Portland, Maine Tours & Activities in 2025

Portland , Maine

From $ 69.00

Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine. Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows! As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor. This is The Real Portland Tour! Check my website for a complete listing of tour days, times, and availability.

Portland , Maine

From $ 69.00

Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailors for centuries, each offering a chance to delve into their rich history. While most lighthouses aren’t open for tours, you’ll still get up-close views and plenty of opportunities to admire their stunning architecture and scenic surroundings. As you navigate through Portland’s picturesque coastline, you’ll be surrounded by breathtaking views that are as storied as they are beautiful. This focused, relaxed tour is the perfect way to connect with maritime past while soaking in the charm of Maine’s coastal landscape.

Portland , Maine

From $ 39.00

This 50-minute sightseeing tour is a fun and unique way to discover Portland, Maine. Board a Vintage Fire Engine and travel back in time as your knowledgeable guide helps relive Portland’s colorful history from a local’s perspective. See lighthouses, Civil War forts, city parks and buildings, interesting stories and a multimedia experience packed with historic images of Maine. This is one family-friendly tour you should not miss out on!

Portland , Maine

From $ 54.00

The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland peninsula. Towards the end of the tour, we make a 20-30 minute stop out at Portland Head Light in Cape Elizabeth.

Portland , Maine

From $ 54.00

Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that guide mariners into Portland Harbor.

Portland , Maine

From $ 48.99

Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commercial Street and continues for 2 hours through the historic Old Port, downtown and waterfront areas, sharing highlights of Portland's history since 1632. Some of the locations we may feature on your tour include; the lobster statue, the home of Henry Wadsworth-Longfellow and his place of worship, the Eastern Cemetery, the Abyssinian Church, the U.S. Customs House and more. ***Tour duration is two "ish" hours, based on guest engagement and pace of the group. Planning on 2.5 hours for arriving early to check-in and make it back to your vehicle post tour is recommended.

Portland , Maine

From $ 49.00

Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising stories largely left out of the history books. Get ready to broaden your sense of what Portland and Maine have been and could be. Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, we'll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. We’ll see where Indigenous Wabanaki leaders made their earliest relationships with European colonizers and walk together through the centuries. Enjoy an inclusive, empowering, and surprising constellation of tales that offers a welcome contrast to the more obvious themes you’re likely to experience on other tours. You'll enjoy 2 hours of narration over a 1.5-mile route with owner and guide, Dugan Murphy. He is Portland's top-rated guide on TripAdvisor!

Portland , Maine

From $ 159.99

- Portland's culinary culture is made up of many kinds of artisan food and beverage entrepreneurs from bakers, brewers and chefs to confectioners and more - wherever taste and creativity meet! - We combine a unique combination of social history, culinary education, the stories of talented entrepreneurs and current award-winning food scene narrated by friendly and engaging local guides - This tour visits 4-5 venues where you will enjoy a mix of Maine/Maine-inspired cultural, up-and-coming, and trending fare, plenty for lunch with a sweet treat to cap it off.

Portland , Maine

From $ 39.00

A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many as four lighthouses can be seen including a close up view of Portland Head Light, Maine’s oldest and most photographed lighthouse.

Portland , Maine

From $ 101.85

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.

Portland , Maine

From $ 39.00

The only tour of Portland on an open-air trolley, the Peek at Portland is a 60-minute, fully narrated tour of Portland's most famous sights and various neighborhoods that still leaves you plenty of time to explore the city further on your own.

Portland , Maine

From $ 65.00

Portland, Maine is known for its culinary scene, including amazing donuts. With this tour, you'll get to sample from the city's best donut shops, while also learning of Maine's connection to the invention of the donut and the city's history. Your tour guide will take you not only to the most famous of them all, The Holy Donut, to skip the line, but also to local favorites, that are equally delicious.

Portland , Maine

From $ 67.00

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Portland , Maine

From $ 159.99

Learn about Maine's most famous crustacean and the men and women who make their living from trap to table. Stroll along Portland's vital working waterfront , view lobster boats often unloading their catch and visit Old Port and waterfront district destinations for a progressive, iconic Maine lunch. - This walking tour is appx. 1 - 1.5 miles visiting local favorites with plenty of food, and food for thought - lots of time for Q/A. - There's always a whole lobster roll, a New England clam or seafood chowder, local craft beer (or soda) plus a whoopie pie or other Maine sweet, and a surprise seafood taste or two along the way. This is our most “classic heritage” Maine experience with a bit of modern flare.

Portland , Maine

From $ 49.00

Trace 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. You'll meet the Black Yankees who founded Maine communities, overturned slavery statewide, drove our maritime industries, gained political influence, crossed color boundaries, and expanded Mainers’ rights in the modern era. Stepping on granite cobblestones crooked with age — that once saw footfalls from national heroes like Frederick Douglass — you’ll pass storefronts once home to Black-owned barbershops where abolitionists whispered intelligence to Underground Railroad conductors. Enjoy 2 hours of entertaining and enlightening historical narration over a 1.5-mile route. Owner and guide, Dugan Murphy, dug through the archives to present an amazing constellation of stories left out of most tours. TripAdvisor named him Portland's #1 guide!

Portland , Maine

From $ 159.00

Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine coast, lighthouses, and Portland’s history. We have made some modifications to the 5 Lighthouse tour in response to COVID-19. We have modified the tour to allow us not to have guests in our vehicles. As a result of this change, guests will begin biking from the Ocean Gateway and return to the Ocean Gateway by bicycle.  Groups will generally see only 4 lighthouses (Bug Light, Spring Point, Portland Head Light, and Ram Island Ledge). Lunch will be provided by the award-winning "Bite into Maine" Food Truck