Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 450 Sailing Trips activities in USA. Sort by Popularity. - Page 2Kauai’s Na Pali Coast Snorkel and Sail Tour
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More
Likely to Sell Out Kauai’s Na Pali Coast Snorkel and Sail Tour
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USA
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Superb566 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Likely to Sell Out Waikiki Sunset Boat Cruise
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USA
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Superb151 reviews4.9
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More
Likely to Sell Out Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
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USA
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Superb1,996 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
Waikiki Turtle Snorkeling Tour with Free Pickup
Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), sea scooters, and more—offeri... More
Likely to Sell Out Waikiki Turtle Snorkeling Tour with Free Pickup
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USA
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Superb192 reviews4.8
Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....
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
Likely to Sell Out 2.5-Hour Small-Group Catamaran Sail with Drinks
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USA
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Superb280 reviews5
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
Likely to Sell Out Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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USA
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Superb171 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
Likely to Sell Out Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
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USA
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Superb22 reviews4.8
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
Classic Tall Ship Cruise in Boston Harbor
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeata... More
Likely to Sell Out Classic Tall Ship Cruise in Boston Harbor
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USA
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Superb645 reviews4.7
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liber....
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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USA
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Superb412 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
Private Tour
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More
Private Tour
Likely to Sell Out 1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
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USA
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Exellent607 reviews4.1
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
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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USA
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Superb117 reviews4.8
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
Private Tour
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
Private Tour
Likely to Sell Out Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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USA
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Superb746 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
Private Tour
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More
Private Tour
Likely to Sell Out Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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USA
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Superb935 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
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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USA
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Superb832 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Private Tour
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
Private Tour
Likely to Sell Out Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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USA
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Superb117 reviews4.6
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Private Tour
'Alihilani Lahaina Sunset Sail
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More
Private Tour
Likely to Sell Out 'Alihilani Lahaina Sunset Sail
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USA
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Superb123 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Private Tour
Boston Harbor Sunset Sail Tour
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More
Private Tour
Likely to Sell Out Boston Harbor Sunset Sail Tour
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USA
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Superb142 reviews4.8
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Private Tour
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Private Tour
Likely to Sell Out Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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USA
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Superb1,443 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Private Tour
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
Private Tour
Likely to Sell Out Newport Sunset Sail on Schooner Adirondack
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USA
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Superb90 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
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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USA
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Exellent453 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