Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 431 Sailing Trips activities in USA. Sort by Popularity.Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More
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Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings
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USA
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Superb1,168 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
Free Cancellation
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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
Miami Millionaires Sightseeing Cruise
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USA
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Exellent1,553 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **W... More
Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure
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USA
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Superb1,347 reviews4.7
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....
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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Superb1,529 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Key West Sunset Sail with Open 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 Open Bar, Live Music and Hors D'oeuvres
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USA
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Superb3,597 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
Kona Signature Catamaran Sunset Sail
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More
Kona Signature Catamaran Sunset Sail
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USA
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Superb232 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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USA
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Superb1,469 reviews4.9
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour....
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More
Likely to Sell Out Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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USA
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Superb826 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail
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
Likely to Sell Out Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail
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USA
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Superb2,224 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Likely to Sell Out Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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USA
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Superb1,390 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
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
Likely to Sell Out Turtles & Tacos Luxury Catamaran Snorkel
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USA
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Superb108 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
Likely to Sell Out
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
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Likely to Sell Out Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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USA
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Superb4,374 reviews4.9
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....
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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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Superb532 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Likely to Sell Out
Key West Signature Sunset Sail with Live Music, Open Bar & Food
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More
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Likely to Sell Out Key West Signature Sunset Sail with Live Music, Open Bar & Food
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USA
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Exellent331 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
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Key West Reef Morning Snorkeling with Breakfast and Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More
Likely to Sell Out Key West Reef Morning Snorkeling with Breakfast and Mimosas
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USA
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Exellent583 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More
Likely to Sell Out Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
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USA
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Superb215 reviews4.7
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....
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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Superb855 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Key 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
Likely to Sell Out Key West's Favorite Afternoon Dolphin Sail
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USA
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Superb155 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
Likely to Sell Out Deluxe Sail & Snorkel to the Captain Cook Monument
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USA
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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
Likely to Sell Out Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
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USA
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Exellent11 reviews4.4
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....