Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 725 Sailing Trips activities in North America. Sort by Popularity. - Page 16Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time
Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers you the chance to unwind on the beautiful sands of Pelícano Beach, where you can enjoy a minimum of 2 hours of free time to soak up... More

Cabo Yacht Tour to Lovers or Pelícano Beach + Beach Time
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North America
Set sail for a day of relaxation on our yacht tour to Lovers Beach. This 45-minute journey offers yo....
Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing) and we will guide you on this wonderful route created for you and your companions (Adventure Tourism, Nature and more). You are looking for TRANQUI... More
Private Tour

Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
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North America
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Superb34 reviews5
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing) and we will guide ....
Private Tour
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More
Private Tour

Key West Sunset Sail Aboard Legendary Schooner Appledore
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North America
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Superb212 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.
Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to ... More
Private Tour

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster....
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North America
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Exellent7 reviews4.4
Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out o....
Private Tour
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More
Private Tour

Sunset Sail Cruise in Key West
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North America
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Superb243 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
Sailing Adventures 3-Hour Activity in Destin
There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stiletto Catamaran. Harnessing the power of the wind as we sail along these beautiful waters is magical. You might even get to experie... More
Private Tour

Sailing Adventures 3-Hour Activity in Destin
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North America
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Superb4 reviews5
There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stil....
Private Tour
Sunset Cruise with the Whales from Anaeho'omalu Bay
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More
Private Tour

Sunset Cruise with the Whales from Anaeho'omalu Bay
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North America
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Superb46 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
Private Tour
Sunset Sail Experience by Catamaran in Waikiki
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More
Private Tour

Sunset Sail Experience by Catamaran in Waikiki
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North America
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Superb6 reviews4.8
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
Private Tour
Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun
This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give you a real caribbean experience. Discover Isla Mujeres and it's beautiful beach with us, our team is certified and you will spend... More
Private Tour

Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun
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North America
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Very Good4 reviews4
This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give ....
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

Luxury Private Yacht Charter in Cabo San Lucas Mexico
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North America
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Superb6 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
Rosé Golden Hour Sunset Sail
Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with complimentary drinks on board. Whether you're going with a big or smal... More
Private Tour

Rosé Golden Hour Sunset Sail
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North America
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Superb11 reviews4.8
Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset crui....
Private Tour
Amazing Romantic Dinner In Cancun On A Spanish Galeon The Best Sunset Activity
Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as th... More
Private Tour

Amazing Romantic Dinner In Cancun On A Spanish Galeon The Best Su....
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North America
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Superb1 review5
Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. ....
Private Tour

Isla Mujeres Snorkeling Catamaran Adventure with Lunch
Join a 7-hour adventure to Isla Mujeres aboard a luxurious catamaran, where the Caribbean Sea's vibrant hues set the backdrop for your day. Dive into the azure waters for snorkeling at a stunning reef, and enjoy the thrill of flyi... More
Free Cancellation
Private Tour
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Isla Mujeres Snorkeling Catamaran Adventure with Lunch
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North America
Join a 7-hour adventure to Isla Mujeres aboard a luxurious catamaran, where the Caribbean Sea's vibr....
Free Cancellation
Private Tour
(Saving 20% )
Snorkeling Adventure in Puerto Morelos Includes snack, Water and Round Trip.
You must live this experience once in your life, This activity is only for travelers that love to be in a unique place in the world. You will discover the 2nd biggest reef wall in the world, you will see a huge variety of fish of... More
Private Tour

Snorkeling Adventure in Puerto Morelos Includes snack, Water and ....
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North America
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Very Good90 reviews4
You must live this experience once in your life, This activity is only for travelers that love to be....
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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Superb4 reviews4.8
Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your ....
Private Tour
Clear Boat to Cabo Lands End, The Arch and more
Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take a tour just where the Pacific Ocean meets the Sea of Cortez, the famous Lands End. In our... More
Private Tour

Clear Boat to Cabo Lands End, The Arch and more
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North America
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Exellent12 reviews4.4
Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most ....
Private Tour
Pastries & Prosecco Aboard a Tall Ship in Boston Harbor
What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. F... More
Private Tour

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor
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North America
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Superb14 reviews5
What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable v....
Private Tour
Chacahua Afternoon Journey
As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out of the same schedules that our fellow colleagues offer this tour is whole afternoon experience that show us al... More
Private Tour

Chacahua Afternoon Journey
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North America
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Superb21 reviews5
As a team we try to create journeys that are worth investing your time and confidence. We try to do ....
Private Tour
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 5... More
Private Tour

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
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North America
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Superb2 reviews5
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - com....
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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Superb144 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
Private Tour