Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 427 Sailing Trips activities in USA. Sort by Popularity. - Page 2Day'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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Superb66 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
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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USA
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Superb900 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
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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Superb826 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
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
St. Augustine Live Music Cruise with Drinks and Sunset Option
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USA
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Superb312 reviews4.8
**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** S....
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
Luxury Catamaran Whale Watch
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USA
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Superb57 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
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
Waikiki Sunset Cocktail Sail with Open Bar
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USA
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Superb547 reviews4.8
Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....
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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Superb533 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
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
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
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USA
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Superb2,109 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
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
Key West Afternoon Reef Snorkeling with Open Bar
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USA
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Exellent416 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Key West Dolphin and Snorkel Experience
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USA
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Exellent332 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
St Augustine Nights of Lights Tour with Live Music and Sunset Opt
Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday magic from the water, giving guests sweeping, unobstructed views of the illuminated bayfront, the Bridge of Lions, and Castillo de... More
St Augustine Nights of Lights Tour with Live Music and Sunset Opt
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USA
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Superb69 reviews4.7
Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday ....
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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USA
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Superb936 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Monterey Bay Whale Watching
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More
Likely to Sell Out Monterey Bay Whale Watching
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USA
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Superb314 reviews4.7
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
Private Luxury Yacht Charters, BYOB & Dolphins
We are a family owned luxury yacht 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 you... More
Private Tour
Likely to Sell Out Private Luxury Yacht Charters, BYOB & Dolphins
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USA
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Superb394 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
Private Tour
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More
Private Tour
Likely to Sell Out Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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USA
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Superb166 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Private Tour
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More
Private Tour
Likely to Sell Out Key West Sunset Sail Aboard Legendary Schooner Appledore
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USA
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Superb238 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More
Private Tour
Likely to Sell Out Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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USA
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Superb160 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
Private Tour
Deluxe Sunset & Day Sail Small Group
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More
Private Tour
Likely to Sell Out Deluxe Sunset & Day Sail Small Group
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USA
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Superb244 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
Private Tour
Key West Champagne Sunset Catamaran Cruise
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail thr... More
Private Tour
Likely to Sell Out Key West Champagne Sunset Catamaran Cruise
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USA
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Superb586 reviews4.7
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....
Private Tour
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
Private Tour
Likely to Sell Out Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
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USA
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Superb188 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Private Tour