Portland, Maine Port Guide

Hop aboard for an authentic 1-hour and 45-minute sightseeing tour of Portland and three lighthouses, led by a guide born and raised in the city. Get an insider’s look at Portland's rich history, current happenings, and hidden gems that other tours often miss. Your guide, a college librarian, provides an informative and entertaining experience packed with little-known facts and a true Mainer's sense of humor.

Discover the wit and grit of the diverse people who built Portland on this walking tour featuring extraordinary stories often left out of history books. Stroll 1.5 miles through the historic Old Port, seeing where Indigenous Wabanaki leaders first met colonizers amidst beautiful Victorian-era buildings. Your locally-raised guide, Dugan Murphy, is Portland's top-rated guide on TripAdvisor and provides two hours of captivating narration.

Trace the steps of Black Portlanders who shaped Maine's history, from founding communities to driving maritime industries and overturning slavery. This 1.5-mile walking tour passes historic sites like storefronts that housed Black-owned businesses and aided the Underground Railroad. Enjoy two hours of enlightening narration from owner and guide Dugan Murphy, who was named Portland's #1 guide on TripAdvisor for his unique, well-researched stories.

Leave the crowds behind on a private 2-hour sightseeing charter aboard a vintage Maine Lobster Boat, culminating in a breathtaking sunset. Navigate through the islands of Casco Bay, passing historic 19th-century forts, iconic lighthouses, and the stunning Maine coastline. This personalized tour is perfect for small groups and families, and includes your first round of local beer or wine.

Skip the city and head straight to the coast on this dedicated tour of Maine’s best lighthouses. You will explore three iconic beacons, getting up-close views of their stunning architecture and scenic surroundings. This focused, relaxed tour is the perfect way to connect with the region's maritime past while soaking in the charm of Maine’s beautiful coastline.

Join this 'Walk Through Time' to learn about Portland's history with railroads, fires, wars, and famous poets since 1632. The tour travels through the historic Old Port, downtown, and waterfront areas, featuring locations like the Abyssinian Church and Henry Wadsworth-Longfellow's home. The duration is approximately two hours, based on the engagement and pace of the group.

Join a 3-hour tour that follows the scenic South Portland Greenbelt Pathway to visit three local lighthouses. Your journey includes stops at Portland Breakwater Light, also known as "Bug Light," Spring Point Ledge Light, and the famous Portland Head Light. The tour passes by Willard Beach, and it is recommended that you bring a lunch or purchase one from a local food truck.

Step aboard a vintage Maine Lobster Boat for a 100% private, 2-hour sightseeing charter for your group of up to six guests. Leave the crowds behind as you cruise through the islands of Casco Bay, passing four iconic lighthouses, historic 19th-century forts, and the stunning coastline. Perfect for families of all ages, this charter departs from the Old Port and includes your first round of local beer or wine.

Explore Portland’s diverse craft beverage scene, which extends beyond its famous breweries to include local spirits and wine. Sample unique creations like small-batch organic rum or wines blended with Maine wild blueberries and apples. The tour concludes at the Portland Beer Hub, where you’ll receive a 10% discount on additional draft and to-go purchases.

Embark on a full-day adventure from Portland to experience the beauty of Acadia and Bar Harbor. Your journey into one of Maine’s most scenic regions includes exploring rugged shorelines and panoramic summits, with two hours of free time in Bar Harbor to shop or dine. The trip also features scenic photo stops at the Fort Knox–Narrows Bridge Overlook and the famous red Victorian home of Stephen King in Bangor.

Immerse yourself in the natural beauty of Maine by capturing the moment in a painting. On this tour, you will hike to a scenic location to interpret and paint the landscape. No experience is necessary, as this class is designed for all skill levels, from complete beginners to more experienced painters.

Embark on an unforgettable boat tour of Casco Bay where nature, history, and beauty intertwine. Your journey includes views of majestic Fort Gorges and historic Fort Scammel, with the chance to disembark on Fort Gorges if the tide permits. You will also cruise by multiple iconic lighthouses, including the famous Portland Head Light, before looking for seals basking on the rocks.

Discover Portland in a unique way on this 50-minute sightseeing tour aboard a vintage fire engine. A knowledgeable local guide will help you relive the city's colorful history as you see lighthouses, Civil War forts, and historic buildings. This family-friendly adventure includes a multimedia experience packed with historic images of Maine.

Explore Portland's bustling inner harbor, Diamond Pass, and the main shipping channel on this boat tour. The route is designed to provide close-up views of historic Civil War era forts. You will also see as many as four lighthouses that have guided mariners into Portland Harbor for centuries.

Explore Portland's culinary culture, made up of talented artisan entrepreneurs from bakers and brewers to chefs. This tour combines social history and culinary education, narrated by friendly and engaging local guides who share the stories behind the food. You will visit 4-5 venues to enjoy a mix of Maine-inspired fare, providing plenty for lunch and ending with a sweet treat.

Embark on a fully narrated, 60-minute scenic cruise through busy Casco Bay and its innermost islands. The tour offers views of lighthouses, forts, lobster boats, and wildlife such as seals and seabirds. You'll see as many as four lighthouses, including a close-up view of Portland Head Light, Maine’s oldest and most photographed beacon.

Discover why Portland is known for its amazing donuts on this dedicated tasting tour. You will sample creations from the city's best shops, including local favorites and the chance to skip the line at the famous Holy Donut. While you indulge, your guide will share stories of the city's history and Maine's connection to the invention of the donut.

Discover Portland and the shores of Casco Bay by bicycle on this tour featuring the Maine coast, lighthouses, and local history. Although it is called the 5 lighthouse tour, groups will generally see four iconic beacons, including Bug Light and the famous Portland Head Light. After your ride, enjoy an included lunch provided by the award-winning 'Bite into Maine' food truck.

Relax and unwind on a 105-minute cruise around the inner islands and lighthouses of Casco Bay at dusk. Enjoy the evening breezes and sparkling city lights on this fully narrated tour. This cruise is a great way to end a hectic day of sightseeing or to begin a romantic evening.

Board the Elizabeth Grace for an exclusive experience visiting Portland Harbor's imposing 19th-century stone fortresses. This one-of-a-kind tour features a private visit to Fort Scammel, the only fort in the harbor to see active combat and a site not easily accessible to the public. Along the way, you’ll cruise past other great sights like iconic lighthouses, but please note this tour has a four-person minimum to operate.