Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 394 Sailing Trips activities in USA. Sort by Popularity. - Page 6Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More
Private Tour

Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun
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USA
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Superb54 reviews4.7
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....
Private Tour
Sunset Sail on Historic Schooner in Key West
Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I return, Bea and I will sail around the world!" Step foot on the gorgeous teak... More
Private Tour

Sunset Sail on Historic Schooner in Key West
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USA
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Superb96 reviews4.8
Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then ....
Private Tour
Private Key West Sandbar and Paddle by Boat
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More
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Private Key West Sandbar and Paddle by Boat
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USA
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Superb31 reviews4.9
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....
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

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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USA
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Superb22 reviews4.8
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Private Tour
Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More
Private Tour

Dolphin Adventure Sail in Cocoa Beach
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USA
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Superb130 reviews5
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....
Private Tour
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More
Private Tour

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
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USA
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Superb22 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Molokini Snorkel and Performance Sail from Ma'alaea Harbor
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More
Private Tour

Molokini Snorkel and Performance Sail from Ma'alaea Harbor
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USA
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Superb198 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Private Tour
Key West's Favorite Afternoon Dolphin Sail
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More
Private Tour

Key West's Favorite Afternoon Dolphin Sail
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USA
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Superb45 reviews4.8
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
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

Sunset Sail Cruise in Key West
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USA
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Superb213 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More
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Small Group Waikiki Sunset Sailing Tour
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USA
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Superb89 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Private Tour

2hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
Free Cancellation
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2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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USA
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Superb48 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
Free Cancellation
Private Tour
(Saving 10% )
Guided Snorkel + Morning Sail - Small Groups with Honest Eco
Guided Snorkel + Morning Sail • Winter Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows you the be... More
Private Tour

Guided Snorkel + Morning Sail - Small Groups with Honest Eco
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USA
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Superb10 reviews5
Guided Snorkel + Morning Sail • Winter Only with Small Groups on an Honest Eco Tour. What Makes....
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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USA
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Superb62 reviews5
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
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
Private Tour

1.5-Hour San Francisco Bay Sailing Tour
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USA
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Superb376 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
Private Tour
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
Private Tour

Windjammer Classic Sunset Sail from Camden, Maine
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USA
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Superb332 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Private Tour
2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More
Private Tour

2-Hour Oahu Sunset Catamaran Sail
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USA
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Superb101 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
Private Tour
Pau Hana Sunset Cruise with the Whales
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More
Private Tour

Pau Hana Sunset Cruise with the Whales
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USA
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Superb46 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
Private Tour
Oahu 3pm Tradewind Sail from Honolulu
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphins, whales and other sea life while getting as close as possible so you c... More
Private Tour

Oahu 3pm Tradewind Sail from Honolulu
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USA
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Superb226 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
Private Tour
New York City Sailboat Day Cruise to the Statue of Liberty
Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides a... More
Private Tour

New York City Sailboat Day Cruise to the Statue of Liberty
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USA
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Superb119 reviews4.9
Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted sc....
Private Tour
Key West Sailing & Snorkeling: A Reef 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
Private Tour

Key West Sailing & Snorkeling: A Reef Adventure
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USA
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Superb127 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Private Tour