Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 708 Sailing Trips activities in North America. Sort by Popularity. - Page 14Private Sunset Sailing Cruise in Puerto Vallarta
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains and the prettiest areas of Down Town Puerto Vallarta. While on tour we provide 2 cour... More

Private Sunset Sailing Cruise in Puerto Vallarta
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North America
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Superb24 reviews5
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on ....

Laguna Grill - Private Boat with on-board BBQ and Drinks Included
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North America
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Superb124 reviews5
One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy natu....
Private Tour
1 Hour Private Charter in New York Harbor for up to 6 people
This is a private tour which means it is just you and your party on board. You will be sailing on our beautiful classic sailboat named Tara. Tara is a classic sailboat and one of a kind in NYC. You will sail past Elis Island and t... More
Private Tour

1 Hour Private Charter in New York Harbor for up to 6 people
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North America
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Superb50 reviews4.9
This is a private tour which means it is just you and your party on board. You will be sailing on ou....
Private Tour
Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks
Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and enjoy this adventure aboard our luxurious French-made sailboats and cat... More
Private Tour

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Dr....
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North America
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Superb12 reviews5
Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel a....
Private Tour
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More
Private Tour

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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North America
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Superb17 reviews4.7
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....
Private Tour
Jolly Roger Pirate Show Cancun with Transportation
Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed sunset cruise on the gorgeous Spanish Galleon for the ideal evening out with the whole family. The buccaneers start greeting you a... More
Private Tour

Jolly Roger Pirate Show Cancun with Transportation
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North America
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Superb12 reviews5
Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed s....
Private Tour

Half Day Sail Orcas Island
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North America
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Superb14 reviews5
Lessons are private and designed so you can brings friends and family with no extra charge. Up to 6 ....
Private Tour
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More
Private Tour

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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North America
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Superb15 reviews4.8
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
Private Tour
Cozumel Private Snorkeling and Charter Experience
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More
Private Tour

Cozumel Private Snorkeling and Charter Experience
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North America
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Superb25 reviews5
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....
Private Tour
Friday Night Firework Cruise in Waikiki
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More
Private Tour

Friday Night Firework Cruise in Waikiki
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North America
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Superb23 reviews4.7
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Private Tour
Private Sailing Tour through the Ten Thousands Islands
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More
Private Tour

Private Sailing Tour through the Ten Thousands Islands
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North America
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Superb143 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
Private Tour
Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht
This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a California day. The multi-colored sky is the perfect backdrop for relaxing and enjoying our complimentary beer and win... More
Private Tour

Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht
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North America
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Superb2 reviews5
This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramati....
Private Tour
Private Sail on the Cape Fear River Aboard a Classic Yacht
Our private charters offer insider access to the Cape Fear River under the guidance of a local captain who has sailed these waters - and the wide Atlantic beyond - professionally for more than a decade. Our steward's comparable ex... More
Private Tour

Private Sail on the Cape Fear River Aboard a Classic Yacht
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North America
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Superb2 reviews5
Our private charters offer insider access to the Cape Fear River under the guidance of a local capta....
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More
Private Tour

South Shore Open Sail from Kewalo Harbor Including Drinks
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North America
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Superb15 reviews5
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More
Private Tour

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
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North America
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Superb18 reviews4.8
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....
Private Tour
New York City Live Jazz Sail
Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around New York Harbor. Sit back and relax while enjoying live Jazz music played throughout this s... More
Private Tour

New York City Live Jazz Sail
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North America
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Superb13 reviews4.8
Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's....
Private Tour
Fireworks Dinner Cruise
See Vancouver’s waterfront sights while you dine on a sunset dinner cruise. This leisurely cruise takes you past the downtown skyline, Canada Place, the North Shore Mountains behind the North Shore, the West Vancouver shoreline ... More
Private Tour

Fireworks Dinner Cruise
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North America
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Very Good3 reviews4
See Vancouver’s waterfront sights while you dine on a sunset dinner cruise. This leisurely cruise ....
Private Tour

Catamaran to Isla Mujeres
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North America
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Very Good6 reviews3.8
Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will s....
Private Tour
4-Hour Sailing Adventure on The Strait of Juan de Fuca
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More
Private Tour

4-Hour Sailing Adventure on The Strait of Juan de Fuca
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North America
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Superb23 reviews4.7
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....
Private Tour
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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Superb328 reviews5
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....
Private Tour