Portland, Maine: Sunset Windjammer Cruise Along the Coast
Sail through the waters of Casco Bay while experiencing Maine's historic craftsmanship (NOTE: This is not a narrated tour, but our crew is happy to answer any question...
Cruises and boat trips.
For the operators we researched and recommend, see our food tours and cooking classes in Portland, Maine, or the experiences overview.
On the water
Portland: Casco Bay Sunset and Lighthouse Cruise
Relax on the water in the evening glow with this Casco Bay sunset cruise from Portland. Travel through the Calendar Islands and feel the ocean breeze as you glide by p...
Portland: Best of Maine Lighthouse Scenic Cruise
Explore the sights and scenes of Casco Bay on a fully narrated scenic cruise. See major sights like Portland Head Light and Spring Point Ledge Lighthouse as well as lo...
Portland: Sightseeing Cruise to Portland Head Light
Climb aboard a spacious boat with indoor and outdoor seating and enjoy a fully-narrated cruise in Portland. Discover Casco Bay and see iconic lighthouses, forts, lobst...
Coastal Maine Day Sail Experience - Public & Private
Enjoy a scenic sail along rugged coastlines and charming harbors. Choose a shared public cruise or a private charter for a more personalized, relaxing experience on the water.
Portland: Private Powerboat Sunset Experience
Experience the magic of a Casco Bay sunset on our Private Extended Sunset Powerboat Cruise. This exclusive 4-hr adventure offers breathtaking views as the sky transfor...
Boothbay Harbor: Puffin & Wildlife Cruise
Embark on a narrated cruise to Eastern Egg Rock and see the puffin colony. Spot seals, blue herons, and other wildlife along the way.
Portland: Land and Sea Tour Duck Tour with a Guide
Step aboard an amphibious vehicle for a thrilling tour of Portland's top sites, exploring colonial districts and Victorian monuments before splashing into Casco Bay fo...
Portland: Schooner Tall Ship Cruise on Casco Bay
Soak in the views of Portland, Maine aboard a famous schooner tall ship. Cruise the rugged coastline of Casco Bay and catch sight of seals, lighthouses, and coastal wildlife.
Portland: Scenic Waterfront Boat Cruise - Public & Private
Experience the beauty of Maine’s rugged coastline on a relaxing powerboat cruise through Portland Harbor and Casco Bay. Cruise past historic forts, lighthouses, and ch...
Portland: Private Island Fort Tour
Pass iconic lighthouses on this sightseeing cruise from Portland to House Island and take a guided tour of the 17th-century Fort Scammel. Enjoy a refreshing alcoholic ...
Portland: Private Charter on Vintage Lobster Boat w/ Drinks
Cruise through Maine's picturesque Casco Bay aboard a vintage lobster boat. Soak up the breathtaking views of Portland's harbor, islands, and iconic lighthouses with a...
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Discover lighthouses perched atop rocky cliffs and on the shores of windswept islands on this sightseeing cruise from Portland, Maine. Relax with an alcoholic drink as...
Portland: Casco Bay Lighthouse Sunset Cruise
Embark on a beautiful evening cruise in Portland, Maine. Glide through the waters of Casco Bay to view the Portland Head Light, and Bug Light Park, complete with a bea...
Coastal Maine Sunset Sailing Experience - Public & Private
Sail along Maine's iconic coastline at sunset as skies glow over lighthouses and barrier islands. Choose a shared cruise or a private charter for a relaxing, unforgett...
Portland: Casco Bay Morning Lighthouse Cruise
Travel along the coast of Casco Bay and view lighthouses on a boat trip in Portland, Maine. Admire Portland Head Light, Bug Light Park, Spring Point Ledge Lighthouse, ...