Our most recommended things to do in Portland, Maine

Portland Maine: Tour in Vintage Fire Engine

1. Portland Maine: Tour in Vintage Fire Engine

Enjoy seeing Portland in an unforgettable way. Hop on board a vintage fire truck with onboard multimedia system, including a large, flat-screen LED TV. Experience Portland in a unique and fun way with this local-led tour aboard a classic fire engine. Explore the city’s peninsula as you drive along the cobble-stoned streets. Enjoy great views of lighthouses, civil war forts, and the historic architecture that make up the wonderful Maine city. Enjoy a 50-minute tour narrated by local guides who love sharing their knowledge of Portland Maine. Get to know the vibrant neighborhoods of this city by the sea from high up on your truck.

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

2. Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Enjoy a 1.5-hour cruise around the islands of Portland's Casco Bay. Pass historic lighthouses, early-19th century forts, and quaint fishing piers as you explore the area at sunset. Guests over 21 can enjoy 1 craft beer or hard seltzers per person. As you cruise, keep an eye out for seabirds and the occasional seal that call Maine's coast home. When the timing's right, the boat will turn its bow towards Portland so you can enjoy the sunset and the city's skyline from the water. GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Portland: Self-Guided Sightseeing Driving Audio Tour

3. Portland: Self-Guided Sightseeing Driving Audio Tour

Start by downloading the Action Tour Guide app, which will function as your personal tour guide, audio tour, and map. Purchase one tour per car, not per person. Everyone listens together! Note: This 10+mile-long tour covers the essentials of Portland in 1-2 hours. 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.  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: Old Port Culinary Walking Tour

4. 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: Hidden Histories Guided Walking Tour

5. Portland, Maine: Hidden Histories Guided 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. Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, on this tour you’ll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. Enjoy two hours to slow down and immerse yourself in the best Portland has to offer. 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. Entertainer-historian Dugan Murphy leads unforgettable jaunts through his hometown, telling an inclusive, empowering, and surprising constellation of tales you won't hear on other tours. Find out why Tripadvisor named him Portland's #1 tour guide!

Portland, Maine: 2-Hour Guided History Tour

6. 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: Maine Lighthouses Sightseeing Cruise with Drinks

7. Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Uncover the beauty of the Portland Harbor and Casco Bay aboard the Elizabeth Grace on this sightseeing cruise from Portland. Sail past iconic lighthouses, historic forts, and rocky islands while sipping on 1 complimentary alcoholic beverage. Hop aboard a comfortable and spacious ship at the Custom House Wharf. Take in views of the city's charming skyline as you embark on your cruise. Unwind with a delectable craft beverage in hand as you sail. Feel the wind in your hair as you cruise by lighthouses, 200-year-old forts, and rocky and stunning islands. Cruise with confidence knowing that the ship is regularly maintained to the highest safety standards. Keep an eye out for local wildlife like loons, black ducks, and buffleheads as you sail. Return to your starting point at the Custom House Wharf at the end of your cruise. GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Portland, Maine: Sunset Kayak Tour with a Guide

8. Portland, Maine: Sunset Kayak Tour with a Guide

The hour just before sunset is the best time to be paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enough along the waterfront or into the islands to enjoy a panoramic view of the sun setting over the city as we paddle back to the East End Beach. This two-hour tour is designed for paddlers of all experience levels -- including first-time kayakers.

Portland, Maine: Local Brewery & Spirits Bus Tour

9. 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: Walking Tour Audio Guide

10. Portland, Maine: Walking Tour Audio Guide

Start by downloading the Action Tour Guide app, which will function as your personal tour guide, audio tour, and map all in one. Purchase one tour per car, not per person. Everyone listens together! Note: This 3+mile-long tour covers the essentials of Portland in 1-2 hours. Once downloaded, your tour begins outside the Visit Portland Center. Here, you'll get your first introduction to Portland's intriguing history, from its dual founding to its reconstruction following the Great Fire. Walking down the city streets, you'll learn about the Burning of Portland, the landmark United States Custom House, and the only newspaper published at sea! You'll delve into the fascinating tales of the Portland Rum Riot and the city's history of conflagration, then journey back to the times of the Underground Railroad and the life of Daniel Colesworthy, a key abolitionist voice in Portland. Stepping into the world of the Wabanaki people, you'll also gain insight into Portland's original inhabitants. The next stop is the beautifully preserved Victoria Mansion, a symbol of the city's architectural wealth. After that is the equally grand Cathedral Church of St. Luke. Stroll by the Augusta Hunt House, take a moment to admire the statue at One Longfellow Square, and learn about the struggle for Women's Suffrage in Maine. Then, pick up some trendy souvenirs in the vibrant Art District! At the Maine Historical Society, explore the Wadsworth-Longfellow House, a reminder of the city's literary heritage. After that, lounge in the beautiful Lincoln Park as you hear the thrilling tale of the Battle of Portland Harbor. Finally, you’ll pass by the University of Maine School of Law, a striking building with a lot of history. Your tour concludes here, back in Old Port where you began.

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What people are saying about Portland, Maine

Overall rating

4.7 / 5

based on 278 reviews

Ross gave us an outstanding tour of Portland, combining his deep historical knowledge with a keen eye for good restaurants/bars, and is a genuinely interesting person. I cannot recommend a tour with him highly enough.

The tour was well worth it. Our guide, Ross, was very informative and interesting. We saw lots of things we would never have found on our own.

Guide was great. Very helpful and informative. Made the tour a lot of fun. Highly recommend.

Guide was great. Very informative and helpful. Made the tour a lot of fun.

Very knowledgeable and personable guide; enjoyed very much!