Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 689 Sailing Trips activities in North America. Sort by Popularity. - Page 3Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! 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 a... More

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb669 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
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

Southwest Florida Sunset Sail
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North America
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Superb407 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
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

Puerto Vallarta, Luxury Sunset Sailing
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North America
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Superb358 reviews4.7
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....

Sunset Boat Cruise: Swim and Cruise Waikiki
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Waikiki Coastline. Be amazed by the natural beauty as day turns to night and twilight blankets us with an array of amazing colors ... More
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Sunset Boat Cruise: Swim and Cruise Waikiki
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North America
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Superb446 reviews4.7
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....
Free Cancellation
(Saving 10% )
El Cielo, Palancar Snorkel & Beach Party Experience
El Cielo is an unspoiled, natural marvel of cobalt crystal clear shallow waters, sand bottom, and Cozumel's jungle in the background; we will relax here after snorkeling at the world famous Palancar Reef offers to snorkelers a col... More

El Cielo, Palancar Snorkel & Beach Party Experience
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North America
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Superb490 reviews4.7
El Cielo is an unspoiled, natural marvel of cobalt crystal clear shallow waters, sand bottom, and Co....
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

Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent235 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
El Cielo Snorkel by Private Boat
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More
Private Tour

El Cielo Snorkel by Private Boat
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North America
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Superb298 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
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

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
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North America
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Superb388 reviews4.6
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....
Private Tour
2 Hour Sailing Cruise on Lake Tahoe
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More
Private Tour

2 Hour Sailing Cruise on Lake Tahoe
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North America
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Superb681 reviews4.9
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....
Private Tour
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
Private Tour

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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North America
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Superb902 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Private Tour
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
Private Tour

Key West Afternoon Reef Snorkeling with Open Bar
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North America
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Exellent340 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
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

Deluxe Sunset & Day Sail Small Group
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North America
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Superb123 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
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

Key West Sunset Sail Aboard Legendary Schooner Appledore
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North America
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Superb141 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
Panama City Beach Sunset Catamaran Sail on The Privateer
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More
Private Tour

Panama City Beach Sunset Catamaran Sail on The Privateer
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North America
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Superb615 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour
Day's End Cocktail Sunset Sail
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More
Private Tour

Day's End Cocktail Sunset Sail
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North America
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Superb19 reviews4.7
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....
Private Tour
Boston 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
Private Tour

Boston Harbor Sunset Sail Tour
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North America
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Superb62 reviews4.7
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Private Tour
Sunset Sail Experience at Kona from Honokohau
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More
Private Tour

Sunset Sail Experience at Kona from Honokohau
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North America
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Superb144 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....
Private Tour
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More
Private Tour

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
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North America
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Superb433 reviews4.6
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....
Private Tour
Kealakekua Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral garde... More
Private Tour

Kealakekua Snorkel and Sail Adventure
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North America
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Superb627 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the....
Private Tour
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More
Private Tour

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
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North America
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Superb290 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....
Private Tour