Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 674 Sailing Trips activities in North America. Sort by Popularity. - Page 33Key West Haunted Night Sail on Schooner America 2.0
Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under the Key West night sky. During this night boat ride, we'll cruise through the waters of Key West while listening to mysterious t... More

Key West Haunted Night Sail on Schooner America 2.0
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North America
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Superb4 reviews5
Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under....
Afternoon Ali'i Adventure
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Afternoon Ali'i Adventure
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North America
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Superb4 reviews5
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....
All Inclusive Private: 40´ Yacht Van Dutch El Cielo Cozumel
It is a private experience with a super fast luxury yacht that will take you to the incredible island of Cozumel to visit the biosphere of Heaven and delight yourself with exclusive dishes created just for you... More
Private Tour

All Inclusive Private: 40´ Yacht Van Dutch El Cielo Cozumel
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North America
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Superb22 reviews4.8
It is a private experience with a super fast luxury yacht that will take you to the incredible islan....
Private Tour

Private Catamaran Sailboat 4hrs 15Pax
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North America
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Superb22 reviews4.8
Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelo....
Private Tour
Sailing Clases in Cancun
From Sailboatcancun we offer sailing courses aboard a 75 feet sailboat with an experience of more than 25 thousand miles sailed by different oceans. The classes have a duration of 4 hours. The schedule is in the morning, but we c... More
Private Tour

Sailing Clases in Cancun
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North America
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Superb1 review5
From Sailboatcancun we offer sailing courses aboard a 75 feet sailboat with an experience of more th....
Private Tour
Magic Night Boat Dinner with Show & Speedboat Experience at Cancun (1 day tour)
Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are looking for an exciting activity, experience an intrepid adventure in our guided speed boat and snorkeling tour. Our speed boats ar... More
Private Tour

Magic Night Boat Dinner with Show & Speedboat Experience at Cancu....
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North America
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Superb1 review5
Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are l....
Private Tour
Private Yacht for up to 12 People
Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip that you will enjoy like no other, you cannot miss its comfortable spaces while the beautiful colors of the sea and the sky make thos... More
Private Tour

Private Yacht for up to 12 People
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North America
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Superb1 review5
Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip tha....
Private Tour
Private 3 hour Bird Watching Tour in Monterey Bay
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail is much quieter and therefore up close encounters with seabirds are common. This tour is great for birders who are looking for an ... More
Private Tour

Private 3 hour Bird Watching Tour in Monterey Bay
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North America
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Superb1 review5
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail ....
Private Tour
NY Luxury Yacht Cruise with Fashion Show and Art Exhibition
Exclusive Venue: The event takes place aboard a luxury yacht, offering a distinguished experience in a stunning setting with panoramic views of the iconic New York City skyline. Fusion of Fashion and Art: The combination of a hig... More
Private Tour

NY Luxury Yacht Cruise with Fashion Show and Art Exhibition
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North America
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Superb1 review5
Exclusive Venue: The event takes place aboard a luxury yacht, offering a distinguished experience in....
Private Tour
Private Luxury Sailboat Charters of Honolulu
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. While aboard this fully renovated 41' vessel, view the most treasured maritime life and landscapes of Oahu on a Day Sail and create gr... More
Private Tour

Private Luxury Sailboat Charters of Honolulu
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North America
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Superb1 review5
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. Whil....
Private Tour
Private all inclusive party on the water!
First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew will make sure that you have a drink in your hand within minutes. You will get to see the world famous Arch, Lover's Beach, Divorce... More
Private Tour

Private all inclusive party on the water!
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North America
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Superb1 review5
First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew w....
Private Tour
Private Sunset Catamaran: 3-Hour Exclusive Cruise in Los Cabos
Highlights of Your Private Sunset Cruise: Exclusive Private Catamaran: Perfect for couples, friends, or family. Breathtaking Sunset Views: Watch the sky light up with vibrant colors over Cabo. Iconic Landmarks: Sail past The Arch,... More
Private Tour

Private Sunset Catamaran: 3-Hour Exclusive Cruise in Los Cabos
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North America
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Superb1 review5
Highlights of Your Private Sunset Cruise: Exclusive Private Catamaran: Perfect for couples, friends,....
Private Tour
Super ATV´s and Romantic Dinner Combo, Transport, Lunch and Dinner included.
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
Private Tour

Super ATV´s and Romantic Dinner Combo, Transport, Lunch and Dinn....
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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 Tour
Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres
A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catamaran tour from Cancun to Isla Mujeres. The day begins with a leisurely sail across the turquoise waters, where you'll enjoy drinks... More
Private Tour

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres
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North America
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Good3 reviews3.3
A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catam....
Private Tour
Sunset Sail on the Black Pearl
Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point Amusement Park from the water, sail past the Marblehead Lighthouse, and... More
Private Tour

Sunset Sail on the Black Pearl
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North America
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Superb4 reviews5
Come experience the tranquility of gliding through the water under sail on the Black Pearl while app....
Private Tour
Waikiki Boat Party Cruise with live DJ
Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, this exclusive 4-hour catamaran party cruise features an open bar with Vodka, Rum, Whiskey, Gin, Tequila, Champagne, Beer, plus Juice... More
Private Tour

Waikiki Boat Party Cruise with live DJ
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North America
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Superb4 reviews5
Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, thi....
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

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
Shared Experience Glass Bottom Boat to the Arch in Cabo San Lucas
Set sail on our spacious and comfortable 30-foot glass-bottom boats, equipped with onboard mattresses, music, and plenty of room to relax. This is not just a tour—it’s an experience! You’ll explore the most iconic spots of ... More
Private Tour

Shared Experience Glass Bottom Boat to the Arch in Cabo San Lucas
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North America
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Superb4 reviews5
Set sail on our spacious and comfortable 30-foot glass-bottom boats, equipped with onboard mattresse....
Private Tour
6-Night Private Charter in Lake Clark National Park
An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the only live aboard yacht on Lake Clark. Enjoy meals prepared by your onboard chef. Relax in our beanbags and hammocks while enjoyin... More
Private Tour

6-Night Private Charter in Lake Clark National Park
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North America
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Superb4 reviews5
An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the ....
Private Tour
SSS Experience. Speedboat, Snorkel, and Sightseeing in Cancun, Must Do Activity
Welcome to the most intrepid and extreme adventure in Cancún. You will be able to known the other face of the Caribbean with the Jungle Tour. On this activity we will drive our speedboat through the calm waters of the Nichupteâ... More
Private Tour

SSS Experience. Speedboat, Snorkel, and Sightseeing in Cancun, Mu....
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North America
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Superb4 reviews5
Welcome to the most intrepid and extreme adventure in Cancún. You will be able to known the other f....
Private Tour