Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 91.5-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
1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb393 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience
Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan that can accommodate up to 25 passengers. It's decked out with a kitchen, bedroom, bathroom, and even water sports gear like kayak... More
Private Tour
Likely to Sell Out Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience
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North America
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Superb393 reviews4.8
Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan ....
Private Tour
Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.
Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to ... More
Private Tour
Likely to Sell Out Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster....
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North America
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Exellent7 reviews4.4
Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out o....
Private Tour
Sunset Cruise with the Whales on our Sailing Catamaran
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More
Private Tour
Likely to Sell Out Sunset Cruise with the Whales on our Sailing Catamaran
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North America
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Superb49 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
Private Tour
Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More
Private Tour
Likely to Sell Out Dolphin Adventure Sail in Cocoa Beach
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North America
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Superb170 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
Private Tour
Likely to Sell Out
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
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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North America
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Superb937 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Free Cancellation
Private Tour
(Saving 10% )
Sailing Tour through the Laguna de los Siete Colores
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More
Private Tour
Likely to Sell Out Sailing Tour through the Laguna de los Siete Colores
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North America
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Superb1,539 reviews5
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....
Private Tour
Key West Dolphin Watch and Sunset Sail on Catamaran
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unob... More
Private Tour
Likely to Sell Out Key West Dolphin Watch and Sunset Sail on Catamaran
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North America
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Superb36 reviews4.7
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lig....
Private Tour
Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks
Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k reviews. Connect your phone & be your own DJ—bring your own food, drinks & alcohol. Our boat is fully equipped with a Bluetooth sound... More
Private Tour
Likely to Sell Out Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks
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North America
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Superb268 reviews4.8
Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k revie....
Private Tour
Los Cabos Catamaran Cruise with Open Bar & Light Snack
Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past its most iconic landmarks. Sail along the dazzling Cabo coastline to The Arch (El Arco), Lover’s Beach, and Divorce Beach, where ... More
Private Tour
Likely to Sell Out Los Cabos Catamaran Cruise with Open Bar & Light Snack
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North America
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Superb260 reviews4.8
Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past i....
Private Tour
Vancouver Sailing Experience on a 50 foot Sailboat
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More
Private Tour
Likely to Sell Out Vancouver Sailing Experience on a 50 foot Sailboat
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North America
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Superb100 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Private Tour
Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar
Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your picture at The Arch, one of Cabo’s main landmarks, and get a glimpse of Lover’s Beach and the Sea Lion Colony. Known as the a... More
Private Tour
Likely to Sell Out Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar
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North America
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Very Good5 reviews4
Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your ....
Private Tour
Bacalar Lagoon Tour Open Bar With Pick Up
Bilingual captain (English, Spanish and French) who shares local stories in a fun way. • Pickup right from your hotel so you can just relax and enjoy. • Cold drinks and Mexican snacks throughout the tour. • Snorkeling and... More
Private Tour
Likely to Sell Out Bacalar Lagoon Tour Open Bar With Pick Up
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North America
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Superb92 reviews4.9
Bilingual captain (English, Spanish and French) who shares local stories in a fun way. • Pickup r....
Private Tour
Private Charleston Harbor Catamaran Sail
Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More
Private Tour
Likely to Sell Out Private Charleston Harbor Catamaran Sail
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North America
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Superb28 reviews5
Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....
Private Tour
Sunset Catamaran Sail in Cocoa Beach
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Floridaâ... More
Private Tour
Likely to Sell Out Sunset Catamaran Sail in Cocoa Beach
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North America
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Superb177 reviews4.9
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private Tour
One Hour Cruise Around Marina del Rey
Explore Los Angeles' best-kept secret on a classic boat tour of Marina del Rey. See the city, admire the yachts of the rich and famous, enjoy the fresh air, and look for wildlife like sea lions.... More
Private Tour
Likely to Sell Out One Hour Cruise Around Marina del Rey
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North America
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Very Good32 reviews4
Explore Los Angeles' best-kept secret on a classic boat tour of Marina del Rey. See the city, admire....
Private Tour
Statue of Liberty Sunset Cruise and New York City Sky Line
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More
Private Tour
Likely to Sell Out Statue of Liberty Sunset Cruise and New York City Sky Line
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North America
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Good45 reviews3.2
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....
Private Tour
Classic Tall Ship Cruise in Boston Harbor
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeata... More
Private Tour
Likely to Sell Out Classic Tall Ship Cruise in Boston Harbor
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North America
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Superb615 reviews4.7
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liber....
Private Tour
Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar
Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous Arch, Land's end, and Sea Lion Colony before you head out of the bay.  Visit a secl... More
Private Tour
Likely to Sell Out Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Ba....
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North America
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Superb373 reviews4.9
Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great ph....
Private Tour
Sunset Sailing Cruise in Monterey Bay
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More
Private Tour
Likely to Sell Out Sunset Sailing Cruise in Monterey Bay
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North America
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Superb35 reviews4.8
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....
Private Tour