Portland Head Light

Casco Bay

Fort Gorges

Victoria Mansion (Morse-Libby House)

Eastern Promenade

United States

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. 

Discover Portland City and Lighthouse Tour

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.

Harbor Lights and Sights Cruise

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. 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.

Sunset Windjammer Cruise Along the Coast of Portland Maine

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. 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.

Afternoon Windjammer Cruise Along the Coast of Portland Maine

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. 

Lighthouse Lovers Cruise in Portland

Portland

Embark on a 5-day road trip through Portland, Boston, Stowe, and Salem, discovering local gems, enjoying leisure & wellness activities, and exploring vibrant markets.

Ultimate New England Road Trip: Portland, Boston, Stowe, and Salem

Discover the vibrant city of Portland in 3 days. Immerse in its unique culture, visit iconic landmarks, and indulge in local cuisine.

Beautiful Portland: Exploring the City of Roses

Embark on a breathtaking road trip from Redwood Meadows to Grand Canyon West. Explore stunning parks, charming towns, and iconic landmarks.

Epic Road Trip: Redwood Meadows to Grand Canyon West

Embark on a thrilling 4-day road trip from Portland to Anaheim, exploring adventure, culture, and fun with the family.

4-Day Family Road Trip: Portland to Anaheim

Discover the vibrant arts scene, rich history, and stunning natural beauty of Portland and Ogunquit on this 5-day itinerary.

Exploring the Best of Portland and Ogunquit in 5 Days

Experience the best of California's main attractions, nature, and food & drink on this 7-day road trip from San Francisco to Los Angeles.

California Road Trip: San Francisco to Los Angeles

Embark on a 3-day road trip through the Pacific Northwest, visiting Portland, New Boston, and Wilmington.

Pacific Northwest Road Trip: Exploring the Natural Wonders

Embark on a thrilling 4-day adventure exploring the best of New York City, Orlando, and Portland.

4-Day Adventure in New York City, Orlando, and Portland

Embark on a scenic road trip through Oregon, exploring Portland, Bandon, Cannon Beach, Diamond Lake, and Umpqua.

Ultimate Oregon Road Trip: Portland to Umpqua in 7 Days

Experience the best of adventure, culture, and natural beauty in New York, Portland, Boston, and Philadelphia.

Portland

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