bike tours from siena italy

THE 5 BEST Siena Bike Tours

Bike tours in siena.

• Gear Rentals
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• Up to 1 hour
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• Chianti Road
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• Anima Toscana Bike Tour
• Via delle Volte
• Tuscany Private Tour
• Castello di Brolio
• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Small Group E-Bike Chianti Tour with farm lunch from Siena

2. Chianti Classico E-Bike Tour

3. Chianti Classico Bike Tour from Siena

4. Half-Day Cycling Tours around Siena

5. E-Bike tour and wine tasting from Siena

6. Siena City Private eBike Experience

Keep the fun going with other experiences in the area.

Greve in Chianti Wine Tasting and Winery Tour

Private Tuscan meal with Wine and EVO oil tasting

Private Wine & Oil Tasting with Lunch

Wine Tour Ebike Experience

Grape stomping in Tuscan farmhouse

3 Hours Truffle Hunting with Pasta Cooking Class and Lunch

Truffle Lunch & Hunting Experience in San Gimignano

Luxury Picnic Experience in Tuscany

Private Tour: San Gimignano Walking Tour

Private Tour in San Gimignano

E-Bike rental in Tuscany

Tour of the cellar and tasting of 6 wines

Wine Tour Experience at Agricola Tamburini

Tour in Volterra with a Licensed Tour Guide

Villa Medicea Di Lilliano Tour with Wine Tasting

Exclusive Lunch Tour and Wine tasting at a Chianti Classic Winery

Private walking tour in San Gimignano with a local licensed guide

Chianti and Castle Small Group Tour from San Gimignano

Wine and food tasting on an organic family farm.

Lunch with Wine Tasting

Pienza - Ebike tour for a full immersion in Val d'Orcia.

Discover Montepulciano!

Tour of the historical cellars in Montepulciano

Truffle Hunting in Tuscany

What travelers are saying.

• Small Group E-Bike Chianti Tour with farm lunch from Siena
• Chianti Classico E-Bike Tour
• E-Bike tour and wine tasting from Siena
• Siena City Private eBike Experience
• Chianti Classico Bike Tour from Siena
• Siena Bike Tour
• Up and Down the Chianti
• Curioseety Siena
• Enjoy Tour Tuscany
• Kilometro Inverso
• Road Bike Tours Italy

•  +39 3288264014
•   [email protected]

Bike Tour Siena

Love for the Terre di Siena and Tuscany Anima Toscana Bike Tour, a Tour Operator whose primary desire is to take you discover the different souls hidden in our land.

San Gimignano Bike Tour

One day bike tour to discover San Gimignano with Vernaccia wine tour and tasting.

Brunello di Montalcino Bike tour

Bike tour in the land of Brunello di Montalcino wine region, riding surrounded by vineyards and woods. During the bike ride we'll visit a winery and taste 3 wines.

Val d'Orcia bike tour

The one day bike tour in Val d’Orcia, UNESCO world heritage site, will make unforgettable your holiday in Tuscany. You will cycle surrounded by the typical rolling hills of the region, through small medieval villages and beautiful views.

Chianti bike tour

Bike tour to discover the Chianti region, the Castle of Brolio and final wine tour and tasting in our selected winery.

Crete Senesi bike tour

A unique naturalistic experience, riding through Crete Senesi to Monte Oliveto Abbey.

Monteriggioni and Castellina in Chianti bike tour

One day bike tour to discover Monteriggioni and Castellina in Chianti

Eroica Bike Tour

One day bike tour to discover the route of L'Eroica.

BIKE RENTAL IN SIENA AND TUSCANY

ANIMA TOSCANA IS YOUR BIKE RENTAL POINT IN TUSCANY. WE RENT HYBRID BIKES, MTB, ELECTRIC BIKES AND ROAD BIKES FOR YOUR BIKE TOUR IN TUSCANY THROUGH SIENA, CHIANTI, VAL D'ORCIA, MONTALCINO AND BUONCONVENTO.

HYBRID BIKE

The hybrid bikes are suggested for the gravel roads of Terre di Siena and Eroica routes.

MOUNTAIN BIKE

Mountain bike with wheels size 29" are perfect for the gravel road and Via Francigena route.

Performance and lightness. The road bike can be used for competition and it's also excellent to discover Tuscany by bike.

ELECTRIC BIKE

The electric bike is the best solution for beginners cyclists and people of every age. The electric motor will make it easier your bike tour in Tuscany.

Anima Toscana will make your trip to Tuscany intense and exciting, thanks to the deep knowledge of our lands and the attention to details that we will devote to your holiday with us. The passionate selection of the itineraries, of the structures, of the “pleasant diversions”, will immerse you into the authentic Tuscan Soul. The selection of every detail is minded personally by Anima Toscana, in the pursuit of the more typical, genuine and welcoming spirit. Itineraries selected by Anima Toscana will bring you through unknown but fascinating and uncontaminated corners, far off routine and mass tourism.

Siena and surroundings: two wheels, endless emotions

The scenery is where one of the key stages of the UCI WorldTour  -  the top world cycling calendar event  - has been held for years, namely  the Strade Bianche, a road cycling race staged every March in the province of Siena . The route combines the main characteristics of two other classics - the Paris-Roubaix for its stretches on uneven road (in France on cobblestones, in Tuscany on dirt - “white” - roads) and the Tour of Flanders for its short stretches with very high slopes.  A difficult race , reserved to the most fearless cyclists, which attracts cycling fans from all over the world to Siena. Back with our feet on the ground, or on the pedals, around the official route used for the championship race, there are  many other routes within everyone's reach  for discovering the Siena area by bicycle with friends or family.

Cycling in the Siena area

We set out by bike from the heart of Siena , Piazza del Campo, on the classic streets of the city center, paved with the typical pietra serena . Then we head east in the direction of the Logge del Papa (late 1400s), alongside the church of San Martino with its wonderful baroque facade. Once past the Contrada della Torre area, you will find yourself in front of the Basilica of San Clemente in Santa Maria Dei Servi (Contrada of Valdimontone), from where you can admire a beautiful panoramic view of Siena . Leaving Valdimontone in the direction of Porta Romana, built in 1327 along the city walls near the ancient Via Cassia, continue along some neighboring streets, and enter the district of Nicchio, then gradually cross the remaining streets to arrive in Via del Casato and back to the starting point: Piazza del Campo.

Piazza del Campo

On two wheels between the gates of siena.

One of the most characteristics features of Siena are the gates to the city that can be found along the ancient defensive walls , and the beauty of this route lies precisely in the fact that it takes you across the most beautiful ones. So, Porta Romana, Porta Pispini and Porta San Marco will be important stops on this excursion. You'll learn about one of the city's oldest water sources , pass under the famous inscription "Cor magis tibi Sena pandit" (Siena opens a heart to you that is bigger...than the gate you're walking through), and discover Baroque and Renaissance treasures in a unique environmental setting . There will also be a picnic area where you can take a break, maybe do some exercise on the open air gym equipment nearby, or finally replenish your water supply. The route treats you to a final twist : you arrive in the breathtaking Piazza del Campo.

Via Lauretana, a paradise for cyclists

The ancient Via Lauretana is now a cycle route leading from Siena to Cortona, along part of a hiking route that is recognized as one of the “Cammini Toscani”. Along this route you can join the Via Francigena and the Sentiero della Bonifica . The many detours you will encounter help you avoid areas prone to road traffic, and will allow you to enjoy the very best of this beautiful route, spanning alternate short asphalted sections and long stretches of dirt roads. There are six possible stopping points along the way, with bike points located in the most important places. The stretch that departs from Sinalunga, passes through Montepulciano , and leads to Cortona is challenging but absolutely beautiful. The more expert, fitter riders among you could finish the tour in one day , but our advice is to take at least 48 hours and experience it slowly , taking the time to enjoy the many beauties you will meet along the way.

Cycling between sheaves of wheat and sunflowers

A route that winds through the rolling hills of Siena and, starting from one of the city’s gates, Porta Romana, you will pedal through the open countryside following the signs marked Via Francigena Sud . Along the route, the Certosa di Maggiano can be reached along a succession of dirt roads and short stretches of asphalted road, in the tradition of the "white roads". The scenery is that of the Val d'Arbia, where gentle climbs and easy descents await you. Here, in the summer, you'll find some of the fields planted with sunflowers in full bloom, or more wheat fields just after harvest, with their round sheaves lying along the slopes. Whatever the season, you will discover the charm of Grancia di Cuna, an imposing red brick building, and one of the best preserved medieval fortified farms. It is also one of the most interesting architectural complexes in the entire province of Siena. Once your eyes are filled with wonder and your heart is brimming with emotion , you can complete the excursion by pedaling in the direction of Porta Romana and returning to Siena.

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• Route planner

Top 10 Bike Rides and Cycling Routes in Siena

Cycling in siena.

Cycling in Siena is one of the most enjoyable ways to explore more of this part of Tuscany. So you can find your perfect Siena bike ride, we’ve reviewed our full collection of cycling routes in the region to deliver the best. Just click on each route to see a full breakdown of detailed information including elevation profiles and surface analyses, and browse real tips and photos uploaded by other members of the komoot community.

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Bagno Vignoni, Pienza e San Quirico d'Orica — Giro ad anello

Da siena ad asciano – giro ad anello.

Let us show you the way with the komoot mobile app

Da siena a castellina in chianti – giro ad anello, da buonconvento a montalcino — giro ad anello, from colle val d’elsa to san gimignano, da siena a monteriggioni e gracciano d'elsa, strade bianche bagnaia e vidritta da siena – giro ad anello, da siena al passo dell'incrocati – giro ad anello, abbazia di sant'antimo e castelnuovo dell’abate da montalcino – giro gravel ad anello, i colori del chianti — giro ad anello.

Our Tour recommendations are based on thousands of activities completed by other people on komoot.

Popular around Siena

Bike Touring Collection by komoot

Find the perfect Tour

Explore the most popular tours in siena, discover the most popular attractions in siena.

Didn’t find what you were looking for? Check out more Cycling Routes throughout Siena below and find the perfect Tour in your destination.

• San Gimignano
• Castellina In Chianti
• Radda In Chianti
• Piancastagnaio
• Monteroni D'Arbia
• Castelnuovo Berardenga
• Riserva Naturale Pigelleto
• Buonconvento
• Colle Di Val D'Elsa
• Riserva Naturale Del Bosco Di Sant'Agnese
• Riserva Naturale Il Bogatto
• Castiglione D'Orcia
• Riserva Naturale Basso Merse
• Riserva Naturale Alto Merse
• San Quirico D'Orcia
• Gaiole In Chianti
• Rapolano Terme
• Nature Reserve Lucciola Bella
• Monteriggioni
• Casole D'Elsa
• San Casciano Dei Bagni
• Chianciano Terme
• Radicondoli
• Riserva Naturale Di Castelvecchio
• Torrita Di Siena
• Nature Reserve Lake Montepulciano
• Montepulciano
• Riserva Naturale Crete Dell'Orcia
• Abbadia San Salvatore
• Riserva Naturale Cornate E Fosini
• San Giovanni D'Asso
• Lake Montepulciano
• Lake Chiusi
• Riserva Naturale Pietraporciana

Explore more of Tuscany : Browse the best Cycling Routes in other regions.

• Massa-Carrara

• Great Britain
• 8 - 10 Days
• 11 - 14 Days
• Self Guided (Open Departure)
• Self Guided (Scheduled Departure)
• Guided (Scheduled Departure)

Siena Self-Guided

Extended Route

Siena is without doubt the showpiece province of Tuscany, and this self-guided cycle tour explores some of the most beautiful cycling routes in Siena Italy. The incomparable impressionist-style landscapes of lush vine and poppy bedecked hills and valleys just beg to be explored and enjoyed from the saddle of a bicycle.

You will begin your journey in Siena cycling to the green pasturelands of Le Crete where tiny roads wind through the fields and along hill crests to connect ancient farmhouses and tiny medieval villages. This area is a scenic delight of bare ridges, solitary cypresses and medieval farmhouses, and it abounds with ancient Roman and Etruscan archaeological sites. South from Le Crete lies the Val d’Orcia where the landscape is one of nature’s inspired works of art. Possibly no other region conjures up such classical images of Tuscany. ... the hamlets and hilltowns, terracotta rooftops, swaying cypress and golden valleys, vineyards and olive groves all contribute to the overall picture. Besides the beauty of the landscape, you will explore the fascinating and beautiful towns of Pienza, Montepulciano and Montalcino. Dropping down from Montepulciano you pedal through the the sunflower, tobacco and corn fields of the Val di Chiana to Monte San Savino before climbing to the spectacular city of Cortona. The final leg of the itinerary is a beautiful ride across the hills to the tranquil Arezzo.

This tour is Tuscany cycling at its very best. Perfect for those who want to experience a cycling holiday in Italy. Each core route is designed to allow time to enjoy the scenery, to explore the en route attractions and to have a leisurely lunch. The route extensions are for the more ambitious riders who want to challenge themselves. It is important to bear in mind that Tucscany is not flat – even on the core routes the terrain is largely rolling. Some of the riding on both core routes and extensions is on the strade bianche - the white dirt roads that are so characteristic of Tuscan landscapes.

The views from Siena’s Torre del Mangia

Siena Cathedral

Sodoma’s frescoes in the Abbazia di Monte Oliveto Maggiore

The Etruscan museum in Murlo

The Castle of Gargonza

The Renaissance town of Pienza

The hot springs in Bagno Vignoni

Sampling a glass of Brunello wine in Montalcino’s Fortezza

The vista across the Val d’Orcia from Cortona’s heights

Arrive into the stunning UNESCO World heritage Site city of Siena, where you will be checked into your hotel and met with your bikes, mapping and introductory talk

Siena-Montalcino (48km core)- Leaving behind the city, you pass through the rolling hills whcih surround Siena, passing through the quaint Radi, before climbing into Murlo, a stunning medieval village where you may wish to visit the Etsuscan Museum. From Murlo, you cycle the tiny lanes through typically beautiful Tuscan countyside, passing Buenconvento, where you may want to stop for lunch, before making the final climb of the day toward the scenic Montalcino.

Montalcino-Montepulciano (48 core)- From Montalcino, you ride East through the Val d'Ocria, a rich, green nature reserve, which produces some of the best wines in the world. Each hilltop town you pass seems more beatiful than the last, with plenty of options for lunch stops or stunning vistas where you may decide to picnic. The final leg involves a steep climb into the breathtaking medieval town of Montepulciano.

Montepulciano Loop Ride (36, 63, 74km)- We have plenty of options available to you on today, with varying distances and difficulty levels. You have the option to ride the famous Strade Bianche white gravel lanes, to visit the famous spa town with its hot springs in Bagno Vignoni, or smaller rides, allowing you the chance to sample some of the world famous red wines in the town and its immediate surroundings.

Montelpulciano- Cortona (45km core)- Dropping down from Montepulciano you pedal through the the sunflower, tobacco and corn fields of the Val di Chiana to Monte San Savino. The valley has plenty of wine and olive oil offerings in each of the medieval towns, as well as being dotted with the famous Chianina cows, one of the oldest breeds in the world. The last leg of the day is the short, steep, but worthwhile climb into Cortona, which boasts some of the best views anywhere in Italy.

Cortona Loop (51km core)- There are again a couple of options on your loop ride down from Cortona. The loop takes you to the shoreline of Lake Trasimeno, as well as to the beautiful castle of Pierle, dating back to at least the 10th century. You may want to spend some of your day walking the cobbled streets and visiting the independent retailers which specialise in handmade crafts and gastronomic delights. Cortona was used extensively in filming for Under the Tuscan Sun.

Cortona to Arezzo (40km core)- There are various options for your final leg of the trip. The core route is a flat, gentle ride through the valley. You have an option to ride some more of the famous white pebbled lanes, as well loner rides out toward Citta di Castello, as well as travelling along some of the well trodden St Francis Way. You final night is spend in the picturesque Arezzo, whose central piazza was used as the backdrop to Roberto Benigni's Oscar winning film Life is Beautiful.

Accommodation

The standard accommodations for the self-guided itineraries are family run hotels. Generally, these have around 10 to 20 guest rooms and the owners live on the premises. Italian hotel are classified by a star rating system – from one to five stars – standards for each category may vary a little from region to region. Most of the hotels that we use fall into the three star category – though we occasionally use two and four star hotels when circumstances or availability dictate. In almost all cases the bathroom facilities are ensuite (self-contained within the room). Some of the smaller hotels do not have a restaurant, but there will always be several options close by, within easy walking distance.

The Italian breakfast is light – a cappuccino and a brioche (pastry). Most hotels serve a continental breakfast of orange juice, coffee, tea or hot chocolate, bread rolls and jam. There may also be yogurt, cheeses, cured meats, pastries and cakes.

When you book a tour, your pre-trip planner will have more details about the specific facilities and services provided by the accommodations.

Examples of our Tuscany hotels include;

• Albergo Il Marzocco, Montepulciano
• Il Giglio, Montalcino
• Ristorante Fiorentini, Sansepolcro

Getting there

The Tuscan airports at Pisa and Florence mostly handle internal and short haul flights. Coming from abroad, Rome may be more convenient. Rome has two airports. Leonardo da Vinci Airport (at Fiumicino) is used by the major airlines, while Ciampino Airport is used by budget airlines such as Ryanair .

Getting to and from the trailheads (Siena, Sansepolcro, Florence) for the Tuscany itineraries involves travel from your arrival airport to the nearest mainline station or bus station for onward transport to the trailhead town.

Most inter-city trains leave Rome from Termini Station. Most inter-city buses leave from the main bus station outside Rome Tiburtina railway station. The Metro (line B) connects the two.

From Leonardo da Vinci Airport the most convenient way to get into Rome is to take the Leonardo Express, a direct train service to Termini (½ hr/every ½ hr).

From Ciampino Airport take a Terravision bus (¾ hr/ every hr) which to Termini. You can book online.

Pisa Airport has a railway station – trains run to Florence Santa Maria Novella Station (1½ hr/every hr). For Siena (2 hr/ every hr), change at Empoli.

Terravision buses run a regular service from Pisa Airport to Florence Santa Maria Novella Station (1¼ hr / every 1½ hr).

Terravision buses run a regular service from Florence Airport to Florence Santa Maria Novella Station (¼ hr/ every 1½ hr).

Note that the train station in Siena is located approximately 2 km from Siena's historical centre. It's a five minute bus ride from the city centre (Piazza del Sale) to the train station and buses run regularly in both directions.

• From Rome Termini Train to Siena (3½ hr /every hr)
• From Rome Tiburtina Sena Line Bus to Siena (3 hr / every 1½ hr)
• From Pisa Train to Siena (change at Empoli)
• From Florence Train to Siena

Tuscany is at its most beautiful in spring when the meadows and waysides are carpeted with wild flowers. Autumn is equally attractive when the beech and chestnut woods become clothed in a blaze of seasonal red and gold. The best months for avoiding the heat and the crowds are May, June, September and October. Easter should be avoided, as accommodation can be hard to come by. In August Tuscans head for the coasts for their annual vacation – and many shops, bars and restaurants are closed.

Tuscany is renowned for its light, which develops a clear golden quality as the days of high summer begin to shorten. Spring and autumn days are warm with plenty of hours of sunshine. July and August are the hottest, driest months, and you must to be comfortable cycling in very hot temperatures if you choose these months for your tour. October is also fine, but there is a greater chance of rainfall.

€855 is the cost per person sharing. The cost includes the following (unless stated otherwise)

• 7 nights' accommodation with breakfast
• Pre-trip planner
• Routes in the form of highlighted maps and cue sheets
• Telephone support
• Meet and greet (if you are renting bicycles)

Luggage Transfers

The standard charge is based on one or two riders. A couple would therefore share the luggage transfer costs. There is then a small additional fee for the third and each additional person. For example:

• Total cost for one or two riders = 325 (162.50 per person based on two people sharing)
• Total cost for three riders = 325 + 25= 350 (117 per person)
• Total cost for four riders = 325+ 25+ 25= 375 (94 per person)

Note that the more riders in the group, the less expensive are the luggage transfers per rider.

Please note that whilst we will try our best to provide you with the exact bike as listed below, due to availability or sizing issues we may not always be able to. The bike you will receive will be of a very similar spec and always in very good condition.

Fuji Absolute Hybrid Bike

• 5 frame sizes
• FX Alpha Gold Aluminium
• FX Alloy fork

Bring your own saddle and/or pedals if you wish and we will fit them to the bike. (You must be able to remove them yourself at the end of your trip).

Fitted with: Rear rack; platform pedals, bottle cage, fenders (mudguards)

Equipment provided: Handlebar bag; map case; spare tube; puncture repair kit; lock; mini pump; multitool.

Available on request: Panniers, helmet, odomoter, gps unit

Kona Touring Bike

• Kona Cromoly Butted Frame
• Disc brakes
• Kona Cromoly Fork

Bring your own saddle and/or pedals if you wish and we will fit them to the bike. (You must be able to remove them yourself at the end of your trip)

Fondriest Carbon Road Bike

• 7 frame sizes
• Monocoque carbon frame
• Reflex fork
• Sleek Italian design

Fitted with: Platform pedals, bottle cage,

Equipment provided: map case; spare tube; puncture repair kit; lock; mini pump; multitool, frame bag

Fuji E-Traverse E-Bike

• Suntour NEX disc fork
• Bafang H400 rear hub motor
• Bafang 5 mode LED display w/walk assist
• Shimano Gearing

Most beautiful biking I've done

Just wanted to let you know we are having best trip of our lives.

Just wanted to let you know we are having best trip of our lives. Loved the route today - especially the single track (forgot about your note regarding flood, obstruction, etc). Most beautiful biking I've done -- and I've been around. Hotels friendly and comfortable. We hope to do another trip within the year. My next destination targets are northern Spain or Scotland. Do you do Croatia?

It was fantastic

It was fantastic, and went as smoothly as one could imagine.

It was fantastic, and went as smoothly as one could imagine. Your not hearing from us for most of the duration of the trip is a sign of good organizing - we were having a good time, didn't get too far lost on the lead sheets, and thoroughly enjoyed the accommodations. The pool at Montalcino was heavenly after the long hot climb. We appreciate your putting together this custom itinerary for us, and I'm totally going to recommend you to any friends considering a similar trip. I may even come back for a longer version!

A great time

We had a great time and would definitely do an Iron donkey cycle tour again.

We had a great time in Italy and would definitely do an Iron Donkey cycling tour again. The ease of having our luggage transferred and great bikes really made the cost worthwhile.

Are you ready to find your next adventure? Leave us your details to make an enquiry.

+44 (0) 7780 496969

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Daily Bike Tour in Siena

• Tour Type: Daily
• Bike Type: Road or e-bike
• Price from: €90,00

Cycling in Siena Overview

Cycling in Siena offers a unique way to discover its breathtaking surroundings: the one-of-a-kind rolling hills and the countryside of Tuscany . Whilst riding on a road bike or e-bike with our professional riding guides, you will encounter many vineyards, medieval villages, and scenic viewpoints, giving you a real sense of the region’s rich history and natural beauty . This area in Tuscany is also famous for its fabulous gravel roads which cannot be missed when riding here. Join one of our daily cycling tours in Siena and enjoy this one-of-a-kind experience!

Kind of Tours

1 Rider: € 185,00 x person

2 Rider: € 150,00 x person

3 Rider: € 100,00 x person

4 Rider: € 90,00 x person

• Professional Riding Guide for up to 4 hours 
• Coffee or gelato
• Bike Rental
• Extra Accessories

1 Rider: € 300,00 x person

2 Rider: € 250,00 x person

3 Rider: € 165,00 x person

4 Rider: € 125,00 x person

• Professional Riding Guide for up to 6.5 hours 
• Light Lunch

Have you ever dreamed about a multi-day bike tour in Italy?

Explore Italy's country roads with our seasoned professionals, boasting over two decades of expertise. Immerse yourself in local history, culture, and cuisine as you ride. Tailored for all levels, from seasoned cyclists to beginners, our multiday bike tours offer a unique Italian experience. Join us and discover Italy like never before.

Looking to rent a bike in Italy?

Rent a premium bike with Ciclismoplus , your key to unlocking remarkable cycling experiences through Italy's captivating landscapes. Positioned prominently in Lucca and Florence , and with expansion plans underway, Ciclismoplus's focus is on delivering top-tier bike rental services throughout Italy.

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Terre di Siena Landscape

Terre di Siena Bike Tour

Authentic bike tour Italy

This Tuscany’s combination of natural beauty, medieval and renaissance art, architecture and friendly people will enchant you. Pedal to lofty hill towns, spin through broad valleys and follow sinuous country roads past cypress-lined lanes and quiet woodland.

Cycling through unparalleled countryside by day complements incredible Tuscan cucina by night. This gastronomic paradise beckons to lovers of sublime provincial cooking and superb wine; fresh pastas, porcini mushrooms, and locally produced pecorino cheese from Pienza  mark the region’s celebrated dishes, which just happen to be the perfect match for its world-class wines.  Every day will bring new experiences enriching you.

Off your bike, discover unforgettable Renaissance art and architecture, visit winery and cellars: you will be in the heart of Chianti Classico, savour meals created from the finest local ingredients and relax in charming Tuscan retreats.

Wow Moments riding Terre di Siena

• Explore some of the region’s most celebrated towns, including Siena, San Gimignano, Gaiole in Chianti
• Sample fine wines before dining on local specialties
• Castelli road: the Chianti castles route: the surprising number of castles, fortified farm houses, towers and fortified Abbeys in the area
• a visit to the famous Castello di Brolio before Gaiole is a must!

Arrival at hotel in Siena on your own. Siena, a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. ften described as Italy’s best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You’ll have time to take a leisurely stroll about this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. Piazza del Campo is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city. Here you’ll have time to shop while exploring the many hidden medieval walkways. Meet and Greet, we’ll fit your bikes and introduce you to each day ride.

Distance: 50 km/31 miles Ride from Siena to Castellina in Chianti, following the “chiantigiana” road. Along the way you can stop at Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlet. Not-to-be-missed is Castello di Brolio, a castle and winery. Gaiole the Eroica town worth to stop. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get in Castellina.

Distance: 52 km/32,5 miles Circular bike ride to Florentine chianti: bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany’s forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honeys and rich olive oil . Have a stop at Greve’s main piazza, characterized by an original formation of irregular triangular shape, defined by beautiful long porticos. Back via Panzano with preserved the old walls, gate and the keep of the medieval castle. relax by the vanishing edge pool spilling into the countryside of endless vineyards

Distance: 50 km Ride to San Gimignano: more vineyards await us today, but you’ll be amazed at how different they look once we get into the district of San Gimignano. Hill climbing with many recovery sites on your way including medieval Barberino and Tavernelle the gateway Soft, colorful, rolling hills of vineyards and sunflowers provide the backdrop to pre-Roman Etruscan remnants on your route to San Gimignano’s “medieval skyscrapers” in the distance you will see the seventeen towers. You’ll have plenty of time to wander through the cobblestoned streets, window shop and buy a few last-minute Tuscan mementos for our friends and…why not, for ourselves too!

Distance: 70 km/43,5 miles Ride back to Siena via casole d’elsa Stop in Casole d’elsa: originally inhabited by the Etruscans that means before roman empire. The fortress and the defensive walls are still visible today, although the town gates have unfortunately been destroyed during the Second World War.You will be soon in quiet road through Santa Colomba and Celsa pass the medieval hamlet “Fungaia” known to the sienese chronicle since 1247, it is on the old medieval pilgrim trail Via Francigena.

optional Loop ride to Montagnola Senese Distance: 60 km/37.5 miles The bike ride is an exploration of Montagnola Senese, pass through charming little villages and borgo: Sovicille, Ancaiano, Simignano, Pieve Scola all medieval village with picturesque houses. You will be in the Via Francigena, the ancient road and pilgrim route running from France to Rome, very important in medieval times. The subsoil, mainly limestone, is full of marble, including the famous yellow marble, being used also for the Duomo of Florence

TOUR REVIEWS

Tour reviews.

Hi Giuliana! Thanks so much for the pictures – we had been meaning to write to you! We had such a wonderful time in Italy. The bike trip was one of our favourite highlights … we told everybody about it. Both Sarah and I had such a blast. We really can’t wait to do it again! I’ve attached a few pictures we took, hope you enjoy. Thanks again … all the best.

We want to thank you for such a great vacation. The biking was the highlight of our stay in Italy. We were able to see such untouched beautiful areas that we just couldn’t have seen otherwise. And, the towns we visited were generally much less touristy than where most people go. Even San Gimignano emptied of the tourists by late afternoon and we were able to wander through this beautiful town in peace. Also, all of the hotels were wonderful and your suggestions of restaurants were all fantastic

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Price & Inclusions

Price  Cost: Euro 1330 per person in double occupancy Single room supplement Euro 350

Inclusions Five nights in excellent three-star superior hotels Five  breakfasts All Baggage transfers RideWithGPS App: tracks, route notes, off-line navigation Trip notes: Sightseeing & meals suggestions Maps with elevation gain Delivery bike at Siena hotel & bike fitting Pick-up of bikes and gear in Siena Keepsake Cicloposse water bottle Sales taxes

Not Included Bike Rental per entire tour Hybrid bike euro 180 Road bike, E-Bike, Gravel      euro 210

City Tax   each village charges a tax per day between euro 0,70 to euro 3,00

Essence of Tuscany by bike

Best wine country & Hamlet

Cycling Tuscan Wine Country

Brunello, Chianti Classico & Nobile

Tuscany Maremma

Pienza | Montalcino | Scansano

• +39.0575.750.000
• [email protected]

Terra di Siena Dream

A bicycle tour from Siena to Sansepolcro (7d-6n)

Moderate - difficult, tour category, self guided bicycle tour, tour details, description.

The curvaceous roads that run from Siena to the Val d’Orcia and from Montepulciano towards Cortona and Val di Chiana is the main gateway into the heart of Central Italy. No other region of Italy conjures up such classic Italian images … the hamlets and hilltop towns, terracotta rooftops, swaying cypress and golden valleys. The roads both paved and dirt are pretty much surrounded by silence, yes …ok … there are hills to climb…but your efforts will be well rewarded by the simply perfect views, the scenery in every season and with any weather seems to be a work of art.

In each of the towns you will stay, the locals gather, just like in old times, in the piazza every afternoon for a walk in their “corso”(old town’s main road) looking for a stroll with friends or a good “espresso.” This simple way of life is the Italy’s best kept secret. Sport and culture can be found on the same roads here and are suited for cycle tourists who love to ride in the shadow of ancient civilizations. Here travelling requires frequent stops in order to take it all in, there are towns and villages that will take your breath away.

After a ride through rolling green wheat fields, vineyards, zig-zaging through lines of cypress, you will taste the true flavours of this land… pecorino cheese, fruity olive oils, the famous Tuscan wines, and the warmth of our hospitality each evening.

Day 1:BENVENUTI!

Welcome to Siena – Bike Fitting

Our representative will meet you in Siena

– Special Event of the day: A walk in Siena, the best preserved Medieval town of the world also called “Medieval Pompeii” , the Campo square, its narrow alleys

Day 2: SIENA – BUONCONVENTO-MONTALCINO

Highlights of the day: Epic ride across the hills South of Siena, the Etruscan territories of Murlo and Vescovado, the village of Buonconvento and the nearby Abbey of Monte Oliveto Maggiore (extension) with masterpieces of Renaissance painting.

Ride details: level: MODERATE – approx 50 km rolling hills

– longer route and optional roads available

– Special Event of the day: a stroll in the historic centre of Montalcino

Day 3: MONTALCINO – PIENZA – MONTEPULCIANO

Highlights of the day: Views of Tuscan towns and countryside, Pienza the dream town of Pope Pius II place of architectural masterpieces, shop for ceramics and sample delectable pecorino cheese, the small hamlets of the Val d’Orcia

Ride details: level: MODERATE – approx 40 km rolling hills

– longer routes (+70 km) and options available

– Special Event of the day: Visit of the town of Pienza or the small villages of the valley, some of the local wineries, olive mills and ewe cheese producers.

Day 4: MONTEPULCIANO – MONTICCHIELLO – PIENZA-MONTEPULCIANO

Highlights of the day: Views of Tuscan towns and countryside , a stroll in Montepulciano one of the most beautiful hilltop towns of Italy, an alternative ride Pienza or the ride to the hot springs of Bagno Vignoni

– longer route available

– Special Event of the day: Visit of the town of Pienza

Day 5: MONTEPULCIANO – CORTONA

Highlights of the day: Views of Tuscan towns and countryside , the Montepulciano wine area and Lake Trasimeno, the largest lake of the Peninsula

– Special Event of the day: Fantastic undulating ride with final climb to Cortona with vistas on Lake Trasimeno and Chiana. A glass of local wine in the Wine bar on Cortona’s Corso

Day 6: CORTONA – SANSEPOLCRO

Highlights of the day: Views of the Northern Umbria woodlands and rural areas, easy riding in the Tiber river Valley surrounded by the Apennine Mountains.

Ride details: level: MODERATE –approx 70 km starting from the very beginning with the only climb of the day

– Special Event of the day: Do not miss the frescoes by Piero della Francesca in Sansepolcro

Day 7: Ciao Ciao!

End of tour after breakfast. Departure: Bus available to reach Arezzo train station connected to Rome, Milan and Florence.

Taxi transfer from Sansepolcro available.

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Cycling Tours & Bike Trips in Italy

Cycle past UNESCO houses in the quaint towns of Puglia , verdant vineyards in the renowned Chianti region, or through the famously historic streets of Tuscany . Explore the charming laid-back Italian way of living and ride through landscapes of olive orchards, limestone cliffs, crystal waters and Baroque towns. Escape to a storybook land where cycling trails lead to quaint towns, marble mountains and Mediterranean shores on a cycling tour of Italy .

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229 italy bicycle tours with 289 reviews.

Cycle Tuscany

The bikes were good,routes good however a few involved heavy traffic. Heavy rain requires some rescheduling

• Food & Culinary

A Fantastic Journey- Tuscany Small Group Bike Tour

This tour exceeded my expectations, on so many levels. The riding was wonderful, the countryside was glorious, the food was outstanding....but the attention to detail, from guides Luca and Rikki, was just phenomenal. If you want to tour Tuscany by bike, in a way that make you feel totally connected to the area, book this trip! It will not disappoint!

Cycling Puglia & Matera

Highly recommend. Unique tour of Puglia, we really enjoyed all aspects of the tour. Region is spectacular and full of surprises. Christina was an excellent skilled cyclist and knowledgeable guide. She was very generous with her time, considerate and friendly. Support driver provided excellent back-up, organising our luggage, snacks etc.

• Self-Guided Cycling

Pisa - Cinque Terre

A great cycling vacation! The individual stages were well chosen (route, length, landscape, hotels) and the navigation has largely worked very well. With the slopes, especially in the heat, a good condition or possibly an e-bike is required.

Women's Adventures

Cycle Cilento & the Amalfi Coast

A bit clumsy in booking details as Exodus did not want us to contact them directly, so all matters had to go through Tour Radar. The trip itself went well - a very attentive tour guide 'Alex' made it even better.

Tuscany Hills and Sea-Luxury/ Small Group Bike Tour

This was such an amazing trip .... I would highly recommend Luca's hosting. Everything was top notch including organization, equipment, safety on the road, hotels, meals ... etc, etc. I will most certainly be returning for another tour.

Veneto Bike & Boat

From beautiful Venice, we cycled on a couple of Venice's outer islands then along the Po to lovely Mantova, and stayed aboard a super comfortable barge. With a mixed group of nationalities, 2 great guides and amiable crew, comfortable bikes and delicious food on board, this was a great experience. I'm not really a cyclist so was a bit nervous, but there was no need as the route is flat. I'm also not usually a group trip type of person, but really enjoyed the experience.

Cycle Dolomites, Lake Garda and Venice

A most enjoyable trip. There were 7 in the group plus Fabio which was the perfect group size. Very sociable and good fun.

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

• Sightseeing

Cycle Puglia

We loved it i! It was an amazing experience. Make sure to get e-bikes. It's not that easy. A great adventure with memories that will last you a lifetime ! Puglia is beautiful region of Italy! Cycling gives you the authentic local nature cultural and environmental feel of the land and it's people!

• Wine tasting

Piedmont Round Trip

Coastline and Culture of Italy’s Heel: Apulia cat. B

A taste of Sicily

Coastline and Culture of Italy’s Heel: Apulia cat. A

Emilia Romagna's Culinary Delights

Fantastic tour, even for the novice cyclist! We didn't start riding bikes until 3 months before the tour started and we had NO trouble keeping up with the daily mileage. The guides on our tour were awesome and made the entire experience a lot of fun and very informative. The food everywhere was AMAZING!!! Hotel accommodations were first class and included a breakfast that would put anything in the USA to shame! We had fresh chocolate croissants every morning! Gorgeous countryside, and even the other people on the tour were a lot of fun and everyone got along wonderfully. Very, very worth it, even if you've never cycled before. Don't miss this experience!

Italy Bike Tour Reviews

Trip of a lifetime. Could not have been any better. Would recommend to others.

The bike tour was fabulous - the itinery covered many interesting towns, great scenery from contry to ocean, much variation and it was never too hard.

Bicycle Tours

• Self-Guided Cycling (61)
• Road Cycling (7)

Regions in Italy

• Northern Italy (98)
• South Italy (59)
• Central Italy (42)
• Italian Alps (41)
• Puglia (34)
• Prosecco (34)
• Apulia (33)
• Tuscany (31)
• Trentino Alto-Adige (27)
• Sicily (22)
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• The Dolomites (16)
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• Sardinia (8)

Travel Styles

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• 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?

•  +39 3288264014
•   [email protected]

Love for the Terre di Siena and Tuscany create the bike tour operator Anima Toscana.

Gran Fondo Strade Bianche 2024

The strade bianche weekend is a celebration of early-season cycling on the white roads around historic sie, march 1 - 4.

Accommodation

Price 4* Hotel

Willier Disc Ultegra

Gravel Bike - Topstone Cannondale

Gran Fondo 2024

Sunday, March 3

From: € 835

Description

• Cost & Book

Gran Fondo Strade Bianche 2024 from March 1 until March 4 Pro Race Saturday, March 2 – Gran Fondo Event date Sunday, March 3 For private groups of 5 persons or more only please send us an email ([email protected])

Only need a bike for GF Strade Bianche 2024? BOOK HERE

Check also the VIP Packages for 2024 – STRADE BIANCHE VIP 2024

Experience the GF Strade Bianche 2024!

GF Strade Bianche 2024 is one of Italy’s new cycling Gran Fondo. It combines the beauty of Siena (a UNESCO World Heritage site) together with the splendid hills of Tuscany. Enjoy the professional organization and the friendly and relaxing atmosphere of the Strade Bianche.

The route of the Strade Bianche leads you through the most charming places in Tuscany. Starting from the city of Siena, you’ll cycle to Montalcino through charming villages in the countryside and over a few gravel roads. From the historic town of Montalcino, you go up to the ski area of Val d’ Arabia also known as Rapolano. From here you continue your way back to the city of Siena. The finish line is at Piazza del Campo, where a huge crowd welcomes the arrival of all participants.

Stay with us in beautiful Tuscany and enjoy the medieval city of Siena. The Strade Bianche weekend is a celebration of early-season cycling on the white roads around historic Siena. The southernmost northern classic has only been in existence since 2007 but it has already established itself as a ‘must see’ and a ‘must do’ event.

Need a bike anywhere else in Tuscany? Check TUSCANY BIKE RENTALS

There are two different course lengths

• Gran Fondo: 142,5 Km, 54,7 km of gravel roads, altitude gain of 2,250 m, gravel altitude gain of 1,285 m
• Medio Fondo: 86,8 Km, 21.6 km of gravel roads, altitude gain of 1,350 m, gravel altitude gain of 545 m

Cycle and Watch the Gran Fondo Strade Bianche!

• 3 nights in 4* hotel in Siena
• The finish line at Piazza del Campo, where a huge crowd welcomes you
• Cycling through medieval villages and spectacular landscapes that’s Tuscany!
• The GF Strade Bianche subscription
• Breakfasts, evening meals, and hotel taxes
• Guided ride on Strade Bianche day with Andrea
• The beauty of Siena (a UNESCO world heritage site)
• Private feed station on the route

• If you plan to fly your luggage, and your bike will be transported from Pisa and Florence airport at set times. The journey to Siena takes approximately 1hr30 - 2 hours.
• Transfer 1 at 12.00 > Depart Pisa Airport at 12.00, so please book a flight that lands in Pisa before 11.00. Collect riders from Florence Airport at 13.00, so please book a flight that lands in Florence before 12.00. You will arrive at our hotel in Siena around 14.15.
• Transfer 2 at 18.00 > Depart Pisa Airport at 18.00, so please book a flight that lands in Pisa before 17.00. Collect riders from Florence Airport at 19.00, so please book a flight that lands in Florence before 18.00. Arrive at our hotel in Siena around 20.15.
• You can bring your own bike to transport bike boxes on airport transfers. Alternatively, you can rent a bike with us for the weekend. You are allowed to store it in your room.
• The mechanic will be available this afternoon at the hotel to assist you with fitting your rental bike or building your own bike after travel.
• The Strade Bianche sets up a limited number of areas located on the course within the final portion of the stage for special access called Club Truck. Guests of the Club will arrive at the finish a little before the cyclist and will have access to the Club Truck, reserved for the top stars and located in a privileged area near the finish line. The Truck will offer snack/coffee bar service, and TV screens will broadcast the final kilometers of the race until the riders come into view.
• The race largely shares the course with the Women's Elite event. The route is twisty and undulating, with no lengthy climbs, but with punchy hills, especially on the unpaved parts. Newly added to the route is the most popular and most challenging sector of Monte Sante Marie, named after Fabian Cancellara, with gradients exceeding 15% on both climbs and descents. There are roughly 55 km of gravel roads (38.4% of the total race route) appearing in 10 sectors (some of which are “new” to both the women’s and men’s Pro race), with a roadbed in good conditions, well-packed ground with no grass invasion, and a little gravel on the surface.
• The final kilometres initially follow the outskirts of the city of Siena, along wide, long and straight roads connected by sweeping curves, first descending, and then climbing slightly, up to 2 km from the finish, where the route takes the Via Esterna di Fontebranda, and the gradient reaches 9%. The road surface becomes paving slabs 900 m before the finish line, just past the Fontebranda Gate. The gradient is over 10%, peaking out at 16% in Via Santa Caterina, around 500 m from the finish. A sharp right-hand turn leads to Via Delle Terme and then to Via Banchi di Sotto. Starting 300 m to the finish, the road is a slight, continuous descent. With 150 m to go, a right curve leads into Via Rinaldini. The route enters Piazza del Campo 70 m before the finish; the last 30 metres are on a 7% gradient descent, while the finish line is on a level road.
• This afternoon and early evening the team will assist you with re-packing your bikes ahead of travel
• Dinner at hotel
• MEDICAL CERTIFICATE Additionally, all riders taking the Day Licence must have a Medical Sports Certificate which was issued within 6 months of the event and must be presented at race registration. This should state: 'The data of the athlete' the indication of the sport for which it required the visit to the doctor: CYCLING the statement of the sports doctor that THE ATHLETE, ON THE BASE OF MEDICAL CONTROL, DOES NOT HAVE CONTRAINDICATIONS
• Florence International Airport is named after one of the most famous Italians: Amerigo Vespucci. There is no train connection from the airport to the city. From Florence railway station there are good connections to all kinds of cities in Italy. The airport lies only 4 kilometers away from Florence. Shuttle buses leave every 30 minutes. Florence airport is only 80 kilometers away from the airport of Pisa, Galileo Galilei.
• Pisa Airport lies directly on the highway Florence-Pisa-Livorno. The airport is close to the city a ride to the center of Pisa does not take more than ten minutes. There are good connections to all kinds of cities in Italy. The airport lies only 4 kilometers away from Florence.

Cost & Book

Booking information.

• All prices are based on double rooms
• For bookings and inquiries contact us at [email protected]

Extra Information

• Fill out and submit the online booking request or send an email to [email protected]
• We tend and try to send all over within 48 hours.
• Please do not make travel plans until you receive our confirmation.
• Please be advised that we make every effort to ensure that all the information given on this site is accurate. All statements and information have been researched and supplied by third parties.
• The information given is accurate and reliable, to the best of our knowledge. Should errors be found, we will rectify them as quickly as possible. However, we accept no responsibility for errors or inaccuracies.
• 3 nights at the 4* hotel Executive in Siena near the start and the finish of the Gran Fondo and the Pro Race
• The bike stored in your room
• Bike mechanic
• Guided ride on Strade Bianche day with Andre
• Detailed Itinerary
• ABTA protected

Not Included

• Airport transfers - Pisa and Florence Airport RETURN transfer service BOTH WAYS €140
• Strade Bianche Entry front grid € 200
• Strade Bianche Entry pen 3 € 155
• Strade Bianche Entry pen 4 € 130
• Willier Carbon Disc €210
• Gravel Bike Cannondale €240
• VIP Start Village hospitality for Non-Riders
• PRO RACE A DAY IN AN OFFICIAL CAR EXPERIENCE 1045 euro
• PRO RACE START AND FINISH EXPERIENCE 300
• PRO RACE START AREA EXPERIENCE 105
• PRO RACE FINISH LINE EXPERIENCE 210

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