Top Portland How to Get Around

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 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.

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.

Visit the top sights of the Columbia Gorge and Mount Hood on this guided tour. You'll stop to take in the views at the historic Vista House, spend time exploring Latourell Falls, Horsetail Falls, Wakheena Falls, and famous Multnomah Falls--and that's all before lunch. You'll also get to take a drive through the Fruit Loop apple-growing area and Mount Hood's Timberline Lodge before returning to Portland.

With our Kayak rental, you can explore the natural beauty of Sebago Lake (on your own) and adjacent streams to spot native birds, fish, turtles, ducks, and the picturesque views of this Maine lake.

Hop aboard a vintage fire engine for this short sightseeing tour of Portland. You'll drive past some of the city's most beautiful sites, including its old lighthouses and pretty buildings. A knowledgeable guide will be onboard to narrate the tour, while photographs provided by the Maine Historical Society will play on a large flat-screen TV!

Spend three hours kayaking through Casco Bay with this small-group tour led by a professional guide. You'll launch from Mere Point in Brunswick and paddle over to a couple of different islands, with the opportunity to see all sorts of marine birds, and maybe even a seal or two, along the way.

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.

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.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.