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The Ultimate 14-Day Italy Travel Itinerary

LAST UPDATED: 2/25/24 – Ultimate 14-Day Italy Travel Itinerary

The country of Italy is a beautiful and exciting place with a seemingly endless number of amazing things to see and do. It is no wonder then, that Italy is one of the world’s top tourist destinations. If you are planning a trip to Italy soon, you will want to review my Ultimate 14-Day Italy Travel Itinerary to make sure you don’t miss out on some of the country’s most popular sights and activities.

Without a proper plan in place, it is very easy to miss out on an important sight or activity and regret it later. Using this itinerary as a blueprint, you can start to build your big Italian adventure knowing that you have a wealth of information and experience at your fingertips.

See Many of Italy’s Top Destinations

While my itinerary doesn’t cover every region of Italy, it does cover some of the most popular tourist destinations within this amazing country. On your two-week Italian adventure, you will get to explore all of the treasures in the amazing cities of Rome, Venice, and Florence. You will also have the opportunity to explore breathtakingly beautiful regions such as the Amalfi Coast and Tuscany. To top it off, you will even get a chance to visit the amazing island of Capri, which is widely considered to be one of the most beautiful places in Italy.

Included in this Italy travel itinerary are numerous links to in-depth guides that I have developed for each of these regions of Italy. As you start to fill out your personal travel itinerary, these guides will be invaluable resources that you can use to choose the proper accommodations, decide which restaurants you want to try, lay out your daily plans for sightseeing in the region, and book fun and exciting tours and excursions that you will remember for a lifetime. With this wealth of information in hand, you can relax and enjoy the process of planning your trip and focus on the fun, less tedious aspects of planning your trip.

Italy Travel Itinerary Overview

This includes tasks such as making sure you have a valid passport and VISA for entry into the country. It also means confirming that you are up-to-date on the vaccinations that are recommended and required. Once you have done that, you will need to understand what you should and should not pack for your trip.

You will also need to determine what time of year to take your trip and how you will get around the country. Using the links below, you can quickly and easily navigate to the relevant sections of this guide as you start to check these items off your list.

Italy Travel Itinerary Guide Navigation Menu

The best times to visit italy.

When planning your big trip to Italy, one of the most important decisions that you will need to make is when to visit. Before you start looking at accommodations and arranging transportation, you need to know when you will be traveling. For many travelers, this is often one of the most stressful parts of planning a trip because there are so many different variables to consider.

In my opinion, the most important of these variables that you will want to consider are the weather and the number of other tourists that will be visiting when you do. The better the weather, the more time you will be able to spend outdoors exploring this amazing country. And with fewer other tourists around, you will have fewer crowds to contend with when you set out to see and do what interests you.

To make things easier for you as you start to plan this trip of a lifetime, I have compiled all of the weather and tourism data that you will want to consider when scheduling your trip to Italy within my Italy travel itinerary. Using this data, you will be able to pick the time of year that you find the weather to be the most enjoyable.

Average Temperature (°F)

One of the most important factors that you will want to consider before deciding when to visit Italy is the average temperature throughout the year. In the graph below, I have compiled the average high and low temperatures for Venice, Rome, Florence, and the Amalfi Coast for each month of the year. Using this data, you can easily determine which month of the year will be the most comfortable for you as you start to put together your Italy travel itinerary.

Average Precipitation Level (Inches)

Another factor that you will want to consider when deciding when to visit Italy is the average amount of precipitation that each region of Italy you will be visiting typically gets. After all, it can be difficult to get outside and enjoy the beautiful landscapes and cities when it is raining a lot. If you take a look at the graph below, you will see the average amount of precipitation for Venice, Rome, Florence, and Amalfi Coast throughout the year.

Using this data, you can decide which time of year gives you the highest probability of having nice weather during your trip as you start to fill in your Italy travel itinerary.

Average Number of Visitors (Millions)

The last major factor that you will want to consider when determining which time of year is the best time for you to visit Italy is the number of other visitors that you can expect to be visiting while you are there. To give you an idea of how many other tourists you can expect to encounter in Italy throughout the year, I used Statista’s analysis of the number of tourist arrivals and guest accommodations in Italy.

In addition to having an impact on the crowds you will encounter, the number of other tourists visiting during your trip will also impact the availability and price of excursions and tours. However, most importantly, it will be a large factor in the price of your airline tickets and accommodations while in Italy.

The Best Months to Plan Your Trip to Italy

As you look at the temperature, precipitation, and visitor numbers for Italy, it is clear that some months are better for visiting than others. For instance, the months of June through August tend to be quite hot in Italy. This is especially true for July and August. If you want to avoid the heat, you should avoid visiting during these months.

I would also avoid visiting during the autumn months of October through December, as those are typically the wettest months of the year in Italy. Not to mention, it can also get quite cool between November and March. Unless you like wet and rainy conditions, I would avoid planning your trip during late autumn or winter.

In my opinion, the best months to visit Italy are the shoulder months of May and September. The weather is typically warm, but not too hot, and there is usually little rain. This gives you the best weather window to get out and enjoy the sites during your adventure in Italy.

How to Get to Italy for Your Trip

There are many different international airports in Italy, so if you are planning on flying in from outside of the country, you have a lot of options to choose from. If you follow the Italy travel itinerary that I have outlined for you here, there are four major international airports that you can choose from to fly into and out of. For your reference, I have listed those airports for your review.

Major International Airports You Can Fly Into for This Itinerary

• Rome – Leonardo da Vinci International Airport (FCO)
• Venice – Venice Marco Polo Airport (VCE)
• Naples – Naples International Airport (NAP)
• Florence – Florence Airport, Peretola (FLR)

To save time, I would strongly suggest that you fly into and out of different airports. This will prevent having to backtrack significantly when it is time to fly home. However, if you would prefer to fly into and out of the same airport, or find significantly cheaper airfare by doing so, then you can easily modify this Italy travel itinerary to meet those needs. As you start to plan your trip, there are several different options that you can choose from when laying out the logistics of your trip.

There Are Multiple Ways to Plan This Trip

You can start by flying into Venice and then work your way down to Naples, where you will fly home. There is also the option of flying into Naples and then working your way up to Venice, where you will end your trip. For the sake of this guide, I am going to outline a modified Italy travel itinerary where you fly into Rome, work your way down to the Amalfi Coast, then work your way back up to Venice, where you will fly home at the end of your trip. This will allow you to fly into and out of two of Italy’s largest airports where there are more flight options. However, feel free to modify this itinerary in any way that you see fit to meet your travel needs.

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Italy Passport Requirements

When visiting Italy, you must have at least 6 months of validity on your passport beyond the date on which you are planning on arriving in the country.  You will also need to have at least two blank passport pages to be processed into the country. 

Presently, you do not need to have a Visa if you are planning on staying in the Schengen area of the EU for less than 90 days, but starting in 2025 American citizens will be required to get a  European Travel Information and Authorization System (ETIAS) authorization . Before you start making your travel plans, I would strongly suggest you review the passport and Visa requirements I have laid out in my Italy travel itinerary guide below.

Recommended Travel Immunizations for Italy

Before you leave for your trip to Italy, you need to make sure you have all of the proper vaccinations.  Not only to protect yourself but to protect others.  You may have questions on what immunizations you need and what to look out for when getting them. If you do, I have included some general guidelines I can pass on to you from my experience below.

• Most specialized travel clinics will not accept insurance so you will have to pay for your travel consultation and immunizations and then request reimbursement from your insurance company later.
• Some immunizations aren’t accepted by every insurance company, so check with your insurance provider before getting your immunizations.
• Check with your regular doctor first, as often they can do a travel consultation for you and write you the necessary prescriptions for your immunizations, even if they aren’t able to give them to you.  This way you can ensure that at least your travel consultant will be covered by your insurance up-front.
• Check with  Walgreens   or other drug stores that give flu shots to see if they have any of the immunization shots that you require before going to a specialized clinic that doesn’t accept insurance to get them.  Walgreens can give you many of the immunizations necessary for international travel, and they accept insurance up-front.
• The  Centers for Disease Control (CDC) website   can be a great resource for answering any travel immunization questions that you have.

Italy Immunization Recommendations

In case you are unsure of what travel vaccinations you might need, I have compiled a list below of some of what you might expect your physician to recommend.

• Hepatitis A & B  (if you haven’t had them).
• Tetanus  (if you aren’t current).
• Transderm SCōP Patch (for motion sickness) or at minimum Dramamine pills if you get motion sickness easily and you plan on getting out on the water or doing adventure activities.

Italy Travel Packing Tips

Outside of knowing the entry and immunization requirements, there is no pre-travel task more important than packing. Don’t worry, I am here to make sure you are packed and prepared for your trip. I have included links to my packing resources in my Italy travel itinerary guide below for you to review.

Planning Your Transportation in Italy

When it comes to arranging your transportation for the trip, getting from Italy is just half the battle.  Once you arrive in Italy, you are going to need a way to get around.  There are several different methods of transportation you can choose from, depending on the amount of time you will be in-country and your comfort level with driving.

The two most popular options to choose from are renting a car and using the train system. Before you decide which method of transportation is best for you, I have outlined the important considerations for each of these transportation methods for you to review in my Italy travel itinerary below.

Renting a Car

If you are comfortable driving a car abroad, renting a car to get around while in Italy is one option that you can consider. Unlike public transportation, you aren’t subjected to a schedule when planning your travel from one place to another. Ultimately, this means you have much more freedom to do what you want when you want to do it while in Italy.

Italy Car Rental Tips

However, it does come with responsibilities that you don’t need to worry about when using public transportation. This includes paying tolls, finding parking, and filling up with gas when you run low. If you are considering renting a car for your trip, I have included some important tips for you to consider below.

Airport Rental Tips

• The main car rental companies in Europe are Avis , Hertz , Budget , Europcar , and Sixt .
• If you choose to pick up your car while at the airport, you will likely get charged an extra fee.  To save money, you can consider renting from a location outside the airport.   Whether the cost savings on the rental is worth it or not will depend on the cost of transportation to pick up the car and the amount of time it will require.
• In Italy, CDW car rental insurance is mandatory in Italy and rental companies will not let you leave the lot with a car without it. You will be asked to sign a waiver stating that you have car insurance that covers you overseas and you will be responsible for all damages to the vehicle you rent. If you plan on purchasing insurance from the rental company, it is almost always cheaper to select when you make the reservation than it is to add it at the rental counter during vehicle pick-up.
• Unless you specify that you want an automatic transmission when you make your reservation, you will almost always be given a vehicle with a manual transmission.
• Most car rental companies in Europe will charge you an extra fee to take your rental car outside the country, so I would check with the car rental company you decide to use before taking your rental car outside of Italy.

Driving Regulation Tips

• The legal driving age in Italy is 18 years of age, but you also need to have your license for a year before you can rent a car. Most car rental companies will charge you an extra fee if you are under the age of 25 years.
• Never drive in zones marked as Zona Traffico Limitato  (ZTL) or  Area Pedonale . These pedestrian zones are often monitored by traffic cameras and you will be fined.
• The maximum speed limit on highways is 130 kilometers per hour and 60 kilometers per hour within most towns, so be aware of your speed when you aren’t sure of the posted speed limit.
• Never turn right on red lights. While this is commonly acceptable in the United States, it is generally against the law in Europe. So unless you see a sign that explicitly says that you are allowed to turn right on a red light, always wait for the light to turn green.
• As long as you have a valid US driver’s license, you should not need an international driver’s license to drive in Italy.
• In Italy, motorists drive on the right side of the road and the driver’s seat is on the left side of the car.
• Italy uses the metric system, so mileage is listed in kilometers instead of miles.

Using the Rail System

If you aren’t comfortable driving while overseas or just want to avoid the hassle of having to find parking for your rental car, navigate from city to city, and deal with the heavy traffic in some of Italy’s largest cities, a popular alternative is to use Italy’s amazing rail system to get from city-to-city and then use taxis or ride share services to get around each of the cities you visit.

Italy Rail System Tips

The downside of using the train system is that you will have to be aware of your time and make sure you plan your train rides well in advance so that you don’t miss out on some of your trips by not getting where you need to go when you need to be there. If you are considering using the rail system during your trip, I have included some important tips for you to consider below.

Purchasing Rail Passes

• If you are only planning on traveling within Italy, it may not make sense for you to purchase a rail pass. Instead, it will likely be cheaper for you to purchase point-to-point tickets for your train rides separately. The rail passes in Italy tend to be more than $50 per day and you will likely spend less than that amount on second-class point-to-point tickets between Naples, Rome, Florence, and Venice. Before you make a decision on whether or not to purchase rail passes, I would suggest using the railway fare map I included below to price out how much you would be charged for all of your point-to-point tickets and then compare that total price to the cost of a rail pass on the Eurail website .
• Be aware, that even with a rail pass, some routes require that you purchase a reservation for some routes. These reservation costs are included in the fare route map I included below but are not included in the cost of the rail pass.
• The Italo trains run between Italy’s largest cities. If you purchase a rail pass, stick to the Le Frecce trains, which are covered by the rail pass and are typically quicker and run more frequently.
• The Circumvesuviana and Campania Express trains run between Naples Pompeii and Sorrento. If you plan on visiting the Amalfi Coast, this will impact you as the Circumvesuviana and Campania Express trains are the main options to use for getting from Naples to the Amalfi Coast region by train. These tickets typically only cost around $5.

Purchasing Train Tickets

• I would recommend purchasing tickets ahead of time if you know when you will be traveling to ensure that you get on the trains that you want. However, if you do need to purchase point-to-point tickets or reservations while in Italy, I would recommend taking advantage of the ticket machines at the train stations as opposed to waiting in the ticket lines to save yourself time.
• If you are 60 or older, you can buy a  Carta d’Argento , which gives you a 15% discount on most train tickets. They cost €30 for individuals between the ages of 60-74 and are free to those over the age of 75.
• Individuals under the age of 25 can purchase a Carta Verde , which gives you a 10% discount on most train tickets.
• Note that children under the age of 3 ride free on Italian trains. And while not free, kids between 4-11 ride for half-price on regional trains, and kids between 4-14 ride for half-price on long-distance routes.

Italy Travel Itinerary Outline

Now that we have covered some of the basics that you will need to know before you start planning your specific Italy travel itinerary, it is time to start putting your itinerary together. To make that process easier for you, I have included my recommended itinerary below. Your trip will essentially be broken up into four different stages, centered around four different major tourist destinations within Italy.

You will Start Your Trip in Historic Rome

You will start by flying into the city of Rome, where you will tour the city and the Vatican City for the first leg of your trip. After getting to see all of the amazing things that Rome has to offer, you will head south to the Amalfi Coast region. Here, you will enjoy the beautiful beaches, amazing coastline, and wonderful seafood that this region is known for.

As soon as you are finished touring the Amalfi Coast, you will head north to the city of Florence. After taking a day or two to tour the city, you will venture into the countryside to experience the beauty of the region of Italy known as Tuscany. In addition to enjoying the rolling hills and beautiful vineyards, you will get to tour some of Italy’s most amazing wineries.

You will End Your Trip in Beautiful Venice

When you have had your fill of wine, you will keep heading north until you get to the final destination on this Italy travel itinerary. In Venice, you will get to enjoy one of this world’s most amazing cityscapes. Between the breathtakingly stunning canals, beautiful bridges, and amazing historical buildings, you will really enjoy your time touring Venice before getting on a plane and heading home.

Day 1: Arriving in Rome

On the first day of the Italy travel itinerary that I have laid out, you will be arriving in Rome, Italy to begin your two-week adventure. When booking your flights, I would recommend trying to find a flight that gets you into Rome as early as possible.

This will give you time to settle into your accommodations and start exploring the city. If you would like some assistance in finding the right accommodations for you, I have included some recommendations on hotels and hostels in Rome in my Quintessential Rome, Italy Visitor Guide for you to review.

I have included an assortment of options at a variety of different price points near the top attractions in Rome to give you options when choosing the right accommodations for your trip. I have also included several restaurants that I recommend in my guide in case you are looking for a good restaurant to try for dinner after getting settled.

Day 2-3: Tour Rome

Rome is an amazing city with a wealth of history to explore. Because there is so much to see and do in the city and the surrounding area, I have set aside two days for you to explore Rome. To help you fill out your itinerary, I have included a link to my Quintessential Rome, Italy Visitor Guide below.

In my guide, I outline the top things to see and do in Rome during your visit. In addition, I have also included several different tours and excursions that I would recommend checking out if you have the time. Using my guide, you should have no trouble getting around the city and seeing all of the wonderful things that the city of Rome has to offer during your visit.

Day 4: Tour the Vatican

On the fourth day of my Italy travel itinerary, I have scheduled some time for you to explore the wonderful Vatican City near Rome. It’s a large and amazing place, so I would recommend setting aside the entire day to fully explore the Vatican.

I would recommend booking a tour of the Vatican rather than exploring it on your own. Not only will it ensure that you see everything and make your visit more memorable, but tours get priority on entrance and it will save you a bunch of time that you would otherwise spend waiting in line.

Expert Tip: I would strongly recommend booking a tour of Saint Peter’s tomb. They only let a very limited number of people tour the tomb each day, so you will need to make sure you book your tour well in advance (at least 3 months in advance). If you are using a tour company to tour the Vatican, I would let them know you are interested in this tour and they can help you get a reservation.

Day 5: Travel to Sorrento

After touring Rome and the Vatican, the next phase of my Italy travel itinerary has you heading south towards Naples, and then on to Sorrento, which will be your base of operations while you tour the Amalfi Coast.

Depending on how much time you want to spend in Rome, you can travel to Sorrento either early in the day on Day 5 of your trip or later that evening. I would recommend not getting in too late so that you can make sure you get settled properly and are ready to get out and explore right away on Day 6.

If you are looking for accommodations and restaurants in the Sorrento area, I would recommend checking out my Definitive Amalfi Coast Visitor Guide for recommendations. I have included an assortment of accommodation and restaurant options at a variety of different price points in my guide so that you can easily find what you need.

Day 6: Visit Capri

On Day 6 of my Italy travel itinerary, I suggest that you take a trip to the island of Capri to explore for the day. The island of Capri is one of the most beautiful places in Italy and an absolute must-see if you are visiting the Amalfi Coast.

You will need to arrange a ferry ride from Sorrento to Capri and back, so make sure you either purchase tickets in advance if you are sure about your travel dates or leave yourself ample time and flexibility to buy your tickets when you get there.

If you would like more information on travel from the island of Capri, as well as what to see and do while you are there, please refer to my Complete Capri Travel Guide linked below for my recommendations.

Days 7-8: Tour the Amalfi Coast

The next stop on the Italy travel itinerary I have laid out for you is one of the most beautiful regions in Italy. The Amalfi Coast is famed for its breathtaking coastline, colorful cities built up on the coastal bluffs, and delicious seafood and citrus fruits.

You will get to spend the next few days traveling down the Amalfi Coast and exploring all of the treasures that this quaint Italian region has to offer. If you are looking for recommendations on what to see, where to grab a bite to eat, and what tours and excursions are recommended in the area, I would suggest that you check out my Definitive Amalfi Coast Visitor Guide linked below.

Day 9: Travel to Florence

Once you have finished exploring all of the beauty on the Amalfi Coast, the next stop on the Italy travel itinerary I have laid out is the amazing city of Florence in Northern Italy. If you decide not to rent a car while in Italy, you will need to take a train from Sorrento to Naples, where you can catch a high-speed train to Florence. Considering the distance, the 3.5-hour train ride really isn’t that bad.

If you are driving, it will take you roughly 5.5 hours to get from Sorrento to Florence, so you might want to consider making your way North slowly or consider doing this trip from the top-down (starting in Venice and ending in Naples) or bottom-up (starting in Naples and ending in Venice). This will save you a considerable amount of driving time on your trip.

If you are looking for accommodations or restaurant recommendations in Florence, I would recommend reviewing my Florence, Italy Visitor Guide for recommendations. I have included an assortment of accommodation and restaurant options at a variety of different price points in my guide so that you can easily find what you need.

Day 10: Tour Florence

Few cities in the world, let alone Italy, have as much wealth of history as the amazing city of Florence. After arriving in Florence on Day 9 of the Italy travel itinerary, you will get to spend the rest of that day and the following day exploring all of the treasures that the city has to offer. I would suggest that you make the most of it, as there are many amazing things to see and do in the Florence area.

If you are looking for suggestions on what to see, where to eat, and what tours and excursions are recommended in Florence, I would suggest reading my Florence, Italy Visitor Guide linked below for my recommendations.

Day 11: Take a Tour to Tuscany

On the eleventh day of your Italian vacation, you will be taking a tour into one of the most popular tourist spots in Northern Italy. The Tuscany region of Italy is famed for its beautiful rolling hills and fantastic vineyards and wineries. If you have some extra time to extend your trip, this is one of the spots where I would recommend spending an extra few days if you have the time.

If you don’t have extra time, you should be able to get a good sense of the region by taking a day tour into the Tuscan countryside and touring some of the most popular vineyards and wineries in the region.

There is a wide range of tours available, so make sure you take the time to research the tour that is the most interesting to you. To give you a head start, I have linked TripAdvisor’s list of the best Tuscany wine tours and tastings for you to review below.

Day 12: Travel to Venice

When you are finished exploring Florence and Tuscany, the last stop on my Italy travel itinerary is one of the most amazing cities you will find in the world. Renowned all across the world for its romantic canals, its amazing annual Carnival festival, and its wealth of history, Venice is an absolute must-see destination when visiting Italy.

It’s roughly a three-hour trip from Florence to Venice, both by car or train, so you will want to decide how you spend your time on this travel day. You can travel mid-day and spend portions of each day touring each of these cities, travel in the evening if you need more time in Florence, or depart early in the morning if you would like to spend more time in Venice.

When I visited Venice, I was able to see what I wanted in one full day, so my personal recommendation is to spend at least some of the travel days further exploring Florence and Tuscany.

Venice is a large city, so there are a lot of options for you to choose from in terms of accommodations. If you are looking for recommendations, I would suggest reviewing my Venice, Italy Travel Guide for my suggestions. If you are interested, I also outline the top restaurants in the city that I would recommend trying during your stay. I have included an assortment of accommodation and restaurant options at a variety of different price points in my guide so that you can easily find what you need.

Day 13: Tour Venice

When most travelers think of Venice, the first thing that comes to mind is the beautiful canals and romantic gondola rides through the city. While this is a popular activity to enjoy while visiting Venice, it is just the tip of the iceberg when it comes to the wonderful things to see and do while visiting the city.

The last full day of my Italy travel itinerary is dedicated to exploring Venice and all of the amazing things there are to see and do. If you are looking for suggestions on what to see, I have included my list of the top things to see and do in the city in my Venice, Italy Travel Guide linked below. I also outline some of the best tours and excursions you should consider during your stay in case you have extra time and would like to try something unique.

Day 14: Depart From Venice

On the final day of my Italy travel itinerary, you will be wrapping up your sightseeing and preparing to depart for home. If you follow my itinerary as I have laid it out for you in this guide, you will be departing for home from the Venice Marco Polo Airport (VCE) in Venice.

In which case, you will want to leave yourself some extra time to get to the airport as you are going to need to catch a boat from the city back to the mainland of Italy. From there, you can take a taxi or rideshare to the airport.

If you adjust this itinerary to follow the top-down or bottom-up options, you will either be flying out of Leonardo da Vinci International Airport (FCO) in Rome or Naples International Airport (NAP) . You will want to ensure that you have your transportation prepared so that you get to the airport in plenty of time to make your flight.

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Published by Josh Hewitt

Avid traveler and photographer who loves to see new places, meet new people, and experience new things. There is so much this world can teach us, we just need to explore! View all posts by Josh Hewitt

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3 comments ›.

Your blog is amazing! We’ve travelled through Italy and your guide is thoroufh and valuable for anyone who is considering Italy as a travel destination.

Thank you so much for the kind words!! You absolutely made my day! 😃

I did not see the price, and what is included within the price , food or anything else?

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Gibraltar is so beautiful, I never thought of visiting this place, your always adorable photography has made Gibraltar even more…

Thank you so much for the kind words!!

Wonderful, very nice article

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Italy Travel Guide

Looking for an in-depth Italy travel guide ?

Then you’re in the right place!

Italy consistently ranks high on the list of most-visited countries in the world, and for good reason. Between its incredible Italian food, rich history and culture, and gorgeous environment, Italy has so much to offer travelers.

Whether you’re looking to sail the Italian lakes and hike through the Tuscan countryside or just enjoy as much Italian cuisine as your stomach will allow, this guide can help you design the perfect adventure in Italy.

Now, there are a few destinations in Italy that you simply can’t miss.

The capital of Rome has been a hub for urban life for thousands of years. Where else can you enjoy a gelato right across from ancient Roman ruins like the Colosseum?

Additionally, the city has plenty of hidden gems to explore beyond the big-name attractions, like Museum Missionario di Propaganda Fide and other little churches and shops hidden in back alleys. You just have to know where to look!

The city of Florence , located in the heart of Tuscany, is renowned for both classic and modern art — including plenty of street art you can enjoy free of charge. You can even make some art of your own at a fresco workshop !

Up north in Milan, wander through a city that is a true mix of old and new. Roman ruins share space with Gothic cathedrals and modern architecture in this fashionable city.

There are also plenty of ways to enjoy Italy while getting a little off-the-beaten path.

In the small walled Tuscan town of San Gimignano, explore Medieval architecture and climb up the bell tower at Torre Grossa for a truly incredible view. The town is also home to plenty of boutique hotels with a local vibe.

From there, you can explore the rest of the region of Tuscany by bike or car, taste some local wines, and get a true feel for Italian life.

Oh, and you can’t miss the Amalfi Coast, one of the most gorgeous seaside regions in the world! Pro tip: If you enjoy being active, hike the Path Of The Gods and then end the day with some beach time and an Aperol Spritz in Positano.

After your Amalfi Coast adventure, spend time in the nearby city of Naples to explore the still-active Mount Vesuvius and savor a slice in the birthplace of pizza before taking a ferry to visit the island of Ischia for a few days of hiking, beaches, castles, and seafood.

Or, if you’re looking for a truly picturesque destination, head to Cinque Terre on the northwest coast. Go beyond the guidebook and visit the little seaside villages along the coast by hiking or by taking a boat — you’ll be glad you did!

Keep reading to dive into resources that will help you with planning a trip to Italy in Europe.

Note: This ultimate guide to Italy travel contains affiliate links to trusted partners!

Use this Italy travel map to begin planning your trip to this incredible country!

Click here for an interactive Google Map version of the above graphic.

Top Italy Destinations

Looking for the best vacation places in Italy ? These travel guides to Italy can help!

Slowing Down In Paradise In Perugia, Italy

Things To Do In Venice, Italy (Beyond The Grand Canal)

One Perfect Day On The Italian Island Of Ischia

Tips About Italy

This Italy travel advice will help you plan the perfect trip!

How To Hike The Path Of The Gods On The Amalfi Coast Of Italy

How To Have An Epic Road Trip Through Italy

Traveling Italy Solo: The Ultimate Guide

Tuscany Travel Guide

You can’t go to Italy without visiting Tuscany. Learn why through these Italy travel guides.

How To Bike Tuscany & See The Region’s Best Views

A Carnivore’s Heaven In Tuscany, Italy

Learning The Art Of Cooking With Olive Oil In Tuscany

Piazza del Vino: A New Concept For Tuscany

A Delicious & Tipsy Journey Through Tuscany, Italy

Florence Travel Guide

Looking for a city guide to Florence as well as to learn about the best day trips from Florence ? Check out:

Learning The Art Of Fresco In Florence, Italy

3 Unique Art Experiences In Florence (Beyond The Uffizi Gallery)

Cinque Terre Travel Guide

If you’re looking for the best Italy places to visit you can’t miss Cinque Terre. Here’s why.

Making Friends Over Food In Riomaggiore, Italy

How To Go Beyond The Guidebook In Cinque Terre, Italy

Rome Travel Guide

Rome is home to some of the best sights to see in Italy , which you’ll discover in these guides.

Italy, Travel: Exploring Rome Beyond The Ruins

Exploring The Hidden Treasures Of Rome, Italy

The Ultimate Rome Solo Travel Guide

20 Best Weekend Trips From Rome

Best Italy Tours

Explore local culture with an Italy tour guide through these unique excursions:

• Skip-The-Line Rome Colosseum Tour with Roman Forum & Palatine with 45′ Guided Tour
• Ancient Rome City Tour
• Cooking Class and Lunch at a Tuscan Farmhouse with Local Market Tour from Florence
• Cinque Terre Day Trip from Florence with Optional Hiking
• Capri and Blue Grotto Day Tour from Naples or Sorrento
• Full-Day Prosecco Wine Tasting from Venice

Renting A Car In Italy

Need a rental car for your Italy trip?

Use Discover Cars to quickly compare your car rental options.

Italy Train Travel

Getting around Italy by train, bus, or ferry?

Omio is a must! I use this tool for all of my public transportation needs, especially when traveling through Europe .

The site is straightforward and user-friendly — and you can pre-book your tickets in advance at a discount.

They even offer flight and car deals!

Italy Hotels

Click here to browse the best Italy travel hotels!

Prefer self-contained stays?

Click here to check out unique local rentals!

You can also use this map to search for local stays:

Italy Travel Insurance

It doesn’t matter if you’re traveling solo or with a group on an Italy tour. When visiting Italy — or any other country in the world — make sure to get travel insurance to protect your health and safety.

In my opinion, the best travel medical insurance for travelers is SafetyWing as they’ve got a large network and offer both short-term and long-term coverage — including coverage if you’re traveling for months as well as limited coverage in your home country).

Additionally, SafetyWing is budget-friendly and offers $250,000 worth of coverage with just one low overall deductible of $250.

With coverage, you’ll have peace of mind as you embark on your Italy travel itinerary.

Click my referral link here to price out travel insurance for your trip in just a few clicks .

Italy Travel Guide FAQ

Below, find answers to frequently asked questions about traveling in Italy .

Q: How much money do you need per day in Italy?

The average traveler spends about $150 USD per day in Italy on accommodations, food, transportation, activities, and more.

Italy is fairly backpacker-friendly and there are plenty of ways to save money on food and other travel expenses. Hostels abound in most cities and many offer free walking tours, which are also a great way to get oriented upon arriving in a city.

Tip: Since many restaurants charge an extra fee if you choose to sit and eat inside, consider grabbing some food to go and having a picnic. With all the delicious food available in Italy, you won’t miss out on the cuisine by eating al fresco.

Q: What are some travel tips for Italy?

There are lots of things to consider when visiting Italy, particularly for the first time.

For one, many cities and towns have been around for centuries and can be tough to navigate without a map. Make sure to download some offline maps before you head out. This is particularly helpful in cities like Venice, where the combination of twisty streets and less-than-stellar navigational service can leave you walking around in circles for hours.

There’s no need to buy water in most major Italian cities. Cities like Rome and Florence have clean drinking water fountains throughout where you can fill up a reusable bottle for free. There are even some natural sparkling water fountains around for those who need their fix of bubbles.

While English is widely spoken in major cities, you’ll want to learn at least a few Italian phrases, particularly if you’re visiting smaller towns. Not only will it help you communicate with the locals but it shows your respect for the people of Italy and their culture.

You will also probably visit at least a few churches during your time in Italy. Note that women are expected to cover their shoulders and legs inside churches, particularly at major religious sites like the Vatican. All visitors are expected to remove their hats, as well.

Covering up can be a challenge in the hot summer months, so packing a shawl or hoodie in your day bag to throw over your shorts or tank top is a smart idea.

Hungry? Make sure to spend some time trying traditional food in Bologna , the food capital of Italy!

Q: Is it safe to travel in Italy?

Italy is generally quite safe for visitors. Though crime rates are on the higher side than other European destinations, they have declined in recent years, and most tourist cities are even safe for those traveling alone ( solo trip to Rome , anyone?).

The main thing to be aware of is petty crime. Pickpocketing does happen, particularly in tourist-heavy areas, so be aware of your surroundings, keep any valuables close to you and out of sight, and learn how to avoid pickpockets by wearing hidden-pocket clothing.

It’s also important to be aware of local laws. For example, drinking alcohol on the street is common in many Italian cities but public drunkenness can come with major fines.

Also, don’t forget to validate your bus, train, or metro ticket before you board. If you get caught without a validated ticket, you can face an on-the-spot fine.

Q: How many days do you need in Italy?

Most experts recommend spending at least 10 days in Italy to enjoy the major cities and top destinations like Tuscany and the coast.

You’ll need at least three days just to explore Rome since the city is chock full of historic sites, including the Vatican.

A two-week trip will allow you to visit a few more places like Pompeii and spend a bit of time on the Amalfi Coast. The length of your trip certainly depends on your priorities — and is the perfect amount of time for a fun-filled Italy road trip !

Q: When is the best time to visit Italy?

While the summer season (from July to early September) is a popular time for tourists to visit Italy, the weather is very hot.

Springtime (April through June) and early fall (mid-September through October) are a bit more pleasant and much less crowded. You’ll also find some better deals if you visit off-season.

Of course, Italy is lovely any time of year, and visiting in the winter has its perks, particularly if you’re looking to do some skiing in the Alps.

Q: How long can a tourist stay in Italy?

Most tourist visas will allow you to stay in Italy for up to 90 days without engaging in any professional activity during your stay.

Q: Do I need an Italy travel visa?

Travelers from the United States, the United Kingdom, Australia, Canada, Schengen Area member countries, and several other countries do not need a visa to visit Italy for a period of fewer than 90 days.

It’s recommended to view your country’s Italy International Travel Information page for the most up-to-date information on entry and exit requirements. You can also contact the Consulate General of Italy.

Q: Where is Italy?

Italy is located in southern Europe and is bordered by France, Switzerland, Austria, and Slovenia to the north as well as the Adriatic Sea, Tyrrhenian Sea, Ionian Sea, and the Mediterranean Sea.

Q: Are credit cards accepted in Italy?

Credit cards — particularly Visa and Mastercard — are widely accepted around Italy, though it is always wise to carry some cash for smaller establishments and in case of emergency.

Q: Can you drink the tap water in Italy?

Yes, it is safe to drink tap water in Italy unless otherwise noted in just a few areas of the country.

Q: What is the local currency in Italy?

The local currency in italy is the Euro (€).

What would you add to this Italy travel guide?

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Italy Tours & Holidays

Cruise canals, peruse piazzas, veer towards the Vatican and polish off the perfect pizza.

Italy may be one of Europe 's most-visited countries, but finding your way around Venice’s canals, choosing the best place for gelato in Rome, and knowing your agnello from your agnolotti are skills best learnt from locals. Our Italy tours & holidays  are all about strolling down cobbled lanes in city backstreets and ancient walled villages in search of la dolce vita. Once here, the opportunities are endless – from tasting balsamic vinegar in a traditional acetaia in Modena and sailing past pastel-hued cliffside villages on the Amalfi Coast , to sampling local wine in Tuscany's vineyards  and admiring lesser-known Renaissance art in Florence . One thing's for sure: you won’t be going hungry.

Our Italy trips

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We also travel to

Italy at a glance, capital city.

Rome (population approximately 2.87 million)

Approximately 59 million

(GMT+01:00) Amsterdam, Berlin, Bern, Rome, Stockholm, Vienna

CALLING CODE

Electricity.

Type C (European 2-pin) Type F (German 2-pin, side clip earth) Type L (Italian 3-pin)

Learn more about Italy

Culture and customs.

The Renaissance, opera, Vespa, Valentino, slow food, espresso, the Colosseum and the Sistine Chapel, the culture of Italy is as rich as its food. And with iconic cities like Rome, Venice, Florence and Naples showcasing historic gems around every corner, it's easy to see why Italians are so very proud of their heritage. Italy drips with sensational artwork, ancient icons, ornate architecture and historic sights. The streets are filled with people and places that exude character and charisma, and the famous Italian artists, inventors and public figures that have contributed so much to the world are openly adored and celebrated.

In general, Italians value family, food and the enjoyment of life. Good quality food made with the best ingredients is preferred over processed products and fast food. Eating is a pleasure to be enjoyed with friends and family, not a necessary inconvenience. Respect for the family unit is paramount, with many families choosing to live close to each other for life. Community is also an important element of Italian life and this can be seen in neighbours enjoying a passeggiata (an after-dinner stroll and chat).

Italians certainly live their lives with passion, and this is evident in their zealous approach to driving, passionate following of football (soccer) matches and exuberant social life. It's common to see Italians debate politics, fashion, sport and current affairs with ferocious verve, which can sometimes be quite confronting for people from meeker cultural backgrounds. But lying underneath the bold, animated exterior of most Italians is a deep, passionate love of life itself.

History and government

Rise of the empire.

The rise of the Roman Empire has been the subject of much fascination, intrigue and interest from scholars, artists, travellers and students around the world. The modern world owes a lot to this civilisation, with many important scientific inventions, art movements, architectural triumphs and philosophical ideas being born from Roman civilisation – most notably during the Renaissance.

Founded sometime around 750 BC, Rome is still considered one of the most important and enduring cities in the world. Home to such famous citizens as Julius Caesar, Emperor Augustus, Claudius, Nero, Mark Antony and Marcus Aurelius, Rome has enjoyed the great highs of dominating the Mediterranean region and the artistic triumphs of the Renaissance, but also the lows of the Great Fire of Rome, which ended up destroying a large part of the city. Rome has survived natural disasters, political turmoil, feuding families, plagues and fierce wars.

Spanning centuries, the story of Ancient Rome is full of dramatic twists and turns, and explains how tourist icons like the Colosseum, Pantheon, Circus Maximus and Palantine Hill came to be.

The Renaissance

The time of the Renaissance in Italy (15th to 16th century) marked the clear transition from the Middle Ages to Modernity. The social and cultural revolution began in Florence, which was under the rule of the Medici family, and spread south to Rome. During this time, there was a reinvigoration of the arts, literature, science, invention and political theory, which influenced all of Europe – all centred in Italy.

People in protest

After the Renaissance, Italy was unified with Sardinia in 1861, becoming the Kingdom of Italy. After World War I, Italy came under the fascist rule of Benito Mussolini, who ruled until 1943. Siding with Nazi Germany in World War II, the Italian Army suffered many losses and ultimately surrendered in 1945. After a referendum in 1946, Italy became a Republic and flourished during the 1950s and 1960s. The post-war period marks a time of economic progress for Italy, also largely reflected by the rest of the world's increased economic stability during a period of relative peace.

From the late 1960s, Italians lived with political upheaval and uncertainty, marked by the ‘Anni di Piombo’ or ‘Years of Lead’. This time was marked by conflict and public protests, and in the years to follow, corruption, organised crime, terrorism and government debt was prominent in Italy. This led to extremist incidents of political terrorism and crisis on the left and the right, with one terrorist group – le Brigaterosse (or the Red Brigade) – a key player in the turmoil.

In 1994, media mogul Silvio Berlusconi was elected to the office of Prime Minister but was forced to step down later in the year after losing support from his political partners. Social unrest died down a little after the turn of the millennium, but Italy’s political system remained fraught with instability. Undeterred, Berlusconi regained power on two separate occasions, both times amid controversy and scandal.

Currently, Italy is run under a unitary parliamentary republic system, and has been since 1946. The final downfall of Berlusconi has marked a shift in Italian politics, with many parties vying for office, and alliances and coalitions the only way to do so.

Top places to visit in Italy

Oh, Venice. The city of romance, gondolas, Piazza San Marco and an endless maze of canals. With plenty of free time to eat, drink, shop and stroll, you’ll lose all sense of direction – but remember, getting lost in Venice is the whole point! Don't forget to sample a big slice of tiramisu (coffee-soaked sponge cake), the region’s specialty.

Explore Venice on our 14 day Best of Italy tour, on our 8 day Highlights of Italy tour, or on our 8 day Italy Real Food Adventure.

2. Cinque Terre

The footpaths between the villages on the enchanting Cinque Terre were once the only way to travel in the region. Hike along the rugged clifftops and discover olive groves, vineyards, breathtaking vistas and five pastel villages perched on the coastline – each more colourful than the last. If hiking isn’t your thing, don’t worry – just jump on the train!

Fall in love with Cinque Terre on our 15 day Barcelona to Rome tour, on our 8 day Cinque Terre: Hike, Bike & Kayak tour, or on our 8 day Northern Italy Family Holiday tour.

3. Amalfi Coast

Discover southern Italy’s dazzling coastline of cliffside villages and rugged terrain by land and sea. You might like to hike the famous Walk of the Gods, sip Campari in Sorrento, or tuck into traditional pizza in Naples – the birthplace of pizza.

Adventure along the Amalfi coast on our 10 day Explore Southern Italy tour or on our 8 day Amalfi Coast: Hike, Bike & Kayak tour.

There's much more to Tuscany than Florence's impressive Renaissance art and architecture – though there'll be plenty of time to explore this! From rolling hills and fruitful vineyards to charming fortified towns with their relaxed vibes, the Tuscan countryside is the Italy that continues to draw you back; the one you fall in love with.

Marvel at Tuscany's picturesque countryside on our 10 day Italy Experience tour or on our 8 day Cycle Tuscany tour.

Italy’s enduring capital, the epicentre of the fierce Roman Empire – Rome is a living, breathing history book. Dive deep into the city’s most iconic sites – the Forum, Colosseum, Trevi Fountain, Spanish Steps – and stumble upon the country within a city: the Vatican. Or simply sip espresso at one of the tiny streetside cafes and watch life go by.

Absorb Rome's history on our 8 day Rome to Amalfi tour or on our 8 day Highlights of Italy in Winter tour.

6. Taormina

If mainland Italy is the boot, Sicily is the football. The further south you go, the more relaxed Italians get – so immerse yourself in an island culture full of charm, and a cuisine packed full of arancini and granita. Take a day trip to the charming city of Taormina and visit the world-famous Greek theatre and cathedral, take a dip in pristine coves or enjoy lunch while looking at the imposing Mt. Etna.

Visit Taormina on our 24 day Rome to Sicily adventure.

Eating and drinking

Italy may be the food capital of the world (not exaggerating), but sometimes it can be difficult to know what to eat and where to go.

When eating and drinking through Italy, be sure to walk a street or two away from the tourist attractions to find a restaurant, as they often are cheaper and much more authentic than the ones close by. Be sceptical of menus entirely in English and those with pictures, as this is, again, not the authentic way. Also, bigger is not always better – often the ‘hole-in-the-wall’ restaurants produce the best food. But above all, go with your gut and follow your eyes and nose, and you will be satisfied.

Sample and sip your way through the best flavours Italy has to offer on our 8-day Italian Real Food Adventure Tour

Must try dishes and drinks in Italy

• Antipasto If any country knows its way around cured meat and vegetables, it’s Italy. Discover salami, olives, artichokes, anchovies, cheeses, grissini and more, with each board changing depending on what region you find yourself in.
• Pizza If you were asked to describe Italy in one word, chances are someone would yell ‘pizza’. This carby dish of 100% joy is found all over, with regional specialities everywhere you go. And if you’re vegan? No stress – just ask for one of the vegetarian pizzas ‘senza formaggio’ (without cheese) and you’ll be set. Expect to be crucified if you ask for pineapple, though. 
• Pasta Different shapes, different sauces and different preparations make this one of the world’s most versatile dishes. From a fiery penne arrabbiata and a creamy spaghetti cacio e pepe to a baked gnocchi alla romana, you really can’t go wrong.
• Gelato Traditional Italian flavours like bacio (chocolate hazelnut), amarena (sour cherry) and limone (lemon) are the perfect accompaniment to sightseeing on a hot summer's day. Stack the gusti (flavours) up on a cono (cone) or in a copetta (cup) for a quick snack.
• Wine Italy produces some of the world's best wine, so savour a glass (or three) of Chianti or Sangiovese with dinner. Most regions of Italy produce their own wine, but the area that everyone talks about is the one and only Tuscany.
• Aperitivo A classic Italian pastime, aperitivo hour calls for two things: to find a local restaurant or bar in the early evening, and to order yourself a drink. This is usually a light and dry tonic, but can be wine or a cocktail. It’s usually accompanied by some complimentary nibbles.

Read more about what to eat in Italy

Read more about what to drink in Italy

Geography and environment

Sharing borders with Switzerland , France , Slovenia and Austria , Italy also encompasses the independent territories of San Marino and Vatican City and includes the islands of Sicily and Sardinia.

Home to mountains, volcanoes, islands, beaches, spectacular cliffs and expansive stretches of coastline, the natural landscapes of Italy provide dramatic scenery as well as popular places to explore and relax for travellers. The major cities of Italy, although industrialised, still retain buildings, churches and relics from the past. It's quite common to see modern shops housed in historic cobblestone streets and new Vespas perched beside piazzas.

In smaller cities and more isolated areas, rural life is a whole lot slower. Permaculture remains popular, with many Italians growing fruit and vegetables in their backyards. The traffic and frenetic pace of the cities give way to idyllic olive groves, vineyards and farmhouses.

8 iconic Italian landscapes

• Capri Be blown away by the shimmering beauty of this sun-bleached island that sits in the middle of a mass of deep blue water. Home to luminous sea caves, stunning cliff faces and whitewashed buildings, Capri is the perfect setting for a romantic escapade, relaxing boat ride or some serious sun-worshipping.
• Tuscany An enchanting mix of rolling green hills, vineyards, simple farmhouses and charming villages, Tuscan landscapes are effortlessly beautiful. Whether you're cycling around vineyards, hiking through the countryside or lying in a field of golden grass, Tuscany is made for life in the slow lane.
• Lake Como Lake Como is considered one of the most picturesque slices of Italy. A vast expanse of deep blue water set to a stunning mountainous backdrop dotted with rustic villas and wildflowers, Como is the sparkling jewel of Italy's north, naturally polished to perfection.
• Mount Vesuvius Sitting on the Bay of Naples, the austere beauty of brooding Mt Vesuvius offers a contrast to the luscious green landscapes of the Mediterranean. Mt Vesuvius is still active, but a hike to the summit is possible – and worth it for the views of the bay below.
• Amalfi Coast A journey along the winding roads of the Amalfi Coast offers panoramic sea views, alluring towns perched on cliffs and beaches bathed in sunlight. Admire landscapes dotted with lemon trees and olive groves and enjoy the gentle sea breezes.
• Sicily Sitting under the watchful eye of moody Mt Etna, Sicily is a taste of authentic Italy. Surrounded by a sea of turquoise speckled with volcanic islands, Sicily boasts diverse landscapes of rocky mountains, rural pastures, ancient ruins and villages steeped in history.
• The Dolomites Carpeted in wildflowers during summer and covered in a blanket of white snow during winter, the Dolomites are a breathtaking sight in any season. Whether you're hiking the trails during summer or skiing downhill during winter, you’ll soon realise why the Dolomites have such a mighty reputation.
• Le Cinque Terre A quintessential Italian sight, the Cinque Terre, or Five Lands, is a destination to be cherished. Walk the rocky path over steep cliffs and past character-filled villages perched beside the sea. Wander past shady trees, gardens and groves as the sea reflects the sun’s rays. This is panoramic perfection!

Italians are known for their style and this is reflected in their designer fashion and furniture. Be prepared to part with money – shopping in Italy can get quite expensive – but the quality of handmade and tailored items is generally exceptional.

Things to buy

• Clothing Milan, Rome and other big cities are packed with high-end designer fashion boutiques, chic outlets and tailors. Wherever you are in Italy you're guaranteed to get the latest fashions straight from the catwalks of Europe.
• Colourful ceramics Vibrant, hand-painted ceramic bowls, jugs and glasses can be found in the shops and markets of the Amalfi Coast and Sicily – a perfect reminder of the Mediterranean. If you do happen to head to the island of Murano in Venice, be sure to check out their renowned glassware.
• Masks Venice is filled with shops selling elaborate, handcrafted masquerade masks. These colourful creations look great hung on walls and are a true Venetian keepsake.
• Leather footwear, bags and accessories Florence and Rome are hotspots for sourcing gorgeous handmade leather items. Splash out on an 'investment purchase' – a leather handbag that will last a lifetime. You deserve it.
• Italian foodstuffs Now, this one you’ve got to be careful with, but if you know your limits, you’ll be eating and drinking authentically when you arrive home. Infused olive oils, syrupy balsamic vinegar, local dried pasta, limoncello and more – all (likely) fine to pack carefully in your luggage and take home. Be careful with anything fresh or unsealed, though, or you might be in for a hefty fine if you try to get them back home.

It's a good idea to check with your local customs officials to ensure that you are able to bring certain items back into your home country. Australia and New Zealand, in particular, have strict quarantine laws.

Top Italian events and festivals 

Keep the ‘festa’ (or party) going in Italy with festivals and events all around the country. If there’s something going on in Italy, you know that food and drink is somehow involved, too.

1. Regata Storica di Venezia (Venice Historical Regatta)

For four days, Venice’s romantic gondolas take second place on the scenic canals to races featuring the world’s best rowers. Dating back to the 13th century, this historic event is held on the first Sunday of September each year.

2. Natale di Roma (Rome’s Birthday Celebrations)

Every April, Rome throws itself an epic birthday bash and parties like it’s 753 BC. Gladiator battles, historic re-enactments, equestrian events, parades and concerts are all part of this three-day throwback to ancient Roman times.

3. Pasqua (Easter)

Beautifully decorated shop windows, colourful painted eggs, church services, parades, feasts and fireworks make Easter a wonderful time to visit and be immersed in traditional Italian cultures. A huge Easter celebration mass is held at St Peter’s Basilica at the Vatican, followed by an address from the Pope at noon. There are many festive recipes rolled out for Easter too, including the colomba – a dove-shaped cake flavoured with almond.

5. Carnevale

Each city may celebrate differently, but Carnevale festivities in the lead-up to Lent are always a raucous affair in Italy. Venice celebrates with masked parties. Viareggio opts for parades featuring floats, costumes and enormous papier-mache puppets, and Turin hosts the Battle of the Oranges – a spectacular food fight with, you guessed it, oranges.

6. Verona Opera Festival

The country that gave the world opera hosts the oldest opera festival in Verona each summer in the historic Verona Arena, a massive first-century Roman amphitheatre.

Read more about festivals in Italy

Further reading

For inspiring stories to prepare you for your Italy adventure, check out these books:

• The Name of the Rose – Umberto Eco
• I’m Not Scared – Niccolo Ammaniti
• The Divine Comedy – Dante Alighieri
• Naples ‘44 – Norman Lewis
• Call Me By Your Name – Andre Aciman
• The Sicilian – Mario Puzo
• Ancient Rome: The Rise and Fall of an Empire – Simon Baker
• A Thousand Days in Venice – Marlena de Blasi

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Italy travel FAQs

Do i need a covid-19 vaccine to join an intrepid trip.

Trips from 1 January 2023 onwards

From 1 January 2023, Intrepid will no longer require travellers to provide proof of vaccination against COVID-19 (excluding all Polar trips and select adventure cruises).

However, we continue to strongly recommend that all Intrepid travellers and leaders get vaccinated to protect themselves and others.

Specific proof of testing or vaccination may still be required by your destination or airline. Please ensure you check travel and entry requirements carefully.

Do you need a visa for Italy?

Generally, you will not need a visa to travel to Italy for a period of up to 90 days. Some citizens of a select few nationalities may need to obtain a Schengen visa before travelling to Italy. For more information, contact the Italian embassy or consulate in your home country.

This page is for general information only and may be subject to change. It is your responsibility to obtain relevant visa and travel information required for entry, departure and travel to each country or region you visit on your trip. You should confirm these with the relevant embassies and/or consulates. 

Last updated: 06/06/2023

Do I need to purchase travel insurance before travelling?

Absolutely. All passengers travelling with Intrepid are required to purchase travel insurance before the start of their trip. Your travel insurance details will be recorded by your leader on the first day of the trip. Due to the varying nature, availability and cost of health care around the world, travel insurance is very much an essential and necessary part of every journey.

For more information on insurance, please go to: Travel Insurance

Is tipping customary in Italy?

Tipping isn’t customary in Italy, but it is appreciated. Feel free to leave a small amount if the service has been particularly good. Some restaurants will add a cover charge or ‘servizio’ to your bill.

What is the internet access like in Italy?

Italy, like the rest of Europe , is well connected. Wi-fi is almost always available at larger hotels and guesthouses, either included in your room price, or for a small additional fee. Some smaller accommodations, such as rural guesthouses and homestays, may not have wi-fi available, or the signal may be patchy.

Many fast food chains, bars and restaurants also offer wi-fi connectivity, often with an access code located on a purchase receipt. Look out for the international wi-fi symbol, or politely ask a waiter if the option is available. Some major Italian cities also offer public wi-fi hotspots with registration.

If you do not have your own device, there are still some internet cafes in Italy’s major cities.

Can I use my mobile while in Italy?

Mobile phone coverage is generally good in Italy. Your best (and often cheapest) option is to purchase a local SIM card when arriving in Italy if your phone is compatible and unlocked.

There is also the option to activate global roaming with your service provider before leaving home. Check the roaming charges before you leave home, as this option can often be highly expensive.

What are the toilets like in Italy?

Western-style flushable toilets are the norm in Italy.

Public toilets are not in abundance in Italy, so your best bet is to use the facilities in museums, galleries, department stores, train stations and restaurants. You may have to pay a small fee to use public toilets – ranging from around EUR 0.50 to EUR 2.

What will it cost for a…?

Italy’s unit of currency is the euro (EUR). Here's what you can expect to pay for a:

• Cup of coffee = EUR € 1.50
• Small gelato cone = EUR € 2-3
• A glass of beer = EUR € 4-5
• Bottle of wine in a restaurant = EUR € 10
• Mid-range meal at a restaurant = EUR € 30-40

Can I drink the water in Italy?

Drinking water from taps in Italy is generally considered safe. For environmental reasons, try to avoid buying bottled water. Fill a reusable water bottle or canteen with filtered water instead.

Are credit cards accepted widely in Italy?

Major credit cards are widely accepted by stores in Italy. Smaller cafes, shops and markets may not accept credit cards, and smaller museums or galleries may charge an entry fee in cash only, so ensure you carry enough cash to cover small purchases.

What is ATM access like in Italy?

ATMs are common in Italy, so finding one won't be a problem in most towns and cities. Beware of transaction fees that ATMs charge and the conversion rates they may offer, as they are often much worse than what your card offers.

What public holidays are celebrated in Italy?

• 1 Jan: New Year’s Day (Capodanno)
• 6 Jan: Epiphany (Epifania)
• *Mar/Apr: Easter Sunday (Pasqua)
• *Mar/Apr: Easter Monday (Pasquetta)
• 25 Apr: Liberation Day (Giorno della Liberazione)
• 1 May: Labour Day (Festa del Lavoro)
• 2 Jun: Republic Day (Festa della Repubblica)
• 15 Aug: Feast of the Assumption (Ferragosto)
• 1 Nov: All Saint’s Day (Festa di Ognisanti)
• 8 Dec: Feast of the Immaculate Conception (Festa dell’Immacolata Concezione)
• 25 Dec: Christmas Day (Natale)
• 26 Dec: St Stephen’s Day (Festa di Santo Stefano)

Please note, Italy public holidays may vary.

Is Italy safe for LGBTQIA+ travellers?

Italy is mostly a safe destination for LGBTQIA+ travellers. Same-sex relationships are legal and are largely accepted, with civil unions entrenched in law since 2016. Same-sex marriage is currently not legal. There are some anti-discrimination laws to protect sexual orientation and gender identity.

In more rural and regional areas, overt displays of affection can attract negative responses in smaller towns, which tend to be more conservative. Rome, Milan and Bologna have the largest gay scenes, and Florence and Naples have a handful of LGBTQIA+-friendly venues too.

For more detailed and up-to-date advice, we recommend visiting Equaldex  or  ILGA before you travel.

If you are travelling solo on an Intrepid group tour, you will share accommodation with a passenger of the same gender as per your passport information. If you don’t identify with the gender assigned on your passport, please let us know at time of booking and we’ll arrange the rooming configuration accordingly. A single supplement is available on some tours for travellers who do not wish to share a room.

When is the best time to visit Italy?

Italy enjoys a temperate climate most of the year, with June, July and August the warmest months. Popular tourist spots get very busy and crowded during the European summer, but don’t let that deter you – the sun will be shining, and the gelato will be served icy cold.

The shoulder seasons of April–May and September–October offer great conditions for travel, with milder temperatures and fewer crowds at main sights and beaches. Even though it’s not as hot, you’re still set for some warmer conditions and more pleasant temperatures to walk around the cities like Rome and Florence.

It can get quite cold in the winter months, especially in the north, with cities like Milan, Turin and Venice often seeing snow, fog and rain in December and January. Major coastal tourist spots like the Amalfi Coast and Cinque Terre can be very quiet during winter with many establishments closing at this time, so it might be best to visit in the warmer months if these places interest you.

What is the weather like in Italy?

As you can tell from a world map, Italy is a pretty long country compared to its European neighbours. This gives it one of the more diverse climates in Europe , with mountainous zones in the north and dry arid landscapes in the south graced with all different types of weather.

Much of the inland northern regions have harsh winters and hot summers, while coastal areas of Liguria, Tuscany and the south of Italy generally fit that Mediterranean stereotype, with hot and dry summers and mild winters. The east coast of the Italian peninsula is not as wet as the west coast, but in winter, the east coast is usually colder.

Generally, Italy’s hottest month in the south is August and can reach upwards of 40°C, while the north hits its peak in July and has slightly milder maximums. January is the coldest month throughout the country.

What to pack for Italy?

You’ll need to consider the time of year you want to travel, plus the places you’re travelling to so you can work out what you should wear in Italy.

In summer, loose-fitting cotton clothing like light t-shirts and shorts or light trousers, is recommended no matter what part of the country you’re in. During the transitioning seasons of April-May and September-October, packing a jacket and long pants is encouraged so you can layer, if needed.

Winter brings snow and sub-zero temperatures to the north of the country, so if you’re travelling in Milan or the Piedmont region, pack warm clothing, such as thermals and thick jackets. A scarf and gloves are encouraged too. For the south, you may not need all the heavy stuff, but having warm, windproof and waterproof gear is advisable.

If you wish to visit the Sistine Chapel and other churches and religious sites in the Vatican City and beyond, it is highly recommended that men and women wear clothing that covers shoulders and knees, any time of year. If you are found to be wearing immodest clothing by security guards or staff, you will be denied entry.

Read more about weather in Italy

Is Italy accessible for travellers with disabilities?

Intrepid is committed to making travel widely accessible, regardless of ability or disability. That’s why we do our best to help as many people see the world as possible, whatever physical or mental limitations they might have. We’re always happy to talk to travellers with disabilities and see if we can help choose the most suitable itinerary and, where possible, make reasonable adjustments to our itineraries.

Despite Italy’s charm and old-town feel, travellers with mobility and sight or hearing impairments may find it difficult to travel around the country independently. Old cobbled streets and pavements blocked by parked cars are the norm, making it difficult for wheelchair users.

Despite this, much of Italy’s public transport system is mobility friendly. The service ‘Sala Blu’ (Blue Hall) is provided to travellers who require assistance at the 14 main train stations around Italy. These services include providing a wheelchair, a representative to accompany you to your train, another to meet at the other end, lift service to get on and off the train, and free use of baggage trolleys.

Many of Italy’s most-visited attractions, like the Colosseum, Vatican museums and the Uffizi Gallery, are almost entirely wheelchair accessible, with ramps and lifts available. Venice may be considered the least accessible, but it is possible. Bridges between canals should be avoided, but vaporettos (or water taxis) can be used, especially the routes along the Grand Canal.

If you do live with a visual, hearing or other impairment, let your booking agent or group leader know early on so they’re aware and suitable arrangements can be made. As a general rule, knowing some common words in the local language, carrying a written itinerary with you and taking to the streets in a group, rather than solo, can help make your travel experience the best it can be.

How do I stay safe and healthy while travelling?

Intrepid takes the health and safety of its travellers seriously and takes every measure to ensure that trips are safe, fun and enjoyable for everyone. We recommend that all travellers check with their government or national travel advisory organisation for the latest information before departure:

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The World Health Organisation also provides useful health information.

How will I be travelling around Italy?

Intrepid believes half the fun of experiencing a new country is getting there, and getting around once there! Where possible, Intrepid uses local transport options and traditional modes of transport – which usually have less of an environmental impact, support small local operators and are heaps more fun.

Depending on which trip you're on while in Italy, you may find yourself travelling by bicycle.

Whether it’s riding through fields of grass scattered with wildflowers or past quaint buildings down cobblestone lanes, taking a quick spin around town or tackling the towering Dolomites, two wheels open up so many options.

What better way to see Italy’s island of Sardinia or the Amalfi coast than on a small-group sailing adventure? Cruise past idyllic islands to fabulous shore stops dotted around the Mediterranean.

What kind of accommodation will I be staying in?

Travelling with Intrepid is a little bit different. We endeavour to provide travellers with an authentic experience to remember, so we try to keep accommodation as unique and traditional as possible.

When travelling with us in Italy you may find yourself staying in a:

Agriturismo (farmstay)

Your time in Italy is further enhanced with an agriturismo, or farmstay, experience. Immerse yourself in a picturesque setting overlooking the countryside, with food and relaxation the main focus.

Does my trip to Italy support The Intrepid Foundation?

Yes, all Intrepid trips support the Intrepid Foundation. In fact, we make a donation on behalf of every traveller. Trips to Italy directly support our foundation partner, Cooperativa Coraggio.

Cooperativa Coraggio

Cooperativa Coraggio set up agricultural projects on unused public land to create local jobs and produce organic food in communities in Italy. Donations help their regeneration project on 22 hectares of land at Borghetto San Carlo Estate, located on the outskirts of Rome.  

Intrepid will double the impact by dollar-matching all post-trip donations made to The Intrepid Foundation.

What is it like travelling on a small group tour?

Whether you’re a seasoned traveller or you’re about to embark on your first trip, travelling can be as intimidating as it is exciting. That's the beauty of a small group tour. From handling the logistics and organising amazing cultural activities to local leaders who know each destination like the back of their hand (like which street has the best markets and where to get the most authentic food), travelling on a small group tour with Intrepid will give you unforgettable travel experiences without the hassle that comes with exploring a new place. Plus, you'll have ready-made friends to share the journey with. All you have to do is turn up with a healthy sense of adventure and we’ll take care of the rest.

Fully Immersive Tour of Italy: Highlights and Hidden Gems

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Countries Visited

Places visited, suggested duration.

The perfect balance of leisure and adventure is available on this 21-day tour of Italy. With destinations, such as Venice and Bologna, you will get a sound introduction to Italy's urban charm that can then be compared to the rustic countryside of Tuscany and the Costa Smeralda. No matter your preference, by the tour's end, you will be well acquainted with the culture and history of this unique Mediterranean world.

Customizable Itinerary

Venice – arrive in the city of canals.

Situated along the windswept shores of the Adriatic, Venice beckons visitors like a light in a storm. The opening leg of your 20-day Italian adventure will start in this city of canals. Here, watery roads carry tourists and locals through a serene setting of picturesque neighborhoods. After landing at the nearby Marco Polo international airport, a private transfer will ensure your smooth arrival at your comfortable accommodations before concluding your day with a charming cruise on an authentic Venetian gondola.

What's Included:

Venice – In the Footsteps of Royalty

A daybreak walk along the waterfront of Venice is a great way to avoid the crowds and see the horizontal light shine brilliantly upon iconic facades, such as St. Mark's Basilica and the Doge's Palace. Today, you will dive into the lively neighborhood and memorable landmarks that make Venice a top destination for all travelers on a private walking tour. As your expert guide regales you with tales from Venice's illustrious past, your imagination will come alive. Today, you will walk in the footsteps of emperors and royalty.

Venice – Explore at Your Own Pace

As Venice's population began to grow, land became scarce, and entire neighborhoods had to be constructed on piers and floating docks. In this environment, waterways replaced roadways, and boats became the preferred method of transportation through the city. Your final day in the capital of Venice will be yours to spend however you wish. Perhaps, you would like to visit the welcoming eatery you passed the night before or tour the magnificent Ponte Rialto. No matter how you choose to conclude your time in Venice, it is hard to avoid the abundance of beauty on display.

Bologna – Eating Your Way

Turning your back on the Adriatic, you will make your way by train to Italy's interior. Gazing from your comfortable train car, the gentle sweep of the hillsides and terraced farmlands will evoke a timelessness that will only increase upon arriving at the town of Bologna. After settling into your accommodation, you will embark on a tour of Bologna's favorite pastime, eating. This walking tour of the city will introduce you to famous food shops where the prosciutto and parmesan are proudly displayed. Afterward, you will visit the famous Lamborghini factory. Here, cars are produced with almost as much care as the wine you sampled earlier.

Bologna – A Self-Guided Day

Bologna occupies a special position as an important city for both native Italians and the visitors who flock here by the thousands. The history alone is enough to dazzle the imagination with the famous visitors who wandered these narrow alleys and mesmerizing piazzas over the centuries. Soon, you will realize that Bologna is also home to Europe's oldest operating university. This diverse and youthful spirit will be one of the first things you notice. Today, you will be able to enjoy the city at your leisure.

Cinque Terre – Into the Five Lands

Perched atop some of the most stunning coastline in the Mediterranean, Cinque Terre exists as a superb specimen of how early life looked for many communities that lived between sea and land. Best of all, the rugged coastline, tiny villages, and charming streets make industrial-grade tour buses a distant memory; the only vehicles here are compact, and most use boats to navigate the coast. After departing Bologna, a private transfer will convey you into this storied landscape, where upon arrival, you can spend the rest of the day exploring at your own pace.

Cinque Terre – Scenic Coastal Voyage

The brisk air that sweeps off the Tyrrhenian sea will help you wake on your first day in the Five Lands. Today, you will be able to enjoy a guided excursion by private boat, which will take you past the pastel villages of Riomaggiore, Vernazza, Monterroso al Mare, and a host of other smaller communities. Green and blue are the main colors you will encounter on this scenic voyage as you pass lush hillsides that are covered in gardens. When you return to the hotel, your appetite will be happily satisfied by the staff.

Siena – Visiting a Hilltop Town

Today, you will return to the Italian interior and depart Cinque Terre. After breakfast, you will make your way into the Tuscany region for your first visit to the winemaking paradise. A medieval rival of Florence, Siena boasts a vast assortment of museums, art galleries, and a bi-annual bareback horserace that never fails to attract thousands of thrilled spectators. Into this intoxicating environment you will step upon arriving at your comfortable accommodation. Wasting no time, your day will conclude with an expert cooking course, during which the gastronomic traditions of Tuscany and your taste buds will come alive.

Siena – Truffle Hunting

Today, you will enjoy a veritable treasure hunt as you embark on your comfortable Sienese accommodation to the countryside in search of truffles. Leading you on this expedition, a 2-legged guide will explain the history of truffles and their modern application, and a 4-legged companion will help you find the buried delicacies. Dogs are ideal truffle hunters and use their keen sense of smell to detect their quarry. After you worked up an appetite, you will be able to enjoy a savory lunch with local ingredients and wine.

Siena – A Day at your Leisure

After a day spent in the Tuscan outback looking for truffles, you will look forward to spending some leisure time to chart your own course through this picturesque landscape. The city of Siena offers travelers a rustic ambiance to kick up their boots and savor what locals call la dolce vita or the sweet life. The city center alone boasts enough cathedrals, piazzas, and palaces to earn the coveted award of being a UNESCO World Heritage Site and presents art lovers a head-spinning array of Renaissance art.

Siena – Your Final Day in Tuscany

Another self-guided day will ensure that you are able to conclude your Tuscan reverie at your own pace. A visit to the Siena Cathedral is an excellent way to survey the mastery of Romanesque-Gothic architecture that is on display across the town. The unfinished walls of the eastern transept speak to the ambition of Sienese builders along with the ravages of the Black Plague. More commercial-oriented travelers can enjoy the chic boutiques and enthusiastic vendors who will be ready to meet your every need.

Sorrento – The Heart of Campania

Leaving Northern Italy behind, you will make your way by train and enjoy a journey through some of the most breathtaking countryside in Italy. You will speed past abandoned villas that have become overgrown with ivy. Your destination will be the bustling Bay of Naples and the rural town of Sorrento, which is an enduring contrast to the urban sprawl of Naples on the northern edge of the bay. After your arrival at your conveniently-located accommodation, you will have the remainder of the day to explore Sorrento at your own pace.

Sorrento – Tour of the Amalfi Coast

It will not take much time after your arrival to hear rumors of a stunning coastline filled with charming villages and impressive panoramas on the other side of the Sorrentine peninsula. The Amalfi Coast has charmed visitors for centuries and is now a well-known destination for romantics and honeymooners. Today, you will step into this scenic environment on a full-day tour of Amalfi and the nearby town of Ravello. You should pay particular attention to the series of stone watchtowers that line the coast and are still ready to warn of imminent pirate raids.

Sorrento – Pearl of the Mediterranean

Finally, the allure of the waves will be too much. Today, you will take to the waves on a voyage to the nearby island of Capri. Capri was once a top destination of bored emperors and wealthy celebrities, and it will not take long for you to see why this little island has such a hold on the imagination. Upon your arrival at the main harbor, you will embark on a tour to the Faraglioni rocks before grotto-hopping between the many natural sea caves that punctuate the coast.

Costa Smeralda – Venturing Off the Grid

Today, you will exchange a small island for a bigger one. After breakfast, you will depart the idyllic ambiance of Capri and Sorrento for the rustic charm and distinct culture of Sardinia.  The island itself has been inhabited for centuries and has seen its fair share of conquerors and kings. As you will see today, it exists as an off-the-beaten-path destination for those hoping to avoid the crowds of the mainland. Upon your arrival, you will have the remainder of the afternoon to spend as you wish.

Costa Smeralda – Along the Emerald Coast

No guide book is capable of capturing the essence of Sardinia, and it requires an unflinching look at this colorful land to fully experience it. Such a fearless approach will be yours today as you enjoy a sea-kayaking experience at the Capo d'Orso or Cape of the Bear. After a brief orientation of your kayak, you will be able to plunge into the cool water and embark on a memorable aquatic tour of the Costa Smeralda.

Costa Smeralda – Leisurely Day in Sardinia

The Mediterranean has long been known as a place where locals know how to live the good life. Sardinia is no different, and the Costa Smeralda is a top destination for those hoping to do just that. Whether reclining on the sandy beaches with a good book, shooting the links at a nearby golf course, or savoring an authentic, three-course meal at a local eatery, there is something for everyone in this idyllic setting. Today, you will be able to rest your weary paddling arms at your own pace on this leisurely day.

Costa Smeralda – Exploring as you Please

Feeling well-rested from your day of leisure, you will enjoy an exploration of the nearby Maddalena archipelago, which is a cluster of granite islets that occupy the Start of Bonifacio between Corsica and Sardinia. This scenic cruise will allow you to plunge into the clear water and stroll along sandy beaches in search of that perfect spot to relax or read a book. By the time this island-hopping tour concludes, you will be refreshed and ready to take on the final leg of this Italian tour.

Rome – A Private Visit to the Vatican

A slight tan and modest collection of shoe sand will be the only evidence of your leisurely visit to Sardinia. On your first day in Rome, you will need more than a bathing suit to begin your tour. After a brief flight, a private transfer will carry you from the Roman airport to your comfortable accommodations. In the afternoon, you will visit the holy heart of the Catholic Church and seat of Papal power. Vatican City offers visitors a conspicuous example of church authority and will be the setting for your private tour of the famous museums, Sistine Chapel, and the vast Basilica of St. Peters.

Rome – Pondering the Past

For your final full day in Italy, an in-depth walking tour will ensure that no site goes unseen.  You will scour Rome's city center in search of the beautiful and historic. Starting with more recent history and working backward, your expert guide will lead you on a private tour of the Spanish Steps, Trevi Fountain, and other delights of the city's artistic masters. Things will take a turn for the ancient in the afternoon when you visit the iconic Colosseum and adjacent Forum, where characters like Julius Caesar once strode. Your tour will end just in time for you to seek out an authentic Italian meal.

Rome – Departure

Unfortunately, you will depart Rome today, and the country in which you have fallen in love. From the north to south and from land to sea, this 21-day tour has delivered a balanced approach to exploring this colorful corner of Europe. Like chocolate, moderation is the best approach to taking in the vast array of cultural and historic sites contained in Italy, and the good news is that there is still so much to see for your return trip.

Trip Highlights

• Stroll along the windswept waterfront of Venice and take in the stunning Adriatic views
• Eat your way across Bologna on a walking tour through the city's savory culinary scene
• Immerse yourself in the history of the Cinque Terre, where dirt paths were once the only highways that linked these colorful villages
• Take to the waves on a scenic voyage past terraced gardens wreathed with Bougainvillea and pastel villages that cascade into the sea
• Enjoy the Tuscan charm of Siena, where the unbuilt remains of a vast cathedral still speak to an illustrious past
• Hunt through an Italian woodland in search of the illusive truffles that lurk just beneath your feet
• Wrap up your stay in Tuscany with plenty of time to yourself to relax or adventure through this rustic land
• Walk in the footsteps of emperors on a tour of Amalfi, where scenic panoramas await just around the next corner
• Enjoy an island-hopping tour through Sardinia's Maddalena archipelago, where crystal-clear water competes with white granite in brilliance
• Conclude your Italian tour with a memorable visit to the country's capital to dive into Rome's alluring past

Starting Price

$16,375  per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

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Explore the Stunning Island of Sicily During an 8-Day Guided Tour of Italy

See every slice of Sicily during this 8-day guided tour. Take off to Paradise Quarry in Syracuse with a Local Expert, who will show you its Ear of Dionysius, an ear-shaped limestone grotto: call out to your fellow travelers here, and your voice may echo as many as 16 times. Visit the Palatine Chapel to marvel at the glittering gold mosaics for a stunning sight. Travel to the quaint fishing town of Cefalú and stroll to the Porta Marina for a picture-perfect view of the harbor. In Taormina, perched above the Ionian Sea, join a Local Expert at the city’s cliffside Greek theater, from which you can see Mount Etna, the island’s active stratovolcano.

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Start Giardini Naxos, Italy. End Catania, Italy.

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How To Spend 5 Days In Italy - 6 Unique Itineraries

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Wonderful Time in Italy We were covered from the moment we landed in Rome. The drivers were great, the connections were flawless, and it was well-planned a...

Welcome to enchanting Italy, where timeless beauty and rich history come together to create a truly unforgettable experience. If you only have a few days to explore this captivating country, fear not, as we have designed six unique 5-day Italy itineraries that will show you how to make the most of this short period of time.

Tailor-made travel itineraries for Italy, created by local experts

8 days  / from 2622 USD

Experience the hit TV show 'The White Lotus' in Sicily

Stay in beautiful Taormina with gorgeous views of Mount Etna and discover Sicily, including famous filming locations. Go on exclusive wine tastings, discover the Greek theater in Taormina with a private guide, visit other Sicilian towns and enjoy the crystal clear water on this week-long trip.

8 days  / from 3258 USD

Enchanting Italian Lakes

Experience the picturesque lakes of Northern Italy, including Lake Garda, Como, Lugano and Maggiore; explore the charming Borromean Islands – former favourites of Ernest Hemingway – and stroll the romantic streets of Verona and Milan. All of this, and much more, with this self-drive trip!

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From Venice to Florence: A Grand Tour of Northern Italy

From the atmospheric canals of Venice and the picturesque coastline of Cinque Terre, to the trendy designer boutiques of Milan and the Renaissance-infused streets of Florence, Northern Italy has plenty to offer. Experience it all with this comprehensive trip.

See our itineraries below, or get inspired by duration: 7-days - 10 days - 14 days - North Italy - South Italy

Itinerary #1: Wine and Food in Tuscany

Stay at a beautiful hotel in San Gimignano, a medieval hill town halfway between Florence and Siena. Tuscany is known for its wines and food and that's what you'll be exploring on this 5-day itinerary - several wine and food pairings await. All are hand-picked by your local travel specialist.

The first day of adventure begins with a private car transfer to a hotel in the charming San Gimignano area, offering free time to unwind and adjust to the new surroundings. The second day allows for a leisurely exploration of the region at one's own pace.

The highlight of day three is a captivating winery experience, featuring a vertical Wine Tasting of 15 Tuscan products, paired with a delectable lunch served amidst the vineyards or in the winery itself. The day encompasses everything from vineyard visits to wine-making techniques, providing a comprehensive understanding of the art behind Tuscan wines.

Day four is dedicated to indulging in the region's traditional cuisine. Guests can savour a selection of mouthwatering dishes while sipping on the finest Chianti wine, all set against the backdrop of the picturesque Tuscan landscape.

On the final day , a private driver ensures a smooth departure, bidding farewell to Tuscany as they are taken to the airport in Florence for their onward journey. The memories of this extraordinary trip, filled with extraordinary experiences, will undoubtedly linger, leaving travellers longing for a return visit to this captivating Italian region. Read more .

City of San Gimignano, a small medieval town in Tuscany, Italy © Vaflya/Shutterstock

Itinerary overview

Check this overview of the 5 days Italy itinerary.

• Transfer from Florence to San Gimignano
• Overnight in San Gimignano
• Free day in San Gimignano
• Overnight in San Gimignano 
• Romantic lunch in the vineyards
• Chianti - food and wine pairing
• Transfer and departure from Florence

Dreaming of exploring? Turn your dreams into reality and book this trip now .

Tuscany Vineyards, Italy @ Shutterstock

Itinerary #2: Eternal Rome for the Weekend

Welcome to the timeless allure of Eternal Rome, a city steeped in history, art, and culture. Embrace the essence of this enchanting destination in just a weekend with our carefully curated 5-day itinerary . From iconic landmarks to hidden gems, immerse yourself in the heart of the ancient world and experience the eternal charm that Rome has to offer.

On the first day , after a warm welcome, enjoy free time to explore the city at your own pace. Day two unveils the Vatican Museums and the awe-inspiring Sistine Chapel, offering insight into the brilliant works of Michelangelo and other renowned artists. The tour then leads to St. Peter's Basilica, where the breathtaking architecture and "La Pietà" masterpiece await.

On day three , venture to the iconic Colosseum, once the stage for gripping gladiator battles. Nearby, immerse yourself in the rich history of the Roman Forum, the political, commercial, and religious heart of ancient Rome.

Day four begins with a small-group walking tour, encompassing symbolic landmarks like the Spanish Steps, Trevi Fountain, and the magnificent Pantheon. The journey concludes at "Piazza Navona," graced by Bernini's Fountain of Four Rivers and a delightful tasting of local Italian products.

As the sun sets on your Roman adventure, day five bids farewell as you check out of your hotel and head to the airport, taking cherished memories and a newfound appreciation for Eternal Rome with you. Read more .

Night view over Fountain di Trevi in Rome © trabantos/Shutterstock

• Arrival in Rome
• Overnight in Rome
• Vatican visiting
• Colosseum - Flavian Amphitheatre
• Rome fountains & square wine tasting
• Rome departure

Ready to embark on an adventure? Book your trip now .

Vatican at night, Italy @ Shutterstock

Itinerary #3: Florence: A Trip Back In Time

Step into the enchanting city of Florence and experience a mesmerising journey back in time with our carefully planned 5-day Italy itinerary . This enchanting destination is a treasure trove of Renaissance art, ancient architecture and rich cultural heritage.

On day one , after a warm welcome at Florence Airport, explore the city at your leisure, with must-see recommendations like the renowned Uffizi Gallery and the Accademia, home to Michelangelo's masterpiece, David.

Day two unveils the mysterious Vasari Corridor, a secret passageway connecting Palazzo Pitti to Palazzo Vecchio. Adorned with a fascinating collection of self-portraits from the 15th century, this hidden gem offers a glimpse into Florence's rich past. Witness the grandeur of the Room of the Five Hundred in Palazzo Vecchio, adorned with artwork by Vasari, Leonardo da Vinci, and Michelangelo.

Venture off the beaten path on day three to Casa di Dante, a museum commemorating the life of the famed poet. Journey through three important stages of Dante's life, tracing his footsteps through 13th-century Florence to his exile and lasting legacy. The tour then continues to the iconic Piazza del Duomo, the Badia Fiorentina, and the awe-inspiring Baptistery with its mesmerizing Gates to Paradise.

Enjoy a free day on day four to explore Florence at your own pace or opt for a picturesque day trip into the Tuscan countryside, visiting enchanting towns like San Gimignano, Siena, or Pisa. The day concludes with a delightful 3-course meal at an authentic, local restaurant, offering a true taste of Florentine cuisine.

As your adventure draws to a close on day five , cherish the memories of this remarkable journey. Depending on your flight time, bid farewell to Florence as you are transferred to the airport, carrying with you the beauty and essence of this enchanting city forever in your heart. Read more .

Florence cityscape © Bob Hilscher/Shutterstock

• Arrival in Florence
• Overnight in Florence
• Exploring the Vasari Corridor and the Palazzo Vecchio
• Experiencing medieval Florence
• Free day in Florence or a day tour to the Tuscan countryside
• Transfer to Florence Airport and departure

Interested? Don't miss the opportunity to book this trip now .

Uffizi art gallery in Florence, Tuscany, Italy @ Shutterstock

Itinerary #4: Romantic Venice

Enjoy a weekend getaway in the most romantic of cities. This compact 5-day itinerary features a pleasant walking tour, which provides a unique insight into the history, art and architecture of Venice, and a gondola ride. You will also have some free time to explore this labyrinthine city.

Day one welcomes you as you arrive at Marco Polo International Airport and are transferred to your hotel, leaving the day free to explore Venice at your leisure.

On day two , embark on a private walking tour, beginning at the Saint Mark's area, where you'll delve into the historical significance of the powerful maritime empire of the Mediterranean. The tour includes iconic landmarks such as The Doges' Palace, St. Mark's Square, and the Basilica, each showcasing unparalleled beauty and historical importance.

Day three commences with a sumptuous breakfast, followed by a picturesque 30-minute gondola ride through Venice's waterways, allowing you to soak in the city's unique ambience. The afternoon is yours to explore at your own pace, culminating in a delightful three-course dinner at a centrally located restaurant (drinks not included).

Enjoy a free day on day four , allowing you to fully immerse yourself in the beauty of Venice and discover its hidden gems.

As your journey comes to an end on day five , check out of your hotel after breakfast. A private transfer will take you to Marco Polo International Airport, leaving you with cherished memories and the desire to return to this mesmerizing destination once again. Read more .

Burano island canal, colourful houses and boats, Italy © StevanZZ/Shutterstock

• Arrival in Venice
• Overnight in Venice
• Venice walking tour
• Exploring Venice
• Free day in Venice
• Departure from Venice

Fascinated by the itinerary? Don't wait, book this trip now .

Gondolas in Venice © Shutterstock

Itinerary #5: Trieste - a combination of hiking and culture

Experience an authentic adventure in Trieste with our exclusive 5-day Italy itinerary . This journey goes beyond just sightseeing; it will allow you to truly experience the city like a local. Immerse yourself in the small daily rituals and discover hidden gems tucked away off the tourist trail.

Day one welcomes you with a warm reception at the train station or airport, followed by a leisurely exploration of the city centre. Marvel at the historic streets and squares, the seafront, and the renowned Piazza Unità. Wander up to the hill of San Giusto for breathtaking views.

Day two takes you on a scenic journey to the Karst plateau. Hop on the iconic Opicina tram, dating back to 1902, to ascend to the plateau. Embark on a picturesque walk with panoramic views of the city and sea, leading you to the splendid Miramare Castle Park.

On day three , embark on a discovery of the equestrian park of Lipica, an oasis of tranquillity and home to the elegant Lipizzan horses. After a guided tour and serene strolls in the estate, visit the valley of the Blessed Virgin of Lourdes, a unique sanctuary dating back to the 1800s.

Day four begins with a trip to the Rosandra Valley Reserve. Walk along the ancient salt road, enjoying views of the Rosandra stream with its waterfall and natural pools.

Conclude your trip on day five with a visit to the awe-inspiring Grotta Gigante, the largest cave in the world. At the end of the visit, you will return to the city. From here, once you have recovered any luggage left at the deposit of your facility, you can continue your journey independently or return home. Read more .

Trieste, Italy @ Shutterstock

• Arrival in Trieste
• Overnight in Trieste
• From the Karst to Miramare Castle
• Lupica Stud farm
• Rosandra Valley Nature Reserve
• Grotta Gigante
• Departure from Trieste

Fisherman, Trieste, Italy @ Shutterstock

Itinerary #6: Exploring Vatican City and Assisi

Soak up sights and delights of Ancient Rome, with this 5-day-long itinerary , including visits to the Sistine Chapel, the Colosseum and St. Peter's Basilica, before journeying to the home of St. Francis of Assisi, Eremo delle Carceri.

Day one will begin with your arrival in Rome, where a transfer will take you to your hotel for an overnight stay and preparation for the adventures ahead.

On day two , you'll immerse yourself in the cultural wonders of Rome as you tour the Vatican Museums, the Sistine Chapel and St Peter's Basilica. Skip the long queues and check out one of the world's most important art collections, and admire the Tapestry Gallery and the Geographical Maps. The day culminates with a visit to the famous Sistine Chapel and the awe-inspiring St Peter's Basilica.

On the third day , you will continue your exploration of Rome's iconic landmarks with visits to the Colosseum, Roman Forum and Palatine Hill. With priority entry and a qualified local guide, you'll discover the fascinating history and stories of ancient Rome.

On day four , you'll venture from the bustling streets of Rome to the serene city of Assisi, the birthplace of St Francis. Discover the Eremo delle Carceri, the first home of St Francis and his followers, as you immerse yourself in the tranquil beauty of this sacred monument. Enjoy a relaxing day of sightseeing before returning to your hotel for an overnight stay.

On the fifth day , at the conclusion of your journey, you will return to Rome airport and fly home, taking with you fond memories of the historical wonders of Rome and the peaceful serenity of Assisi. Read more .

Piazza San Pietro in Vatican City

• Vatican Museums, Sistine Chapel and St. Peter's Basilica
• Exploring Ancient Rome
• a day in Assisi
• Overnight in Assisi
• Transfer and departure from Rome

Captivated by the possibilities? Don't hesitate and book this trip now .

Assisi, Italy @ Shutterstock

You might also want to browse our customisable Italy itineraries, or talk to our local Italy experts .

Related articles from the blog

The Rough Guides to Italy and related travel guides

In-depth, easy-to-use travel guides filled with expert advice.

Travel advice for Italy

From travel safety to visa requirements, discover the best tips for traveling to Italy

• Eating and drinking in Italy
• How to get to Italy
• Getting around Italy: Transportation Tips
• Shopping tips for Italy
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• Travel Tips Italy for planning and on the go
• Best time to visit Italy
• How to spend 7 days In Italy - 8 unique itineraries
• The Best 10-Day Italy Travel Itinerary
• How To Spend 14 Days In Italy - 5 Unique Itineraries
• How to get from Rome to Florence

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updated 18.09.2023

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The Best 2-Week (14-Day) Tours in Italy

Looking for the perfect 14-day getaway to Italy with a fantastic guided tour? We've carefully analyzed all of the possible two-week tour options to Italy based on price, comfort, service, guest ratings, cuisine, and activities in order to find the absolute best multi-day organized tour options available. Whether you're seeking a relaxing getaway or an action-packed expedition, these guided tours offer the perfect length to indulge in the best of both worlds. From captivating excursions to tantalizing cuisine, get ready to experience the ultimate 2-week escape to Italy that will leave you with unforgettable memories and a renewed sense of wanderlust. Great for museums & attractions, food, nightlife, and beaches, Italy is a terrific destination. So, check out our curated list of tours below to get started!

• Italy's Best 14 Days, $2839.00
• Splendours of Italy (13 Days) 13 Days, $2725.00
• Highlights of Sicily & Southern Italy 14 Days, $3899.00

Which 14-day tour options are available in Italy?

Here are the important factors:

• 28 trip options analyzed
• $316 average price per day (USD)
• 13 to 14 days in length
• 4.72 of 5 average rating
• 32 people or less on average

Curious about the diverse range of tours lasting 2 weeks? Prepare to be amazed by the array of options available to suit every traveler's preferences. It comes as no surprise that visitors adore these tours, given their exceptional average guest rating of 4.72 out of 5 stars. When it comes to group sizes, the average maximum capacity stands at 32 people, allowing for a comfortable and sociable experience. The shortest tour is 13 days, while the longest is 14 days. As for physical activity options, the tours are thoughtfully categorized as easy and moderate, with the most being easy. For transportation , the tours are marked as coach / bus, ocean cruise, and train & rail, with a prevalent number on coach / bus tours. With a comprehensive analysis encompassing 28 tours lasting 2 weeks, you can rest assured that Italy has something tailored to your interests and preferences, promising an unforgettable experience for all.

(All tour prices are in US Dollars before taxes, and come from a base price that is reported by TourRadar. Peak season prices can vary significantly, particularly in destinations where seasonal travel fluctuates dramatically.)

So, let's get to it and see...

The 10 Best 2-Week Tours in Italy

Italy's best.

• Great Value: the daily price is lower than average for tours lasting 2 weeks.
• High Quality: guest ratings are higher than average.

This exceptional trip offering by Cosmos has received a 4.9 out of 5 rating. On this 14-day trip you can unwind while also making new memories. Along the way, this journey encompasses 17 destinations, including Pompeii, Sorrento, Pisa, and Montecatini. You'll start and end this amazing trip in Rome. With a group size of 50 people, it's suitable for travelers from 5 and up. This extraordinary adventure also revolves around local culture and family-friendly activities. This remarkable trip is priced at an unbeatable $203 per day.

• Coach / Bus
• In-depth Cultural

Splendours of Italy (13 Days)

• On Sale: 15% Off See Prices

Check out this journey that has received rave reviews, earning a stellar 4.2 out of 5 rating, visiting Italy and Vatican City (Holy See). This itinerary covers 12 captivating destinations, with stops in Venice, Verona, Lugano, and Saronno, among others. Rome will be both the start and end of your journey. Spanning across 13 unforgettable days, this voyage offers an intimate group experience with 52 participants, and it's great for travelers from 5 to 80 years old. Brought to you by the renowned Costsaver , this exceptional opportunity is priced at an incredible $178 per day - an unbeatable value. Hurry and secure your spot while this incredible sale lasts!

Highlights of Sicily & Southern Italy

This 14-day trip is ideal for travelers from 5 to 80 years old. And priced at only $279 per day, it's a great value, too. You're in for an epic adventure with a strong emphasis on local culture and family-friendly activities. Immerse yourself in a travel experience that includes 13 destinations, featuring Bari, Lecce, Alberobello, and Matera. Beginning in beautiful Rome, you'll have a terrific journey that ends in Palermo. It's offered by Globus , a very popular company with rave reviews and knowledgeable guides.

Italian Glory (13 Days)

Priced at just $288 per day, this terrific 13-day journey is ideal for travelers from 5 and up. Uncover the beauty of 9 destinations on this itinerary, with highlights such as Venice, Florence, Maiori, and Amalfi. Milan will mark the start of your journey, while Rome will serve as its final destination. Organized by the reputable Trafalgar , this is one of the best tours on this list.

Best of Italy (Summer, 13 Days)

Check out this incredible journey that has received a 4.6 out of 5 rating from previous guests. With an emphasis on local culture and family-friendly activities, you know you'll have an amazing adventure. With a duration of 13 days, this journey ensures an intimate group size of 50 people, and is good for travelers from 5 and up. Traverse through 12 enchanting destinations, with Como, Pisa, Florence, and Pompeii among the must-see stops along the route. Begin and conclude your remarkable journey in the gorgeous destination of Rome. This fantastic option, organized by Trafalgar , presents an unbeatable value at just $292 per day.

Italian Mosaic

Spanning over 13 days, this trip, visiting Italy and Switzerland, has a maximum size of 46 individuals. Welcoming travelers from 5 to 80 years old, it is organized by Globus , a very popular company with plenty of great reviews. This trip visits 13 destinations, including Padua, Assisi, Sorrento, and Capri along the way. You'll start and end your journey in beautiful Rome. And since the priority is on local culture and family-friendly activities, this tour is a great choice. Available at an unbeatable price of only $338 per day, this option also has a rating of 5 out of 5 stars from previous guests.

A Taste of Italy: 14 Days

Here's your chance to take off on an exceptional trip, visiting Italy and Vatican City (Holy See), that has garnered a 4 out of 5 rating. With a duration of 14 days, this jouney will have 45 participants, and it warmly welcomes travelers from 8 and up. Expertly organized by Omega Tours , this amazing trip is an incredible value at just $291 per day.

Italian Escapade (Classic, 13 Days)

This memorable trip, visiting Italy and Vatican City (Holy See), is offered by Insight Vacations which has received plenty of positive reviews. The trip itself has a guest rating of 4.5 out of 5 stars, and is priced affordably at $369 per day. Explore 14 incredible locations on this trip, including Giudecca Island, Assisi, Pompeii, and Sorrento. You'll start and end this amazing trip in Rome. This extraordinary adventure also revolves around local culture and family-friendly activities. The maximum group size is 40 people, welcoming travelers from 5 and up.

Country Roads of Switzerland (Classic, 14 Days)

• On Sale: 20% Off See Prices

Set off on an extraordinary journey, visiting Switzerland and Italy, that has been awarded a 5 out of 5 stars by previous guests. This terrific trip also highights local culture and family-friendly activities. With a duration of 14 days, this trip offers an intimate group setting, accommodating 40 individuals, while extending a warm welcome to travelers from 5 and up. Discover a journey that spans 16 destinations, with notable stops in Sion, Zermatt, Brig, and Lake Maggiore. Zurich will be both the start and end of your journey. Brought to you by Insight Vacations , this exceptional deal is an incredible steal at a mere $416 per day. Act quickly to seize the current limited-time sale and reserve your spot now.

Mamma Mia! - 13 Days/12 Nights

• On Sale: 10% Off See Prices

With this option you can experience an unparalleled journey for 13 unforgettable days. It ensures an intimate group setting with 15 participants at most. This trip takes you on an adventure to 12 destinations, including Amalfi, Positano, Naples, and Florence. Rome will mark the start of your journey, while Venice will serve as its final destination. Italy on a Budget Tours , the organizer of this journey, extends a warm invitation to guests travelers from 18 to 45 years old. This extraordinary opportunity offers exceptional value at only $135 per day.

See also The Best Family-Friendly Tours to Italy , The Best Hiking & Trekking Tours in Italy , The Best Historical Tours in Italy , The Best 10-Day Tours in Italy , The Best One Week (7-Day) Tours in Italy , The Best 3-Day Tours in Italy , The Best Bicycle Tours in Italy , Tours for Outdoor and Nature Lovers in Italy , The Best Christmas & New Years Tours in Italy , The Best Coach Bus Tours in Italy , The Best Adventure Tours to Italy , The Best Eco Tours in Italy , The Best Train & Rail Tours in Italy , The Best Thrill-Seeking Tours in Italy , The Best Sightseeing Tours in Italy , The Best Cultural Tours in Italy , The Best Vineyard & Wine Tours in Italy , The Best Food and Culinary Tours in Italy , The Best Music Tours in Italy , The Best Romantic Tours for Couples in Italy , The Best Walking Tours in Italy , The Best Tours Under $1000 in Italy , The Best Luxury Tours to Italy , The Best Budget Tours to Italy , The Best Tours for Seniors to Italy , The Best Contiki Tours to Italy , or The Best G Adventures Tours to Italy for more tour ideas. With so many options, there's a guided tour or vacation package for every type of traveler.

Also, if you're departing from a specific destination, see The Best 3-Day Tours from Rome , The Best 3-Day Tours from Florence , The Best One-Week (7-Day) Tours from Rome , The Best One-Week (7-Day) Tours from Venice , The Best One-Week (7-Day) Tours from Catania , The Best One-Week (7-Day) Tours from Naples , The Best One-Week (7-Day) Tours from Florence , The Best One-Week (7-Day) Tours from Milan , The Best One-Week (7-Day) Tours from Palermo , The Best One-Week (7-Day) Tours from Bari , The Best One-Week (7-Day) Tours from Pisa , The Best One-Week (7-Day) Tours from Bolzano , The Best One-Week (7-Day) Tours from Merano , The Best One-Week (7-Day) Tours from Olbia , The Best One-Week (7-Day) Tours from Bologna , The Best One-Week (7-Day) Tours from Cagliari , The Best One-Week (7-Day) Tours from Alberobello , The Best One-Week (7-Day) Tours from Como , The Best One-Week (7-Day) Tours from Montecatini , The Best One-Week (7-Day) Tours from Siena , The Best One-Week (7-Day) Tours from Turin , The Best One-Week (7-Day) Tours from Civitavecchia , The Best 10-Day Tours from Rome , The Best 10-Day Tours from Venice , The Best 10-Day Tours from Palermo , The Best 10-Day Tours from Catania , The Best 10-Day Tours from Milan , The Best 10-Day Tours from Naples , The Best 2-Week Tours from Rome , The Best 2-Week Tours from Venice , The Best 2-Week Tours from Milan , or The Best 2-Week Tours from Palermo for more package tour options.

How much do 14-day tours to Italy cost?

After analyzing 28 tours lasting 2 weeks in Italy, we found the average price to be a remarkably economical $316 per day. Naturally, this region has many fantastic options for tours lasting 2 weeks with a variety of prices. The individual costs will vary by the destinations, travel style, available dates, and other factors. If you're interested in more information about tours here, see our guide to tour prices in Italy .

And for more information on Italy, see Italy Travel Costs and Italy Hotel Costs .

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*Prices below are per person based on double occupancy and include airline taxes, surcharges and fees of $0, which are subject to change until final payment is made. All tour prices (excluding airline taxes, surcharges, and fees) are guaranteed.

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Sicily in Depth

Crossroads of the Mediterranean…the “toe” in Italy’s boot…“God’s Kitchen”…Sicily is all this and much more, as we see on our stellar small group journey around this Italian island. It’s lively cities and ancient ruins, temples of man and of nature, hospitable people and delectable cuisine…a feast for all the senses.

Tour Details

From $4,074

Small Group Highlights

• Palermo’s Arab-Norman UNESCO sites
• Street food experience in Palermo
• Stunning Monreale Cathedral (UNESCO site)
• Medieval walled town of Erice
• Trapani Nature Reserve and salt pans
• Agrigento’s Valley of the Temples (UNESCO site)
• Outstanding mosaics at Villa Romana del Casale (UNESCO site)
• Archaeological Park of Neapolis in Syracuse (UNESCO site)
• Wine tasting
• Taormina touring
• Mt. Etna excursion
• Farmhouse lunch
• Distinctive, well-located small group hotels

Day-by-Day Itinerary

Located in the heart of Palermo within walking distance of the Palermo cathedral and the famed Via Maqueda, the Centrale Palace occupies the old Palazzo Tarallo building, retaining the original structure along with vintage frescoes and furniture.  The hotel also forms part of the Arab-Norman route, declared a World Heritage Site by UNESCO, where the Phoenicians, Romans, Byzantines, and Arabs raised their places of worship.  Hotel amenities include a restaurant serving traditional Sicilian fare and a terrace bar, both with panoramic views of Palermo and its surrounding mountains; complimentary Wi-Fi access; fitness center; and laundry and dry-cleaning services (for a fee).  Air-conditioned guest rooms include private bath with hair dryer, minibar, TV, and in-room safe.

Baia di Ulisse stands along the southern coast of Sicily, just a short drive from Agrigento and the only hotel in the area with direct access to a private beach.  The hotel boasts classic Sicilian décor and offers amenities including a restaurant and bar, spa with sauna and whirlpool (services available Fri–Sun for a fee), and complimentary Wi-Fi internet access in common areas.  Each air-conditioned guest room has a balcony and features private bath with hair dryer, minibar, TV, and phone.

The Hotel Borgo Pantano sits on the site of a restored 19 th century manor in the rolling green countryside outside Syracuse.  This family-run property was opened in 2010 and boasts four dining and drinking options: a restaurant, outdoor grill, thatch-roof poolside bar, and lobby bar.  Set within sweeping manicured grounds with an array of covered sitting areas is an expansive outdoor swimming pool and lounge area.  Additional amenities include laundry and dry-cleaning service (for a fee) and complimentary Wi-Fi internet access.  Each air-conditioned guest room has a unique layout and furnishings, is decorated with art created by local artists, and includes private bath with hair dryer, minibar, tea-making facilities, TV, and phone.

The elegant NH Collection Taormina is nestled high on the rugged wooded hillside along which the city of Taormina is built.  The hotel offers a restaurant, café, rooftop swimming pool with poolside bar, fitness center (with spa, sauna, solarium, and steam bath, for a fee), laundry and dry-cleaning service (for a fee), and complimentary Wi-Fi internet service.  Air-conditioned guest rooms have private bath with hair dryer, minibar, in-room safe, tea- and coffee-making facilities, TV, and phone.

Tour Price Includes

• Round-trip air transportation from listed cities
• 10 nights’ accommodations in Deluxe, Superior First Class, and First Class hotels
• 22 meals: 10 breakfasts, 5 lunches, 7 dinners
• Extensive sightseeing as described, including all entrance fees
• Services of an Odysseys Unlimited Tour Director
• Private motorcoach transportation throughout your trip
• Luggage handling for one bag per person
• Gratuities for local guides, dining room servers, airport and hotel porters, and all drivers
• $100 frequent traveler credit towards your next Odysseys Unlimited tour ($200 after three tours; $300 after 10 tours)

Average Daily High by Month (°F )

Average temperature (°f ), dates & prices.

Airline upgrades (subject to availability; pricing subject to change) on round-trip Trans-Atlantic flight: Business Class – $3,795 per person in 2024; $3,995 per person in 2025. Premium Economy – $1,595 per person in 2024; $1,795 per person in 2025

Apologies, we were unable to retrieve the latest tour information at this time.

Regrettably, we do not currently have any available departure dates for this tour.

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Tour Directors

“We enjoyed spending time with Dania. She was thoughtful, knowledgeable, and always positive. She has the perfect temperament for a tour leader.”

Rekha & Craig Arness McLean, VA

“Absolutely outstanding! Very knowledgeable about Sicily and Italy, and the Italian way of life. Kept us entertained with stories and piano playing.”

Dennis & Sharon Marks Vero Beach, FL

“Lisa is one of the best tour directors we have ever had. She was caring, conscientious, knowledgeable and was able to adapt to any situation that required a change in the program.”

Andrea & Donald Gray Tuscon, AZ

"Giulia was amazing! She was incredibly accommodating and it was very apparent that her number one priority was making sure that everyone had an awesome trip."

Brandon & Sharlee Sara Herriman, UT

Odysseys Unlimited Tour Director

“Andrea was outstanding in all aspects. His attention to every detail was perfect! He also had a great personality that added fun to every part of the trip!”

John & Kristine Pagano Cheshire, CT

“Daniela was exceptional. Her caring attitude and knowledge of Italy were exceptional. She truly made the tour come alive.”

Gregory E. Peterson Tyngsboro, MA

"Sara was amazing! She was upbeat, warm, helpful, knowledgeable, patient, and passionate! She greatly enhanced our experience!"

Susan Kossak & Howard Saltz Kissimmee, FL

“There are simply no superlatives worthy of Maurizio’s talents as a guide. He is always organized…[and] always ready to deal quickly and efficiently with the unexpected.”

Owen & Laurie Guitteau Santa Barbara, CA

"I cannot say enough about Eva. She is a gem! So wonderful! She went out of her way to help us and let us get a full experience. The best!"

Grace Ratliff Garner, NC

“Osciri Chageg was splendid. He was knowledgeable, enthusiastic, personable, and understanding…true star.”

Nancy Maffucci East Rockaway, NY

"Diana was outstanding. She was very informative and shared her love of her country in a special and genuine way…another one of your outstanding guides!"

Marylin & Clark Bunton Anaheim, CA

“Marina was on top of everything, from waiting for us at the airport, to each activity, each question.  Her knowledge and love of Sicily was thorough and a part of all she shared.”

Grace Berestecki Needham, MA

Destination Insights

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Physical Activity Level

• Walk 2-4 miles per day, often on uneven terrain or cobblestones
• Occasional long walks from motorcoach drop-off to sights and hotels
• Uneven natural terrain at Mt. Etna and at Agrigento archaeological site
• Steep grades while walking in Taormina
• Many stairs of varying height throughout the tour
• Embarkation/disembarkation from multiple boats

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Italy Small Group Tours

Discover new and exciting adventures in Italy with an unforgettable small group tour experience. Make time on your holiday to visit the Sistine Chapel, hike along the Dolomites , spend time in Florence and sample delicious seafood in Sicily .

250+ Italy small group tours with 2,246 reviews

• In-depth Cultural
• Local Living
• Christmas & New Year

Local Living Italy—Sorrento

Carla was very kind and helpful on our tour

• Food & Culinary
• Hiking & Trekking

Small Group Tour of Sicily: Highlights (Maximum 8 Guests)

Had a great time and met some really nice people. Also all the guides were very nice and were very educated.

• 10% deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Small Group Sicily Food & Wine Tour (Maximum 8 Guests)

I had the best experience with Sicily Activities. The tour was super fun and I don’t think I would have experienced everything without being in this tour. The tour guides were so friendly, especially Orozio, Antonio and Stefania. It was worth every penny, a trip I will remember forever ❤️

Local Living Italy—Amalfi Coast

This was my first hiking tour and I'm happy to say it exceeded all my expectations. It was exactly the type of holiday I wanted, hiking in beautiful scenery with good company and fabulous food. The food was absolutely fantastic - homemade and some homegrown. The hosts at our accommodations were wonderful and wend above and beyond for us. Our tour guide Elisa was perfect for this trip, she helped to make a great itinerary even better. She was very knowledgeable , accommodating and fun. The best kind any group can only dream of.

• Coastal Walks

Amalfi Coast Walking - Agriturismo

I’loved it every minute! We had the most amazing, patient and understanding guide our awesome Matteo! There was nothing that he wouldn’t help everyone with individual problems! Talk about problems and you name it all! No worries because all was taken care! Very very good tour! Love all about it!

• Coach / Bus

Sicilian Landscapes: Catania-Catania (8 days/7 nights)

Meals need to be improved, especially dinners. Stop at the mall was waist of time. We were not informed about swimming opportunities so we left our swim attire on the bus.

• $50 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Cycle Tuscany

Well organized, good fun and good explanations of what was happening and what we were about to do. Good exposure to lesser known, local, yet good accommodations and activities. Difficulty level of the tour was appropriate. Walter’s style if leading was good.

Best of Italy

mecol was great. went above and beyond

Best of Sicily - 8 Days (Small Group Tour)

Very pleased with the tour. The guides were personable and well informed. The hotels very nice and the chosen restaurants and variety of offered foods exceeded expectations. Only complaint is that I wish tips had been included. There was a lot of confusion as to who should get tipped and what was the appropriate amount. All in all I feel that it was a great mix of seeing Sicily yet having free time to explore independently.

• Sightseeing

Deluxe Italian Escape with picturesque Cinque Terre

TourRadar was excellent. The tours they scheduled were well-run by knowledgeable and amiable guides. Of course, the Italy locations were superb. The office staff kept in constant contact, but unobtrusive. And when I changed plans on the fly, the staff was responsive and thorough. I definitely cannot wait to book my next adventure with TourRadar!

Amalfi Coast Experience

The perfect way to explore Sorrento, Capri and the Amalfi Coast. Giovani was fantastic at bringing the group together, communicating options and giving local tips and facts. I recommend the extra package if possible- the dinner was delicious and the chairlift in Capri was a highlight. This tour gives flexibility and freedom if you want free time or if you want to stay with the group in locations. Accomodation was a fun way to see a camp site in Sorrento and has a pool, mini market and restaurant.

• $100 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Taste of Salento-Authentic Culinary Experience

Just got done with Taste of Salento with Emilio and Carla. Fantastic tour. If your looking for a small group experience or solo tour that is relaxed and eating fantastic food then this tour is for you. Family oriented , professional and friendly. They really went above and beyond. taking you to many different places

• Train & Rail

Venice, Florence and Rome escorted small group by train

Other than the heat, the entire tour was wonderful. Venice was special and wish we had more time. The hotels were clean and comfortable as was the bus transportation. Everything was very well organized and when something happened unexpectedly, Annamaris was on the phone fixing the situation. Some of our people go stuck at the airport the day of arrival and she got them to the hotel. Our taxis didn't show for a transfer and she found a solution and got us to the train station on time. Annamaria is professional. Knowledgeable

Mamma Mia! - 13 Days/12 Nights

Excellent tour! Emma and Manolo were very knowledgeable and accommodating. Great tour to see a lot in the 13 day time frame.

Discover Matera and Taste of Salento Tour

This was an outstanding experience from start to finish. I would highly recommend it. With Emilio and Clara and their family in Salento, I got to experience authentic Italian life as well as sightseeing some incredible towns. I felt like I was staying with good friends who had so much knowledge and desire to showcase the typical foods from the region. Emilio runs a restaurant at the olive oil farm and each meal was delicious. Understanding the production of olive oil was fascinating. And they give flexibility on the time you wish to spend at each place. Each day was different and they change the schedule to suit the weather so you get the best out of the places you visit. My time in Matera was just as outstanding. Mr Cosimo, my guide was very kind and shared so much history of the town with me. He looked after me like a good friend. It was amazing. He gave me great suggestions about restaurants for my free time. The hotel was stunning and had a Roman bath where I could relax. Omar from Soleto Travel was always very helpful in answering any questions and prompt. I am so happy I found this tour.

Reviews of Small Group tours to Italy

This tour was the very best experience we have ever had traveling overseas. The booking process was seamless and painless. We felt especially grateful that while the group was limited to 8 participants, it was guaranteed to proceed with 2 people. As it ended up, our trip was just me and my husband and we felt so fortunate to have had the attention of the guides in such a personal way. The guides were all tremendous and I am confident that a larger group would have felt equally tended to. Special thanks to our guides and drivers: Denise, Orazio, Roberto, Carlos, Fabio and Massimo. Part of what was truly evident was how passionate they each were about Sicily and how many of them had connections with people at the restaurants, local businesses and attractions that we went to. We felt like we were in such good hands during the time we were with all of the guides. Each tour and activity was enlightening and educational. The included lunches and other meals were top notch. The opening night walking food and wine tour was a great way to kickoff the trip. There were some others who joined us for that portion, and it was most welcome. I don't think it would have been as much fun for the restaurants and enoteca to have just 2 people and the guide show up, and we knew the rest of the trip we would have individual attention. We felt pampered with our lunches on the Mafia tour, at the winery on Etna, in Marzememi and Agrigento. There was never a feeling of penny-pinching, more plush and like what we would have chosen for ourselves! The selected hotels were excellent! Centrally located, each with a fantastic breakfast spread and fun bar/restaurants. We would happily go back to any of them again and recommend them. We loved the scheduling each day and felt like we had a great mix of free time to explore on our own. Lastly, Graziana was out lifeline while we were traveling. She connected with us daily to check in, and to share the next days plan and name of our guide and where they would meet us. She made dinner reservations for us while we were there and provided recommendations that were helpful. We didn't encounter any issues, but felt that we had a ready ally if needed. Massimo also checked in midtrip, so we truly felt like everyone was interested in us having the best possible trip. I cannot wait to return to Sicily. We have recommended Sicily Activities to many people since our return and would book again in a heartbeat.

The food and guides were great! Hotels were very comfortable. Drivers were excellent!

• Italy Travel Guide | All You Need to Know
• Itinerary Ideas for 10 Days in Italy, 2022-2023
• Best 7 Day Italy Itineraries 2024/2025 (with Reviews)
• Discover the Best Italy Vacation Packages 2024/2025
• What is the best time to visit Italy in 2024/2025?

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Travel to italy like an insider with the best local experts.

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A trip to Italy is too special to get wrong. Here's how to do it right. (San Gimignano, Tuscany)

I absolutely love Italy, for many different reasons. But I hate the way in which many Americans go about planning trips there. Survey after survey shows it is the number one dream destination for U.S. leisure travelers, but the way those travelers get their information and advice gives me nightmares.

Throughout the years I’ve heard people say over and over that “I was told to do this in Italy,” or “I was told not to do this in Italy.” By who? “A friend.” I have close friends who recently planned their entire 12-day trip on the basis of another couple they knew who gave them advice—after their first visit. I’ve heard of many people who skipped Rome because “we heard it was too busy, just another big city.” Or passed on Venice, one of the world’s most magical destinations, because, “I heard it was touristy.”

There are American tourists who say you should skip Venice. They are wrong.

It goes on and on, but suffice to say, I have been to Italy in the neighborhood of two dozen times, summer and winter, for food, wine, skiing, golf, hiking, cycling and more food, from north to south and east to west and islands too, and I know a lot about Italian cuisine, but I still ask real experts for advice every time I go. I specifically ask for advice on where to eat, what to see, and who to choose as guides. And by experts, I mean people how live in Italy, specialize in particular areas of travel, and know their subject matter.

“We get multiple guests a year who want to wing it,” says Cherrye Moore, owner of My Bella Vita travel. Moore moved to Calabria two decades ago after falling in love with the region on a visit, and opened a bed and breakfast, learning about what her visitors were looking for. Her company now specializes in planning trips—especially foodie and ancestry trips—to the area in Southern Italy where many Italian Americans trace their heritage. “They say, ‘My neighbor just showed up in their family’s hometown and it went great for them,’ or, ‘Our friends went to Italy last year and said we don't need a driver.’ It’s true that you can rent a car and drive to your family’s hometown, but that experience is vastly different from having a dedicated driver and a heritage specialist who has done research on your family’s history, who has already identified the home your grandfather was born in, and who has arranged meetings with locals upon your arrival.”

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Anyone can tour the Vatican, but only the right guides can get you a private visit.

I just got back from an exploration of Turin followed by a weeklong hiking trip in surrounding Piemonte, Italy’s most prestigious wine region, which included multiple winery visits. For restaurants and guides and sightseeing in Turin I used an Italian-based travel specialist that is the choice of many of the best luxury travel agents/advisors in this country (the best travel agents are savvy enough to know what they do not know and regularly rely on local experts). For the hiking trip, I used an Italy-based active travel specialist that does nothing else, and does it with a food-centric spin. It was another fantastic Italy trip, one amazing day after another, featuring many meals, wineries and experiences I never would have found by myself, especially by asking random friends or watching You Tube influencer videos by people with far less Italy experience than myself.

“We don’t focus on stars or diamonds, we focus on really special one-of-a-kind experiences and lodging that lets you discover our Italy,” said Heather Dowd, who lives in Turin and along with her Italian husband Beppe Salerno. They run Tourissimo , the active travel company we used. We had several friends hiking with us who were on either their very first or second trip to Italy, and when we reviewed our experiences at the end for the trip, one place we stayed, an 18 th century castle turned boutique hotel, was the overwhelming favorite. It did not have whirlpool tubs or Frette linens, it did not have a concierge or room service, but it had excellent food and beautiful gardens in which we had an epic dinner. It had cooking classes, a great location, a fun aperitivo evening cocktail session, and most of all, incredible charm..

Everyone wants the perfect meal in Italy, but not everyone knows where the locals go to find it.

It was exactly what my first timers dreamed Italy would be like, and it was a place we never would have found online. It was perfect, and even in Italy not every place is, but the reality is that Heather and Beppe and their guides spend a lot of time behind the scenes visiting small hotels and vetting them, way more time than the people who rate their stays on booking websites. One of my friends was so impressed he is already planning an extended family hiking trip to Sicily with Tourissimo next year.

If you want to have an insider experience in Italy, and see the places locals go, you need a local insider to help you out.

“Our goal is for guests to experience Calabria like we do, so we’ve built experiences that aren’t available online,” said My Bella Vita’s Moore. “Nowhere else can you find a multi-course lunch hosted at Zia Pina’s or a picnic prepared and delivered by Signora Francesca. Lunch in the home of our friend, Chef Massimo, isn’t available on Google. When creating or reviewing experiences I always think of my sister in Texas. If she were visiting, would I take her here? If that answer is yes, I know we have a winner.” That is exactly the standard by which I’d like my Italy travels to be judged.

A trip to Italy is a beautiful, special, and almost sacred experience, so don’t screw it up by taking bad advice. I do not know every local specialist—and I hope to keep finding more—but I know several experts I would recommend for different kinds of travel. Or use a good travel advisor, something I recommend for all travel (Read my article Why You Need A Travel Agent More Than Ever here at Forbes ), and communicate with them to ensure they are on the same page in terms of sourcing these kinds of local experts. If they are good, they will already be familiar with several of these companies.

Active Travel

All of Tourissimo's cycling and hiking trips in Italy emphasize food and wine, which is how it ... [+] should be.

Italy has long been the dream destination of cyclists, with Tuscany atop the Bucket List for global road riding destinations. But for the past few years the fastest growing sector of cycling has been “gravel grinding,” and with hundreds of miles of its stunning unpaved “white roads,” Tuscany has also emerged as the world’s top travel spot for gravel lovers. There are also plenty of other amazing places to ride in Italy, including Piemonte, Sardinia, Puglia, the Lakes region, and many other areas. World class hiking abounds, especially the stunning Dolomites—a UNESCO World Heritage Site of beauty unmatched by most other mountain regions on earth. Beyond this there are the Alps in the east, the Cinque Terre, Sardinia, and many other great options.

Italy is so well known for cycling and hiking that every major active travel company in the world runs trips there. But for my last two active trips, one hiking and one biking, I chose a tour operator that is actually based there, founded by an Italian with a passion for cycling and food. Tourissimo may be Italian, but they cater to the American market, and founder Beppe Salerno worked for am American cycling company as a guide before realizing he could do the real Italy better himself—to me, the perfect startup rationale. Over the years since, Tourissimo has grown its library of offerings, with both with an array of scheduled group trips and private custom options. While they do mostly road riding, they are notably one of the only tour operators scheduling gravel trips, and can also arrange custom mountain biking itineraries, with years of expertise in cycling and hiking.

Superstar Chef Mary Sue Milliken has led about galf a dozen Chef's Cycling Tours in Italy for ... [+] Tourissimo.

In addition, Tourissimo has also been a pioneer in “Active Culinary Travel,” a hot new category I have written about here at Forbes (and for other magazines and newspapers). They offer an annual series of six group rides (and a hike) each hosted by an acclaimed chef like Mary Sue Milliken, an award-winning chef, restaurateur, cookbook author (five!) and co-host of the popular PBS cooking show Two Hot Tamales . She is also an avid cyclist and has led the Tourissimo Chef Bike Tours for several years, along with other big names. These trips are a unique option for serious foodies who also ride, while the other trips cater to just about anyone. Otherwise they offer several styles of trips, from Bici Basics for new riders to Ambitious Tours for the more hard core.

Tourissimo puts a focus on local, choosing small and often historic hotels that they have curated and vetted (like the castle I just stayed at in Piemonte), places that you would never be able to distinguish from hundreds of other non-chain options online. Same for restaurants, wineries, and all the other ways they take you behind the scenes and into their real Italy. Their Mission Statement? “We don't want to be the biggest adventure travel company. We want to design and run the best tours in Italy. We strive to be the most authentic and the most beneficial to local communities.” Fantastico!

Bellagio on Lake Como is one of the most famous destinations in Italy — and the perfect place for a ... [+] food-centric bike tour!

Bike It! Bellagio offers another insider biking experience on a much different scale, providing a great one-day experience for visitors to Italy’s most famous lake town. This bike shop on Lake Como is run by a former pro racer and his wife. They rent bikes (road, mountain and e-bikes) out, but also offer one-day guided tours with multiple food and drink stops. Given that the owner grew up here and knows everyone, it’s not surprising that the food and drink spots are insider picks. The shop sits near the iconic Madonna del Ghisallo climb, the most famous in the Giro di Lombardia, a race more than a century old, and several days a week the shop offers guided group rides with a climb of the pass, on road or e-bikes—Bianchi bikes of course!

There are scheduled tours Monday through Saturday, as well as wide range of customizable private tours. These are often taken by families with mixed ages, but for more aggressive riders they offer longer road tours, mountain biking and gravel riding, along with a wide range of less demanding e-bike tours, including some even more focused on food and wine. They also offer a handful of multi-day tours and can put these together as custom on demand, usually for groups, including an iconic coast to coast traverse of Italy. If you are a guest of one of the many stunning (and pricey) ultra-luxury hotels around Bellagio, and ask the concierge to arrange a bike tour, they are likely going to call this shop anyway (and mark it up) so just do it yourself.

Luxury Travel in Italy

From planning your entire itinerary with flights, hotels, and transfers to just booking the best tours, guides and VIP access (often to non-public highlights), it pays to use a top local specialist.

Last year I attended the annual Virtuoso Travel Week in Las Vegas, which has been called “the Oscars of the travel industry.” Virtuoso is the leading global luxury travel consortium, and many of the best travel advisors on earth belong, So does just about every top hotel, resort, safari lodge, cruise line, and luxury tour operator. Virtuoso CEO Matthew Upchurch was explaining the many advantages of using a travel advisor (I wholeheartedly agree) and something he said really stuck with me. He explained that with all of the new online tour booking companies, it was easier than ever to book a tour or guide in just about any destination on earth, but harder than ever to judge the quality. The caveat was that, “you can book a guide, but you can’t book my guide.”

One of Italy's greatest hidden gems, Turin was the nation's first capital and a Winter Olympic host. ... [+] It's worth getting a good guide if you visit.

The Vatican is the Vatican and the Colosseum is the Colosseum, so when you opt for a guided tour, what really matters and makes it a good, bad or great experience is the guide—and their special access, like a tour of the Vatican when no one else is there.

For my recent trip to Turin, I called Imago Artis Travel , an Italy-based luxury travel specialist. They are what is known in the travel industry as a destination management company or DMC, the same companies luxury travel agents call to arrange local details for their clients. There are great DMCs all over the world, and local knowledge is valuable everywhere, but many of them do not deal directly with travelers, while in Italy the best ones do.

I wanted a private day tour of Turin and its surrounding attractions for my wife and I, most importantly the Reggia di Venaria Reale, aka the “Italian Versailles” (one of two places in Italy with this lofty but accurate nickname). The guide they got for me was a licensed guide, and lifelong resident of Turin, and spoke excellent English, which was all good, but she was also an architect, which was great in a city where so much is driven by architecture. That’s not so easy to find on global tour aggregator website. Imago Artis also gave me a list of their favorite restaurant recommendations, which were spot on, then made my reservations for me. At a minimum this eliminates the language barrier of calling or the technology barrier of booking through often tricky (or non-functional) Italian restaurant reservation websites, but in many cases it also gets you a better table and instant VIP treatment—which definitely does not happen when I book myself.

Italy is rich in world-class crafts, and companies like Imago Artis can take you behind the scenes ... [+] to meet the makers.

Imago Artis Travel is a Virtuoso member, which means when you book through them, if you book your luxury hotel, you get extras like room upgrades, late checkout, spa credits etc., one of the big advantages of working with Virtuoso travel advisors. If you have a bigger budget than I do, they can handle all sorts of luxury transport, private jets, helicopters, boat charters, and also offer VIP Meet and Greet services at just about every airport in Italy. They can even arrange private security details. On a more accessible luxury level, they specialize in exclusive experiences, unlocking historic buildings and art collections not open to the public, and taking you behind the scenes with many artisans of Italy, from custom shoemakers to sculptors to jewelry designers. They know food, they know the guides, and I especially like their mission statement, “Our mission is simple: Getting You to the Heart of Italy.” That’s what it is all about.

Another top luxury DMC that is also a member of Virtuoso that I have used in the past with great success is IC Bellagio . They offer a similar array of luxury services and are very well connected, but they also specialize in Villa rentals as well as 5-Star hotels. Differentiating villas in Italy may be the single biggest challenge, more so than restaurants, with so many options and so few valid reviews. IC Bellagio has also boldly acknowledged the overtourism problems some of the most popular parts of Italy face, and are pushing “Slow Season Travel,” which varies in each of the country’s 20 regions but is something they are expert in. Last winter I went to Venice in the off-season, and it was spectacular, and I just traveled in a slow season to Piemonte. It was much, much better than fighting the crowds.

Skiing in Italy is awesome, and it's the best place in the world to stay in mountain rifugios — but ... [+] you need help for the perfect trip.

Skiing in Italy remains a bit under the radar for Europe, especially compared to France and Switzerland. Well, let the crowds go to other countries, because Italy has two different major ski regions, both of which have hosted the Winter Olympics, and the Games are returning to Milan and Cortina in 2026. The interconnected Dolomiti SuperSki lift and trail network in the Dolomites is arguably the largest “ski resort” in the world, and inarguably one of the most beautiful mountain landscapes on the planet. The towns are charming, the food is great, there are spectacular hotels from non-chain independent hidden gems to world-class luxury (Aman, Mandarin Oriental, Relais & Chateaux, etc.) and it’s cheaper than much of the rest of Europe. Did I mention the food?

I first went to the Dolomites to go hiking, and was so wowed I thought, “I have to come back and ski here.” I came back the next winter and skied, and the following year I got a group of friends together and went back. I have skied all over the U.S., and all over the world and never had the same compulsion to return to the same place immediately. That’s how good skiing in Italy is ( read much more in my Italy skiing piece here at Forbes ).

I’ve only used one company for ski travel in Italy and see no reason to switch gears, especially since the local logistics (a great guide/instructor, transfers, the best on-mountain meals and staying a couple of nights in the region’s unique on-mountain rifugios) is very hard to organize on your own. The company is Dolomite Mountains , a specialist in both resort ski vacations and backcountry touring trips (using skins and alpine touring or AT gear). They too are a U.S. facing company with mainly American clientele.

Like many active travel companies, they offer both group trip scheduled departure options and private custom trips to fit whatever you want. The group option is called the Dolomites Ski Safari and is a 7-day trip mixing stays in amazing rifugios with in-town hotels (4 and 5-stars on the Italian system) and includes all breakfasts and dinners, a full-time guide, ski pass, luggage transfers and more. Custom options include the same kind of trip for your own group, or anything you want, and while its name suggests local expertise—quite true—Dolomite Mountains also handles ski trips in the rest of Italy, like Courmayeur, and connected border regions of France, Switzerland and Austria, as many lift systems here know no national boundaries (ski with your passport!). They are also a Virtuoso member.

Calabria & Southern Italy

Many Italian Americans trace their ancestry to Southern Italy's Calabria, and if you want to visit, ... [+] make sure you do it right.

My Bella Vita travel focuses on this area, including both small group trips and custom privates. Their specialties include “Heritage Tours” for those interested in their ancestry, and a food focus for the rest of us. For instance, Taste of the South is a 12-day gastronomic journey through Calabria, Basilicata and Naples—the birthplace of pizza! Food & Wine of Calabria is an 11-daty trip and just what it sounds like.

These are some of the scheduled small group tours offered, but the rest of their business is private trip planning and custom options.

“Italy is deceivingly large, and travelers think two weeks is enough time to see everything. It isn’t,” insists Moore. “You can’t even experience all of Calabria in two weeks. Our team collectively spends about six months a year scouting new hotels, restaurants, and experiences in Calabria and we are constantly re-evaluating and tweaking our recommendations.”

There are some other Italy specialists I have not personally experienced, but that come highly recommended by some of my other experts:

My Bella Vita’s Cherrye Moore says, “ In Sicily, I recommend Lucia Davies of Sicily Tour , one of a trio of British expats who have lived in Siracusa, Sicily for decades.” A family-owned tour-guiding company based in Siracusa, they have nearly 40 years of experience on the island and create trips fostering cultural exchange between Italy and English-speaking visitors, specializing in small group and custom tours.

Food & Wine

Life is too short to go to Italy and not eat well.

Beppe and Heather Dowd of Tourissimo recommend Lazy Italian Culinary Adventures , a company that has also earned kudos from other travel industry folks I know. Owner Francesca Montillo grew up in Southern Italy where her father was greengrocer. An Italian-American cookbook author, she launched the company a decade ago, and she personally leads the tours. She does numerous scheduled tours to different regions each year, and also offers custom private itineraries.

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