Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 34Private Yacht for up to 30 People
This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a length of 50 feet, it can accommodate up to 30 guests. Renting the Carver 50 is the perfect option for a variety of events and cr... More

Private Yacht for up to 30 People
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North America
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Superb3 reviews5
This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a....
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

Private Sightseeing Charter in Frenchman Bay
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North America
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore t....
Private Tour
VIP Sailing Experience Puerto Vallarta
Choose between an afternoon stroll, a refreshing splash in the water or a sunbathing siesta with your toes in the sand. Ada Sailing provides masks, snorkels, fins and life jackets for children and adults. This tour is only availab... More
Private Tour

VIP Sailing Experience Puerto Vallarta
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North America
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Superb11 reviews5
Choose between an afternoon stroll, a refreshing splash in the water or a sunbathing siesta with you....
Private Tour
Private 2-Hour Wind and Wine Sunset Sail in Key West
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More
Private Tour

Private 2-Hour Wind and Wine Sunset Sail in Key West
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North America
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Superb81 reviews4.9
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from ....
Private Tour
Key West Wreckers Race Aboard Schooner America 2.0
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More
Private Tour

Key West Wreckers Race Aboard Schooner America 2.0
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North America
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Superb9 reviews4.9
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....
Private Tour
Banderas Bay Sailing adventure Private Sailboat
Join an unforgettable sailing experience led by a captain who has single handily crossed the Pacific 4 times! You’ll explore the breathtaking beauty of Banderas Bay in comfort and style aboard a 40 foot sloop. Private charter lu... More
Private Tour

Banderas Bay Sailing adventure Private Sailboat
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North America
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Superb9 reviews4.9
Join an unforgettable sailing experience led by a captain who has single handily crossed the Pacific....
Private Tour
Discover Maine's Coastal Charms: Half-Day Scenic Sail
Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day excursion. Traverse the serene waters of the Saco River and Saco Bay with its eight gorgeous islands as you uncover their hidden sec... More
Private Tour

Discover Maine's Coastal Charms: Half-Day Scenic Sail
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North America
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Superb3 reviews5
Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day ex....
Private Tour
Waikiki Boat Party Cruise with live DJ
Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, this exclusive 4-hour catamaran party cruise features an open bar with Vodka, Rum, Whiskey, Gin, Tequila, Champagne, Beer, plus Juice... More
Private Tour

Waikiki Boat Party Cruise with live DJ
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North America
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Superb3 reviews5
Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, thi....
Private Tour
Private Yacht for up to 12 People
Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip that you will enjoy like no other, you cannot miss its comfortable spaces while the beautiful colors of the sea and the sky make thos... More
Private Tour

Private Yacht for up to 12 People
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North America
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Superb3 reviews5
Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip tha....
Private Tour
Tall Ship Sailing Tour in Chicago with Fireworks Display
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely... More
Private Tour

Tall Ship Sailing Tour in Chicago with Fireworks Display
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North America
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Superb3 reviews5
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....
Private Tour
Sailing Trip to Dia Island - All Inclusive
Our qualified team brings years of experience and a deep passion for the art of sailing. We take immense joy in every moment spent on the open sea, and it is our pleasure to extend that feeling to our valued customers. Relaxation ... More
Private Tour

Sailing Trip to Dia Island - All Inclusive
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North America
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Superb3 reviews5
Our qualified team brings years of experience and a deep passion for the art of sailing. We take imm....
Private Tour
Basic Catamaran to Isla Mujeres from Cancun
Oceanix Isla Mujeres Essential Tour, a 6-hour trip full of fun, relaxation and unforgettable moments in the stunning Mexican Caribbean. Designed for those looking for the perfect combination of sailing excitement, unlimited drinks... More
Private Tour

Basic Catamaran to Isla Mujeres from Cancun
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North America
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Superb3 reviews5
Oceanix Isla Mujeres Essential Tour, a 6-hour trip full of fun, relaxation and unforgettable moments....
Private Tour