Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 2Four 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

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb774 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Sunset & Dolphin Catamaran Cruise with Island Time
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Sunset & Dolphin Catamaran Cruise with Island Time
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North America
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Superb1,472 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!
Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never before! Perfect for any special occasion, this VIP experience promises unforgettable memories Adventure Highlights Biscayne Bay ... More
Private Tour

50ft Luxury Yacht Tour in Miami Beach Captain, Champagne & Party!
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North America
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Exellent39 reviews4.5
Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never....
Private Tour
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
Private Tour

Sunset Sail in Key West with Beverages Included
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North America
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Superb767 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Private Tour
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of Los Cabos’ Land’s End Arch! First, you’ll enjoy a beautiful sightseeing stop at Pelican’s Rock where you’ll have a cha... More
Private Tour

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
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North America
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Superb746 reviews4.9
Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of....
Private Tour
Turtles & Tacos Luxury Catamaran Snorkel
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More
Private Tour

Turtles & Tacos Luxury Catamaran Snorkel
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North America
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Superb11 reviews5
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
Private Tour
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
Private Tour

Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb446 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
Private Tour
Kona-Kohala Coast Sunset Sail by Catamaran
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More
Private Tour

Kona-Kohala Coast Sunset Sail by Catamaran
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North America
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Superb334 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
Private Tour
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
Private Tour

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
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North America
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Exellent416 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
Private Tour
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
Private Tour

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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North America
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Superb133 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
Cabo San Lucas Sunset Sailing Shared Cruise
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More
Private Tour

Cabo San Lucas Sunset Sailing Shared Cruise
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North America
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Superb692 reviews4.9
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....
Private Tour
Afternoon 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
Private Tour

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb663 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Private Tour
Private Luxury Sailing Charters, BYOB & Dolphins
We are a family owned luxury sailing 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 y... More
Private Tour

Private Luxury Sailing Charters, BYOB & Dolphins
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North America
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Superb339 reviews5
We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing t....
Private Tour
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More
Private Tour

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Superb84 reviews4.8
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Private Tour
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
Private Tour

Puerto Vallarta, Luxury Sunset Sailing
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North America
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Superb347 reviews4.7
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....
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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Superb91 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE COME SEE OUR COMPLETELY REIMAGINED VESSEL! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off o... More
Private Tour

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB
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North America
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Superb598 reviews4.9
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....
Private Tour
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for a romantic evening or just to enjoy time with friends. Please arrive 30 minutes prior to ... More
Private Tour

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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North America
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Superb1,190 reviews4.9
Cruise into the sunset with wines from all around the world, imported and domestic beers as well as ....
Private Tour
Cabo San Lucas Private catamaran Tour for Six People
Have your own private boat to cruise, snorkel, relax at the beach or swim in different places of the beautiful bay of Cabo San Lucas. Visit all landmarks such as the arch, sea lion colony, neptunes finger, lovers beach, divorc... More
Private Tour

Cabo San Lucas Private catamaran Tour for Six People
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North America
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Superb286 reviews4.9
Have your own private boat to cruise, snorkel, relax at the beach or swim in different places of t....
Private Tour

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
Free Cancellation
Private Tour
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Sunset Boat Cruise: Swim and Cruise Waikiki
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North America
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Superb437 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
Private Tour
(Saving 10% )