Top Portland Cultural Tours

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation, or renting a car, on this guided tour of Portland's must-see sights. Stop in downtown Portland, and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.

This self-guided GPS audio walk brings you through one of the most beautiful vistas in Portland, Maine. It starts with a spectacular overlook of Portland Harbor, Casco Bay and the islands, and continues down by the waterfront to East End Beach. Along the way, you’ll hear stories from a local about what it was like growing up on Munjoy Hill and having access to the Eastern Prom. As you cross the railroad tracks, you’ll hear from the engineers that keep the historic steam engines running. Included are tips on what birds to look out for depending on the time of year. Put on a pair of headphones and start the tour by downloading the app. The audio plays automatically at exactly the right place using your smartphone’s GPS. This self-guided tour is narrated by Dianne Ballon - a sound artist, sound designer and an avid bird watcher. She invites you to discover through sight and sound the Eastern Promenade — a place she returns to in all seasons.

Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made her who she is today. Your locally-raised tour guide will captivate you with extraordinary, exciting, and surprising stories about the hardy folks who destroyed and rebuilt Portland time and again over 400 years while you stroll historic streets past spots you’ll surely want to come back to explore. We’ll see where Indigenous Wabanaki leaders made their earliest relationships with European colonizers and walk through the centuries in the historic Old Port and working waterfront. The Portland Hidden Histories Tour includes 2 hours of entertaining and enlightening historical narration over a 1.5-mile route through downtown Congress Street, the Old Port, and working waterfront along Commercial Street. Owner and guide, Dugan Murphy, takes guests to the most intriguing landmarks and presents an inclusive collection of hidden histories not included on other tours.

Running the factories or running for office, Portland women boldly shaped our city’s culture while continually moving the country toward equal rights. Hear stories of women who achieved remarkable things, like the Indigenous Penobscot performer who reframed immigration policy, the Chinese immigrant and laundress who won American Mother of the Year, the white tavern keeper who went up against the British Navy, and the enslaved Black maid who abolished slavery statewide. Experience the charm and depth of a city that was almost lost were it not for the impact of women’s collective energy and passion. Stories are told with heart, humor, and humanity by locally-raised and exceedingly-excited tour guide, Dugan Murphy. See museums, stately row houses, soaring churches, regal Federal-style mansions, and other landmarks on this 2-hour guided walking tour over 1.3 miles in Portland's Arts District and West End neighborhood.

Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.

Learn about Portland's history with this walking tour, which will take you through the Old Port, downtown, and waterfront areas. You'll see all sorts of historic attractions, including the home of Hendry Wadsworth-Longfellow, the Eastern Cemetery, and the Abyssinian Church, all with a professional guide on hand to share stories about the city's past.

See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.

Explore the Portland Peninsula by bike with this guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide takes you to the Old Port to see some of Portland's prettiest old brick buildings, and you learn the significance of local food, history and culture of this area.

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses and natural feature, and you're welcome to bring food and beverages, even the adult kind, on board.

Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.

Discover the lighthouses and coastal landmarks of Portland on a small-group biking tour. Hop on a provided bicycle and follow your guide to the Bug Light, Spring Point Ledge, and Portland Head lighthouses. Along the way, learn about their storied histories. Other highlights include the Liberty Ship Memorial, Cape Elizabeth, and Willard Beach. Set at a leisurely pace, the adventure also includes a complimentary lobster roll lunch at an award-winning food truck.

Welcome to Portland, Maine, a seaside city known for its architecture, marine industry, art, and bustling vibes. This in-app audio tour will walk you through the memorable sights of Portland, letting you explore the area at your own pace. Fall in love with Portland with your private self-guided audio tour. Take a historical stroll and find the first house made entirely of bricks. Look at the Romanesque, Shingle, and Colonial Revival architectural styles. Feel yourself in the paradise for foodies and craft beer lovers'. Get artistic touch and dive into the spirited atmosphere of the city. The mobile app helps you explore Downtown Portland with a private audio tour (included). Download tours in advance to listen without WiFi. The audio guide on the mobile app is the best way to enjoy the tour at your own pace. WeGoTrip app is available on the App Store and Google Play and works offline. Enjoy your party only!

Our Mellow two-hour tour of the coast of South Portland is designed to be accessible, low stress and friendly suited for all people, but especially those who want to take it slow and unwind on a bicycle.