Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 399 Sailing Trips activities in USA. Sort by Popularity. - Page 2Na Pali Coast Kauai Snorkel and Sail
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More

Na Pali Coast Kauai Snorkel and Sail
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USA
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Superb509 reviews4.8
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....
Key West Snorkeling with Breakfast and Unlimited Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Key West Snorkeling with Breakfast and Unlimited Mimosas
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USA
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Exellent505 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Private Luxury Sailing Charters, BYOB & Dolphins
We are a family owned luxury sailing 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 y... More
Private Tour

Private Luxury Sailing Charters, BYOB & Dolphins
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USA
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Superb350 reviews5
We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing t....
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

Afternoon Sail & Snorkel to the Captain Cook Monument
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USA
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Superb671 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Private Tour
Deluxe Sail & Snorkel to the Captain Cook Monument
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 adventure will begin in the turquoise waters a... More
Private Tour

Deluxe Sail & Snorkel to the Captain Cook Monument
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USA
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Superb460 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
Private Tour
Turtles & Tacos Luxury Catamaran Snorkel
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More
Private Tour

Turtles & Tacos Luxury Catamaran Snorkel
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USA
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Superb17 reviews4.7
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
Private Tour
Waikiki Sunset Cocktail Sail with Open Bar
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More
Private Tour

Waikiki Sunset Cocktail Sail with Open Bar
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USA
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Superb474 reviews4.8
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....
Private Tour
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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USA
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Superb131 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Tour
Sunset Boat Cruise: Swim and Cruise Waikiki
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Waikiki Coastline. Be amazed by the natural beauty as day turns to night and twilight blankets us with an array of amazing colors ... More
Private Tour

Sunset Boat Cruise: Swim and Cruise Waikiki
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USA
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Superb446 reviews4.7
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....
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

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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USA
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Superb1,215 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
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

Southwest Florida Sunset Sail
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USA
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Superb413 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
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

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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USA
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Superb783 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
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

Evening Colors Sunset Sail Tour in Seattle
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USA
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Superb416 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Private Tour
Kona-Kohala Coast Sunset Sail by Catamaran
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More
Private Tour

Kona-Kohala Coast Sunset Sail by Catamaran
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USA
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Superb341 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
Private Tour
2 Hour Sailing Cruise on Lake Tahoe
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More
Private Tour

2 Hour Sailing Cruise on Lake Tahoe
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USA
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Superb681 reviews4.9
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....
Private Tour

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
Free Cancellation
Private Tour
(Saving 15% )

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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USA
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Superb204 reviews4.9
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Free Cancellation
Private Tour
(Saving 15% )
Panama City Beach Sunset Catamaran Sail on The Privateer
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More
Private Tour

Panama City Beach Sunset Catamaran Sail on The Privateer
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USA
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Superb619 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour
Day's End Cocktail Sunset Sail
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More
Private Tour

Day's End Cocktail Sunset Sail
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USA
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Superb21 reviews4.7
Bring the whole family along for this upscale evening of outstanding food and beverages. We set 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

Key West Afternoon Reef Snorkeling with Open Bar
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USA
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Exellent344 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Private Tour
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More
Private Tour

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
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USA
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Superb53 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Private Tour