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.... More

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, do... More

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a ... More

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 sto... More

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise through the islands of Casco Bay, passing four iconic lighthouses, hi... More

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 stori... More

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 wa... More

Our 3-Hour tour leaves at 11:00 am and follows the scenic South Portland Greenbelt Pathway to three local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will ... More

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... More

Private Casco Bay Cruise – Up to 5 Guests Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves,... More

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses and our unique 14-passenger RIB b... More

As we cruise the waters around Portland Harbor we will make stops at Portland Breakwater Light, Spring Point Light and Ram Island Ledge Light before stopping at Maine’s oldest and most iconic lighthouse, Portland Headlight. This... More

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking Maine sunset. We’ll navigate through the islands of Casco Bay, pas... More

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 wil... More

Embark on an exclusive private tour of Maine's enchanting central coast and starting in the vibrant city of Portland. In just one day, immerse yourself in the region's finest highlights. Led by knowledgeable local guides, our priv... More

Set off on a refined culinary adventure through the serene waters of Casco Bay. Your journey begins at Portland Beer Hub, where you’ll gather before being escorted to the waterfront to board your boat. As you glide past the stun... More

Escape the crowds and embrace adventure with a cruise aboard our classic motor yacht, the Calista Ann! Whether you're a seasoned sailor or a first-timer, our Coast Guard certified professional captains will ensure an unforgettable... More

Step back in time and immerse yourself in the rich history of Portland, Maine, with this engaging walking tour through the heart of the city. Your expert guide will lead you through Portland’s charming streets, sharing stories o... More

The most immersive way to see Historic Portland is on foot. Our 60-minute walking tour takes you down the cobblestone pathways of our historic city in search of spirits that linger from times long past. Our knowledgeable guides w... More

Discover the best of Portland’s vibrant wine scene with the Portland Walking Wine Tour. Perfect for wine lovers and curious explorers alike, this leisurely walking tour takes you through the city’s charming streets to three ha... More