Sailing Trips in Maine
Top 10 Best Maine Sailing Trips
Found 13 Sailing Trips activities in Maine. Sort by Popularity.Portland Tall Ship Cruise on Casco Bay
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
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Portland Tall Ship Cruise on Casco Bay
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Maine
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Exellent222 reviews4.5
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
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2-Hour Windjammer Sailing Trip in Maine with Licensed Captain
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Maine
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Very Good389 reviews4
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
Windjammer Classic Sunset Sail from Camden, Maine
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More
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Windjammer Classic Sunset Sail from Camden, Maine
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Maine
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Superb332 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More
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Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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Maine
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Superb71 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Portland Tall Ship Private Charter on Casco Bay
What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. ... More
Private Tour
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Portland Tall Ship Private Charter on Casco Bay
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Maine
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Superb71 reviews4.6
What better way to see the delights than in the style of a private charter for you and five friends ....
Private Tour
Windjammer Classic Day Sail from Camden, Maine
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More
Private Tour
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Windjammer Classic Day Sail from Camden, Maine
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Maine
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Superb334 reviews4.7
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Private Tour
Schooner Eastwind Sunset Sail to see the Maine Coastline
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More
Private Tour
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Schooner Eastwind Sunset Sail to see the Maine Coastline
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Maine
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Exellent33 reviews4.5
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Private Tour
Luxury Catamaran Sailing Charters in Maine
Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Maine, and our luxurious yacht makes for a relaxing and fun experience. Our catamaran is stable and does not bounce in waves, providin... More
Private Tour
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Luxury Catamaran Sailing Charters in Maine
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Maine
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Superb85 reviews4.9
Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Main....
Private Tour
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More
Private Tour
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Schooner Applejack Sunset Sail Tour in Boothbay Harbor
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Maine
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Superb19 reviews4.9
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Private Tour
Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor
Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More
Private Tour
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Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor
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Maine
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Exellent20 reviews4.3
Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Private Tour
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 5... More
Private Tour
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2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
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Maine
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Exellent20 reviews4.3
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - com....
Private Tour
2-Hour Private Morning Charter on Heart's Desire in Casco Bay
Sail aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in ... More
Private Tour
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2-Hour Private Morning Charter on Heart's Desire in Casco Bay
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Maine
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Exellent20 reviews4.3
Sail aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and fea....
Private Tour
Private Sightseeing Charter in Frenchman Bay
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore the Porcupine Islands and Egg Rock. See beautiful views of Acadia National Park from the sea. Learn some history of coastal Maine a... More
Private Tour
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Private Sightseeing Charter in Frenchman Bay
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Maine
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore t....
Private Tour