Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 16Waikiki private Day Tour and Sunset sail for couples
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More
Private Tour
Likely to Sell Out Waikiki private Day Tour and Sunset sail for couples
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North America
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Superb17 reviews5
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....
Private Tour
Waikiki Turtle Snorkeling Adventure(8am)
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
Likely to Sell Out Waikiki Turtle Snorkeling Adventure(8am)
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North America
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Superb55 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
New York Day Sail to the Statue of Liberty on Schooner America
Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, elegant and smooth at 105-feet in length with 3600 square... More
Private Tour
Likely to Sell Out New York Day Sail to the Statue of Liberty on Schooner America
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North America
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Superb65 reviews4.8
Offering a premium sailing experience, the Schooner America is a tribute to the original America t....
Private Tour
Ultimate Miami Boat Party with Free Open Bar & Live DJ
Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience. This 3-hour Miami booze cruise offers a unique nightclub atmosphere on the water, complete with a FREE open bar serving unlimited... More
Private Tour
Likely to Sell Out Ultimate Miami Boat Party with Free Open Bar & Live DJ
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North America
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Superb65 reviews4.8
Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience.....
Private Tour
San Salvador Spanish Galleon Adventure Day Sail with General Admission
Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the ... More
Private Tour
Likely to Sell Out San Salvador Spanish Galleon Adventure Day Sail with General Admi....
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North America
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Superb5 reviews4.8
Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step o....
Private Tour
Navy Pier Chicago: Private Sailboat Charter with Captain
On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is th... More
Private Tour
Likely to Sell Out Navy Pier Chicago: Private Sailboat Charter with Captain
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North America
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Superb5 reviews4.8
On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-n....
Private Tour
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering
Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More
Private Tour
Likely to Sell Out Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering
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North America
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Superb40 reviews5
Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....
Private Tour
Sunset Dolphin Sail Aboard the Daydreams Sailboat
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More
Private Tour
Likely to Sell Out Sunset Dolphin Sail Aboard the Daydreams Sailboat
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North America
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Superb37 reviews4.9
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....
Private Tour
Private 90-Minute Harbor Sailing Charter in Key West
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some fri... More
Private Tour
Likely to Sell Out Private 90-Minute Harbor Sailing Charter in Key West
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North America
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Superb19 reviews4.9
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-mi....
Private Tour
Sail Seattle's Iconic Lake Union All Year Around
Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to explore. Your captain, Grant, born and raised in the great Northwest, has bee... More
Private Tour
Likely to Sell Out Sail Seattle's Iconic Lake Union All Year Around
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North America
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Superb2 reviews5
Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the c....
Private Tour
Chacahua Afternoon Journey
As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out of the same schedules that our fellow colleagues offer this tour is whole afternoon experience that show us al... More
Private Tour
Likely to Sell Out Chacahua Afternoon Journey
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North America
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Superb57 reviews4.8
As a team we try to create journeys that are worth investing your time and confidence. We try to do ....
Private Tour
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams
This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fu... More
Private Tour
Likely to Sell Out Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams
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North America
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Superb2 reviews5
This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow....
Private Tour
Relaxing Saco River Public Sunset Sail
Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque views of Biddeford Pool, Camp Ellis, and the iconic Wood Island Lighthouse. ... More
Private Tour
Likely to Sell Out Relaxing Saco River Public Sunset Sail
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North America
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Superb1 review5
Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. G....
Private Tour
Sailboat Cruise on Chesapeake Bay
Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered only by wind! This cruise sails at 9 am, 12 Noon and 3 pm, Tuesday - Sunday and on Mondays fo... More
Private Tour
Likely to Sell Out Sailboat Cruise on Chesapeake Bay
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North America
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Superb39 reviews4.8
Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides th....
Private Tour
Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing and Curiosities of Mayan Culture) and we will guide you on this wonderful route created for you and your companions (Adventure Tourism, Nature and mo... More
Private Tour
Likely to Sell Out Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
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North America
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Superb50 reviews5
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing and Curiosities of ....
Private Tour
Private Sailboat tour in Cabo San Lucas with Papillon Yachts
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More
Private Tour
Likely to Sell Out Private Sailboat tour in Cabo San Lucas with Papillon Yachts
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North America
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Superb203 reviews5
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....
Private Tour
Likely to Sell Out Key West Ultimate Beach Pass with Parasailing
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North America
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Very Good26 reviews4
Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are....
Private Tour
Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More
Private Tour
Likely to Sell Out Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu
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North America
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Superb1,335 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
Private Tour
Likely to Sell Out
Isla Mujeres Full Day Catamaran Adventure from Cancun
Set sail on a delightful catamaran cruise to Isla Mujeres, where the Caribbean Sea meets tropical charm. This full-day adventure begins with a scenic journey along Cancun's coastline, allowing you to soak in the stunning turquoise... More
Free Cancellation
Private Tour
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Likely to Sell Out Isla Mujeres Full Day Catamaran Adventure from Cancun
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North America
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Superb1,335 reviews4.6
Set sail on a delightful catamaran cruise to Isla Mujeres, where the Caribbean Sea meets tropical ch....
Free Cancellation
Private Tour
(Saving 20% )
Likely to Sell Out
Private Catamaran Sunset Sail in Waikiki
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Private Catamaran Sunset Sail in Waikiki
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North America
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Superb11 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Free Cancellation
Private Tour
(Saving inf% )