Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 713 Sailing Trips activities in North America. Sort by Popularity. - Page 13Windjammer Classic Sunset Sail from Camden, Maine
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More
Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb525 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Public Daytime Sailing Cruise
Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests, this intimate sailing adventure is perfect for anyone looking to escape th... More
Public Daytime Sailing Cruise
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North America
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Superb50 reviews5
Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, ....
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
Sunset Catamaran Sail in Cocoa Beach
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North America
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Superb198 reviews4.9
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private sailing tour of Bacalar Lagoon
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More
Private Tour
Private sailing tour of Bacalar Lagoon
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North America
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Superb495 reviews5
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....
Private Tour
Luxury Camden Sailing Experience
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North America
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Superb19 reviews4.9
Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....
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
Dolphin Adventure Sail in Cocoa Beach
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North America
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Superb238 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
Private Tour
Bacalar Private Sailing Boat Tour with Pick up
Discover the beauty of Bacalar’s Lagoon of Seven Colors on an unforgettable private sailing adventure, with convenient hotel pick-up and drop-off included. Explore some of the lagoon’s most beautiful spots, including Piratesâ... More
Private Tour
Bacalar Private Sailing Boat Tour with Pick up
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North America
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Superb35 reviews5
Discover the beauty of Bacalar’s Lagoon of Seven Colors on an unforgettable private sailing advent....
Private Tour
Key West Wreckers Race Aboard Schooner America 2.0
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More
Private Tour
Key West Wreckers Race Aboard Schooner America 2.0
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North America
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Superb15 reviews4.9
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....
Private Tour
Sunset Sailboat Cruise on Winyah Bay
As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone who wants to end the day on the water. Step aboard for an unforgettable evening on the water ... More
Private Tour
Sunset Sailboat Cruise on Winyah Bay
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North America
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Superb2 reviews5
As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for co....
Private Tour
Isla Mujeres Plus by Albatros Catamarans
Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise of the Mexican Caribbean, enjoy the delicacies of Mexican food, dance to Latin rhythms and forget a... More
Private Tour
Isla Mujeres Plus by Albatros Catamarans
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North America
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Exellent341 reviews4.1
Delight all your senses aboard a boat that will take you to one of the best islands in the world, sw....
Private Tour
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More
Private Tour
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
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North America
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Superb15 reviews5
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....
Private Tour
Catamaran to Isla Mujeres
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North America
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Good8 reviews3.4
Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will s....
Private Tour
3 Hours Ultimate Watersports Excursion in Miami
All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable and stable Catamaran for an unforgettable all-inclusive water experience. Highlights: - Extreme Watersports: Feel the thrill wi... More
Private Tour
3 Hours Ultimate Watersports Excursion in Miami
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North America
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Good8 reviews3.4
All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable....
Private Tour
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Private Tour
Waikiki small group turtle snorkeling & sailing
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North America
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Superb109 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
Maui Sunset Sail
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More
Private Tour
Maui Sunset Sail
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North America
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Superb225 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Private Tour
Afternoon Sightseeing and Sailing Tour
Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico. Cruises are narr... More
Private Tour
Afternoon Sightseeing and Sailing Tour
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North America
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Superb37 reviews4.8
Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers....
Private Tour
Waikiki Turtle Snorkeling Adventure(8am)
Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the opportunity to snorkel with Hawaiian green sea turtles ... More
Private Tour
Waikiki Turtle Snorkeling Adventure(8am)
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North America
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Superb141 reviews5
Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our sp....
Private Tour
Private Therapy Sailing Adventure
Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean elegance along Southern California’s glitteri... More
Private Tour
Private Therapy Sailing Adventure
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North America
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Superb49 reviews4.8
Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUIS....
Private Tour
Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise
Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to dance, sing Tiki-Oki, slip down the on board water slide, or just relax and enjoy the sunset, this cruise will ... More
Private Tour
Likely to Sell Out Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise
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North America
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Superb4 reviews5
Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. W....
Private Tour
Tiki Pub Amazing Dolphin Eco Adventure
Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and a myriad of sea creatures and incredible Birds! The best part is that then y... More
Private Tour
Likely to Sell Out Tiki Pub Amazing Dolphin Eco Adventure
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North America
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Exellent11 reviews4.5
Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water i....
Private Tour