Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 430 Sailing Trips activities in USA. Sort by Popularity. - Page 2Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
-
USA
-
Superb10 reviews4.6
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
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
-
USA
-
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
-
USA
-
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
Free Cancellation
(Saving 10% )
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
-
USA
-
Superb2,112 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Free Cancellation
(Saving 10% )
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
-
USA
-
Superb920 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
-
USA
-
Superb823 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
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
Likely to Sell Out Day's End Cocktail Sunset Sail
-
USA
-
Superb72 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Likely to Sell Out
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
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
Free Cancellation
(Saving 12% )
Likely to Sell Out Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
-
USA
-
Superb537 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 12% )
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
Likely to Sell Out Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
-
USA
-
Superb713 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
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
Likely to Sell Out Waikiki Sunset Cocktail Sail with Open Bar
-
USA
-
Superb557 reviews4.7
Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....
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
Likely to Sell Out St. Augustine Live Music Cruise with Drinks and Sunset Option
-
USA
-
Superb328 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
Likely to Sell Out Luxury Catamaran Whale Watch
-
USA
-
Superb74 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
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
Likely to Sell Out Kauai’s Na Pali Coast Snorkel and Sail Tour
-
USA
-
Superb546 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
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
Likely to Sell Out Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
-
USA
-
Exellent622 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
Sunset Sail Along the San Diego Skyline
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water. Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More
Likely to Sell Out Sunset Sail Along the San Diego Skyline
-
USA
-
Superb605 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
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
Likely to Sell Out Key West Sunset Sail Aboard Legendary Schooner Appledore
-
USA
-
Superb281 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
Likely to Sell Out Waikoloa Signature Catamaran Sunset Sail
-
USA
-
Superb399 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
2.5-Hour Small-Group Catamaran Sail with Drinks
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More
Likely to Sell Out 2.5-Hour Small-Group Catamaran Sail with Drinks
-
USA
-
Superb230 reviews4.9
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....
Small-Group San Diego Sunset Sailing Excursion
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More
Likely to Sell Out Small-Group San Diego Sunset Sailing Excursion
-
USA
-
Superb597 reviews4.9
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....
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
Likely to Sell Out Southwest Florida Sunset Sail
-
USA
-
Superb483 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....