Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 51-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
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North America
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Superb1,395 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
9am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

9am Turtle Canyon Snorkel Adventure
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North America
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Superb239 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
San Francisco Bay Cruise
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

San Francisco Bay Cruise
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North America
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Exellent261 reviews4.4
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....
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

Day's End Cocktail Sunset Sail
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North America
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Superb13 reviews4.6
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....
Sail and Turtle Snorkeling Tour in Waikiki
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More

Sail and Turtle Snorkeling Tour in Waikiki
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North America
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Superb227 reviews4.9
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....
JFarwell Sunset Wine and Cheese Yacht Sailing
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More

JFarwell Sunset Wine and Cheese Yacht Sailing
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North America
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Superb116 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
Buccaneer Pirate Cruise
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Buccaneer Pirate Cruise
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North America
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Superb28 reviews4.9
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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North America
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Superb132 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
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North America
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Superb88 reviews4.6
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....
Private Guided Sunset and Dolphin Cruise up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Private Tour

Private Guided Sunset and Dolphin Cruise up to 6 Passengers
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North America
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Superb57 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
Monterey Bay Whale Watching
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More
Private Tour

Monterey Bay Whale Watching
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North America
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Superb276 reviews4.7
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
Private Tour
2-Hour Sunset Sail on the San Francisco Bay
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More
Private Tour

2-Hour Sunset Sail on the San Francisco Bay
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North America
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Superb359 reviews4.8
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Private Tour
Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More
Private Tour

Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests
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North America
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Superb30 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
Sunset Cruise in Los Cabos with Jazz and Wine
Cruise the Los Cabo's Coastline while listening to smooth jazz and instrumental aboard the Tropicat. Your tour also features an international bar and a meat & cheese selection as you sail past main landmarks such as Lover's Beach,... More
Private Tour

Sunset Cruise in Los Cabos with Jazz and Wine
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North America
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Superb186 reviews4.6
Cruise the Los Cabo's Coastline while listening to smooth jazz and instrumental aboard the Tropicat.....
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 adve... More
Private Tour

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb215 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Private Tour
Visit Private Beaches around Puerto Vallarta in a Private Yacht
Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More
Private Tour

Visit Private Beaches around Puerto Vallarta in a Private Yacht
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North America
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Superb81 reviews5
Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....
Private Tour
Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
Join us on Cozumel's largest and most luxurious catamaran with the First Lady Charters Team! Embark on a guided snorkeling tour at Cozumel's renowned Marine Park Reef, with all necessary snorkeling gear provided in different sizes... More
Private Tour

Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
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North America
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Superb11 reviews4.6
Join us on Cozumel's largest and most luxurious catamaran with the First Lady Charters Team! Embark ....
Private Tour
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More
Private Tour

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
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North America
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Exellent283 reviews4.4
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....
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
1.5-Hour San Francisco Bay Sailing Tour
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More
Private Tour

1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb374 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
Private Tour