Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 22Private Chica SAILING Adventure Puerto Vallarta ALL INCLUSIVE
Explore the stunning Bay of Banderas aboard the 41-foot Chica Sailing Adventure. Customize your tour to suit your desires—whether you’re after a romantic sunset cruise, adrenaline-pumping sailing, or a tranquil journey to a se... More
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Private Chica SAILING Adventure Puerto Vallarta ALL INCLUSIVE
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North America
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Superb41 reviews4.9
Explore the stunning Bay of Banderas aboard the 41-foot Chica Sailing Adventure. Customize your tour....
Private Tour
Sunset Cruise on the Scenic & Calming Chesapeake Bay
Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with beautiful photos of the sunset. You must call 24 hours before your cruise time to see if the minimum... More
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Sunset Cruise on the Scenic & Calming Chesapeake Bay
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North America
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Superb11 reviews4.7
Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way t....
Private Tour

Catamaran to Isla Mujeres
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North America
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Very Good5 reviews4
Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will s....
Private Tour
Discovering Isla Mujeres on a Double Decker Catamaran
Start your day with a hotel pickup or directly at the marina, then head out to open sea through the spectacular mangrove channels. The bar opens soon after departure. Snorkel at open sea for 30-45 minutes. In addition to the colo... More
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Discovering Isla Mujeres on a Double Decker Catamaran
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North America
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Very Good12 reviews3.8
Start your day with a hotel pickup or directly at the marina, then head out to open sea through the ....
Private Tour
Sunset in Private Sailboat 4 hrs up to 15 pax
Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other important event. You will receive the best service where you will see the sunset very close during this 4-hour tour... More
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Sunset in Private Sailboat 4 hrs up to 15 pax
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North America
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Very Good15 reviews4
Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other importa....
Private Tour
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More
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Schooner Applejack Sunset Sail Tour in Boothbay Harbor
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North America
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Superb19 reviews4.9
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Private Tour
Catamaran and snorkel in isla mujeres
Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel (depends on weather) and spend time in the exclusive beach club where you will have a delicious buffet.... More
Private Tour

Catamaran and snorkel in isla mujeres
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North America
Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will s....
Private Tour
All Inclusive Tulum: Luxury Yacht 50´ Cranchi, 4hrs
An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day just for you and your family. You can visit different exclusive places... More
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All Inclusive Tulum: Luxury Yacht 50´ Cranchi, 4hrs
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North America
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Superb27 reviews5
An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day ....
Private Tour
All Inclusive Cozumel: Coast & Relax 4hrs Luxury Yacht
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
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All Inclusive Cozumel: Coast & Relax 4hrs Luxury Yacht
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North America
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Superb23 reviews5
Situated in the azure waters of the Mexican Caribbean, Cozumel stands as a jewel of unparalleled bea....
Private Tour
Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos
Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-seekers with our two exciting options: Option 1: All-Inclusive Adventure We'll take you from your Cancun hotel to two incredible sno... More
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Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos
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North America
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Very Good75 reviews3.7
Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-see....
Private Tour
Key West Sail and Snorkel Day Trip from Fort Lauderdale
Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More
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Key West Sail and Snorkel Day Trip from Fort Lauderdale
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North America
Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....
Private Tour
Private New Orleans 2-Hour Sail Aboard a Luxury Yacht
Escape the ordinary, just 8 miles from the French Quarter! Relax and leave your cares behind while you explore the lake side of New Orleans on a private 2 hour sail. Hop aboard a 47' luxury Beneteau sailboat called "Roux Stir", na... More
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Private New Orleans 2-Hour Sail Aboard a Luxury Yacht
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North America
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Superb41 reviews5
Escape the ordinary, just 8 miles from the French Quarter! Relax and leave your cares behind while y....
Private Tour
Captain Steve's Sailing Experience on Long Island
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspecti... More
Private Tour

Captain Steve's Sailing Experience on Long Island
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North America
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Superb6 reviews5
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best ....
Private Tour
3hr Shared Sailing Adventure
Availablie Daily May-Sep Your sailing experience is a great choice to introduce yourself to the sailing world in a casual, relaxed setting. This trip requires no prior sailing knowledge or experience. You have the option of parti... More
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3hr Shared Sailing Adventure
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North America
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Superb8 reviews5
Availablie Daily May-Sep Your sailing experience is a great choice to introduce yourself to the sai....
Private Tour
Sailing Adventure on Okanagan Lake 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
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Sailing Adventure on Okanagan Lake from Penticton & Naramata BC
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North America
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Superb43 reviews5
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....
Private Tour
Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun
If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable evening with that special someone with a dinner to choose between vegetarian, meat o... More
Private Tour

Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun
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North America
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Very Good4 reviews3.8
If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on o....
Private Tour
Enjoying A Beautiful Day With Mother Nature Cruises
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 Mother Nature's wind! This cruise sails at 9 am, 12 Noon and 3 pm, Tuesday - Sunday a... More
Private Tour

Enjoying A Beautiful Day With Mother Nature Cruises
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North America
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Superb31 reviews4.8
Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides th....
Private Tour

Private Sunset Sail for Two
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North America
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Superb6 reviews5
A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Sky....
Private Tour
Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar
Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your picture at The Arch, one of Cabo’s main landmarks, and get a glimpse of Lover’s Beach and the Sea Lion Colony. Known as the a... More
Private Tour

Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar
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North America
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Superb3 reviews4.7
Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your ....
Private Tour
Family Friendly Private Sailing Experience up to 8 Guests
Join us on San Diego Bay for a memorable sailing aboard a private sailing yacht. Our sail yacht can accommodate up to 6 of your friends and family while we enjoy a peaceful daytime sailing experience. Set sail on San Diego Bay whi... More
Private Tour

Family Friendly Private Sailing Experience up to 8 Guests
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North America
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Superb7 reviews5
Join us on San Diego Bay for a memorable sailing aboard a private sailing yacht. Our sail yacht can ....
Private Tour