Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 686 Sailing Trips activities in North America. Sort by Popularity. - Page 6BYOB Waikiki Sunset Swim and Diamond Head Sailing
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

BYOB Waikiki Sunset Swim and Diamond Head Sailing
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North America
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Superb154 reviews5
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
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North America
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Superb91 reviews4.6
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....
1.5-Hour San Francisco Bay Sailing Tour
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb382 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
New York City Sunset Jazz Sail aboard Clipper City
Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantage point of the harbor. Order a drink from our full bar as we raise canvas and leave Manhattan behind as the melodies of live jazz ... More

New York City Sunset Jazz Sail aboard Clipper City
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North America
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Exellent102 reviews4.4
Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantag....
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

Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb342 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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North America
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Superb222 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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North America
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Superb30 reviews4.8
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

Day Sail from Traverse City with Food, Wine, & Cocktails
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North America
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Superb129 reviews4.9
For a full description please visit our website at https://www.winddancertc.com/ where you can learn....
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Dagger and set sail in search of treasure! But wait it's not... More

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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North America
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Superb650 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
Wrightsville Beach Sunset Cocktail Sail
Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while you cruise our local waterways and watch the sunset. Wind permitting, we'll turn off the engines and enjoy the beauty of sailing!... More

Wrightsville Beach Sunset Cocktail Sail
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North America
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Superb5 reviews5
Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while....
Newport Sunset Sail on Schooner Adirondack
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailbo... More

Newport Sunset Sail on Schooner Adirondack
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North America
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Superb40 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Key West Reef Snorkel & Sail Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Key West Reef Snorkel & Sail Adventure
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North America
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Superb515 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Sailing Experience on a 50’ sailboat
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Sailing Experience on a 50’ sailboat
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North America
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Superb72 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Sunset Catamaran Sail in Cocoa Beach
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Florida�... More

Sunset Catamaran Sail in Cocoa Beach
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North America
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Superb146 reviews5
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private Yacht Tour Miami
Discover the vibrant allure of Miami from the luxurious vantage point of our yacht tours. Embark on a journey where turquoise waters meet golden shores, with panoramic views of iconic landmarks like South Beach and the Miami skyli... More
Private Tour

Private Yacht Tour Miami
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North America
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Very Good6 reviews4
Discover the vibrant allure of Miami from the luxurious vantage point of our yacht tours. Embark on ....
Private Tour
Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More
Private Tour

Classic Key West Schooner Sunset Sail with Full Open Bar
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North America
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Superb128 reviews5
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
Tall Ship Silva Sailing Cruise Ft. a Live Musician
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More
Private Tour

Tall Ship Silva Sailing Cruise Ft. a Live Musician
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North America
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Exellent205 reviews4.1
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....
Private Tour
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More
Private Tour

Half-Day Deluxe Molokini Snorkel Excursion in Maui
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North America
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Superb80 reviews4.9
Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....
Private Tour
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore pristine beaches and beautiful sights while savoring fresh guacamole and a selection of delicious snacks. This pe... More
Private Tour

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb64 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
Private Tour
Private Guided Sunset and Dolphin Cruise up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Private Tour

Private Guided Sunset and Dolphin Cruise up to 6 Passengers
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North America
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Superb64 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour