Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 408 Sailing Trips activities in USA. Sort by Popularity. - Page 20San Diego Private Morning Sail up to 12 guests
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More
Private Tour

San Diego Private Morning Sail up to 12 guests
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USA
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Superb29 reviews5
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....
Private Tour
NY Yacht Cruise with High Couture Show, Art Exhibit & Appetizers
- VIP access to "The Haute Couture Boat" event. - Firsthand viewing of Empório Aragão's new collection launch. - Showcase of 7 other international designers' collections. - Access to "Art Biennale sur Mer" art exhibition by São... More
Private Tour

NY Yacht Cruise with High Couture Show, Art Exhibit & Appetizers
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USA
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Superb4 reviews5
- VIP access to "The Haute Couture Boat" event. - Firsthand viewing of Empório Aragão's new collec....
Private Tour
Private 3 hour Bird Watching Tour in Monterey Bay
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail is much quieter and therefore up close encounters with seabirds are common. This tour is great for birders who are looking for an ... More
Private Tour

Private 3 hour Bird Watching Tour in Monterey Bay
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USA
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Superb1 review5
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail ....
Private Tour
Private 2-Hour Wind and Wine Sunset Sail in Key West
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More
Private Tour

Private 2-Hour Wind and Wine Sunset Sail in Key West
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USA
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Superb89 reviews4.9
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from ....
Private Tour
Nights of Lights Sailboat Tour St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More
Private Tour

Nights of Lights Sailboat Tour St Augustine Sailing
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USA
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Superb3 reviews5
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....
Private Tour

San Diego Private Boat Tour
Offering the BEST ‘one-of-a-kind’ ocean experience. Your invitation to what we call “CHAMPAGNE SAILING”! We offer the most spacious small group boat experience which includes a USCG Captain. Tell us your PARTY preferences ... More
Free Cancellation
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(Saving 20% )

San Diego Private Boat Tour
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USA
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Superb3 reviews5
Offering the BEST ‘one-of-a-kind’ ocean experience. Your invitation to what we call “CHAMPAGNE....
Free Cancellation
Private Tour
(Saving 20% )
San Diego Afternoon Sail
Join our father-son team of licensed Captains for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy breathtaking views of iconic attractions and watch for playful sea lions, dolphins, pelicans, an... More
Private Tour

San Diego Afternoon Sail
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USA
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Superb3 reviews5
Join our father-son team of licensed Captains for an unforgettable 2-hour sailing experience aboard ....
Private Tour
Spectacular Midday Sail
Join our father-son team of licensed Captains for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy breathtaking views of iconic attractions and watch for playful sea lions, dolphins, pelicans, an... More
Private Tour

Spectacular Midday Sail
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USA
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Superb3 reviews5
Join our father-son team of licensed Captains for an unforgettable 2-hour sailing experience aboard ....
Private Tour
Private Sunset Sail for Two
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More
Private Tour

Private Sunset Sail for Two
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USA
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Superb5 reviews5
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....
Private Tour
Experience Santa Cruz Private Sailing
We offer an experience like no other in Santa Cruz. Our Navel Academy 44’ was built in 1939 and was among twelve that were designed and built to train the midshipmen at the Annapolis Navel Academy. As an ocean going wooden yacht... More
Private Tour

Experience Santa Cruz Private Sailing
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USA
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Superb5 reviews5
We offer an experience like no other in Santa Cruz. Our Navel Academy 44’ was built in 1939 and wa....
Private Tour
Private Luxury Sailboat Charters of Honolulu
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. While aboard this fully renovated 41' vessel, view the most treasured maritime life and landscapes of Oahu on a Day Sail and create gr... More
Private Tour

Private Luxury Sailboat Charters of Honolulu
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USA
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Superb5 reviews5
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. Whil....
Private Tour
Afternoon Charleston Historic Harbor Sail - Lux Catamatan
Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 50-foot catamaran offers the perfect vantage point to experience the city’s charm from the water, away from the ... More
Private Tour

Afternoon Charleston Historic Harbor Sail - Lux Catamatan
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USA
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Superb3 reviews5
Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s histor....
Private Tour
Themed and Special Event Cruise in Chesapeake Bay
This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversa... More
Private Tour

Themed and Special Event Cruise in Chesapeake Bay
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USA
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Superb1 review5
This cruise is a unique way to celebrate that special event in your life while cruising on your very....
Private Tour
Nighttime Sailing Trip from San Diego
Come aboard a 36-foot (11-meter) yacht for a nightcap on this 2-hour sailing trip from San Diego! Your knowledgeable captain and crew will take you past the Maritime Museum and the majestic city lights of San Diego. Whether you’... More
Private Tour

Nighttime Sailing Trip from San Diego
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USA
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Superb1 review5
Come aboard a 36-foot (11-meter) yacht for a nightcap on this 2-hour sailing trip from San Diego! Yo....
Private Tour
Private Luxury Yacht in Miami
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s top destinations—Haulover Sandbar, Oleta River State Park, Biscayne Bay & Sands Key, and Raccoon Island—in style! This sleek 3... More
Private Tour

Private Luxury Yacht in Miami
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USA
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Superb1 review5
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s ....
Private Tour
Private Dolphin Catamaran 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

Private Dolphin Catamaran Sail In Cocoa Beach
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USA
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Superb1 review5
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....
Private Tour
Private Long Island Sound Sailing Experience
Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast un... More
Private Tour

Private Long Island Sound Sailing Experience
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USA
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Superb1 review5
Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled ....
Private Tour
Private Sightseeing Charter in Frenchman Bay
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore the Porcupine Islands and Egg Rock. See beautiful views of Acadia National Park from the sea. Learn some history of coastal Maine a... More
Private Tour

Private Sightseeing Charter in Frenchman Bay
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USA
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore t....
Private Tour
Two Hour Private Sailing Charter
Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter option is available morning, afternoon, and evening, and it is a great option for a quick getaway. We sail you around lower Manhattan w... More
Private Tour

Two Hour Private Sailing Charter
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USA
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Superb3 reviews5
Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter optio....
Private Tour
Public Schooner Sail in Greenport
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More
Private Tour

Public Schooner Sail in Greenport
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USA
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Superb1 review5
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....
Private Tour