Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 3Sunset Catamaran Cruise in Ft. Lauderdale
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More
Sunset Catamaran Cruise in Ft. Lauderdale
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North America
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Superb695 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More
Day's End Cocktail Sunset Sail
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North America
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Superb77 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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North America
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Superb727 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
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 Sparrow and set sail in search of treasure! But wait it's no... More
Likely to Sell Out Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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North America
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Superb678 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
Private Luxury Yacht Charters, BYOB & Dolphins
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More
Private Tour
Likely to Sell Out Private Luxury Yacht Charters, BYOB & Dolphins
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North America
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Superb402 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
Private Tour
Key West Afternoon Reef Snorkeling with Open Bar
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More
Private Tour
Likely to Sell Out Key West Afternoon Reef Snorkeling with Open Bar
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North America
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Exellent435 reviews4.4
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Private Tour
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More
Private Tour
Likely to Sell Out Key West Sunset Sail Aboard Legendary Schooner Appledore
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North America
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Superb321 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
Sunset Sail Along the San Diego Skyline
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water. Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More
Private Tour
Likely to Sell Out Sunset Sail Along the San Diego Skyline
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North America
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Superb616 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
Private Tour
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Private Tour
Likely to Sell Out Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb829 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Private Tour
Half-Day Luxury Sailing Experience in Tulum with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Private Tour
Likely to Sell Out Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent255 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More
Private Tour
Likely to Sell Out Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
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North America
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Superb2,117 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Private Tour
Evening Colors Sunset Sail Tour in Seattle
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More
Private Tour
Likely to Sell Out Evening Colors Sunset Sail Tour in Seattle
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North America
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Superb594 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Private Tour
Likely to Sell Out Key West Dolphin and Snorkel Experience
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North America
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Exellent349 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Private Tour
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
Private Tour
Likely to Sell Out Waikoloa Signature Catamaran Sunset Sail
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North America
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Superb401 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
Private Tour
Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More
Private Tour
Likely to Sell Out Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
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North America
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Exellent299 reviews4.5
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....
Private Tour
Bimini or Grand Bahama Island by Ferry
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Florida! Picture this: pristine white beaches, crystal-clear turquoise waters, and tons of fun activities waiting for you. We'll pick... More
Private Tour
Likely to Sell Out Bimini or Grand Bahama Island by Ferry
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North America
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Good18 reviews3.5
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....
Private Tour
2-Hour Sunset Sail on the San Francisco Bay
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More
Private Tour
Likely to Sell Out 2-Hour Sunset Sail on the San Francisco Bay
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North America
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Superb399 reviews4.8
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Private Tour
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More
Private Tour
Likely to Sell Out Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
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North America
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Superb438 reviews4.6
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....
Private Tour
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More
Private Tour
Likely to Sell Out Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar
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North America
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Superb2,317 reviews4.8
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....
Private Tour
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More
Private Tour
Likely to Sell Out Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb732 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Private Tour