Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 3Boston Harbor Sunset Sail Tour
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More
Likely to Sell Out Boston Harbor Sunset Sail Tour
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USA
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Superb158 reviews4.8
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
Likely to Sell Out Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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USA
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Superb188 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
'Alihilani Lahaina Sunset Sail
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More
Likely to Sell Out 'Alihilani Lahaina Sunset Sail
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USA
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Superb156 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Kauai: Deluxe Na Pali Sunset Cruise aboard 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
Likely to Sell Out Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
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USA
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Superb1,598 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More
Likely to Sell Out Seattle's Original Sunset Sail (Est. 1984) - 70ft Boat - BYOB
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USA
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Superb211 reviews4.9
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....
St. Augustine Live Music Sail with Drinks & Sunset Option
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, or unwind on a 90-minute After Dark Live Music Cruise (no sailin... More
Likely to Sell Out St. Augustine Live Music Sail with Drinks & Sunset Option
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USA
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Superb384 reviews4.7
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....
Sunset Sailing Cruise on a Tall Ship in Boston Harbor
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More
Likely to Sell Out Sunset Sailing Cruise on a Tall Ship in Boston Harbor
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USA
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Superb452 reviews4.6
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....
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
Likely to Sell Out Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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USA
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Superb965 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Kauai: 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
Likely to Sell Out Kauai: Leila Na Pali Sunset Dinner Sail
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USA
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Superb582 reviews4.6
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
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
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USA
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Superb314 reviews5
Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....
Newport Sightseeing Day Sailing Experience on Schooner Adirondack
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More
Likely to Sell Out Newport Sightseeing Day Sailing Experience on Schooner Adirondack
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USA
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Superb110 reviews4.9
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....
New York Sunset Schooner Cruise on the Hudson River
Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More
Likely to Sell Out New York Sunset Schooner Cruise on the Hudson River
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USA
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Superb231 reviews4.9
Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
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
Likely to Sell Out Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
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USA
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Superb25 reviews4.8
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
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
Likely to Sell Out Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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USA
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Superb200 reviews4.8
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
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
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USA
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Superb569 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
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
Likely to Sell Out Sunset Sail in Key West with Beverages Included
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USA
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Superb974 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More
Likely to Sell Out Sailing on Historic Schooner Yacht in Salem, MA
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USA
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Superb206 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
Sunset Catamaran Cruise in Ft. Lauderdale
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More
Likely to Sell Out Sunset Catamaran Cruise in Ft. Lauderdale
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USA
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Superb706 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Sparrow and set sail in search of treasure! But wait it's no... More
Likely to Sell Out Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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USA
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Superb711 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
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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USA
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Superb844 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....