Sailing Trips in Portland
Top 10 Best Portland Sailing Trips
Found 9 Sailing Trips activities in Portland. Sort by Popularity.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... More

Sunset Windjammer Cruise Along the Coast of Portland Maine
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Portland
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Superb77 reviews4.8
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....
Afternoon 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 win... More

Afternoon Windjammer Cruise Along the Coast of Portland Maine
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Portland
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Superb96 reviews4.6
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....
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

Portland Tall Ship Cruise on Casco Bay
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Portland
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Superb226 reviews4.6
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Casco Bay Morning Windjammer Sail
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. See Fort Gorges, Bug Li... More

Casco Bay Morning Windjammer Sail
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Portland
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Superb5 reviews5
Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the per....
Sunset Lighthouse Cruise Along Casco Bay
Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your fav... More

Sunset Lighthouse Cruise Along Casco Bay
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Portland
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Superb12 reviews5
Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four ....
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

Portland Tall Ship Private Charter on Casco Bay
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Portland
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Superb12 reviews5
What better way to see the delights than in the style of a private charter for you and five friends ....
Private Tour
Casco Bay: Private Afternoon Charter on Heart's Desire
This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John... More
Private Tour

Casco Bay: Private Afternoon Charter on Heart's Desire
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Portland
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Very Good1 review4
This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special ....
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

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
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Portland
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Very Good1 review4
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

2-Hour Private Morning Charter on Heart's Desire in Casco Bay
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Portland
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Very Good1 review4
Sail aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and fea....
Private Tour