Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 2Key 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
Key West's Favorite Afternoon Dolphin Sail
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North America
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Superb151 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
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
Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb540 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
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North America
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Exellent10 reviews4.3
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
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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North America
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Exellent313 reviews4.4
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
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North America
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Superb1,663 reviews4.8
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More
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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
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North America
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Superb2,112 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Free Cancellation
(Saving 10% )
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the C... More
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
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North America
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Exellent1,471 reviews4.3
Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire th....
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More
Sunset Sail in Key West with Beverages Included
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North America
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Superb919 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
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
Likely to Sell Out Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb823 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Puerto Vallarta, Luxury Sunset Sailing
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More
Likely to Sell Out Puerto Vallarta, Luxury Sunset Sailing
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North America
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Superb419 reviews4.6
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....
Private Catamaran Escape for 2–6 Guests: Celebrate Your Way
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More
Private Tour
Likely to Sell Out Private Catamaran Escape for 2–6 Guests: Celebrate Your Way
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North America
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Superb324 reviews4.8
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....
Private Tour
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More
Private Tour
Likely to Sell Out Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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North America
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Superb710 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
Private Tour
Waikiki Sunset Cocktail Sail with Open Bar
Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More
Private Tour
Likely to Sell Out Waikiki Sunset Cocktail Sail with Open Bar
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North America
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Superb556 reviews4.7
Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....
Private Tour
St. Augustine Live Music Cruise with Drinks and Sunset Option
**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** Sailing Catamaran tours will resume on March 2nd. Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all ... More
Private Tour
Likely to Sell Out St. Augustine Live Music Cruise with Drinks and Sunset Option
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North America
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Superb326 reviews4.8
**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** S....
Private Tour
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
Private Tour
Likely to Sell Out Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
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North America
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Exellent621 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
Private Tour
Luxury Catamaran Whale Watch
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More
Private Tour
Likely to Sell Out Luxury Catamaran Whale Watch
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North America
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Superb72 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Private Tour
Kauai’s Na Pali Coast Snorkel and Sail Tour
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More
Private Tour
Likely to Sell Out Kauai’s Na Pali Coast Snorkel and Sail Tour
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North America
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Superb545 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
Private Tour
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More
Private Tour
Likely to Sell Out Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
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North America
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Superb428 reviews4.6
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....
Private Tour
Half-Day Luxury Sailing Experience in Tulum with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Private Tour
Likely to Sell Out Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent250 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
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
Private Tour
Likely to Sell Out Day's End Cocktail Sunset Sail
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North America
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Superb71 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Private Tour