Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 3Sunset 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
Sunset Sail Along the San Diego Skyline
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North America
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Superb605 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
Luxury Whale Watch Cruise to The Arch Los Cabos
Whale season is from mid-December thru mid-April, you can book this tour all year round but to travel only during the Whale Season (Dec 15 thru April 15th). Enjoy 2 hours spectacular adventure looking for whales, who travel thousa... More
Luxury Whale Watch Cruise to The Arch Los Cabos
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North America
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Superb136 reviews4.6
Whale season is from mid-December thru mid-April, you can book this tour all year round but to trave....
Waikiki 2-Hour Sunset Sailing Catamaran – Splash & Sail Adventure
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More
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Waikiki 2-Hour Sunset Sailing Catamaran – Splash & Sail Adventu....
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North America
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Superb537 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
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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
Key West Sunset Sail Aboard Legendary Schooner Appledore
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North America
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Superb274 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Cabo San Lucas Sunset Sailing Shared Cruise
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More
Cabo San Lucas Sunset Sailing Shared Cruise
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North America
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Superb787 reviews4.9
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....
El Cielo Snorkel by Private Boat
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More
Private Tour
El Cielo Snorkel by Private Boat
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North America
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Superb342 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
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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Superb2,282 reviews4.8
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....
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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Superb399 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
Private Tour
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin at Pelican’s Rock, dive into crystal-clear waters filled with hun... More
Private Tour
Likely to Sell Out Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
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North America
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Superb817 reviews4.9
✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unfor....
Private Tour
2.5-Hour Small-Group Catamaran Sail with Drinks
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More
Private Tour
Likely to Sell Out 2.5-Hour Small-Group Catamaran Sail with Drinks
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North America
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Superb227 reviews4.9
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....
Private Tour
Small-Group San Diego Sunset Sailing Excursion
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More
Private Tour
Likely to Sell Out Small-Group San Diego Sunset Sailing Excursion
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North America
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Superb597 reviews4.9
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....
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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Exellent295 reviews4.5
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....
Private Tour
Southwest Florida Sunset Sail
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More
Private Tour
Likely to Sell Out Southwest Florida Sunset Sail
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North America
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Superb481 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
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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Exellent425 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
Buccaneer Pirate Cruise in Destin
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More
Private Tour
Likely to Sell Out Buccaneer Pirate Cruise in Destin
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North America
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Superb96 reviews4.9
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
Private Tour
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More
Private Tour
Likely to Sell Out Sunset Sail Cruise in Key West
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North America
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Superb263 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More
Private Tour
Likely to Sell Out Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
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North America
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Superb94 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Whale-Watching Pirate Ship Cruise in Los Cabos
Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in search of these amazing creatures. You will be accompanied by an experienced bilingual guide ... More
Private Tour
Likely to Sell Out Whale-Watching Pirate Ship Cruise in Los Cabos
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North America
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Superb117 reviews4.7
Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pa....
Private Tour
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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Superb397 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
Private Tour
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More
Private Tour
Likely to Sell Out Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Exellent158 reviews4.5
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Private Tour