Portland Tours

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

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 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.

Maine is known for its seafood, and with this tour, you'll get to learn all about the industry, with the chance to sample some local delicacies along the way. You'll take a walk along the waterfront where lobster boats dock to unload their catches before heading out to a lunch of lobster rolls served with clam or seafood chowder and craft beer or soda pop.

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.

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 the magical Ecola State Park and gaze at stunning views of the rugged and lush Oregon coast. Revel in the misty coastal rainforests which abound with wild berries, ancient Sitka Spruce trees, dozens of species of ferns and lichens and myriad other exotic species! Stroll through the quaint coastal town of Cannon Beach, known for its long stretch of sandy beach, Haystack rock, art galleries and boutique shopping. Travel along scenic Highway 101 stopping at secluded beaches along the way and enjoy the hearty Oregon surfers who brave the mighty Pacific! Look for gray whales, sea lions, seals, rare seabirds (Tufted Puffins!), bald eagles, ospreys, majestic herds of Roosevelt Elk and countless other beautiful examples of exciting fauna (& flora) throughout the day from windswept basalt cliff perches. This tour includes snacks, beverages, luxury van transportation and a naturalist guide.

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.

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.

The Maine Donut Tour - Portland is Maine's ONLY donut tasting tour that provides skip the line access to all (3) Downtown donut shops, and the only guided access to sample (6) different flavors and/or styles of donuts, with access to flavors that often sell out.

Our 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble, before returning to the bike shop.

Explore the lighthouses of the South Portland Greenbelt Pathway by bicycle with this guided tour. You'll visit Bug Light, Point Ledge Light, and Portland Head Light with a local guide. You'll also have the chance to stop at a local food truck for a lunch of lobster rolls before returning to your starting point.

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.

See some of Maine's most picturesque scenery with this private tour from Portland. Your driver will pick you up at your hotel or vacation rental and take you out for a day of exploration, stopping by coastal towns, iconic lighthouses, viewpoints, and other areas of interest along the way.

Take a guided walk tracing the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality. Maine’s earliest settlements couldn’t have existed without Black labor, skill, and insight—and since those first moments, Black Yankees have agitated and organized to resist indignity and realize power. You'll meet the people who founded Maine communities, overturned slavery statewide, drove our maritime industries, gained political influence, founded houses of worship, crossed color boundaries, and expanded Mainers’ rights in the modern era. The Portland Black History Tour includes 2 hours of entertaining and enlightening historical narration over a 1.5-mile route through the Old Port and East End neighborhood. Owner and guide, Dugan Murphy, dug through piles of research and historic documents to present an amazing constellation of stories left out of most tours.

Combine a tour of Portland's lighthouses with a visit to the waterfront fish pier with this private tour. You'll visit Portland Head Light, the Spring Point Ledge Lighthouse, and Bug Light Park, with the chance to learn about the lobster industry at the waterfront fish pier once you are done.

Learn to paint while taking in Maine's natural beauty with this private painting class for all levels. Your instructor will meet you and your party and take you out to a beautiful, scenic spot within a 15-minute drive of Portland. Once you've arrived, your instructor will be on hand to teach you tricks for capturing the scenery in front of you.

Get to know Peaks Island on this cycling day trip from Portland. Traveling via bicycle means you're not trapped behind bus or car windows and you can really experienced the island air. Pedal around the island, stopping for lunch, with a small group; this group size ensures personalized attention from your guide and plenty of chances to ask questions.

Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay. Keep your eyes open for potential seal sightings, as well as the multiple lighthouses, islands, and forts you will see while cruising around. We will turn the bow toward Portland so you can take in a Maine sunset from the water and then cruise through Portland Harbor as the city’s nighttime skyline illuminates. You won’t find a more spectacular experience in Maine!

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.

Take in the famous autumn foliage of New England during a private 2.5-hour sightseeing cruise from Portland. With room for six people, it's an ideal intimate experience for couples, friends, or families. It’s also a great opportunity to photograph the leaves and wildlife from a unique perspective. Learn about the area from your private guide as you cruise at a gentle pace.

Spend two hours kayaking on Sebago Lake with this guided tour led by a professional guide, suitable for experienced kayakers and complete beginners. As you paddle along the gentle waters, your guide will tell you all about the local area. Expect to see all sorts of birds, fish, and turtles as you paddle against the backdrop of the setting sun.

Discover the beauty of Northwest Casco Bay on a 3-hour morning kayaking tour. No experience is necessary, as you get a crash course before the tour begins and your guide is on hand at all times. Double kayaks are available, if you prefer to paddle tandem. See Brunswick and its native wildlife from a unique vantage point. Then enjoy complimentary snacks and a brief land excursion, before your return.

Have you seen these iconic beacons from the water? Now is your chance! Board the Elizabeth Grace to cruise around Portland Harbor on this one of a kind sightseeing cruise. It is the perfect way to see the lighthouses, historic stone forts, and rocky islands that make Casco Bay a world-renowned destination. Relax with a drink as you take in the scenery!