Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 418 Sailing Trips activities in USA. Sort by Popularity.Official Miami Millionaires Sightseeing Cruise
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More

Official Miami Millionaires Sightseeing Cruise
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USA
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Exellent1,186 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
Deluxe Na Pali Sunset Tour on the Lucky Lady
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More
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Deluxe Na Pali Sunset Tour on the Lucky Lady
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USA
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Superb1,420 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Free Cancellation
(Saving 10% )
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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USA
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Superb4,342 reviews4.9
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
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USA
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Superb2,112 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
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USA
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Superb3,395 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
Waikiki Turtle Snorkeling Boat Tour and Adventure
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **Waikiki coastlin... More

Waikiki Turtle Snorkeling Boat Tour and Adventure
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USA
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Superb1,189 reviews4.7
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURSION in the US!! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMIUM snorkel equipment inclu... More

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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USA
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Superb1,188 reviews4.9
2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....

Key West Signature Sunset Sail with Live Music, Open Bar & Food
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More
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Key West Signature Sunset Sail with Live Music, Open Bar & Food
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USA
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Exellent292 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
Free Cancellation
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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
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USA
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Exellent588 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
Sunset & Dolphin Catamaran Cruise with 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

Sunset & Dolphin Catamaran Cruise with Island Time
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USA
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Superb1,855 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
St. Augustine Live Music Sunset Sail with Drinks Included
Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

St. Augustine Live Music Sunset Sail with Drinks Included
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USA
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Superb254 reviews4.8
Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....
Turtles & Tacos Luxury Catamaran Snorkel
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Turtles & Tacos Luxury Catamaran Snorkel
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USA
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Superb77 reviews4.8
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
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

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
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USA
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Exellent599 reviews4.1
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
Waikoloa Signature Catamaran Sunset Sail
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

Waikoloa Signature Catamaran Sunset Sail
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USA
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Superb380 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Day's End Cocktail Sunset Sail
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USA
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Superb53 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
San Francisco Bay Cruise
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

San Francisco Bay Cruise
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USA
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Exellent301 reviews4.4
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s local favorite ARVO Café, served with a selection of Anahola Granola bars—Original, Chocolate Chip, Tropical, and Mango & Ginger. ... More

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
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USA
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Superb1,575 reviews4.8
This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....
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

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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USA
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Superb760 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Sunset Boat Cruise: Swim and Cruise Waikiki
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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Sunset Boat Cruise: Swim and Cruise Waikiki
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USA
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Superb507 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
Free Cancellation
(Saving 8% )
Kona Catamaran Sunset Sail
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Kona Catamaran Sunset Sail
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USA
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Superb179 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....