3 day cruises from portland maine

Specialty Cruises

Whether you have all day or just a couple of hours, the best way to see Casco Bay is from the deck of one of our ferries! Most people know us as Portland’s iconic ferry system transporting people to and from the islands. But if you’re just looking to get out on the water, Casco Bay Lines offers a variety of specialty cruises with different destinations, durations, and departure times.

We make it easy to cruise the bay—just pick your cruise from the list below, pack a bag with refreshments of your choosing, sunscreen, and an extra layer, grab your ticket at our terminal located on the Maine State Pier, and come aboard!

Click on any of the cruises below for schedule are fare information. Trip times vary based upon route and cargo volume.

• Mailboat Run

Duration: 2.5-3.5 hours (roundtrip)

Hop on the Mailboat! The locals’ favorite way to experience Casco Bay – this true working boat carries passengers, mail and freight to Little Diamond, Great Diamond, Long, Cliff and Chebeague Islands. Year-round availability.

Narration provided with 10 or more cruise passengers.

• Diamond Pass Run

Duration: 1.75-2 hours (roundtrip)

Take this scenic cruise of the Inner Bay past island cottages on the shorelines of Little and Great Diamond Island and Peaks Island. Catch a glimpse of island life as we travel to four different stops. Seasonal availability.

Duration: 2.5-2.75 hours (roundtrip)

Portland shimmers in the distance as you enjoy your picnic spread and relax in the twilight of a perfect Maine day. Year-round availability.

• Sunrise Run

Duration: 2-2.5 hours (roundtrip)

Pack a thermos and join our crew, the sea birds, local lobstermen and the occasional seal as they all begin another day on Maine’s Casco Bay. Year-round availability.

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Portland, ME

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Walk Maine’s largest city and follow in the footsteps of your fellow seafarers, past and present, on a Carnival cruise to Portland. Perched on green bluffs overlooking Casco Bay, Portland is a place where lobstermen still ply the briny Maine seas and wooden fishing boats chug through the harbor. Portland cruises pull into a modern-day seaport of sleek high-rises towering over a revitalized Old Port area, alive with brewpubs, restaurants, and shops.

• Meander the colorful streets of Old Port, or see a slice of 19th-century life in the Victoria Mansion.
• Get a panoramic view of Maine’s craggy coast from the cliff-top Portland Head Lighthouse.
• Learn why the other Portland (in Oregon) was named for this east coast original.
• Stroll the Eastern Promenade Pathway above bustling Casco Bay.

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Portland ME (Maine)

Cruise port schedule, live map, terminals, news.

Region East Coast USA and Canada New England

Local Time 2024-04-19 05:28

Port Portland ME cruise ship schedule shows timetable calendars of all arrival and departure dates by month. The port's schedule lists all ships (in links) with cruises going to or leaving from Portland ME, Maine. To see the full itineraries (ports of call dates and arrival / departure times) and their lowest rates – just follow the corresponding ship-link.

Portland is Maine's second largest cruise port - following Bar Harbor . This port city is located on a peninsula (Maine USA's east coast) and north of Boston MA . On the West Coast USA is the namesake Portland Oregon .

Portland ME features historical and architectural attractions, and is also a major commercial, shipping and fishing centre. The port is a gateway to the resort islands in Casco Bay. There's a historic trail and lighthouse in the town. The nearby Kennebunkport is also worth visiting. Its art colony and Seashore Trolley Museum display more than 200 authentic streetcars.

Established in 1632, the town was destroyed in 1676 by Indians, and again in 1690 by Indians and the French. The settlement (then part of Falmouth) was damaged by the British in 1775. In 1786, after being separated from Falmouth, it was named after Portland England .

In 2015, the visiting around 55,000 cruise tourists had an economic impact of USD 5,8 million. In 2016, the cruise port handled 70 ship calls. In August 2016, the port had its ever largest cruise ship docked -  RCI' s  Anthem of the Seas , bringing to the city 4974 passengers and 1480 crew. Cruising season 2016's economic impact was USD 11 million.

In 2017, the port reported a record year as the number of visiting cruise passengers for the first time ever exceeded 100,000. Port's statistics showed a 6% increase in passenger volumes and a 10% increase in crew numbers over 2016. In 2018, the port handled total 32 ship calls (23% over 2017) and around 39,000 passengers. For season 2019 were booked 40 berths.

On March 16, 2018, was announced a plan to fund the USD 2 million ferry terminal's upgrade project. The Ocean Gateway terminal serves all ferries connecting Maine USA with Nova Scotia (NS Canada). The primary funding party will be the Canadian company Bay Ferries Ltd (headquartered in Charlottetown, Prince Edward Island ), which together with the NS government would pay for most of the upgrades. The decision was made after the US Customs and Border Protection (CBP) agency threatened to close the terminal's customs service as it didn't meet USA's federal standards. Bay Ferries is a subsidiary of Northumberland Ferries Ltd (parent NFL Holdings Ltd) and is subsidized by the NS taxpayers.

Portland ME cruise terminal

Cruise ships in Portland ME dock at Portland Ocean Terminal. Following the berth extension and dredging project (completed in April 2017), now the port can dock ships with LOA length 340 m (1115 ft) and max draft 11 m (36 ft). Port's total berthing space is around 2000 m (6560 ft).

The city is linked by  ferries  with Nova Scotia. In November 2017, the ferry service from Ocean Gateway terminal was terminated after US Customs required a terminal renovation (around USD 7 million in upgrades) in order the passenger facility to meet federal standards. The ferry service Maine - Nova Scotia will start again only if Portland provides USD 2 million for the project.

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Portland, Maine, US

Squint your eyes and admit it: Doesn’t that skinny, bearded hipster walking down the cobbled street look a lot like a 19th-century sea captain heading to the wharf to check his ship? Modern Portland, first settled in 1633, carries the marks of both subsets of Mainers. The restored brick buildings and warehouses of the Old Port and the fine upright houses of prosperous captains, merchants and shipbuilders make the city’s past a living part of its present. And the waterfront is a going concern, not a museum: Fishing boats chug into and out of their berths, buoys clang, harbor seals bark. Those shop windows aren’t displaying hardtack, rope or hand salve, though. Juice joints, art galleries, bookstores (and comic-book stores!), worshipful temples to coffee, locavore bistros with national press, bespoke menswear designers and gelato shops all jostle for attention. Don’t limit your visit to the Old Port, though. Wander through the terrific art museum or take a tour of one of the city’s historic homes. Jump on a ferry or whale-watching boat and get out into the busy harbor. Head to the coast—craggy, windswept, dramatic—a glorious and undeniably New England panorama. Get out and take it all in. Welcome to Vacationland.

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Cruise to Portland, Maine

Portland shore excursions, amazing experiences coming soon., sorry, there are no excursions for this port at this moment., things to do in portland.

Lighthouse Tour

A close up view of the Portland Head lighthouse

Situated on the ocean, in the heart of Casco Bay, the Portland area is home to six lighthouses, all within 20 minutes of the city center. The Portland Head Light at Fort Williams Park is the most iconic. Walk the paved oceanside trail afterward for views of the ocean.

Indulge Your Taste Buds

Homemade fritters topped with sugar

Portland put Maine on the culinary map. The food scene is full of creativity and flavor, with dishes can be as local or as international as you'd like. Enjoy the catch of the day at Portland Lobster Company. If it's sweets you're craving, head to The Holy Donut. For a twist on New England cuisine, check out EVO Kitchen + Bar. Finish with a nightcap at Blyth and Burrows.

Breweries by Bicycle

Pedal along the ocean as you sip local brews and learn all about the city's rich history — and its equally rich beer culture during your cruise to Portland. With over 25 microbreweries in Portland, there are beers here for every palette.

Local Cuisine

In just the last five years, the food scene in Portland has blossomed into one of the country's best. From historic pubs to nationally recognized restaurants, the food and drink here doesn't disappoint. Many of the best eateries are just outside the Old Port on Middle Street: Head there for oysters at Eventide (get there early on the weekends) or Belgian fries and paninis at Duckfat.

No matter what trinket you want to bring back from Maine, you can find it in downtown Portland during your cruise. Local and national stores alike line the cobblestone streets of Portland. The Old Port is where you'll find the most distinctive shops; head there for boutique and high-end fashions, home goods and souvenirs.

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Cruises to Portland, Maine

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Portland, Maine Cruise Port Guide

Explore one of the prettiest coastal towns on the East Coast on a cruise to Portland, Maine. Perched on a peninsula jutting out into the island-specked Casco Bay under vast skies, the scent of the ocean on the breeze, this enchanting spot is rich in history. Having been a fishing and trading port since 1632, Portland is defined by its impressive lighthouses, not least Portland Head Light.

Downtown, you’ll find an old-fashioned ambiance in the cobblestone lanes, old brick buildings, and 19th-century warehouses, as well as a creative, arty community served by some excellent museums. There are fabulous restaurants, too; on your New England cruise , sampling the sweet lobster for which the city is famed is a must.

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Top sights & attractions on cruises to portland, maine, the portland head light.

New England is known for its picturesque lighthouses. The Portland Head Light is one of the most famous, having stood on the lonely, rocky peninsula of Fort Williams Park since 1791. Visit the museum in the former Keeper’s Quarters to learn about the history of the light and see displays of navigational aids and old photographs. After your tour, you can hike the coastal trails in the park, taking in magnificent views as waves pound the rocks.

Portland Observatory Museum

The Portland Observatory Museum is the last remaining maritime signal tower in the U.S. and is a National Historic Landmark. The seven-story tower was built in 1807 on Munjoy Hill. Today, it serves as a museum where you can learn about the evolution of Portland and its role in maritime history. You’ll also enjoy magnificent views down over the city and harbor, as well as Casco Bay, dotted with islands.

The Wadsworth-Longfellow House & Longfellow Garden

The Wadsworth-Longfellow House is famous for being the oldest standing structure on the Portland peninsula as well as being the childhood home of the American poet Henry Wadsworth Longfellow. The house was built in 1785, and its interiors are rich with furniture and art from the 18th and 19th centuries. Join a tour to learn more about Longfellow and the impact he had on the New England political and literary scene.

Learn More About Portland Shore Excursions

Things to do in portland, maine, visit the portland museum of art.

Founded in 1882, the Portland Museum of Art is the oldest and largest public art institution in Maine. It provides visitors with a look into the regional art culture and aesthetic of Maine in addition to its permanent collection of American, European, Asian, and contemporary pieces. Admire works by Georgia O’Keefe, Vincent Van Gogh, Andy Warhol, and Claude Monet. One of the most famous paintings housed in the museum is Monet’s Water Lilies, painted in 1914 and one of a priceless series.

Cycle the Eastern Promenade Trail

Join a guided cycle ride along Portland’s beautiful Eastern Promenade Trail, with wonderful views of the beaches and rocky shoreline. You’ll pass Bug Light, the smallest coastal lighthouse in the U.S., and take in views of Casco Bay and Fort Georges. Cycle tours also visit Mackworth Island, encircled by a walking trail that leads through stands of pine and spruce, with tantalizing views of the sea.

Explore Kennebunkport Village

The quaint fishing village of Kennebunkport, its streets lined with handsome Victorian mansions,  is famed as the summer home of the Bush family. The town also attracts celebrities all summer long who come for the art scene, the quirky shops, the farm-to-table restaurants, and endless, sweeping sandy beaches. Come here on a day trip and, after browsing the downtown area, jump on a boat for a scenic cruise of the wild, rocky shores, with a chance to peek at Walker’s Point, the Bush estate.

Top Food & Drink in Portland, Maine

Portland, Maine is known for two culinary treats—fresh lobster and craft beer—although the city’s highly-rated food scene extends far beyond these two. As well as beer, you can try locally produced mead and cider, as well as wines from Maine’s own vineyards. You’ll also find classy coffee roasteries, mouth-watering bakeries, and traditional pubs that reflect the town’s strong Irish heritage. 

Look out for seafood of all kinds on the menus, like lobster, oysters, delicious chowders, and fresh fish straight from the Atlantic. Farm-to-table produce is abundant here, too. Dine in a waterfront restaurant, or wander the streets and wharves around the Old Port and take your pick. Portland is famed for its food trucks, too, which offer anything from artisan gelato to gourmet donuts.

Culture & History of Portland, Maine

Portland’s history has long been tied to the sea. The long peninsula on which it’s located was called Machigonne (“Great Neck”) by the Native Americans who first lived here. When the British began building colonies in America, they also found the peninsula to be an alluring piece of land and established it as a trading and fishing settlement in 1632.

Originally called Casco and then Falmouth by the British, the name was changed after the Revolutionary War to Portland. The city continued to grow as a commercial port and shipping center. When Maine became a state in 1820, Portland served as the state’s first capital until 1832, when it was switched to more centrally located Augusta.

Portland, Maine Cruise Port Facilities & Location

Portland has two terminals: the Portland Ocean Terminal (also referred to as the Maine State Pier) and the Ocean Gateway Terminal. The two terminals are located just a few blocks apart adjacent to Commercial Street. Larger cruise ships will dock at the Portland Ocean Terminal.

From the cruise terminals, you’re within walking distance to downtown Portland and all its popular neighborhoods, including the Old Port shopping district and the Arts District. There’s a tourist information center at the terminal and in summer, a free guiding service from Downtown District Guides.

Transportation in Portland, Maine

Taxis wait outside the cruise terminal, and rideshare services operate in the city. You can explore beautiful Casco Bay on the local ferry service, Casco Bay Lines; ferries depart from their own terminal, around 15 minutes’ walk from where cruise ships dock.

Portland also has a Metro bus system that operates within the Greater Portland area and has a service to Freeport. You can rent a car downtown. A highly enjoyable way to get around is on two wheels, with bike rentals available close to the port.

Shopping in Portland, Maine

The city’s Arts District is full of galleries and antique shops, while the Old Port area has everything from clothing boutiques to homewares. Items to look out for include foodie gifts such as chocolate and spicy sauces, upcycled bags and purses, nautical memorabilia, artisan candles and soaps, ceramics, jewelry, tasteful homeware, and local fashion.

Local Currency & Tipping Customs

Portland and the rest of Maine use the U.S. dollar, and there are numerous ATMs located around the city. Credit cards are accepted in most places, although you should check when hailing a taxi whether they take cash or card. Tipping is customary in the USA, with 15% to 20% of the total bill or fare being the norm.

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Maine Coast and Harbors Cruise

At a glance.

On this 8-day Maine Coast and Harbors Cruise sailing round-trip from Portland, ME aboard the 100-passenger ships, travel to charming ports famous for their shipbuilding, as well as to beautiful national parks with magnificent views and abundant wildlife. Explore quaint historic districts and charming villages, and dine on the freshest, locally sourced seafood prepared by our team of master chefs.

Maine is home to one of most spectacular coastlines in the country, set against a backdrop of a stunning national park with majestic mountains that reach up to the sky and native wildlife that embellishes the landscape. On this enchanting journey, discover the rich maritime heritage that leads you past the magnificent homes of sea captains and through a dynamic working waterfront. Admire the classic schooners of Camden Harbor and stroll through the picturesque gardens of Boothbay Harbor.

Experience the preparing and unveiling of a traditional, old-fashioned lobsterbake luncheon on the shores of Rockland, serenaded by a local blue grass band. Savor delicious clams, mussels, and buttery corn as you enjoy the picturesque New England landscapes.

In the evening, delight in the company of guests and crew as you return to your home away from home. Relax in comfort and admire the view as your small ship winds through scenic rivers, sparkling bays, and historic harbors.

Maine Coast and Harbors Cruise Details

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Pre-Cruise: Pre-Cruise Premium Package

American Cruise Lines custom Pre-Cruise Package provides you with a seamless way to experience Portland and easily board the ship. Arrive the day before your cruise and American Cruise Lines will handle the rest. The package includes a 1 night stay at the Marriott Residence, located in the heart of downtown and steps away from the dock.

Pre-Cruise Packages must be reserved at least 30 days before your cruise date.

Day 1: Portland, ME

Portland is a region that perfectly blends the present with the past. The Old Port waterfront is made up of working fishing wharves and converted warehouses that now host a variety of eclectic restaurants and shops.

Begin your adventure with a calm afternoon on the sun deck looking for whales and enjoying the stunning natural beauty of Maine’s rugged coast. Cape Elizabeth marks the entrance to the Portland Harbor where you can witness spectacular views as you start your journey with us.

Day 2: Bar Harbor, ME

The natural beauty that surrounds Bar Harbor is accented with ocean cliffs, glacier‐formed lakes and valleys, stunning mountain vistas, and pine forest. This beauty has been captured in the works of Thomas Cole, Frederic Edwin Church, and many other great artists.

Lobstering is a centuries‐old industry that continues to thrive in Bar Harbor as well as boat building, another traditional business that is an important part of the economy. Though Bar Harbor region is best known for its outdoor activities, it is also home to small museums, cultural attractions, and historically significant landmarks.

Day 3: Bucksport, ME

Explore the historic seaport town of Bucksport, with a beautiful waterfront ornamented with scenic gardens and reflective fountains. Bucksport was a central hub for paper-making industry once upon a time. Though, the town’s paper mill closed in 2014, it now serves as a training center for the Maine Maritime Academy.

The town is also particularly well-known for the Penobscot River and the iconic Penobscot Narrows Bridge and Observatory, which is taller than the Statue of Liberty. From this vantage point, view spectacular 360-degree views of the Bay, the Maine countryside, and the distant western mountains.

Day 4: Camden, ME

Full of classic schooners, this charming village is considered the “Tall Ship Capital of Maine.” Enjoy the warm summer sun and refreshing sea breezes as you relax and watch beautiful ships sail into the harbor. Walk Camden’s streets lined with shops and art galleries. Bring your camera to capture sweeping ocean vistas, placid coastlines, and panoramic views of Camden, Penobscot Bay, and the surrounding islands from atop Mount Battie.

Day 5: Rockland, ME

Rockland is an exciting town with a vibrant art culture and thriving lobster industry. Spend your time touring one of Rockland’s unique museums, including the Owls Head Transportation Museum and the Farnsworth Art Museum. Explore downtown Rockland which features an eclectic collection of art galleries or relax on a park bench and watch classic schooners sail through the harbor.

Day 6: Boothbay Harbor, ME

Known as the “Boating Capital of New England,” Boothbay Harbor overflows with fishing vessels and pleasure crafts in equal numbers. Walk along Boothbay Harbor’s flower-lined streets, dotted with art galleries, antique stores, and specialty shops. Don’t forget to visit the famous Coastal Maine Botanical Gardens.

Day 7: Bath, ME

Long known as the “City of Ships,” Bath finds its identity in shipbuilding. From its architecture and cultural offerings to its urban downtown, Bath’s shipbuilding roots define its character. Walk Bath’s streets and admire the seaport’s tree-lined avenues, graced with classic examples of American architecture. Or explore the nationally acclaimed Maine Maritime Museum, which offers a variety of exhibits about Maine’s nautical history.

Day 8: Portland, ME

After a refreshing and relaxing week of cruising Maine’s coast and harbors, end your journey where it began, in idyllic Portland. Enjoy breakfast on board, before departing the ship. You may decide to stay longer to explore this charming city, located in the heart of Casco Bay and steeped in maritime history.

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Dates and rates are effective the date the information was updated on this site. Dates and rates may have changed by the cruise line prior to an update here. Contact Sunstone Tours & Cruises for the latest dates & rates.

Prices displayed are per person based on double occupancy.

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American Eagle

At a capacity of just 100 guests, American Eagle offers the best qualities of expedition adventure cruising with the refinement, luxury, stability, and land proximity of river cruising. The design of the ship allows rare access into small ports and ability to travel on almost any river or waterway in the U.S. With land never out of sight, American Eagle is a practical alternative to ocean expeditions, allowing for more time to explore each port in depth.

American Eagle Details …

American Glory

The 100-guest American Glory blends the best qualities of expedition adventure cruising with the refinement, luxury, stability, and land proximity of river cruising. Observation and sitting areas will be available at the bow, while a unique Swim/Activity Platform at the stern of the ship features a tender for local exploration. The shallow draft of the vessels allows rare access into small ports and ability to travel on almost any river or waterway.

American Glory Details …

American Independence

The 100-passenger American Independence is owned and operated by American Cruise Lines and sails overnight coastal, river, and inland waterways within the continental United States.

American Independence Details …

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New England Wanderlust

Maine  ·  August 3, 2022

15 Awesome Day Trips From Portland, Maine (2024)

Portland is a wonderful city in its own right, but it’s also centrally-located to some other amazing places. If you live in Portland or are new to the city, and are looking to get out and explore more of the region, or if you’re planning a longer stay and are wondering what your options are for day trips from Portland, Maine, this post is all about the absolute best options to give you plenty of ideas.

Even with just a day trip from Portland, you’ll be able to see some incredible coastal landscapes and lighthouses, go on some awesome tours, eat some delicious food and feel like you had a true vacation while only being gone a day. Having travelled all over Maine for over 10 years , I’ve seen so much of what the Pine Tree State has to offer, and I’ve scouted out the places that are worth your time!

With that, let’s jump into my favorite day trips from Portland, Maine!

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Best Day Trips From Portland, Maine (2022)

Below is a list of my favorite day trips from Portland, Maine, and the destinations are organized by shortest to furthest distance from Portland. Most day trips from Portland, Maine on this list are less than 2 hours away, with the longest being 2 hours and 30 minutes away. And be sure to keep reading below for bonus seasonal suggestions, as to find out if a day trip from Portland to Acadia is worth it!

1. Kennebunkport, ME

Distance From Portland: 40 minutes

The easiest, and also one of the best day trips from Portland, Maine is Kennebunkport. I love Kennebunkport because there’s so much to do, but it’s also a small town that’s easily manageable for a day trip. It’s packed with tons of charm, has some great beaches, awesome shops and restaurants and feels like a true escape from city life in Portland.

Some of the best things to do on a Kennebunkport day trip from Portland:

• Explore the shops & restaurants along Dock Square.
• Go for a swim or walk on the shoreline of Gooch’s, Mothers or Colony Beach.
• Take a drive on Ocean Avenue.
• Get a lobster roll at The Clam Shack.
• Walk along the coast of Cape Arundel on the Parson’s Way Trail.

A really great tour option in Kennebunkport if you’re a foodie is a culinary walking tour . Each tour is different based on the season, but it lasts for 2.5 hours, and you’ll get the inside scoop from a local on all the best foods to eat in town. They’ll take you to some off-the-beaten path places, and you’ll meet with food artisans to sample locally-caught lobster, chowder, Maine whoopie pies, the absolute best ice cream in town, and so much more. For everything you get with this tour, I think the cost is very reasonable!

Click here to book your Culinary Walking Tour in Kennebunkport!

2. Ogunquit, ME

Distance From Portland: 1 hour

Ogunquit is another one of the best options for day trips from Portland, Maine. It’s very close to Kennebunkport, and you can definitely do both in one day if you’re feeling up for it (although, there’s so much to do in each town that you can easily fill up a full day in each place).

Ogunquit is best known for having one of the longest stretches of sandy shoreline in all of Maine, so if you’re looking for a beach day without having to go far, this is one of the best places for that in Maine. Ogunquit’s town is also very quaint and easily walkable, and packed with adorable shops and great restaurants.

Some of the best things to do in Ogunquit on a day trip from Portland:

• Walk from Ogunquit’s town to Perkins Cove along Marginal Way for one of the most scenic walks in Southern Maine! Perkins Cove has its own town little town, so be sure to budget time to explore it.
• Visit the shops and restaurants downtown.
• Walk along the shoreline of Ogunquit Beach.

Bonus Suggestion : From Ogunquit, it’s also very easy to see Nubble Lighthouse on Cape Neddick, which is only about 20 minutes away, and is worth the excursion. Also close to York, which is home to some more beautiful scenery and the Stonewall Kitchen flagship store, this lighthouse lives on its own little island, and there’s a park that offers a fantastic view of the lighthouse for a gorgeous photo opportunity!

Psst! I have an entire post on things to do in Ogunquit if you need more ideas!

3. Portsmouth, NH

Portsmouth is a lovely little coastal town in New Hampshire that’s just over the Maine border, and only a short drive from Portland. Portsmouth’s downtown is so charming, and has a lot of really great shops, restaurants, cafes and breweries, as well as waterfront walkways, and even a small little lighthouse just outside of town. For all these reasons, it’s one of the best day trips from Portland, Maine.

Some of the best things to do in Portsmouth, NH on a day trip from Portland:

• Taste the local beer at these awesome breweries: Portsmouth Brewery , Loaded Question Brewing and Great Rhythm Brewing .
• Visit the cute shops in Market Square. Two of my favorites are Jane Gee for natural skin and body care products, and Sault New England for East-coast inspired clothing.
• Get some sweet treats at Elephantine Bakery .
• Stroll through Prescott Park.

If you’re looking to see as much of Portsmouth as you can, as well as take in some of the best water views, I recommend checking out this bike tour through town and the local islands . This is a guided tour that last about two hours, and is a casual cruise around town, as well as the surrounding islands. Led by a local expert, you’ll hear stories about the town’s history, as well as be able to stop for some awesome photo opportunities.

Click here to check out this bike tour in Portsmouth!

4. Boothbay Harbor, ME

Distance From Portland: 1 hour and 10 minutes.

One of my favorite small waterfront towns in all of Maine is Boothbay Harbor, and this makes for one of the best day trips from Portland, Maine. Even though it’s such a short drive away, you’ll definitely feel like you’re in a different world. Between the charming downtown, beautiful waterfront restaurants and amazing opportunities to tour the waters and see wildlife, you’re sure to have a great day in Boothbay Harbor.

Some of the best things to do in Boothbay Harbor on a day trip from Portland:

• Walk the streets of downtown to visit the shops and eateries.
• Cross the footbridge for views of town and the water.
• Head out onto the water for a wildlife and lighthouse tour (see my suggestions below!).
• Have an awesome waterfront lunch or dinner at Boathouse Bistro .
• Get an ice cream from Downeast Ice Cream Factory .

If you come to Boothbay Harbor for your day trip, I highly suggest you consider a boat tour. There are so many options in Boothbay, and the views are incredible. My favorite boat tours in Boothbay are the wildlife and lighthouse tours.

A great tour option for your day trip from Portland, Maine is the Lighthouses, Lobsters & Seals Tour . For the price, I think this tour offers a lot a fun and spectacular views. During this tour, you’ll pass by two lighthouses, spot seals lounging on the rocks, and also learn all about the local lobstering community, as well as what it takes to haul lobster traps. And with packing all that into only 1.5 hours, it allows you spend the rest of your day trip exploring the town.

Click here to check out the Lighthouses, Lobsters & Seals tour in Boothbay Harbor!

Another great option if you love lighthouses is this cruise along Kennebec River , where you’ll get to see 7 lighthouses, and also learn about the local maritimes and ship-building history. Tour guides will also help you spot shore birds and other wildlife during the cruise.

Click here to check out the Kennebec River Cruise!

Lastly, definitely consider this Puffin Tour during your day trip to Boothbay Harbor. This tour is about 2.5 hours, and takes you out to Eastern Egg Rock to see a puffin colony. During the tour, you’ll pass by lighthouses and gorgeous scenery, and the you’ll be guided by a member of the National Audubon Society to learn all about the puffins and other shore birds.

Click here to check out the Puffin Tour in Boothbay Harbor!

Psst! I have en entire post on fun things to do in Boothbay Harbor , which includes more tips for your puffin tour, so be sure to check out if you need more information.

5. Newburyport, MA

Distance From Portland: 1 hour and 15 minutes

Newburyport in Massachusetts is another one of the best day trips from Portland, Maine. I love visiting this little town because it’s both a gorgeous place packed with beautiful, colonial-style homes and quaint side streets, but also has a charming downtown, a waterfront park and even the stunning Plum Island to explore. You’ll definitely be able to fill up a full day here.

Some of the best things to do in Newburyport on a day trip from Portland:

• Stroll through the shops downtown.
• Walk along the paths in the waterfront park.
• Get lost in the charming residential side streets.
• Head out onto the water (see my suggestion below!).
• Explore Plum Island and the scenic trails at Parker River National Wildlife Refuge .

A great option for a boat tour in Newburyport is this cruise through the harbor on a Yankee Clipper . There are a few different tour options available, including a narrated history tour, a Parker River National Wildlife Refuge tour, as well as a sunset cocktail cruise if you want to end your day out on the water.

Click here to check out this boat tour in Newburyport!

Psst! I have an entire post on things to do in Newburyport and Plum Island , if you’re looking for more ideas for your day trip!

6. Sebago Lake, ME

Distance From Portland: 1 hour and 20 minutes

Sebago Lake is one of the best options for day trips from Portland, Maine if you’re looking for a peaceful day. While it’s a popular destination, it doesn’t often feel super crowded, and definitely has a very chill atmosphere. There are also a good amount of of kid’s activities here, including mini golf places, and lots of opportunity to get out onto the lake.

Since Sebago Lake is the second largest lake in Maine, it covers a pretty big area, and there are a few different towns that surround the lake, which each offer really fun things to do.

Some of the best things to do in on a day trip to Sebago Lake from Portland:

• Walk around the lake on the Outer Loop Trail inside Sebago Lake State Park.
• Rent Jet Skis and head out onto the water.
• Hike the trails at Hacker’s Hill Preserve.
• Grab some snacks, Maine whoopie pies and other delicious baked goods at Gemmes General Store.
• Eat fresh lobster at Stoney Brook Lobster Pound.
• Taste the local beer at Sebago Brewing Company

One of the best ways to get out onto the lake for a peaceful afternoon is by renting kayaks and spending a few hours enjoying the views from the peaceful water. Along with your kayak rental, you’ll get a life jacket, as well as a map of the lake so you know the best areas to explore.

Click here tochecko it this Kayak Tour on Sebago Lake!

7. Conway, NH

Distance From Portland: 1 hour and 30 minutes

A great option for a day trip from Portland, Maine is Conway, NH, which is located in the White Mountains region. While this is a great destination year-round, I think it’s especially enjoyable in the fall season to really take advantage of the fall foliage views. There’s actually so much to do in Conway that you probably can’t experience it all in a day, but it definitely makes for a great day trip to get some fresh mountain air.

This is also a great destination if you’re traveling with children, as there are lots of kid-friendly activities such as the Conway Scenic Railroad, roller coaster rides at Cranmore Mountain Resort and the Kahuna Laguna Water Park.

Some of the best things to do in Conway on a day trip from Portland:

• Explore the cute downtown and visit the shops.
• Visit all the waterfalls at Diana’s Baths.
• Drive or hike up to Cathedral Ledge View Point.
• Tour the local covered bridges.
• Get some sweet treats to bring home (or eat on the drive!) at one of the town’s many bakeries.
• Have a memorable meal at Chef’s Bistro.

8. Lake Winnipesaukee, NH

Distance From Portland: 1 hour and 45 minutes

Another great destination in New Hampshire that also makes for an awesome day trip from Portland, Maine is Lake Winnipesaukee, which is also the state’s largest lake. Mostly known as a summer destination, Lake Winnipesaukee is also a very scenic fall day trip because the amazing foliage colors.

Lake Winnipesaukee is actually comprised of eight different towns, each with something unique and fun to offer.

Some of the best things to do on a Lake Winnipesaukee day trip from Portland:

• Rent a jet ski or boat to spend the day on the water.
• Go ziplining at Gunstock Mountain Resort.
• Do a little shopping for unique finds at the Old Country Store in Moultonborough.
• Enjoy a ride on the Winnipesaukee Scenic Railroad.
• Visit the mountain top mansion Castle In The Clouds for awesome mountain views.
• Feel like a kid again at Weirs Beach, and ride the roller coasters, play arcade games and go kart.
• Go beer tasting at the local breweries (there’s quite a few here!).

One of the most fun tours to take in Lake Winnipesaukee is a ride in an antique boat ! During your day trip, you’ll want to consider booking a tour on the Millie B, where you’ll get to take in the spectacular views of the region, and maybe even spot a loon or two. With each tour on Millie B, guests get free admission to the Boat Museum as well.

Click here to check availability for your vintage boat ride tour on Lake Winnipesaukee!

9. Camden, ME

A great option to consider when looking at day trips from Portland, Maine is Camden. Camden is a beautiful town along the New England coast that has a really great Main Street with shops and restaurants, a really lovely waterfront park, lots of opportunities for sailing, an amazing state park with an incredible view point, and lots of coastal charm at every turn.

Some of the best things to do in Camden on a day trip from Portland:

• Drive or hike up Mount Battie in Camden Hills State Park for an awesome view of Camden Harbor from above.
• Visit the shops and eateries downtown and along Main Street.
• Walk along the waterfront to admire the gorgeous sailboats.
• Get a lunch picnic from Camden Deli and bring it to a picnic table at the water front park.
• Stop in Owl’s Head on your way there or back to visit the lighthouse (it’s worth the extra stop!).

One of the best things to do in Camden, though, is to head out on a sailing tour . Camden has some gorgeous vessels you can climb aboard, and you’ll have the opportunity to admire the landscapes from a unique perspective out on the water. This Windjammer tour is an awesome option, and they have two types of tours: one is a day sail, and the other is a sunset sail if you want to end your day out on the water. You’ll also be able to see Mount Battie and Curtis Island Lighthouse during either sail.

Click here to check out the Windjammer Daytime Sailing Tour in Camden!

Click here to check out the Windjammer Sunset Sailing Tour in Camden!

10. Boston, MA

Distance From Portland: 2 hours

Even though you’re coming from a city, Boston is always a good idea (at least, that’s just my opinion!). Boston is one of my all-time favorite cities because of its deeply-rooted history, gorgeous architecture, amazing restaurants and charming streets. While Portland also has a lot of that, I still think Boston is one of the best day trips you can take because the two destinations are different enough to make it worth your while.

Boston can easily be done in a day, and while you won’t see it all, you’ll be able to cover a lot of ground, depending on what you’re looking to do. And definitely don’t forget to make a reservation for dinner if you’re hoping for a special meal out!

Best things to do in Boston on a day trip from Portland:

• Stroll through the Public Gardens.
• If you like to shop, be sure to hit up Newbury Street and Copely Place.
• Explore the most charming streets in the Beacon Hill neighborhood (my favorite thing to do!).
• Grab a famous cannoli from Mike’s Pastry.
• Walk around one of the many waterfront parks.
• Get off-the-beaten-path at the Isabella Stewart Gardner Museum.

Best Boston Day Trip Tours

I highly recommend checking out a tour while in Boston, especially if it’s your first visit, or you’re looking to explore something new. Boston has so many amazing tour options led my local experts that share tons of tips and knowledge.

One great tour to consider on your day trip from Portland, Maine is a Freedom Trail Walking Tour . The Freedom Trail is one of the best things to do in Boston for history buffs (and anyone who wants to appreciate the country’s earliest years). You can definitely walk the trail yourself, and do the whole thing or just parts of it. But if you love history, consider this tour by a local historian to get even more out of your experience.

Click here to check out Freedom Trail History Walking Tour in Boston

For day-trippers, a Hop-on, Hop-off trolley tour is a great choice to cover more ground, and also learn something along the way. Once you get to Boston, I always recommend you park your car for the day and explore on foot, but a trolley tour will allow you to see more sites without having to worry about getting around a historic city in your own car.

Click here to check out the Hop-On, Hop-Off Trolley tickets in Boston

For foodies, definitely check out this North End Foodie Tour , which is led by a local culinary expert that knows all the very best spots. You’ll get recommendations for places to eat during the rest of your visit, and get to sample some amazing treats along the way like meats, cheeses, baked goods, drinks and pizzas. This is a walking tour, so you’ll also get to see some charming streets in the North End for a well-rounded day trip to Boston.

Click here to check out the North End Foodie Tour in Boston

How To Get From Portland, ME To Boston Without A Car

If you don’t have access to a car in Portland, you can take the Amtrak Downeastern train from Portland to Boston for your day trip. The best option is to drive because the train will take you three hours one-way, but if you don’t have access to a car, this is a great option!

11. Rockport, MA

Rockport is one of the best destinations for day trips in Maine if you’re looking to see one of the most charming and unique towns along the Massachusetts coast. It’s definitely my most favorite town in the North Shore region of Massachusetts, and probably one of my all-time favorite destinations in all of New England.

Rockport is small, but feels very special and memorable. The downtown area is packed with awesome and unique shops and eateries, there’s a big local artist scene here, and everywhere you go, you kind of feel like you’re in a postcard. It’s no wonder that Rockport has been used in a lot of movies!

Best things to do in Rockport on a day trip from Portland:

• Admire the most painted building in the U.S. – Motif 1.
• Stroll through Bearskin Neck and visit all the shops.
• Grab a lobster roll at Roy Moore Lobster Company.
• Walk on the Rockland Breakwater.
• Visit all the art galleries.
• Hit the trails at Halibut Point State Park.
• Kayak out to Thacher Island to see the lighthouse.
• Take a boat tour of the harbor.
• Get an ice cream at the cutest little ice cream shack on the East Coast!

Psst! I have an entire post on all the amazing things to do in Rockport to help you plan your visit!

12. Marblehead, MA

Marblehead is another amazing day trip from Portland, Maine. It often gets over-shadowed by the neighboring Salem (more on Salem later in the post, though!), but it’s definitely worth a full-day visit, or even a whole weekend. Marblehead has an awesome historic district with beautiful houses to admire, cute little shops and cafes, plenty of waterfront to explore and is even home to some Hocus Pocus filming locations!

Best things to do in Marblehead on your day trip from Portland:

• Explore Chandler Hovey Park and Marblehead Lighthouse.
• Visit Devereux Beach.
• Pick up some sandwiches and see what else you can find at Shubie’s Marketplace .
• Walk around Old Burial Hill Cemetery (a Hocus Pocus filming location). Be sure to find the gazebo at the top to admire the views.
• Grab a lobster roll at Little Harbor Lobster Company.
• Take in the views at Castle Rock.

Psst! I have an entire post on the best things to do in Marblehead, MA if you need even more ideas.

13. Gloucester, MA

Gloucester is a great day trip from Portland, Maine to consider, and is also only about 15 minutes from Rockport, so you can easily combine the two into one trip if you wanted. Both are excellent destinations to dedicate a full day to, however, so it’s entirely up to you!

Gloucester is packed with maritimes history, and also has lots of waterfront to explore. On top of that, though, you’ll find amazing restaurants, a quaint little downtown, a beautiful lighthouse and lots of tour options that get you out onto the water.

Best things to do on a day trip to Gloucester from Portland:

• Explore the Gloucester HarborWalk.
• Visit Hammond Castle to feel like you’ve been transported to Europe.
• Walk along the shore at Good Harbor or Wingaersheek Beach.
• Head over to Eastern Point Lighthouse and walk almost a half mile out on the breakwater.
• Have a lovely lunch at Sugar Magnolia’s.

One of the best places to go whale watching in the entire world (yes, world!) is actually right here in Gloucester, so this is definitely something you’ll want to consider for your day trip. Whale Watch tours from Gloucester head out to Stellwagen Bank, a national marine preserve that’s only 12 miles offshore. This particular tour is great for day-trippers because the vessel is a high-speed catamaran, so you’ll be able to cover more ground in the same amount of time, allowing you to really maximize your time.

Click here to check out this Whale Watching Tour in Gloucester

To get around Gloucester faster and easier, a great option for your day trip is to rent e-bikes ! E-bikes are so much fun to ride, and allow you to pack more into your schedule than just walking. And with e-bikes, you’ll be able to ride some of the bikes through all of Cape Ann since you’ll have them for 8 hours, allowing you to see even more of this gorgeous region.

Click here to check out renting e-bikes in Gloucester

14. Rangeley Lake, ME

Distance From Portland: 2 hours and 30 minutes

The furthest day trip from Portland, Maine is still definitely worth your time! Rangeley Lake in Maine is located in the Northwestern corner of the state, and is a beautiful destination to consider. And actually this region is home to several lakes, and covers a lot of ground, so you’ll have lots of options when it comes to towns to visit, activities on the water and places to eat. Rangelely Lake is also a quiet and peaceful destination, which makes for a wonderful escape from the city.

Best things to do on a day trip to Rangely Lake from Portland:

• Take a scenic drive along the Rangeley Lakes Scenic Byway.
• Cool down at the swimming holes at Small Falls.
• Enjoy the views at the Height of Land Overlook.
• Drive to the top of Quill Hill for more amazing bird’s eye lake views.
• Explore the charming shops in downtown Rangeley.
• Rent a kayak and head out onto the water.
• Have a lakefront dinner at the Loon Lodge Inn.

For something really fun and special (and a bit of a splurge that’s totally worth it), consider booking a seaplane tour over the region. This tour often spots moose from above on the lake shorelines, so if seeing a moose in Maine is on your list, this will be a great option. You’ll pass over two lakes and get to spot other wildlife as well. Even though it’s a splurge, the price is very fair for a private tour, especially in such a gorgeous area.

Click here to book your Seaplane Tour in Rangeley Lake!

Day Trips From Portland, Maine In the Fall

15. salem, ma.

Distance From Portland: 1 hour and 30 minutes.

Pretty much any destination in New England is wonderful to visit in the fall, but one of the best day trips from Portland, Maine in the fall is Salem, MA , especially during the month of October. I think Salem is a great town to explore year-round, but of course, there’s something extra fun and special about it in the fall season. From haunted tours, to fun street fairs, to a picture-perfect New England streets covered in leaves, this is one of the best day trips from Portland, Maine you can take during the autumn season.

One of the best tours in Salem is this Hauntings & History walking tour , and you can select either a day option, or a night option if you want to increase the spooky factor. The tour is led by a local historian and shares stories of the town’s incredible history, which dates back to the 1600s.

Click here to book your Hauntings & History Walking Tour in Salem!

If you’re a fan of the movie Hocus Pocus (and honestly, who isn’t?), then you may enjoy this walking tour of the movie’s filming locations in Salem. You’ll see five movie locations, learn some fun trivia about the movie, and also hear about the town’s fascinating history to get the best of both worlds.

Click here to book your Hocus Pocus Filming Locations Tour in Salem!

If you’re looking for a super spooky tour and lots of goosebumps, then you’ll love the Voodoo, Vampires & Ghosts Walking Tour . Done at night, this tour is led by a local history expert and takes you to some of the most haunted locations in town. You’ll also listen to authentic stories from the Salem Witch Trials and hear about ghost sightings around Salem.

Click here to book your Voodoo, Vampires & Ghosts Spooky Walking Tour in Salem!

Psst! I have an entire post on taking a day trip to Salem, MA , if you’re looking for more information!

Day Trips From Portland, Maine Without A Car

In all honestly, getting outside of Portland to explore the local areas without a car is very difficult, and sometimes not even possible. New England in particular really requires a car to get around, and public transportation between towns isn’t great, unless you’re going from one city to another.

But if you’re willing to stay in Portland, and head out for fun tours that will feel like day trips, this is an excellent option if you don’t have a car! Below I’ve also listed two options for companies that will drive you around Maine in a private tour if it works in your budget, and well as one tour in Portland that will feel like an escape.

Best Day Tours From Portland, Maine

A great option for day trips from Portland, Maine without a car is this full-day Maine in the fall tour . This tour will start at Portland Head Light, and take you out to Camden, Bangor and some of the best sites in Acadia National Park, including to the top of Cadillac Mountain and Bass Harbor Lighthouse. You’ll even have time to explore downtown Bar Harbor for a bit. This is a private tour for your group, and considering how much ground you’ll cover, the price for the whole group is very fair! Keep in mind that this is a fall-specific tour, and it’s not available year-round.

Click here to check out this full-day private fall tour from Portland!

If you’re willing to stay in Portland and explore the coastline, this awesome bike tour is 5-hours long, and will make you feel like you’re away from the city. You’ll head out to Cape Elizabeth, and explore the local lighthouses and dramatic coastline views, and also stop for an amazing lobster roll from a food truck that’s included in the tour cost.

Click here to check out this bike tour (with a lobster roll!) around Portland’s coast!

This company offers customized and private luxury tours throughout Maine, and if you’re looking to get around the state from Portland and don’t have access to a car, it’s worth reaching out to them to plan your perfect day trip.

Click here for more information on customized and luxury private day tours from Portland!

Can You Do A Day Trip From Portland, Maine To Acadia?

Yes, you can, but just keep in mind that it will be a long day and you’ll have to carefully plan what sights you really want to see and be strategic. Especially in the summer because of traffic and crowds. The drive is 3-hours one-way, but if your only opportunity to get to Acadia National Park is by taking a day trip, it’s definitely worth it!

There’s so much to do in Acadia that I usually recommend at least 2-3 nights, but you can also see a lot on a day trip. With a day, I would recommend doing Ocean Path (walking from Sand Beach to Otter Cliffs), one hike (Great Head or Gorham are both great choices), and then heading into downtown Bar Harbor for dinner before driving home. If your schedule allows, see if you can also do lunch at Jordan Pond House inside the park overlooking the mountains.

Here’s my guide on the perfect Acadia National Park itinerary if you need some day trip ideas, or are planning to spend a few nights there!

Hiking Day Trips From Portland, Maine

The destinations from this list that offer amazing hiking opportunities as a day trip from Portland would be Acadia National Park, Camden (Camden Hills State Park), Conway, Sebago Lake and Rangely Lake.

Day Trips From Portland, Maine In The Winter

Kennebunkport and Ogunquit are excellent options for days trips from Portland, Maine in the winter because of their holiday celebrations. The Kennunkport Christmas Prelude is one of the best Christmas festivals in New England, and Ogunquit’s Christmas by the Sea event will fill you with all kinds of holiday cheer. And since these two towns are so close to one another, you could easily combine them into one festive day trip.

Once the holiday season is over, a great option for a day trip from Portland, Maine in the winter is to head just a few minutes north to Freeport and explore the charming town covered in snow, explore the trails at Wolfe’s Neck Center & Farm and then head back into town for a very cozy meal at Tuscan Brick Oven Pizza.

Conway, NH from this list is also an awesome day trip in the winter. Known as an incredible ski destination, you’ll be able to hit the slopes, or just enjoy the quaint town and its attractions covered in a beautiful blanket of snow.

More Of My Maine Travel Guides:

• Maine In November: Is It Worth Visiting?
• Maine In The Spring: Where To Go & What To Do
• Maine In October: Best Fall Foliage Spots & Things To Do
• Maine In The Winter
• Portland, Maine In The Winter
• Best Stops To Make On A Portland, Maine To Acadia National Park Road Trip
• Best Breweries In Portland, Maine
• Where To Find The Best Whoopie Pies In Maine
• The Best Maine Lighthouse Road Trip Itinerary
• Blueberry Picking In Maine
• My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary
• Maine In The Summer

You may also enjoy:

• Best Christmas Towns In New England
• Best Day Trips In New England
• The Most Incredible New England Lighthouses To See

That’s A Wrap On The Best Day Trips From Portland, Maine

Now that you know all about the best day trips from Portland, Maine, you’re armed and ready to plan your own perfect day. Whether you’re excited to head to Boston and relive history and enjoy the amazing culinary scene, or you’re looking forward to a quiet day at one of the best lakes in the region, the opportunities for seeing amazing landscapes and taking some awesome tours are endless. Happy planning!

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3 Best Day Trips from Portland, Maine

By Alexandra Hall

When in Maine, way just tends to lead on to way. One minute you’re happily ensconced at a diner in Portland , the next you're marveling at the natural beauty within an hour’s drive. Before you know it, you’re haggling over handmade pottery and biking in Kennebunkport, strolling along the Atlantic’s crashing waves in Ogunquit, or hiking to the rare nesting grounds of osprey in Freeport. When you get the urge to explore some of the most memorable sights around the city, here are a few spectacular places and ways to do it, all of them easy to fold into your next Maine trip. Read on for our picks for Portland's best day trips.

Click the link to read our complete Portland, Maine city guide .

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THE KENNEBUNKS

It was the shipbuilding, farming, and fishing industries that set the stage to turn Kennebunkport and Kennebunk into two ridiculously cute seaside summer resorts in the first place. But for more than a century now, it has been the historic mansions, charming inns, posh shops, soft-sand beaches, and renowned restaurants that have bolstered its cachet. The two sibling towns meet at the Kennebunk River, home to Dock Square’s slew of boutiques and art galleries, and the working harbor where you can catch a whale watch, eat a lobster roll, or sip a hoppy locally brewed ale.

White Barn Inn, Auberge Resorts Collection Arrow

Ever since Kennebunk's White Barn Inn & Spa opened in 1973, the 26-room, 19th-century main house and two renovated barns have attracted couples seeking enchantment and celebrities seeking discretion. They’ve indulged in all the decadent property has to offer—the infamously rich lobster fettuccine with cognac coral butter sauce; the 90-minute Himalayan Salt Stone Massage in the spa ; the hand-packed picnic baskets made for sunrise (or sunset) beach picnics. What's most remarkable about The White Barn Inn is the extent to which they seem to have thought of everything: You walk away from a stay here wondering why all of life can't be this seamless.

Sandy Pines Campground – Glamping Arrow

Known for years in Kennebunkport as Salty Acres Campground, it was bought and renamed Sandy Pines by local hoteliers Tim Harrington and Debra Lennon, who have also produced a handful of upscale and luxury spots around town. The entire campsite was renovated and reopened in 2017 with glamping tents and retro-cool mobile homes, a nostalgia-driven general store (peddling everything from s’mores fixings to lobster rolls), a heated saltwater pool, sparkling new bathhouses, and a swanky, modern lodge centered around games and a fireplace.

Dock Square Arrow

Window shopping is elevated to an art form in this cluster of boutiques, art galleries, and curiosity shops around Kennebunk's Lower Village and Kennebunkport's downtown neighborhoods. It's an ideal stomping ground for those who treasure independent and local stores crammed with creative and clever wares. Be prepared to bring home paintings, sculptures, and jewelry by local artists; high-end clothing; handmade goods like candles or furniture; and plenty of touristy gifts for your friends and family.

Jessica Puckett

Anna Borges

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Goose Rocks Beach Arrow

As Maine beaches go, this one is exceptional for one thing: its powdery white sand. You can walk barefoot on the entire three miles here without worry that you'll go home bruised and battered from kicking rocks. The beach is very DIY, unless you're a guest of The Tides Beach Club or one of its sister restaurants (in which case you'll be provided with chaise lounges and umbrellas). You'll have to hit up the Club's restaurant for food, too. 

Hidden Pond Arrow

Drive down the subtly marked dirt road into the resort, and the first thing you come upon is a garden on your right and a small pond on your left. Slowly, you realize that tucked between them and the countless birch trees are cottages and treehouse suites. Hidden Pond has been expanding over the decade-plus since it opened, adding private bungalows and cottages and one of the standout restaurants in the entire state in Earth. Personal, quiet, and soothing, but with plenty of activities for all ages, this is one of those places people come back to again and again.

Batson River Brewing & Distilling Arrow

With a notably strong craft cocktail game, Batson River brings in plenty of people for drinks made with its own spirits, like the "Whatsa Matcha," made with the house's Riparian Gin, matcha, and honey. Or the Rhubarb Sour, a mix of lemon, rhubarb, and Batson's Langsford Road Whiskey. That said, the beers here have their own fan club; a rotating list of about ten IPAs, pilsners, and ales are sampled from with gusto (and no shortage of analysis and discussion) by regulars and beer tourists alike. The food menu is its own delicious reason to come. Fried chicken comes with delectable duckfat cornbread and jalapeño and jicama ginger slaw. It's the perfect foil to any of the soothing ales. 

The Tides Beach Club Arrow

The restaurant at this hotel sits directly across the street from, and looks out to, Goose Rocks Beach , a gorgeous slice of shoreline. From the kitchen, though, you won't find any culinary acrobatics, precious ingredients, or esoteric dishes. The lobster roll comes on a meticulously grilled roll, either cold with a light dress of garlic aioli and scallion, or hot with a pour of tarragon and brown butter. The short ribs are braised in apple cider and fork-tender. The chicken sandwich arrives fried to a light crispiness on the outside, is moist as can be in, topped with pickled green cabbage, and locally made maple mustard.

Cliff House Maine Arrow

Just a few steps in the front door, and you're confronted with the hotel's raison d'être: the jaw-dropping cliffs. Framed by epic floor-to-ceiling windows, they dominate the lobby, tumbling down from the resort's perch down to the crashing ocean waves. The rooms are in keeping with the rest of the resort's quiet coastal cool aesthetic. Navy buffalo check bedding beneath the Cuddledown comforters here, subtle striping on drapes and carpets there. But just as in the lobby, the real star is outside the window, where the Atlantic Ocean does its thing with waves crashing or lapping, gulls crying, and breezes soothing beneath your private terrace.

It isn’t just the juxtaposition of culture and nature that makes this former shipbuilding village a standout. Though there certainly is that, the area's status as a longtime artist colony is made even more resplendent set against its shores and sprawling beaches. But then there’s the other juxtaposition—crowds of families all summer here for the beaches; city slickers hanging at the trendy bars; and LGBTQ+ tourists and business owners, many of whom have decided they love it here so much, they now visit year-round.

Ogunquit Beach Arrow

Running alongside the town of Ogunquit, this beach couldn't be easier to access. The 3.5-mile-long stretch of soft sand is a big hit with families for its consistently gentle surf and its collection of tide pools that both toddlers and parents love. The clean, clear waters are fantastic for swimming, and at low tide, there's extensive room for long walks onto sand bars. The middle section of the beach is called Footbridge Beach, and it's where you'll find public restrooms, gift shops, changing rooms, and snack bars.

Meadowmere Resort Arrow

The personal qualities of an inn with the functionality of a motel, The Meadowmere is an independent property owned and run by the Cavaretta Family since 1983. The fanciest inn around, it's not. But on vacation, that can be an attribute. Its staff is friendly as can be, and its handsome and well-kept rooms, plethora of amenities (from the spa to the indoor/outdoor pools to easy access to downtown Ogunquit's shops and restaurants) have made it an annual favorite of families visiting the area.

Ogunquit Trolley Arrow

The hop-on, hop-off Ogunquit Trolley is a convenient and inexpensive way to get around downtown Ogunquit's crowded streets in the summertime, but it's also a great way to see the town's biggest attractions, from Perkins Cove to Marginal Way to Ogunquit Beach. While trolley drivers aren't formal tour guides, they oftentimes provide information about the town and share some of their own stories. There's no need to buy tickets in advance—just pay the driver the $2 fare for adults, $1.50 for kids. They run every 15 minutes and operate seasonally, from late June through mid-October.

M.C. Perkins Cove Arrow

Even if they didn't have one of the most buzzed-about burgers in New England (the $26 Kobe burger has its own, very committed following), co-owners and James Beard Award-winning chefs Mark Gaier and Clark Frasier would be packing the house on the strength of the rest of their chic bistro menu. While the waves crash and roll just outside the expansive windows you'll be dining on Maine chowder with haddock, clams, hominy corn cake, and smoky tomato butter or the delectable, sweet-tart duck confit with peach-lemongrass sauce and tamarind.

Marginal Way Arrow

Named for being a "margin" between land and sea, Marginal Way is a stunning cliff walk. Along the 1.25-mile paved path are 39 benches perfect for soaking up the incredible views of crashing Atlantic waves, and perhaps peep some sea life. It's paved and open year-round, but you'll want to be careful in winter—there can be icy patches. Strolling the trail is free, and anyone who adores nature walks and the ocean will delight in the experience.

Freeport, Maine

Yes, of course it’s about the giant duckboot, as well as all the other designer outlets that spiral out from L.L. Bean’s world headquarters. But that’s far from Freeport’s only lure. What distinguishes this retail haven from others is how seamlessly it has woven in local businesses, the area’s history, and its stunning natural setting, which includes coastal and mountain hikes, and farmlands. All of it is under an hour drive from Portland.

Harraseeket Inn Arrow

At the Harraseeket Inn, you'll find traditional New England decor in a 1850 Greek Revival filled with wood-burning fireplaces and antiques at nearly every turn. This legendary Freeport hotel is owned by the inimitable Nancy Dyer Gray, a champion and pioneer of Maine tourism, and her family. Their personal dedication is evident in details throughout the hotel and you see it in the staff (many of whom have worked for the hotel for two decades) and their connection to the regulars who visit from inside and outside of the state.

Maine Beer Company Arrow

Maine Beer Co. has a fervent and an ever-widening local and regional fan base, which shows up at the brewery's Tasting Room all day and past dinnertime to sample the company's many creations (there are 20 draft lines, plus bottles the company offers only on-site and not in retail stores). Beer lovers relax on the patio in warm weather, dig into wood-fired pizza, hang at the bar, and shmooze at the water fountain, sipping each brew and discussing it with a seriousness that only real beer nerds can muster.

Wolfe's Neck Woods State Park Arrow

Wolfe’s Neck Woods State Park in Freeport is coastal Maine at its finest. The winding hiking paths bring you through pines, hemlocks, and birches, set on salt marshes and along Casco Bay's rocky shoreline. With multiple trails, hikes can be as short as 20 minutes to as long as a few hours, so visitors can easily customize their time spent here, depending on hiking ability and interest level. Want a more relaxing day in the park? Plenty of people come simply to sit on a rock and enjoy the view, while others come for a picnic.

Freeport Village Station Arrow

Anchored by the world retail headquarters of outdoor equipment and gear outfitter L.L. Bean, Freeport Village Station is a stable of discount designer shops and independent boutiques. It also has worked hard with the Town of Freeport to maintain the area's history and rural nature, so even while the outlets are all about shopping, all you have to do is walk five minutes off of Main Street and you're among historic homes. Stroll a few more minutes away, and you're in the wilderness of Casco Bay.

Thos. Moser Showroom Freeport Arrow

Thos. Moser is one of the most esteemed artisans in the country, crafting museum-quality wooden furniture and hand-carved gifts. Colleges and museums across the country have invested in their heirloom pieces, like a Cumberland dining table or a Pasadena rocker, and you can too if you some money to spend. If you're not ready to open your wallet quite that wide, this is also home to the outlet annex, a trove of deeply discounted floor samples and still-beautiful seconds.

Harraseeket Lunch & Lobster Company Arrow

A true seafood shack of the red-beadboard-and-old-wooden-tables variety, this Freeport landmark has been operated by the Coffin Family since 1970, and not a lot has changed in that time. The Harraseeket Lunch and Lobster Company is a magnet for boaters pulling up to the dock who are seeking some of the best seafood around. There are absolutely no culinary sound barriers being broken at this restaurant, but what it does, it does extremely well. Some favorites include fried clams and lobster rolls, and the homemade desserts—especially the whoopie pies and blueberry pies—are worth a trip on their own.

Bradbury Mountain State Park Arrow

Think of Mount Bradbury as a one-size-fits-all hike—there are trails for almost all skill levels and uses; mountain biking, horseback riding, snowmobiling, and dogs are all welcome. It's easy to get to from downtown Freeport, has plenty of parking, and is open year-round. (In winter, there are snow shoe rentals available; in summer it's popular for camping.) All year long, there are spectacular views across its 800 forested acres.

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Welcome to Maine Windjammer Cruises

The original windjammer fleet.

EXPLORE OUR OVERNIGHT CRUISE SCHEDULES & PLAN YOUR TRIP TODAY!

QUESTIONS? (800) 736-7981

The intimate 6-passenger Swift offers the joys of sailing and socializing in a smaller modern setting.

2024 Swift Schedule

  Our online  reservation system is ready for your use,  but please feel free to call us if you need assistance.

We will offer three and six-night trips, boarding either on Sundays or Wednesdays.  Our season begins June 2 and runs through early October.

Charters will be arranged on a case-by-case basis for any length of time.

 Reservations are processed in the order they are received.  Please be patient as we take care of all of our eager passengers.  Bookings made over the weekend sometimes cause a little delay, but rest assured that you will receive confirmation via email and regular mail once your reservation is fully processed.

Annual Calendar

Each year since the 1990s we have produced our annual calendar for those who have sailed with us or shown interest in our cruises. This year’s calendar features our new flagship.

DOWNLOAD 2024 CALENDAR

DOWNLOAD INSTRUCTIONS:  click on the above link and download to your computer.  Print on good quality 8 1/2 X 11 paper or card stock . We hope this brings you daydreams of summer and sailing on the bay!  

If you are unable to download and print, please contact us and we get a copy to you.

Cruise Options

Weekly Trips Throughout the Season – We Have a Cruise That’s Right For You! Our Windjammer vacations are all-inclusive.

A $300 per person deposit is due when you make your reservation; the trip balance is due in full 6 weeks prior to your trip.  We understand that personal circumstances sometimes change, and you may find it necessary to cancel your trip.  Seven Corners Insurance specializes in sailing vacation coverage.

Cancellations must be made in writing prior to 8 weeks ahead of your trip.  A 10% per person handling fee of the total fare price will be retained and credited toward a future trip on a space available basis.

Cancellations made less than 8 weeks ahead of your trip can not be refunded unless we are able to rebook your cabin(s).  We do have a wait list, or you are welcome to find someone to take your place.  In the event we are able to re-book your berth, we will refund all but a 10% per person fare price handling fee.

PRE-SEASON THREE  or SIX DAY CRUISE  ABOARD THE  SWIFT

Off-season rates, coupled with long days and uncrowded anchorages mean you will see more for less.

In June, crew and passengers are anxious to get started on a new season, and the windjammers are often the only vessels on the bay. The sailing is great and enthusiasm is high.

THREE DAY CRUISE – PRE-SEASON

These cruises are an excellent introduction to the world of windjamming. You may choose from the first or second half of the week. This can be a grand change of pace or the highlight of a longer Maine vacation. A Lobster Feast is included in all three-day cruises.

Board Sunday evening at 5:30 PM and meet your new shipmates. You will be on your own for dinner in town, but will sleep aboard your vessel.

After a hearty breakfast Monday, we get underway for our short adventure exploring the islands of Maine. You will return to Camden Harbor between 10 a.m. and Noon Wednesday. Often, people who take the first half pre-season 3-day cruise have such a good time, they ask to stay on for the second half.  IF SPACE ALLOWS, you can stay for the second half of the cruise, at an additional discounted fee.

SECOND HALF

The usual boarding time is 5:30 PM on Wednesday, but we may ask  you  to be in the area earlier and check in with us by phone.  In either case, you will return by 10 am on Saturday.

SIX-DAY CRUISE

Offered exclusively in the Pre-Season, these trips have it all. They are the best value with long days to sail and explore, a shore-side lobster bake, and lots of time to relax and unwind. Board Sunday evening and return Saturday by 10 a.m.

SUMMER SAILING

Available on the Swift.

THREE-DAY CRUISE

This cruise is an excellent introduction to the world of windjamming. Board Sunday or Wednesday evening, meet your new shipmates and have dinner on your own in Camden.  You will sleep aboard, and after a hearty breakfast the following morning, you’ll be underway for your adventure exploring the islands of Maine. This cruise can be a grand change of pace and certainly the highlight of a longer Maine vacation. A Lobster Feast is included in all three-day cruises. You will return to Camden Harbor by 10 a.m. Wednesday or Saturday.

FALL FOLIAGE CRUISES

This is a very special time of the year. Reduced fares make these trips  the perfect time to vacation in Maine. The beauty of the fall colors adds a new dimension to already breathtaking scenery. Crisp, clear days with brisk winds offer the best sailing of the season.  Trips board Sundays and Wednesdays.

Windjammer Events

Always on Labor Day weekend. Celebrate Camden’s rich maritime heritage as our schooners take part in the weekend festivities!

 WOODEN BOAT SAIL IN:    Mid-September.   Windjammers converge on Brooklin, Maine home of Wooden Boat School & Magazine. Refreshments, live entertainment and tours of the grounds & school. Be sure to bring your cameras and be ready for a great time!

FOR THE STAR GAZERS

Skies out on the water are always beautiful. With little light pollution the stars pop and the full moon becomes a beacon sparkling across the water. The annual Perseid Meteor Showers provide a spectacular light show producing up to 30 shooting stars an hour. At its peak it can produce up to 100.

FULL MOON DATES:   JUNE 21,  JULY 21,  AUGUST 19 and & SEPTEMBER 17

BEST STAR GAZING:  NEW MOON DATES:  JUNE 6, JULY 5, AUGUST 4 & SEPTEMBER 2

PERSEID METEOR SHOWER:  AUGUST 12-13 peak

Special Occasion and Private Sailing Excursions Let Us Help You Plan Your Event Aboard Our Schooners

WE’LL PUT THE WONDERS OF THE MAINE COAST AT YOUR FINGER TIPS!  Our windjammers are available for weddings, reunions, family celebrations, team building and other activities.

Is your dream a windjammer wedding? Even if you reside out of state, it’s now simple to get a marriage license in Maine, and our captains can legally perform a wedding ceremony. Would you like to enjoy your wedding reception on Penobscot Bay or offer a trip on our schooners to out-of-town wedding guests?

NON-PROFIT ORGANIZATIONS

Sea Scouts, Boy Scouts, Girl Scouts, Military Units, Summer Campers, foreign exchange students, and specialized travel groups have also enjoyed trips with us.

We work with college alumni and other nonprofit groups to create fundraisers and unique travel opportunities. Even if you don’t have enough people to fill a boat, discounts are available for  groups of ten or more.

Day Charters are sometimes possible on turn-around dates Wednesday and Sunday. Most trips are from noon to 4 p.m. We can carryup to 12 guests on  the Swift . Please call for availability and prices. 800-736-7981

MORE REASONS TO CHOOSE MWC

Brides and grooms and those renewing their vows aren’t the only ones who look to a New England sailing vacation for a special event. Loved ones will never forget a birthday, anniversary, family reunion, graduation, or surprise party celebrated on a Maine windjammer. Our cruises are also popular for college and high school alumni reunions and sorority, fraternity, and professional society gatherings.

We can also provide a trip appropriate for a funeral service or memorial gathering. We look forward to helping you or your organization plan your special event.

OUR MAINE FARE

Food for your charter can be provided from our standard menu that includes lobster, fish chowder, and other traditional Maine fare, but we are willing to work with you for some adjustments or special requests.

Testimonials Click to view testimonials given to Maine Windjammer Cruises™ by passengers of some of our chartered cruises.

Rates vary with the number of passengers, length of cruise, and time of year.

Please plan early to reserve your special date, even if the season is already underway.

We require one-third of your payment at the time of your confirmed reservation, one-third between the reservation and balance date, and one-third 45 days before your departure date. Rates are all-inclusive. Other payment plans can be discussed.

Charters are nonrefundable, so we recommend trip insurance through a sailing insurance specialist such as Seven Corners.

A MAINE WINDJAMMER WEDDING CRUISE 

Is your dream a windjammer wedding?

ELABORATE OR SIMPLE – Whether a cruise with friends and family, a reception sail, a quiet sunrise/sunset ceremony as part of your cruise or trips for out of town guests, we are ready to assist in fulfilling your wedding dreams.

“Couldn’t have found a better wedding venue!!! ……Jan Marie

Contact Maine Windjammer Cruises by phone or email to let us help you plan your special day.

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3 Days in Portland, Maine Itinerary | A Long Weekend Guide + Map

Nov 13, 2023

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Portland, Maine, is a city brimming with coastal flair, historic buildings, and the small-town charm worthy of an epic New England getaway.

This port city is dotted with excellent eateries and bars, as well as art galleries on every corner, and gives you easy access to southern Maine beaches and state parks.

A long weekend in Portland, Maine, is nothing short of a foodie and adventurer’s dream.

Between the fresh produce markets, the picturesque lighthouses, and the most delicious lobster in the U.S., you may want to stay longer.

In this guide, I unpack the best ways to explore this charming city through an extensive Portland, Maine weekend getaway 3-day itinerary.

Now without further ado, let’s dive into the ultimate Portland, Maine, weekend trip.

Tip: If you don’t have three days, explore the town’s highlights on a day trip to Portland, Maine .

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Disclaimer: Hey explorer! This post contains affiliate links which means I earn a small percentage of each purchase made through my links. I only ever recommend products I believe in and appreciate your support if you decide to use my links—thank you!

Your Portland, Maine Weekend Trip At A Glance + Map

Coffee + breakfast, cruise or mailboat to casco bay, walk from commercial street to old port, lunch at little tap house, portland observatory tour, join the first friday art walk, dinner on the waterfront.

• Coffee on Congress Street
• Stroll through the Portland Farmers Market at Deering Oaks Park

Go on a Lobstering Tour

Catch a ferry to bug light park + lunch, beer tour + dinner, coffee + donuts, visit friends of the kotzschmar organ, peruse portland, maine’s bookstores + lunch, head to the eastern promenade + dinner.

Here is a map you can use on your trip.

Click here for a live version of the map !

Read Next: The Best Camera Gear for Travelers

Day 1 in Portland

Everyone knows a good adventure starts with a delicious cup of coffee and a tasty breakfast.

Portland, Maine is abundant with quaint coffee shops; one chain that you’ll find dotted across the city is Coffee by Design.

Try the one on Diamond Street, where you’ll discover an artisan roastery, coffeehouse, and cupping room.

On Franklin Street, there’s Coffee ME UP, where you can enjoy your specialty coffee beverage with a selection of light pastries, sandwiches, and tasty smoothies.

Once you’re pumped on caffeine, hop on the first ferry to Casco Bay.

You can catch a gorgeous sunrise via a cruise or a mailboat run at 10 am.

And in case you’re wondering, yes, a mailboat is exactly what you think it is — a boat delivering mail to the island.

Locals enjoy commuting to Casco Bay via a mailboat.

The daily runs from Portland, Maine, cost $17 per adult, take about 2.5 to 3.5 hours, and stop at five islands. This should be enough time to explore your chosen destination. 

Wanderer Tip: If a cruise is more your style, charter a tall schooner ship tour and sail the rugged Casco Bay coastline, catching sights of lighthouses, seals, and other coastal wildlife.

Upon returning to the mainland, stroll down Commercial Street, and discover some of the best spots in Portland, Maine.

Walk along the working waterfront with fishing boats, lobster spots, jewelry, and pottery shops.

Take some time to explore the historic tourist district and learn more about Portland through guided walking tours to Old Port.

You can browse through cute boutiques, art galleries, restaurants, and bookshops.

The charming bookshops range from family-owned stores with a dog-friendly atmosphere selling works by local artists to book shops where you can grab a snack, a coffee, or a beer.

After all that walking, you must be famished.

Head down to  Little Tap House on High Street from Old Port for local delights. The farm-to-table gastropub serves scratch-kitchen cuisine — the fish and chips are delicious and generously portioned.

Wash your meal down with a refreshing cocktail, a light wine, or a mimosa. Ready for your next attraction? That’s great because it’s right across the street.

 A skip away from Little Tap House, you’ll stumble upon the Portland Observatory.

The maritime signal tower is the country’s only surviving one of its kind.

From atop the tower, you’ll see stunning views of Casco Bay. Walk a little further, and behold the Portland Museum of Art.

Take a tour of the museum’s extensive collection and varying displays of contemporary art and film, then head over for some photo snapping at the outdoor sculpture park.

Is it Friday? Then you know what to do in Portland, ME.

Enjoy strolling through the city’s galleries, alternative art studios, and museums, as well as vibing to live music at Congress Square Park.

This art walk also boasts paths lined with pop-ups, coffee shops, jewelry, and pottery vendors.

The event happens every first Friday of the month, and doors open from 5 pm to 8 pm. Oh, and did I mention the entrance is absolutely free?

Portland, Maine’s waterfront is buzzing with fantastic eateries, bars, and bistros.

You’ll be spoiled for choice between the hand-crafted meal on Fore Street, and Boone’s Fish House & Oyster Room—their lobster mac n cheese is delightful.

Boone’s is quite a popular spot attracting large crowds and a lively atmosphere. 

Day 2 in Portland

Coffee on congress street .

Kickstart day two of your weekend trip to Portland, Maine, with a fresh caffeine brew on Congress Street.

If you’re in the mood for a casual vibe and a fresh sandwich made at the counter, Yordprom Coffee Shop is the perfect spot for you.

For a more modern aesthetic, Tandem Coffee and Bakery take the cup. Their freshly baked pastries are excellent, and the chai latte may be the best you’ve ever had.

Stroll through Portland Farmers Market at Deering Oaks Park

Shop from Maine’s top farmers and food producers in one stop, surrounded by gorgeous green spaces and expansive water fountains. 

The farmers’ market is open for the summer season on Wednesdays and Sundays from 7 am to 1 pm, May through November.

And in the wintertime, it’s open Sundays from 9 am to 1 pm, December through April, at the Maine Girls Academy gymnasium.

One thing you must do when in town, even if you’re only spending one day in Portland, Maine, is going lobstering! 

There are plenty of tour providers along the shore. You’ll find Lucky Catch Cruises and Rocky Bottom Fisheries.

Not only do you see the catching process, but you also get to help with measuring the lobster and emptying the traps.

Tip: If all that lobstering gets you hungry, why not join a seafood and lobster walking tour and sample some of Portland, Maine’s favorite local delicacies?

Kickback and relax to stunning skyline views and gorgeous Portland Harbor vistas at this nine-acre manicured parkland.

Home to the picturesque Portland Breakwater Lighthouse, Bug Light Park is the perfect place to kill time before the next adventure begins.

If you like, you can pack a picnic basket and enjoy a tranquil lunch on the lawn. Or opt for a gourmet lunch at one of South Portland’s famous eateries.

North 43 Bistro serves classic American cuisine, like smash burgers, and has excellent marina views.

For seafood delights, stop by Saltwater Grille for an upscale ambiance and Portland skyline views.

Other things you can get up to at Bug Light Park include biking, saltwater fishing, and boating.

Take a three-hour South Portland bicycle tour and explore four gorgeous lighthouses.

This includes the Portland Head Light, one of the most photographed landmarks in the city. Its white façade contrasts the rocky shores surrounding it and the azure backdrops of the sea and sky.

Nature lovers will appreciate walking the half-mile-long beautifully landscaped Cliff Walk to get to the lighthouse.

Portland, Maine, has the second most breweries per capita in the U.S. after Vermont. 20 breweries and over 700,000 people — now that’s a lot of beer!

It goes without saying that you won’t see all these breweries in one go, so choose the one that serves grub of equal standard.

Some of the best breweries in Portland, Maine, for a seating experience, include Foulmouthed Brewing and Foundation Brewing, with an expansive variety of crafts from sour ales and farmhouse ales to IPAs and porters.

For a mobile beer experience, join a Maine Brews Cruise tour and enjoy delicious craft beer on a biking tour, beer bus, or walk from one spot to another. 

Day 3 in Portland

A trip to Portland, Maine, is incomplete without tasting the city’s delicious desserts.

Donuts are popular, and there’s nothing wrong with a little sugar rush to start your last day in Portland. 

Try the tasty donut holes at The Cookie Jar in South Portland, or opt for a creative donut made with locally sourced potatoes at the famous Holy Donut on Commercial Street.

The Holy Donut also serves gluten-free and vegan options.

The Kotzschmar Organ is one of only two municipal organs in the U.S., a true Portland hidden gem.

You can see this colossus by either touring or attending a concert at Merrill Auditorium in the City Hall.

Thanks to the Friends of the Kotzschmar Organ organization, the instrument is still in use, and if you’re lucky, you may catch the annual classic — The Phantom of the Opera .

While Portland, Maine, is often hailed for its lobster rolls and craft breweries, one industry that bears mentioning is the town’s vibrant literary scene. 

The city has about 13 independent bookstores, selling every kind of new, used, and comic book you could possibly imagine.

Check out some interesting spaces like Longfellow Books, Sherman’s, and the cozy Print: A Bookstore.

For lunch, stop by LB Kitchen for something refreshing and healthy to munch on. The bright and colorful eatery serves delicious lunch bowls, salads, and creative smoothies.

The Eastern Promenade is a 68-acre green space on Munjoy Hill designed by the Olmsted Brothers landscape firm, also renowned for creating New York’s Central Park and the Boston Commons.

This expansive lush space offers the best picnic spots and a two-mile scenic hiking and walking trail in Portland, Maine. Catch the kaleidoscopic sunset or kick back on the beach.

The Eastern Promenade is also great for starting your Portland, Maine, day trip to Acadia National Park .

But if you’re running short on time, a hearty dinner and wine at a nearby eatery will do just fine.

Check out Jing Yan for a unique Asian experience. The Front Room and Blue Spoon offer classic American fare and tasty craft beverages.

Where To Stay in Portland, Maine

Now one thing you don’t want to skimp on during your Portland, Maine getaway is the accommodation. The best area to call home is undoubtedly the Downtown / Old Port district.

This part of town is where you’ll find an abundance of luxury chain hotels and budget-friendly Airbnb.

You’ll also be in the heart of the city, allowing you to walk to nearby restaurants, art galleries, and local breweries.

Some places to consider include:

The Press Hotel, Autograph Collection — Embrace the New England atmosphere at this elegance-inspired boutique hotel in the Portland Downtown Historic District. Not forgetting the chic on-site restaurant, where you can enjoy tasty seafood and wine pairings.

Canopy By Hilton Portland Waterfront — If you like shabby chic and contemporary decor with a touch of wooden oak furnishings, this is the hotel for you. Canopy is home to Luna Rooftop Bar, serving great cocktails and waterfront views thanks to its accordion glass walls.

Aloft Portland, Maine — Funky and colorful; and the art-deco furnishings make Aloft one of the best hotels in Portland, Maine. Spend some downtime riding bikes along the waterfront, playing billiards, or cocktailing it up at WXYZ Bar.

Getting Around

Portland, Maine, has sophisticated transportation methods ranging from buses and taxis to ferries and trains.

But the best way to explore the city is by walking or biking along the cobblestone streets downtown and the waterfront.

List of Things To Do in Portland, Maine

Here’s a quick roundup of Portland, Maine’s best things to do. These top attractions and activities make a great addition to your New England road trip . 

Walk Around Old Port — Discover the historical buildings, quaint bookshops, and charming eateries dotted across the Old Port. See the city’s iconic landmarks, from the bustling Commercial Street to the scenic waterfront.

Visit the Portland Observatory — This 86-foot tall octagonal tower is one of Portland, Maine’s trademarks, with excellent cityscape views.

Tour the Portland Museum of Art — Within a two-minute walk from the observatory, you’ll stumble upon Maine’s largest and oldest public art institution.

Stroll Through the Portland Farmers Market — Buy everything from Portland’s local farmers, from fresh produce and baked goods to meats, jams, and sauces.

Explore Casco Bay via a Mail Boat — Enjoy the locals’ favorite way of experiencing Casco Bay via a mailboat run.

Take a Craft Beer Tour Through the City — If there’s one thing you’ll find scattered across Portland, Maine, it’s breweries. There are over 32 breweries for you to choose from.

Walk or Bike Along the Eastern Promenade — Catch the most stunning views of Casco Bay and Portland Harbor.

Marvel at the Portland Head Light — This historical lighthouse along the shores of Fort Williams Park in Cape Elizabeth has spectacular ocean and rocky Maine coastline views.

Enjoy a Picnic at Bug Light Park — Pack a picnic basket, grab an exciting book, and relax on the vast grassy lawn facing the city at this charming park.

Join the First Friday Art Walk — The first Friday of each month belongs to the arts in Portland, Maine, no matter the weather.

Go Bookshop Hopping — If you’re a book lover, the independent bookstore scene in Portland is really something you should take a gander at.

Hop on a Ferry to Peaks Island — Get unparalleled ocean views from Casco’s most populous island. Peaks Island is home to stunning public beaches, art galleries, and museums like the quirky Umbrella Cover Museum.

Go on a Lobstering Tour — Portland, Maine, is synonymous with lobster — lobster bisque, lobster rolls, or an authentic lobster bake. If you’re interested in seeing where the lobster comes from, why not join a lobstering tour?

Hop on a Lighthouse Trolley Tour — Spot Portland’s beautiful lighthouses, from the picturesque Spring Point Ledge Lighthouse to the famous Portland Head Light.

Admire the Kotzschmar Organ — Go off the beaten path and marvel at this gorgeous instrument with over 7,000 pipes.

Portland, Maine Itinerary 3 Days | Wrapped Up

Well, there you have it — 3 days in Maine’s largest and most vibrant city. Visiting Portland, Maine, is a must-add to any foodie’s and adventurer’s bucket list. 

From stunning waterfront views and historical landmarks to scores of quaint bookshops, breweries, and the tastiest lobster rolls in the U.S., you’re set to have a wonderful time.

And if you only have a day in Portland, Maine, explore the city’s highlights via a quirky, vintage fire truck tour .

So what are you waiting for? Pack your bags, book your stay, and gear up to have a fantastic time exploring and eating your way through Portland, Maine.

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I'm a burrito loving explorer who got fired from corporate America and turned that into my dream career as a photographer and blogger. Now I'm here to help you explore life's magic. Thanks for stopping by!

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• Sep 1, 2022

Portland, Maine: Perfect 3-Day travel itinerary for a summer long weekend

If you're looking for an easy long weekend, 3-days in Portland, Maine is the perfect summer getaway. Did you know Portland has been named in the past as the best food destination in the USA? And is home to some of the best-voted lobster roll restaurants in the country too? In this guide, you can expect to find the best places to eat and explore all planned out in an easy-to-follow 3-day travel itinerary including lighthouse spotting, island hopping and plenty of good food.

Where to stay in Portland, Maine:

We'd recommend 1 of two options for accommodation:

Note - This post contains some affiliate links if you use them we will receive a small commission at no extra cost to you.

If you don't have a car: Old Port

Old Port is full of the cutest cobblestone lanes, red brick buildings housing bars, restaurants, cafes and stores, plus is located right on the waterfront overlooking Casco Bay, with direct access to the piers where many of the ferries for island day trips and tours depart. Everywhere within Old Port is centrally located and within walking distance making it the perfect spot if you don't want to rent a car as part of your trip.

Hotel Options in Old Port, Portland, Maine:

If you rent a car: South Portland by Willard Beach:

This is a great option for a more relaxed neighbourhood feel. The suburb is filled with beautiful beach houses and is within walking distance of the beach and cafes. There aren't many hotels located here, so the best option would be an Airbnb if you want to stay in this area.

Top things to see, do, eat and drink in Portland, Maine: A 4-Day itinerary

Day 1: South Portland, Willard Beach & Old Port

Morning Day 1:

Breakfast at Scratch Bakery , South Portland - Don't miss their bagels, arrive early as they sell out fast. They also do great coffee and pastries.

Visit Fort Prebble & Spring Point Lighthouse , walking distance from Scratch. Take the 20-minute coastal walk along Willard beach through to the lighthouse and back

End the morning with a swim at Willard Beach , also don't miss visiting Fishermans Point for the best views overlooking the beach

Afternoon Day 1:

Have lunch at Duck Fat Frites in Old Port and don't miss their Poulet, which is fries coasted in duck fat with gravy and shredded duck. Their original milkshakes are also great.

After wander around Old Port through the cobblestone streets. Be sure to stroll down Wharf Street and stop in the shops around Exchange and Market Streets. Commercial Street is great for restaurants and bars.

Evening Day 1:

Grab some takeaway food, we recommend the clam chowder from Gilberts and watch the sunset at Bug Light park and lighthouse in South Portland (10-minute drive from Old Port)

Day 2: Visit Boothbay Harbour & Wiscasset

Morning Day 2:

Take a 1.5-hour scenic drive to Booth Bay Harbour. Have a quick breakfast along the waterfront at Red's Coffee House (We recommend the blueberry scrolls).

Book a tour with Cap n' Fish cruises , they have 1-hour harbour sightseeing cruises, as well as longer 2-3 hour cruises including whale and puffin watching. We booked the Puffin watching, which we would recommend. If you do this one bring binoculars or a camera with a good zoom lens.

Afternoon Day 2:

Driving back in the direction of Portland, stop to try Red's Eats Lobster Rolls or Sprague Lobster in Wiscasset.

Red's Eats has been voted as the best Lobster rolls in Maine and has been featured on numerous travel shows like Somebody Feed Phil. You can expect to wait up to 2 hours to order here with long queues forming daily. If you don't want to wait, located right across the road is Sprague Lobster which we opted for and was the best lobster rolls we had of the trip. Be sure to order it with the melted butter.

After lunch take a de-tour drive through Bailey Island , stopping to enjoy the coastal walks and views.

Evening Day 2:

Have dinner at The Honey Paw (Asian Fusion) or Via Vecchia (Italian Food) in Old Port depending on what you are feeling like. If you can we recommend making a reservation in advance.

The Honey Paw:

Via Vecchia:

Day 3: Portland Head Lighthouse, Fort William Park, and Peaks Island

Morning Day 3:

Have breakfast in Old Port, picking up pastries from The Standard Baking Co (expect a queue if visiting over the weekend so arrive early) or the Holy Donut (Amazing potato-based donuts, their salted chocolate is their best seller).

Drive 20 minute south to explore Fort William Park and Port Headland Lighthouse. Be sure to take some of the coastal walking trails while there.

Have lobster rolls for lunch in Fort William Park from the Bite Into Maine food truck (Also featured as one of the best eats in Portland on Somebody Feed Phil).

Afternoon Day 3:

Take the ferry from Casco bay to Peaks Island, It's just a 15 minute ride across, with the ferry running around every hour

Getting around Peaks Island: The island is 4 miles around, and will take about 2 hours to explore . You can rent a bike from Brad's located just a 5 minute walk from the ferry terminal for $20 for 2hrs. Alternatively you can also rent golf buggies on arrival too for around $90 an hour, be sure to pre book these before your visit as they sell out (Try Peaks Island Rental).

Places to see: don't miss the Battery Steele and Civil War Museum.

Have dinner at the High Roller Lobster Co , for more amazing lobster rolls, the fresh oysters are great there too.

We hope you enjoyed our long weekend travel guide to Portland, Maine. To see more of our other USA destination guides click here .

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WE ARE: An Australian and British married couple living in Australia, which we recently moved back to after 7 years exploring Asia. By week we manage data forecasting and engineering projects. By the weekend we wander. This is the story of our weekend travels. We are passionate travellers who love taking photos, eating and going on adventures.  We hope you enjoy our travel blog.

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Portland, Maine: A Scenic 3 Day Road Trip Itinerary

Table of Contents

Last Updated on April 14, 2024 by Jackie

Get ready for a whirlwind 3-day adventure through Maine that’ll have you exploring lighthouses, savoring fresh seafood, and soaking in stunning lake and coastal views. This itinerary is packed with excitement and promises to leave you with unforgettable memories of the Pine Tree State!

Maine easily earns a spot in my top five list of the most breathtaking states in America. Its coastal towns, rugged shores, and lobster fishermen capture the essence of the region perfectly. Portland, in particular, adds to the state’s charm with its rich history, artistic flair, and vibrant atmosphere. During our visit, we spent a day wandering Portland’s cobblestone streets, exploring art galleries, devouring freshly caught seafood, and watching lobstermen at work in the bustling harbor.

Over the next two days, we ventured on short road trips to the picturesque destinations of Kennebunkport, Cape Elizabeth, and Sebago Lake. Despite being Maine’s largest city, with just over 66,000 residents, Portland retains a captivating 19th-century charm, especially in the impressive Old Port—the largest in New England. The greater Portland area, where most residents live, buzzes with vibrant shopping centers, art museums, and a lively nightlife.

Interestingly, Portland was the birthplace of national prohibition in 1851. However, today it boasts one of the highest numbers of bars per capita in the U.S., along with an abundance of breweries and distilleries. Besides enjoying drinks, Portland is renowned for its lobster rolls, which you can savor at top-notch restaurants or from the numerous food trucks dotting the city streets.

Portland, Maine Visitor’s Guide

Things to see and do in and around portland.

There are numerous exciting activities and attractions to enjoy in and around Portland, Maine. Here are some suggestions for a 3 day road trip through this stunning area of the United States:

Suggested Itinerary for Day One: Portland, Maine

Self-guided walking tour.

Once you’ve unpacked and settled into your digs, kick off your adventure with a Self-Guided Walking Tour using GPSMyCity . Just download the app, pick a tour (or create your own), and hit the streets at your own pace.

We crafted our own route through Old Port and Commercial Street, meandering along the cobblestones and then sauntering over to the waterfront. There, we soaked in the salty, fishy air and watched the fishermen’s lively antics on the docks. Of course, we couldn’t resist popping into charming boutiques, art galleries, and antique shops along the way—and indulging in a lobster roll or two!

Paid City Tours

If you don’t want to attempt seeing the sights on your own, check out these city tours provided by Viator .

Downtown Portland’s beating heart is the captivating Old Port, where cobblestone streets and historic warehouses create an enchanting vibe. This lively area boasts a smorgasbord of exceptional restaurants to tantalize your taste buds. Dive into the charm of the district by perusing the delightful array of quaint shops. Plus, if you’re itching to explore beyond the city limits, the Old Port offers easy access to ferry services ready to whisk you away to other captivating destinations in this stunning state.

Get a Lobster Roll at Luke’s Lobster

Sinking your teeth into a fresh Maine lobster is pure bliss, especially when it’s hugged by a buttery glaze and a hint of zesty lemon aioli, all snuggled in a warm, freshly baked roll. Luke’s Lobster , at the pier’s end in the quaint Old Port, is a real treasure. Don’t let the term “shack” fool you—Luke’s spreads across two floors, inviting you to relish their mouthwatering seafood while soaking in breathtaking views of the shimmering water.

Discover the Portland Museum of Art

Check out Maine’s vibrant art scene at the Portland Museum of Art! This treasure trove boasts an impressive collection of American and European masterpieces, showcasing works by renowned artists like Winslow Homer and Andrew Wyeth.

Enjoy the Portland Observatory

Climb to the top of the Portland Observatory, a historic maritime signal tower. Take in panoramic views of the city, harbor, and surrounding areas while learning about Portland’s maritime history.

Discover the Victoria Mansion

Visit the Victoria Mansion, an exquisite example of 19th-century architecture and design. Take a guided tour to admire the opulent interiors and learn about the mansion’s fascinating history.

Have Dinner at DiMillo’s on the Water

On our first night in Portland, we rendezvoused with friends at DiMillo’s on the Water , a unique floating restaurant with a fascinating history. Originally a car ferry back in 1941, this gem transformed into a restaurant in 1982. Its location offers stunning water views, adding to the charm of the dining experience.

We dove into some of the most delicious clam chowder, bursting with flavor. And of course, we couldn’t resist another round of their famous lobster rolls, loaded with juicy lobster and topped with a heavenly brown butter aioli, all nestled in a buttery brioche roll.

But fear not, non-seafood lovers! My husband Michael, a proud member of this club, opted for a burger and was pleasantly surprised by how juicy and perfectly cooked it was, satisfying his taste buds.

DiMillo’s is open Monday to Saturday from noon to 9 pm, ensuring plenty of opportunities to indulge in their scrumptious offerings.

Suggested Itinerary for Day Two: Day Trip to Sebago Lake

We’re incredibly lucky to have friends who spend their summers in the charming town of Raymond, nestled on the beautiful shores of Sebago Lake. Just a short, picturesque 45-minute drive from downtown Portland, this serene spot became our go-to destination when our friends kindly invited us to stay at their magnificent lakeside home.

Sebago Lake boasts the title of being the deepest and second largest lake in all of Maine. Its waters are exceptionally pristine and clear, making it a perfect spot for those brave enough to take a refreshing dip in its cool summer waters. The lake is also renowned among boating and fishing enthusiasts, offering endless opportunities for aquatic adventures. With two public boat launch sites, numerous campgrounds, and various recreational facilities dotting the lakeshore, Sebago Lake caters to the diverse interests of its visitors.

Go Fishing or Take a Leisurely Boat Ride

For those eager to dive into the tranquility and splendor of Sebago Lake, look no further than the Lake Sebago Marina ! This top-notch spot offers pontoon boat rentals, setting the stage for unforgettable adventures like fishing, swimming, or simply cruising the pristine waters of the lake.

Renting a pontoon boat from Lake Sebago Marina is the perfect way to explore the vast lake at your leisure. Whether you’re a keen angler looking to reel in the lake’s plentiful fish or a group of friends and family craving a refreshing swim in the crystal-clear waters, these versatile boats provide the perfect platform for your chosen activities.

Enjoy Jet Skiing, SUP or Sailing

For those who prefer a dose of speed and excitement over leisurely cruises, TP’s RAD Jet Ski Rentals is your go-to spot. They offer jet ski and jet boat rentals, perfect for thrill-seekers craving high-speed adventures on the water. And the best part? They’ll deliver the jet ski or jet boat right to your doorstep for a hassle-free experience. At the end of your exhilarating day, they’ll pick it up, leaving you with nothing but memories of your thrilling ride.

If you’re more into a relaxed day on the water, TP’s RAD Jet Ski Rentals also has kayak and stand-up paddle board rentals. These options let you soak in the tranquility of Sebago Lake, paddling at your own pace and exploring its peaceful corners.

For those dreaming of sailing or wanting to brush up on their sailing skills, Sebago Sailing is the place to be. As the sole sailboat school and rental facility on Sebago Lake for over 20 years, Sebago Sailing is committed to providing top-notch sailing instruction and rental services.

If you’re ready to swap your water wings for golf clubs, Point Sebago Golf Course is calling your name! This course is not just a run-of-the-mill fairway; it’s a slice of golfing paradise. Nestled in a 500-acre forest, this 18-hole, par-72 championship course offers stunning views and a memorable round of golf.

Eat Some “Moose Tracks”

When it comes to ice cream, the Mosquito Ice Cream Shop in Raymond really knows how to make your taste buds dance! Their Moose Tracks flavor is a legendary mix of creamy fudge and peanut butter cups that will have you screaming for more. And let’s talk portions—these scoops are so generous, it’s like getting a hug from your dessert. Plus, the staff is as sweet as the treats they serve. Just remember, when winter rolls around, Mosquito takes a break to hibernate, so get your fix before September hits!

Suggested Itinerary for Day Three: Day Trip to Cape Elizabeth & Kennebunkport

On day three of our Portland escapade, we hit the road in our trusty rental car, heading south to the delightful duo of Cape Elizabeth and Kennebunkport. The drive to Cape Elizabeth was a breezy 20 minutes, where we were welcomed by the stunning coastal views. After savoring the sights of Cape Elizabeth, we cruised on for another 50 minutes to reach the charming town of Kennebunkport.

Cape Elizabeth

Just a quick 20-minute drive south of Portland, Cape Elizabeth awaits with its charming blend of rolling hills, sandy beaches, and, of course, those iconic lighthouses that give the town its unique flair. As you wind your way through the picturesque countryside, you’ll feel the stress of the city melt away, replaced by a sense of calm and wonder. When you finally hit the coast, you’ll be greeted by expansive beaches and the soothing sounds of the ocean waves crashing against the shore. But it’s the lighthouses that really steal the show here. From the historic Portland Head Light to the twin beacons of Two Lights State Park, these towering structures are more than just navigational aids—they’re symbols of a bygone era, standing tall against the test of time.

Springpoint Ledge Lighthouse

We made a stop at the Spring Point Ledge Lighthouse in South Portland on our way to Cape Elizabeth. This working lighthouse has stood at the end of a 950-foot jetty in Casco Bay since 1897. Tours of the lighthouse are available in person ,   

Portland Head Light & Fort Williams Park

Portland Head Light, the grand dame of Maine’s lighthouses, has a charm that’s simply irresistible—no wonder it’s the world’s most photographed beacon! Perched majestically on the cliffs, it offers breathtaking views of the rugged coastline, perfect for your next Instagram post.

While you can’t peek inside the lighthouse, Fort Williams Park has plenty to keep you entertained. For just a couple of bucks, you can park your car and explore over 90 acres of picnicking spots, hiking trails, and cliffside walks. Don’t forget to check out the playgrounds for some fun and games!

And let’s not forget about the food. Treat yourself to a mouthwatering lobster roll or a scoop of gelato from one of the park’s quaint eateries. As you munch away, soak in the stunning views and the peaceful vibe of the park.

Kennebunkport

Our adventure took us to the delightful coastal town of Kennebunkport, the epitome of charming Maine. With its sandy beaches and abundance of lobster shacks, this town screams coastal New England charm.

As we arrived, we were immediately taken in by the town’s cozy and welcoming vibe. The beaches beckoned us to take a leisurely stroll, the crashing waves providing the perfect soundtrack to our seaside explorations.

But let’s talk about the lobster shacks—these places were a seafood lover’s dream come true! From classic lobster rolls to lavish lobster feasts, every dish was bursting with the freshest, most flavorful lobster you can imagine.

Colony Beach

After a quick drive through town, we decided to stretch our legs with a leisurely stroll along Colony Beach, also known as Arundel Beach. Tucked between a jetty and some large rocks, this little slice of coastal heaven is what’s known as a pocket beach.

As we ambled along the shoreline, we were mesmerized by the natural beauty all around us. The beach’s idyllic setting, with the waves gently lapping at the shore, created a peaceful vibe that practically begged us to relax and soak it all in.

Colony Beach even has a free parking lot, making it super convenient to access this hidden gem. Just be aware that there aren’t any restroom facilities on-site, so plan accordingly!

Mabel’s Lobster Claw

After our beach stroll, our rumbling bellies led us straight to Mabel’s Lobster Claw , where we dove into even more scrumptious fresh lobster. This place is a Bush family favorite, and it’s easy to see why!

At Mabel’s, we could dine indoors or outdoors, soaking up the lively vibes of this iconic spot. Or, if we were feeling adventurous, we could hit up the walk-up window and enjoy our meal on the move or find a scenic spot to chow down.

Mabel’s dedication to top-notch food was evident in every bite. Their menu, bursting with a variety of mouthwatering seafood dishes, truly captured the essence of Maine’s coastal cuisine. And with Mabel’s open every day for lunch and dinner (except Tuesdays), we were spoiled for choice when it came to satisfying our lobster cravings!

Things to Do With an Extra Day in Portland

If you still have a little time left and need a few more things to do, check out these awesome adventures:

Attend a Brewery Tour

Portland is known for its thriving craft beer scene. Join a brewery tour and sample a wide array of local brews while learning about the brewing process and the city’s beer culture. Here are a few suggestions:

• Best of Portland Spirits and Brewery Bus Tour : Embark on a captivating 3.5-hour small-group tour that will take you on a delightful journey through Portland’s thriving craft alcohol scene. This immersive experience allows you to explore two breweries and a meadery while sampling a flight of delectable brews and gaining insider knowledge about Maine’s cutting-edge craft brewing.
• Pubs of Portland : Uncover the captivating allure of Portland, Maine, a city that is quietly emerging as one of the most enticing destinations for beer enthusiasts. Embark on a half-day tour that will take you to three exceptional breweries: Fore River Brewing Company, Maine Mead Works, and Lone Pine Brewing.
• Portland Beer Discovery Evening Brewery Tour : Spend the evening in the company of a guide learning about Portland’s beer scene. You’ll taste several samples, munch on vegetarian snacks and hear commentary about the history of brewing in the city.

Take a Casco Bay Cruise

Embark on a scenic cruise around Casco Bay , departing from Portland’s waterfront. Enjoy breathtaking views of the islands, lighthouses, and picturesque coastal landscapes. Some cruises also offer lobster boat tours or visits to historic forts.

Explore Peaks Island

Take a short ferry ride from Portland to Peaks Island, a tranquil retreat with picturesque beaches, hiking trails, and charming neighborhoods. Rent a bike or golf cart to explore the island at your own pace.

Top Tours in and Around Portland

Tall Ship Cruise on Casco Bay

Old Port Culinary Walking Tour

The Real Portland Tour:  City & 3 Lighthouses with a Local

Private Sunset Charter on Vintage Lobster Boat

Best of Maine Private Full Day Tour

See all Viator Tours for Portland and the surrounding area.

Annual Festivals and Events

Plan a trip around one of Portland’s annual festivals and events .

Best Time to Visit Portland Maine

The best time to visit Portland, Maine, depends on what you’re after! If you’re all about sunshine and outdoor adventures, aim for the summer months from June to August. You’ll soak up the warm weather, enjoy festivals like the Old Port Festival, and indulge in all the lobster rolls you can handle. For those who prefer cooler temps and colorful foliage, fall (September to November) is your jam. The city transforms into a picturesque autumn wonderland, perfect for scenic drives and cozy sweater weather. Winter (December to February) brings a magical vibe with holiday lights and winter sports like skiing and ice skating. Just bundle up! And if you’re a fan of crisp air and blooming flowers, spring (March to May) is ideal for exploring the city’s parks and gardens as they come to life. Whatever the season, Portland’s charm and delicious food scene never disappoint!

How Long Should You Spend in Portland, Maine

Although this itinerary is designed for 3 days, it’s important to note that extending the road trip to 4 or 5 days would allow for a more leisurely and immersive experience. While the 3-day timeframe offers a glimpse of the Portland, Maine highlights, such as Sebago Lake, Cape Elizabeth, and Kennebunkport, a longer duration provides the opportunity to fully embrace the local culture, engage in outdoor activities, and savor the culinary delights that define each destination along the way.

Is Portland Safe?

Portland, Maine is generally considered a safe city to visit.

Estimated Budget

A moderate daily budget for a visit to Portland, Maine would range from $100 to $200 per person, excluding accommodation. However, this estimate can vary based on personal preferences and the specific activities and dining choices you make during your trip.

How to Get to Portland

The Portland International Jetport (PWM) is only about 10 minutes away from downtown Portland.  

To get from the airport to downtown, you can rent a car, take a shared or private airport shuttle or take an Uber.  Also, you may want to check with your hotel to see if they are one of the many hotels in Portland that provide free shuttle service to and from the airport.

See how to get the best deals on flights .

Getting Around Portland

Getting around Portland, Maine is relatively easy and convenient. Here are some transportation options available:

• Walking: Portland’s downtown area is compact and pedestrian-friendly, making it an ideal city to explore on foot. Many attractions, restaurants, and shops are within walking distance of each other. Download a map of the city here.
• Bicycles: Portland has a bike-friendly infrastructure with bike lanes and dedicated paths. You can rent bicycles from several bike rental shops in the city, offering hourly or daily rentals. There are also bike-sharing programs available , such as the popular Tandem Mobility bike-sharing system.
• Public Transportation: The METRO Bus system operates throughout the Greater Portland area, including downtown Portland. It provides an affordable and convenient way to travel within the city and to neighboring towns. You can check the METRO Bus website for routes, schedules, and fare information.
• Taxis and Rideshares: Taxis and rideshare services like Uber and Lyft are available in Portland. You can easily hail a taxi or book a ride using a rideshare app on your smartphone.
• Car Rentals : Although you won’t need a car in the city itself, you will need one to explore outside of the city. Several car rental companies have offices located at the Portland International Jetport and throughout the city. See my tips and tricks for renting a car .
• Ferries : The Casco Bay Lines operates ferry services that connect Portland to several nearby islands, including Peaks Island, Great Diamond Island, and Little Diamond Island. These scenic ferry rides offer an alternative mode of transportation and allow you to explore the picturesque islands.

Parking is available in downtown Portland, but it can be limited and sometimes expensive. It’s recommended to check for public parking lots or garages and be aware of any parking regulations or restrictions.

Where to Stay in Portland

Portland, Maine offers a range of accommodation options to suit different preferences and budgets. Here are some popular areas to consider when choosing where to stay in Portland:

• Old Port : The Old Port district is the historic heart of Portland and a vibrant area with cobblestone streets, charming brick buildings, and a lively atmosphere. It’s a popular choice for visitors due to its proximity to restaurants, bars, shops, and waterfront attractions. Staying in the Old Port puts you in the midst of the city’s bustling energy.
• Downtown : Downtown Portland offers a mix of hotels, boutique accommodations, and bed and breakfasts. This area provides easy access to the city’s amenities and attractions, including the arts district, museums, and theaters. It’s a convenient location for exploring the city on foot and accessing public transportation.
• West End: The West End is a residential neighborhood known for its Victorian architecture, tree-lined streets, and a quieter atmosphere compared to the bustling downtown area. This area offers a more residential feel while still being within walking distance to the downtown attractions.
• Waterfront : If you prefer waterfront views and being close to the harbor, consider staying in the waterfront area. There are hotels and inns along the waterfront that offer beautiful views and easy access to activities like boat tours, waterfront dining, and shopping.
• Arts District : Portland’s Arts District is home to galleries, theaters, music venues, and a thriving arts scene. Staying in this area allows you to immerse yourself in the city’s cultural offerings and be within walking distance of the Portland Museum of Art and other artistic attractions.

Get the best deal on accommodations in and around Portland by going to Booking.com .  See my post on finding and booking accommodations .

Traveling With Pets?

Pet friendly hotels in portland.

If you’re traveling with a pet and looking for pet-friendly hotels in Portland, Maine, there are several options available. Here are a few pet-friendly hotels in the area:

• Residence Inn Portland Downtown/Waterfront : This hotel welcomes pets and offers pet-friendly rooms. There may be additional fees for bringing pets, so it’s best to check with the hotel beforehand.
• Hilton Garden Inn Portland Downtown Waterfront : This hotel allows pets and offers designated pet-friendly rooms. Additional charges and restrictions may apply, so it’s recommended to contact the hotel in advance.
• Embassy Suites by Hilton Portland Maine : This hotel is pet-friendly and accommodates pets for an additional fee. It’s advisable to check the hotel’s pet policy and any restrictions before making a reservation.
• Hyatt Place Portland-Old Port : This hotel allows pets for a fee. Make sure to inquire about their specific pet policies and any size or breed restrictions.
• La Quinta Inn & Suites by Wyndham Portland : This hotel is pet-friendly and typically allows pets to stay without any additional fees. However, it’s always recommended to confirm the hotel’s pet policy before booking.

Pet Friendly Beaches and Parks in Portland

Portland, Maine offers some pet-friendly beaches and parks where you can enjoy outdoor activities with your furry friend. Here are a few options:

• East End Beach: Located on the Eastern Promenade, East End Beach is a popular spot for both locals and visitors. Dogs are allowed off-leash from October 1st to April 30th, and on-leash from May 1st to September 30th.
• Willard Beach: Situated in South Portland, just across the Casco Bay Bridge from Portland, Willard Beach is a lovely sandy beach that allows dogs on-leash throughout the year. It’s a great place to take your pet for a leisurely walk along the shore.
• Quarry Run Dog Park: This fenced-in dog park is located on Park Avenue in Portland. It provides a safe and designated space for dogs to play and socialize off-leash. The park is open daily and is a popular spot for local dog owners.
• Baxter Woods: Baxter Woods is a wooded park in Portland that allows dogs on-leash. It features walking trails where you can take your pet for a stroll amidst nature.
• Payson Park: Payson Park is another green space in Portland that welcomes leashed dogs. It has open fields, walking paths, and picnic areas where you can enjoy outdoor activities with your pet.

Pet Friendly Restaurants in Portland

Portland, Maine offers several pet-friendly restaurants where you can dine with your furry companion. Here are a few options:

• The Thirsty Pig : This hot dog and craft beer joint has a pet-friendly outdoor seating area where you can enjoy delicious sausages and a wide selection of local beers with your canine companion.
• The Holy Donut : Known for their unique and tasty potato-based donuts, The Holy Donut has an outdoor seating area that is pet-friendly. Treat yourself to some sweet treats while your pet relaxes by your side.
• Bayside Bowl : Bayside Bowl is a fun and vibrant spot that combines bowling, food, and drinks. They have an outdoor patio where dogs are welcome, so you can enjoy a meal or drinks with your four-legged friend.
• The Porthole Restaurant & Pub : Situated right on the waterfront, The Porthole offers scenic views and a pet-friendly deck where you can enjoy seafood dishes and drinks while overlooking the harbor.

Watch These Popular TV Shows and Movies Filmed in Portland

Portland, Maine has served as the backdrop for several TV shows and movies over the years. Some notable productions filmed in and around Portland include:

• Storm of the Century” (1999): Although set in the fictional town of Little Tall Island, Maine, this TV miniseries filmed several scenes in and around Portland. The historic Portland Head Light and Fort Preble are among the recognizable locations featured in the series.
• “Wet Hot American Summer” (2001): This cult comedy film, starring an ensemble cast including Janeane Garofalo and Paul Rudd, was partially filmed in North Bridgton, Maine, which is a short drive from Portland.
• “Olive Kitteridge” (2014): Based on the Pulitzer Prize-winning novel by Elizabeth Strout, this miniseries starring Frances McDormand was set and filmed in various locations in Maine, including Portland.
• “The Sounding” (2017): This drama film, featuring a woman who refuses to speak and instead communicates through Shakespearean quotations, was shot in different locations in Maine, including Portland.
• “Murder in the First” (2014-2016): While not exclusively filmed in Portland, this crime drama series, starring Taye Diggs and Kathleen Robertson, was set in San Francisco but also included some scenes filmed in Portland.

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Report names portland the best city in the country for working from home.

The new report ranks Portland 7th in the entire world, based on several key criteria

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A lot of people got used to working from home during the COVID-19 pandemic and many people continue to work from home.

A new report from remote.com finds that Portland is the best city in the country to work from home in — and the seventh best in the entire world.

The report, titled The Best Destinations for Remote Work, looked at thousands of locations around the world and assessed them based on 25 series of data, spanning eight components:

• Internet Infrastructure
• Attractiveness ( a destination’s draw on visitors, which may include natural, urban, cultural, and any other type of attraction)
• Openness (a societal willingness to accept the other, as well as a degree of government transparency.
• Incentives for remote workers
• Cost of living
• Quality of life

The top destinations, according to the report, are:

• Madrid, Spain
• Madeira, Portugal
• Toronto, Canada
• Auckland, New Zealand
• Tokyo, Japan
• Paris, France
• Portland, Maine
• Taipei, Taiwan
• Stockholm, Sweden
• Reykjavik, Iceland

The next highest cities in the United States on the list are Honolulu, Hawaii, at 19; Des Moines, Iowa, at 20; New York City, at 21; and Concord, New Hampshire, at 21. Montpelier, Vermont, came in at 32 and Boston was 36.

The unemployment rate in Maine in February was 3.4 percent, the same as it has been since October 2023. According to the Maine Department of Labor, the labor force participation rate was 59.3 percent, and there were 656,200 nonfarm wage and salary jobs in the state, which was up 700 over the last month and 9,400 over the last year.

Jobs in health care and social assistance in Maine increased 6,000 over the year, accounting for close to two-thirds of net job growth, according to the Department of Labor.

For every unemployed person in Maine, there are two job openings, on average.