Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 671 Sailing Trips activities in North America. Sort by Popularity. - Page 30Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic of the Mexican Caribbean, snorkeling in Isla Mujeres and Cancun's ... More
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Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....
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North America
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Superb12 reviews5
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....
Private Tour
Key West Private Romantic Sunset Sail for Couples
Cruise the iridescent waters of Florida Keys coast on a romantic 2-hour sailing trip at sunset. Enjoy the intimate atmosphere of this private sailing trip as you admire Florida Keys sparkling skyline at dusk . Allow your expert sk... More
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Key West Private Romantic Sunset Sail for Couples
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North America
Cruise the iridescent waters of Florida Keys coast on a romantic 2-hour sailing trip at sunset. Enjo....
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Sunset Boat Tour Includes Open Bar and Dinner
No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boat tour that covers all of your bucket list checks! Open bar, light food, a sunset boat tour and memories to last a lifetime!... More
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Sunset Boat Tour Includes Open Bar and Dinner
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North America
No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boa....
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3 in 1 Snorkeling, Parasailing, with Meco Ruins Free
Have a funny and incredible experience full of nature, doing 3 activities at water and land in a tour package! Fly and see the gorgeous views of the Carribean at 260 ft. By the way, you feel free and you liberate adrenaline! ... More
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3 in 1 Snorkeling, Parasailing, with Meco Ruins Free
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North America
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Superb1 review5
Have a funny and incredible experience full of nature, doing 3 activities at water and land in a tou....
Private Tour
2-hour Customizable Private Day Sail in Key West
This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon one of our historic schooners. This trip has a capacity of up to 26 people, and a selection of sodas, beer, and wine are included... More
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2-hour Customizable Private Day Sail in Key West
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North America
This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon....
Private Tour
Private Experience in Punta Mosquito Holbox
If you come to Holbox you cannot miss a visit to Punta Mosquito, one of the most beautiful beaches on the entire Holbox Island, visit the flamingos and enjoy the beaches, the water and the beautiful sand banks of Punta Mosquito on... More
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Private Experience in Punta Mosquito Holbox
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North America
If you come to Holbox you cannot miss a visit to Punta Mosquito, one of the most beautiful beaches o....
Private Tour
Themed and Special Event Cruise in Chesapeake Bay
This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversa... More
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Themed and Special Event Cruise in Chesapeake Bay
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North America
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Superb1 review5
This cruise is a unique way to celebrate that special event in your life while cruising on your very....
Private Tour
Private Sunset Sail in Key West Florida
Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More
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Private Sunset Sail in Key West Florida
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North America
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Superb1 review5
Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just ....
Private Tour
Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs
Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting nautical activities! If you are looking to live a unique and unforgettable experience with family or friends, this is the perfect plac... More
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Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs
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North America
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Superb1 review5
Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting naut....
Private Tour
All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs
It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and delicious dishes and our host will serve you 'refreshing cocktails.... More
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All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs
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North America
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Superb2 reviews5
It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and....
Private Tour
San Diego Private Morning Sail up to 12 guests
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More
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San Diego Private Morning Sail up to 12 guests
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North America
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Superb30 reviews5
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....
Private Tour
Sailing Charter
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More
Private Tour

Sailing Charter
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North America
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Superb30 reviews5
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....
Private Tour
Aloha Wednesday Sunset Sail - All Drinks Included - Lux Catamaran
Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More
Private Tour

Aloha Wednesday Sunset Sail - All Drinks Included - Lux Catamaran
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North America
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Superb1 review5
Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....
Private Tour
Isla Mujeres in Private Catamaran, Snorkeling North Beach
We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More
Free Cancellation
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Isla Mujeres in Private Catamaran, Snorkeling North Beach
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North America
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Superb9 reviews5
We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....
Free Cancellation
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(Saving 5% )

Private Catamaran Sailboat 4hrs 15Pax
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North America
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Superb9 reviews5
Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelo....
Private Tour
Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp
Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop at any of the following places: El meco, Sac Bajo, El Farito, or... More
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Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp
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North America
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Superb12 reviews5
Experience the Caribbean like never before with our sophisticated seafarer guiding you through its p....
Private Tour
Private Yacht for up to 30 People
This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a length of 50 feet, it can accommodate up to 30 guests. Renting the Carver 50 is the perfect option for a variety of events and cr... More
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Private Yacht for up to 30 People
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North America
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Superb12 reviews5
This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a....
Private Tour
Public Schooner Sail in Greenport
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More
Private Tour

Public Schooner Sail in Greenport
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North America
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Superb12 reviews5
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....
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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Superb12 reviews5
Set sail on our spacious and comfortable 30-foot glass-bottom boats, equipped with onboard mattresse....
Private Tour
It doesn't get better than this all inclusive 95ft luxury yacht
This all inclusive Baller Package isn't for everyone. If you want THE luxury yacht in Cabo this 95ft is THE one. Hot tub, bedrooms, bathrooms, we are talking 95ft baller baby! Contact us directly to make sure we can get you the ex... More
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It doesn't get better than this all inclusive 95ft luxury yacht
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North America
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Superb12 reviews5
This all inclusive Baller Package isn't for everyone. If you want THE luxury yacht in Cabo this 95ft....
Private Tour