Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 221 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
Likely to Sell Out 1 Hour Private Charter in New York Harbor for up to 6 people
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North America
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Superb52 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
Hidden Beach - Marietas Islands
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursion, departing from Puerto Vallarta. Even those without experience can feel comfortable participating in guided snorkeling excursion... More
Private Tour
Likely to Sell Out Hidden Beach - Marietas Islands
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North America
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Exellent44 reviews4.4
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursio....
Private Tour
Monterey Private 3 - 4 Hour Whale Watching Cruise
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a private guided tour and can accommodate up to 6 people. Whale sightings are NOT guaranteed. However, this tour is designed to give... More
Private Tour
Likely to Sell Out Monterey Private 3 - 4 Hour Whale Watching Cruise
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North America
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Superb2 reviews5
Enjoy a 3 - 4 hour sailing cruise on the Monterey Bay. This Marine Mammal and Wildlife Safari is a p....
Private Tour
Likely to Sell Out
Deluxe private Sunset & Day Sail
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More
Free Cancellation
Private Tour
(Saving 20% )
Likely to Sell Out Deluxe private Sunset & Day Sail
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North America
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Superb2 reviews5
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....
Free Cancellation
Private Tour
(Saving 20% )
Cozumel All Inclusive: Coast & Relax 4h on 51' Leopard
Situated in the azure waters of the Mexican Caribbean, Cozumel stands as a jewel of unparalleled beauty. Recognized as Mexico's largest island, it draws travelers with its captivating charm and natural wonders. Diving enthusiasts ... More
Private Tour
Likely to Sell Out Cozumel All Inclusive: Coast & Relax 4h on 51' Leopard
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North America
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Superb38 reviews5
Situated in the azure waters of the Mexican Caribbean, Cozumel stands as a jewel of unparalleled bea....
Private Tour
Private Oahu Sunset Charter with Tasting and Drinks
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More
Private Tour
Likely to Sell Out Private Oahu Sunset Charter with Tasting and Drinks
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North America
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Superb49 reviews5
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....
Private Tour
Likely to Sell Out Private Sailing Tour of Bodega Bay
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North America
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Superb86 reviews4.8
This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be i....
Private Tour
Private Catamaran Tour
Our starting point is the iconic Casa China with incredible views of the lagoon from its 360° lookout tower. Our friendly bilingual staff enlivens the tour with stories of the place and important facts about the local ecosystem. ... More
Private Tour
Likely to Sell Out Private Catamaran Tour
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North America
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Superb173 reviews5
Our starting point is the iconic Casa China with incredible views of the lagoon from its 360° looko....
Private Tour
2-Hour Morning Sail in San Diego
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More
Private Tour
Likely to Sell Out 2-Hour Morning Sail in San Diego
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North America
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Superb27 reviews4.9
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....
Private Tour
Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will board the catamaran and we will begin our tour together with our guides and entertainers so that you have a pleasant time. You can as... More
Private Tour
Likely to Sell Out Deluxe Catamaran Tour to Isla Mujeres, Drinks, Snorkeling, Buffet
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North America
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Good24 reviews3.5
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will boa....
Private Tour
Luxury Private Yacht Charter in Cabo San Lucas Mexico
You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to 6 people maximum, remember that the trip is totally private, only your group and the crew (captain and first mat... More
Private Tour
Likely to Sell Out Luxury Private Yacht Charter in Cabo San Lucas Mexico
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North America
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Superb8 reviews5
You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a ....
Private Tour
Okanagan Lake Sailing Tour from Penticton & Naramata BC
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More
Private Tour
Likely to Sell Out Okanagan Lake Sailing Tour from Penticton & Naramata BC
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North America
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Superb48 reviews5
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....
Private Tour
Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres or just sail on the bay. Snorkel and discover the natural beauty of the great reefs of Cancun. Private... More
Private Tour
Likely to Sell Out Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
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North America
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Exellent69 reviews4.3
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go....
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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Superb18 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
Likely to Sell Out Sailing Snorkel Adventure
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North America
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Exellent6 reviews4.5
Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....
Private Tour
BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
Private Tour
Likely to Sell Out BYOB Friday Night Fireworks Cruise
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North America
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Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Private Tour
Private Sailing Charter: Up to 24 Passengers
Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting... More
Private Tour
Likely to Sell Out Private Sailing Charter: Up to 24 Passengers
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North America
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Superb1 review5
Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....
Private Tour
Let's Go Sail the York River in Gloucester Point, Virginia
Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More
Private Tour
Likely to Sell Out Let's Go Sail the York River in Gloucester Point, Virginia
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North America
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Superb141 reviews5
Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....
Private Tour
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More
Private Tour
Likely to Sell Out Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
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North America
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Superb23 reviews5
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....
Private Tour
3hr Discover Sailing Adventure
Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager to explore the basics of sailing. Guided by experienced instructors on our specially designed First 22 yacht, you’ll dive into es... More
Private Tour
Likely to Sell Out 3hr Discover Sailing Adventure
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North America
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Superb9 reviews5
Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager t....
Private Tour