Things to do in Portland, Maine

Our most recommended things to do in Portland, Maine

Portland: Old Port Culinary Walking Tour

1. Portland: Old Port Culinary Walking Tour

Enjoy this experience that showcases the culinary culture of Portland, Maine comprised of talented food and beverage artisans, from bakers and brewers to confectioners, chefs, and more. Visit the spots the locals enjoy visiting on a daily basis. Join a friendly and engaging tour guide as they take you to several Old Port and neighboring artisanal shops, restaurants, and pubs. You’ll sample a delectable mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods, and beverages.  Meet and greet culinary artisans along the way, learn what inspires them and how they got their start with a lively narration from your guide. Along the way, your guide will dish about the colorful, social, and culinary history unique to the “Port City” with lots of additional recommendations on how to dine and imbibe. You are sure to leave full of delicious food and local history. This experience works with gluten (not celiac), seafood, nut, and vegetarian dietary preferences and sensitivities to the best of our ability. Guests may pick and choose their participation for any further food issues. Your foodie experience may include: fresh-picked lobster, from-scratch confections, locally-sourced temaki (raw fish) roll, Maine seafood “chowdah”, iconic Maine craft beer, Maine honey wine, and dark chocolate truffles made with Aroostook County potatoes.

Portland, Maine: 2-Hour Guided History Tour

2. Portland, Maine: 2-Hour Guided History Tour

Meet your local guide, a history lover who will bring the stories and facts from Portland’s past alive throughout the tour. Starting on Commercial Street, walk through the cobble stone streets of the historic Old Port, downtown, and waterfront areas.  Some of the locations that may be featured as part of the tour include the lobster statue, the home of Henry Wadsworth-Longfellow, the Eastern cemetery, the Abyssinian Church, and more. Your tour will finish on a sweet note with a local treat.

Portland: Schooner Tall Ship Cruise on Casco Bay

3. Portland: Schooner Tall Ship Cruise on Casco Bay

Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at the ship's wheel if you feel inspired. Whether you're nine years old or 99, sailing aboard a Maine schooner is a unique adventure. Learn more about the wooden windjammers which are all listed on the National Register of Historic Places and were built in Maine.

Portland: Self-Guided Sightseeing Driving Audio Tour

4. Portland: Self-Guided Sightseeing Driving Audio Tour

Travel through the neighborhoods of Portland on a self-guided driving tour. Learn about the city’s history and culture from an audio-guided app on your smartphone and get panoramic views from the Eastern Promenade.  Start by downloading the app, which will function as your personal tour guide, audio tour, and map all in one. Once downloaded, your Portland tour begins at the Visit Portland Center. Drive down Commercial Street and hear about the industrial beginnings of the city. Along the way, you’ll see the wonderfully preserved Victoria Mansion, dating back to 1858. That’s followed by the even older Danforth Inn, which goes all the way back to 1823. As you drive up the Western Promenade, you’ll hear about some famous folks who were laid to rest in Portland, including the poet Henry Wadsworth Longfellow (a statue of whom you’ll see next, in Longfellow Square). Go to the Art District (perfect for picking up a souvenir), followed by a church that was once destroyed by the British.  Continue toward the shore, passing the site of an observatory that once guided ships into Portland’s occasionally treacherous harbor. Spot a couple of picturesque lighthouses perfect for any photo collection. Explore the Eastern Promenade, a 68-acre seaside park sporting plenty of unforgettable ocean views. You’ll see the strange and controversial “baked beans” building, before passing through Old Port again for a second chance to stop at one of the neighborhood’s many restaurants and boutiques. Pass by a statue of Portland’s own John Ford. Cross the Casco Bay Bridge into South Portland, home to a quieter community than its buzzing northern neighbor. Finally, you’ll arrive at Fort Williams Park, full of beauty and history. The tour concludes here.

Portland, Maine: Hidden Histories Downtown Walking Tour

5. Portland, Maine: Hidden Histories Downtown Walking Tour

Discover Portland's hidden histories on a guided walking tour of the Old Port, downtown, and the working waterfront. Marvel at images of the past and at the colorful storytelling your guide shares with you to make the past come alive. Hear stories only a local knows about the city's sights, streets, and buildings. Explore the Old Port, Portland's major public buildings, and the working waterfront, winding through intimate cobblestone streets along the way. See the city's charming red-brick buildings, its waterfront filled with seafood restaurants and sea views, and more. Learn fascinating anecdotes and facts about Portland, sharing them with friends down the line to show your newly-gained local knowledge. End your tour in a waterfront park, about a 5-minute walk from where you started, surrounded by boutiques, restaurants, and other activity opportunities to continue your own discovery of the city.

Portland, Maine: Local Brewery & Spirits Bus Tour

6. Portland, Maine: Local Brewery & Spirits Bus Tour

Satisfy your taste buds with a variety of brewery bus tour options of different breweries throughout greater Portland, Maine. Generous portions of alcohol products made at each different location are included, along with local snacks and an optional lunch. Beerunch Brewery Tour (3 Hours) Visit the famous Bissell Brothers Brewing before they open their doors to public, then travel to East Bayside to Belleflower Brewing for another exclusive visit before they open their doors to the public. The last stop is at Goodfire Brewing before being dropped off in downtown Portland, Maine. Drinks About Town: Brewery and Spirits Tour (3 Hours) This afternoon bus tour explores different craft alcohol products made in the city of Portland. Start at Shipyard Brewing Company for beer, then Après for hard seltzers and alcoholic ciders, and last Three of Strong Spirits for craft, high-quality rum. All tours end with drop-off at Old Port Spirits and Cigars, a perfect place to pick something up to indulge in later in the night after exploring lively downtown Portland.

Portland, Maine: Old Port Brewery Walking Tour

7. Portland, Maine: Old Port Brewery Walking Tour

Spend the day walking, talking, and tasting your way through the historic city of Portland, Maine. Led by a local guide, this 3-hour walking tour takes you through the interesting history of the city's beer culture. From becoming the birthplace of Prohibition in 1851 to establishing the first craft brewery in all of New England in 1983, Portland has a riveting story to tell.  Walk, Talk, & Taste (3 hours) Walk and talk with a local beer history guide through Portland's Old Port with tasting stops at Shipyard Brewing Company, Gritty McDuff’s, and Liquid Riot Bottling Company All tours end with drop-off at Old Port Spirits and Cigars, a perfect place to pick something up to indulge in later in the night after exploring lively downtown Portland.

Portland, Maine: Black History Guided Walking Tour

8. Portland, Maine: Black History Guided Walking Tour

Wind through the brick sidewalks and cobblestone streets of Portland's Old Port and working waterfront on this guided walking tour. Immerse yourself in the rich story of the Black community in the East End neighborhood. Meet your local guide at the First Parish Church, Portland's oldest church, and begin your journey back in time. Discover the monuments, places of business, and civic institutions where Black Yankees drove the economy and organized for political power. Head to the East End neighborhood to see the homes of Black sailors and stevedores that served as stations on the underground railroad. Admire the churches where Black families worshipped, celebrated, and learned together from the 19-century up to the present day. Learn how Maine's earliest colonial settlements could not have survived without Black insight, skill, and labor. Uncover the story behind the enslaved Black maid who abolished slavery in Maine during the Revolutionary War. Discover the exceptional figures who shaped Portland and the State of Maine over 400 years of Black history. Printed images of the past together with gifted storytelling will bring the past to life. Hear the stories that usually get left out of history tours. A portion of every ticket sale will help fund the restoration of the Abyssinian Meeting House, Maine's oldest and America's third-oldest standing Black church. End your tour at Eastern Cemetery, one-half mile from where it began.

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What people are saying about Portland, Maine

Overall rating

4.8 / 5

based on 57 reviews

One of the best tours ever! The guide was very knowledgeable and passionate about Portland and had lived there most of her life. Great value for the money. We went on a cold day but it didn’t feel cold on the tour at all. It seems that the best seats are towards the front and on the left side as you go up the rear steps because you will have a better view of the bay. The tour location was easy to find because it was the only fire engine parked on the main road in downtown Portland. We will go again the next time we are there.

I took my parents on this tour to get to experience Portland like a local and it did not disappoint! Our guide, Ross, was very knowledgeable in Portland’s history and even sang us a few ole’ Portland songs. We learned so much and had a wonderful time. The delicious cookie at the end of the tour was the icing on the cake. I highly recommend this tour if you’re in Portland for a few days visiting or even if you’re a Portland local…anyone can learn from this tour!

Really enjoyed learning about Portland. Easy to use. The directions were easy to follow.

Ross our tour guide was very knowledgeable and prepared. We enjoyed it…

Knowledgeable and informative presented with humor