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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Exellent990 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
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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Superb4,076 reviews4.9
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....
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
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Waikiki Turtle Snorkeling Boat Tour and Adventure
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USA
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Superb1,087 reviews4.7
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....
Free Cancellation
(Saving 9% )
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

2 Hour Sailing Cruise on Lake Tahoe
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USA
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Superb793 reviews4.9
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....
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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Superb1,711 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

Sightseeing Day Sail around Boston Harbor
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More
Free Cancellation
(Saving 15% )

Sightseeing Day Sail around Boston Harbor
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USA
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Superb458 reviews4.8
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
Free Cancellation
(Saving 15% )
Key West Sunset Sail with Full 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 Full Bar, Live Music and Hors D'oeuvres
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USA
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Superb3,287 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
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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Superb2,029 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
2-Hour Seattle Sailing Harbor Tour
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

2-Hour Seattle Sailing Harbor Tour
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USA
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Superb423 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
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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Exellent454 reviews4.1
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
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

Evening Colors Sunset Sail Tour in Seattle
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USA
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Superb517 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Leila Na Pali Sunset Dinner Sail
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Leila Na Pali Sunset Dinner Sail
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USA
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Superb488 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
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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Superb1,018 reviews4.9
2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....
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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Superb1,518 reviews4.8
This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....
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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Exellent525 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
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

Deluxe Na Pali Sunset Tour on the Lucky Lady
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USA
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Superb1,358 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
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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Superb48 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
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

Sunset Boat Cruise: Swim and Cruise Waikiki
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USA
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Superb468 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
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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Superb207 reviews4.7
Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....
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

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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USA
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Superb800 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....