Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 35Sunset Fiesta Cruise: Open Bar, Dancing & El Arco Views
Dance, drink, and sail into the sunset on Cabo’s original party cruise! The Pez Gato offers the perfect mix of sightseeing and non-stop fun, cruising past iconic landmarks like the Arch, Lover’s Beach, and sea lion colony befo... More
Sunset Fiesta Cruise: Open Bar, Dancing & El Arco Views
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North America
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Superb4 reviews5
Dance, drink, and sail into the sunset on Cabo’s original party cruise! The Pez Gato offers the pe....
Sailboat on the Mayan Riviera at sunset
Ready to set sail on a catamaran at sunset? The Riviera Maya is the ideal place to do it. This incredible coastal region is home to some of the calmest waters in the world and the most picturesque landscapes. Board one of our full... More
Sailboat on the Mayan Riviera at sunset
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North America
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Superb1 review5
Ready to set sail on a catamaran at sunset? The Riviera Maya is the ideal place to do it. This incre....
Super ATVs and Romantic Dinner Combo, with transport & dinner
Would you like to give your partner the best birthday or anniversary gift during the holidays? Join us in this great adventure that takes you to experience the Caribbean jungle during the day and the best dinner in Cancun at night... More
Super ATVs and Romantic Dinner Combo, with transport & dinner
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North America
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Good3 reviews3.3
Would you like to give your partner the best birthday or anniversary gift during the holidays? Join ....
Private Catamaran Sailboat 4hrs 15Pax
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North America
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Good3 reviews3.3
Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelo....
Private Tour
Bacalar Seven Colors Lagoon Adventure with Boat Ride and Lunch
What truly sets this experience apart is the perfect blend of nature, history, and comfort in one seamless adventure. You won’t just visit Bacalar — you’ll fully experience it. Sail across the breathtaking Seven Colors Lago... More
Private Tour
Bacalar Seven Colors Lagoon Adventure with Boat Ride and Lunch
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North America
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Good3 reviews3.3
What truly sets this experience apart is the perfect blend of nature, history, and comfort in one se....
Private Tour
75ft Sailboat Courses in Isla Mujeres
Gain sailing skills and confidence on a 75-foot ocean sailboat equipped with the latest navigation technology. Two course options are available: the Basic day course, perfect for beginners or those seeking practice, and the compre... More
Private Tour
75ft Sailboat Courses in Isla Mujeres
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North America
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Good3 reviews3.3
Gain sailing skills and confidence on a 75-foot ocean sailboat equipped with the latest navigation t....
Private Tour
JFarwell Sip & Sail aboard the Reverie
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More
Private Tour
Likely to Sell Out JFarwell Sip & Sail aboard the Reverie
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North America
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Superb19 reviews5
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....
Private Tour
Oyster Bay Three Hour Sailing Experience
Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard WINDSWEPT, a Jeanneau 36i. This charter offers flexible departure times, allowing you to choose a start time that suits your sche... More
Private Tour
Likely to Sell Out Oyster Bay Three Hour Sailing Experience
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North America
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Superb19 reviews5
Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard....
Private Tour
Private Luxury Sailboat for 12 people 4 hrs
Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to have fun with your friends in private. It is a beautiful sailboat, comfortable, spacious, and excellently equipped. Interior: Sp... More
Private Tour
Likely to Sell Out Private Luxury Sailboat for 12 people 4 hrs
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North America
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Superb19 reviews5
Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to....
Private Tour
Spend the Day on Buzzards Bay - Powerboat Cruises
Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are welcome aboard. Whether you crave adventure, relaxation, or both, our charters prom... More
Private Tour
Likely to Sell Out Spend the Day on Buzzards Bay - Powerboat Cruises
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North America
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Superb1 review5
Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per ho....
Private Tour
4 Hours Private Yacht in Puerto Vallarta with Snorkeling and Beach
Enjoy an exclusive getaway on a private yacht in Puerto Vallarta, where adventure and relaxation meet. On this 4-hour tour, sail to the stunning Arches of Mismaloya and explore the natural beauty of Playa Paredón. With snorkeling... More
Private Tour
Likely to Sell Out 4 Hours Private Yacht in Puerto Vallarta with Snorkeling and Beac....
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North America
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Superb1 review5
Enjoy an exclusive getaway on a private yacht in Puerto Vallarta, where adventure and relaxation mee....
Private Tour
4th Of July Fireworks Cruise Experience in Lake Chatuge
Celebrate Independence Day with a festive 4th of July fireworks boat experience on Lake Chatuge. Travelers are collected from the pickup location to cruise past scenic lake houses and neighborhood celebrations, concluding the even... More
Private Tour
Likely to Sell Out 4th Of July Fireworks Cruise Experience in Lake Chatuge
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North America
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Superb1 review5
Celebrate Independence Day with a festive 4th of July fireworks boat experience on Lake Chatuge. Tra....
Private Tour
Bertram Yacht 58 Feet Up to 25 People 4 hrs
This is a beautiful and comfortable Yacht, ideal for planning an excellent vacation and having a fun and spectacular party. The magnificent 58-foot-long boat has the capacity to simultaneously accommodate up to 25 people. Renting ... More
Private Tour
Likely to Sell Out Bertram Yacht 58 Feet Up to 25 People 4 hrs
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North America
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Superb1 review5
This is a beautiful and comfortable Yacht, ideal for planning an excellent vacation and having a fun....
Private Tour
Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise
There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything you need, and bring the party with custom curated playlists, Tiki-Oki, a... More
Private Tour
Likely to Sell Out Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise
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North America
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Superb2 reviews5
There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Yo....
Private Tour
6-Night Private Charter in Lake Clark National Park
Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group of up to six guests. Settle into three queen guest cabins, each with ... More
Private Tour
Likely to Sell Out 6-Night Private Charter in Lake Clark National Park
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North America
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Superb1 review5
Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot saili....
Private Tour
Private Daytime Sailing Cruise on Lake Champlain 12 Passengers
Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adirondack and Green Mountains await. This private two-hour cruise accommodates groups of 2 to 12, allowing you to share the experience wi... More
Private Tour
Likely to Sell Out Private Daytime Sailing Cruise on Lake Champlain 12 Passengers
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North America
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Superb5 reviews5
Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adironda....
Private Tour
Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran
Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sail through the stunning waters of Los Cabos, immerse yourself in breathtaking views at every turn — from the iconic Lover’s Bea... More
Private Tour
Likely to Sell Out Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran
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North America
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Superb5 reviews5
Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sai....
Private Tour
Private Afternoon Snorkel with Sunset Sail in Key West
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More
Private Tour
Likely to Sell Out Private Afternoon Snorkel with Sunset Sail in Key West
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North America
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Superb4 reviews5
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....
Private Tour
Hobie Cat rental or sailing lessons
Rent a Hobie Cat and experience the Bacalar lagoon in a fun, fast and adventure-filled way. This lightweight and agile sailboat is perfect for both experienced boaters and beginners who want to learn about the water. In rental mo... More
Private Tour
Likely to Sell Out Hobie Cat rental or sailing lessons
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North America
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Superb4 reviews5
Rent a Hobie Cat and experience the Bacalar lagoon in a fun, fast and adventure-filled way. This lig....
Private Tour
Private Couples Sunset Sailing Tour in San Diego
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Your sunset saili... More
Private Tour
Likely to Sell Out Private Couples Sunset Sailing Tour in San Diego
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North America
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Superb4 reviews5
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....
Private Tour