Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 689 Sailing Trips activities in North America. Sort by Popularity. - Page 2Isla 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

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Superb98 reviews4.7
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
TRAVELER’S FAVORITE SNORKELING TRIP! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the ... More
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Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
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North America
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Exellent1,313 reviews4.3
TRAVELER’S FAVORITE SNORKELING TRIP! Set off for a great Adventure to the Caribbean and admire t....
Free Cancellation
(Saving 5% )
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
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North America
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Superb789 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

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb779 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
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

Cabo San Lucas Sunset Sailing Shared Cruise
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North America
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Superb704 reviews4.9
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....
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

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....
Key West Snorkeling with Breakfast and Unlimited 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

Key West Snorkeling with Breakfast and Unlimited Mimosas
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North America
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Exellent501 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Small-Group Sunset Sailing Experience on San Diego Bay
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

Small-Group Sunset Sailing Experience on San Diego Bay
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North America
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Superb540 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
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

Turtles & Tacos Luxury Catamaran Snorkel
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North America
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Superb12 reviews5
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
Waikiki Sunset Cocktail Sail with Open Bar
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Waikiki Sunset Cocktail Sail with Open Bar
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North America
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Superb470 reviews4.7
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....
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

Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb457 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
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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Superb350 reviews5
We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing t....
Private Tour
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
Private Tour

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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North America
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Superb1,208 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Private Tour
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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North America
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Superb128 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
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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Superb339 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
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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Superb754 reviews4.9
Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of....
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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Superb140 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
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
Private Tour

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....
Private Tour
Los Cabos Luxury Sunset Sail with Light Apetizers and Open Bar
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More
Private Tour

Los Cabos Luxury Sunset Sail with Light Apetizers and Open Bar
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North America
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Superb1,795 reviews4.8
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....
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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Superb293 reviews4.9
Have your own private boat to cruise, snorkel, relax at the beach or swim in different places of t....
Private Tour