Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 684 Sailing Trips activities in North America. Sort by Popularity. - Page 30Private 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
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Good3 reviews3.3
If you come to Holbox you cannot miss a visit to Punta Mosquito, one of the most beautiful beaches o....
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....
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4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres
Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catamaran, with room for up to 60 guests, and enjoy a premium experience from start to finish. Our team is dedicated to providing except... More
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4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres
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North America
Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catama....
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Ft Myers Beach Tiki Pub Tropical Beach Getaway Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More
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Ft Myers Beach Tiki Pub Tropical Beach Getaway Cruise
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North America
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Superb13 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
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3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
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3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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North America
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Superb13 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
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Isla Mujeres Private Dream Getaway
If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with a transfer to the dock, where your guide will take you out by boat to the island of Is... More
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Isla Mujeres Private Dream Getaway
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North America
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Superb12 reviews4.9
If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres,....
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Private Luxury Yacht for up to 12 people
A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, luxurious and sophisticated, it is specially designed to satisfy the demands of the best tastes and turn moments into memories that ... More
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Private Luxury Yacht for up to 12 people
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North America
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Superb12 reviews4.9
A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, lu....
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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Superb12 reviews4.9
Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting naut....
Private Tour
Private 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 reviews4.9
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....
Private Tour
Discover Catamaran CaboMar: Authentic Mexican Flavor!
Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, with approximately 40 minutes spent at each captivating point along the route. As you glide through the stunning landscapes of Cab... More
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Discover Catamaran CaboMar: Authentic Mexican Flavor!
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North America
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Superb12 reviews4.9
Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....
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
JFarwell Private Yacht Wine & Cheese Sunset Sail
This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine upon boarding, and then set sail. With the engines off and fully under wind power,... More
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JFarwell Private Yacht Wine & Cheese Sunset Sail
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North America
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Superb14 reviews4.9
This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests wil....
Private Tour
Romantic Sunset Sailing in Cabo
Designed with couples in mind, the tour provides a romantic setting aboard a sailboat, where you can enjoy the gentle breeze of Los Cabos while savoring a glass of wine and a gourmet picnic basket. Unlike other tours, this experie... More
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Romantic Sunset Sailing in Cabo
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North America
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Superb14 reviews4.9
Designed with couples in mind, the tour provides a romantic setting aboard a sailboat, where you can....
Private Tour
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating
Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in the South's picturesque setting, this 2-hour sail gives yo... More
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Morning Charleston Harbor Sail Lux Catamaran Shade and Seating
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North America
Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the....
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Snorkeling and Sailing Adventure In the Riviera Maya
Our tour isn’t just an adventure—it’s a one-of-a-kind experience designed to immerse you in the natural beauty and vibrant culture of the Riviera Maya. Here’s what sets us apart: 1️⃣ Exclusive Snorkeling Spot: Swim in... More
Private Tour

Snorkeling and Sailing Adventure In the Riviera Maya
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North America
Our tour isn’t just an adventure—it’s a one-of-a-kind experience designed to immerse you in th....
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
Private Tour

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
Full-Day Sailing Adventure to Isla Mujeres
This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun to Isla Mujeres aboard a wind-powered catamaran with an experienced and friendly captain and crew. Lounge, swim, eat, and drink at ... More
Private Tour

Full-Day Sailing Adventure to Isla Mujeres
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North America
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Good4 reviews3.5
This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun t....
Private Tour
Early Sail with the Whales from Ma'alaea Harbor
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More
Private Tour

Early Sail with the Whales from Ma'alaea Harbor
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North America
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Good3 reviews3.3
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
4 Day Alaskan Excursion
This is a Tour that no other Company in the World offers. You will be sailing and enjoying the Alaskan wilderness. Each day is unknown because the climate here is so unpredictable. But we always make the best with what we have got... More
Private Tour

4 Day Alaskan Excursion
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North America
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Good3 reviews3.3
This is a Tour that no other Company in the World offers. You will be sailing and enjoying the Alask....
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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Good3 reviews3.3
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....
Private Tour