Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 32Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing catamaran. Explore the island through authentic storytelling, coastal beauty, and handcrafted island specialties, both sippable and sa... More
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
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North America
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Superb1 review5
Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing cata....
Private Sailing Experience along the Southern Maine Coastline
Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you to soak in the stunning scenery while learning about the rich history of the area, i... More
Private Tour
Private Sailing Experience along the Southern Maine Coastline
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North America
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Superb1 review5
Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of ....
Private Tour
Private 43' Azimut Yacht 4h – Drinks & Food Included
What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a luxurious escape, our crew tailors every detail to your preferences — from the... More
Private Tour
Private 43' Azimut Yacht 4h – Drinks & Food Included
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North America
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Superb6 reviews5
What truly sets this tour apart is the level of privacy and customization we offer. Whether you're c....
Private Tour
3 in 1 Snorkeling, Parasailing, with Turtle
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
Private Tour
3 in 1 Snorkeling, Parasailing, with Turtle
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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
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More
Private Tour
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
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North America
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Superb1 review5
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become par....
Private Tour
Sunset Boat Tour on Baja Blast 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
Private Tour
Sunset Boat Tour on Baja Blast Includes Open Bar and Dinner
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North America
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Superb1 review5
No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boa....
Private Tour
Los Cabos Catamaran Private Sunset Sail with Snorkel Gear
Enjoy a fully private catamaran cruise where your group has the entire vessel to yourselves—no crowds, just personalized VIP service. Sail past Los Cabos’ most iconic landmarks, including El Arco, Lover’s Beach, and the Sea ... More
Private Tour
Likely to Sell Out Los Cabos Catamaran Private Sunset Sail with Snorkel Gear
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North America
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Superb1 review5
Enjoy a fully private catamaran cruise where your group has the entire vessel to yourselves—no cro....
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
Private Tour
Likely to Sell Out 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
Private Isla Mujeres Adventure & Free Time
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 ... More
Private Tour
Likely to Sell Out Private Isla Mujeres Adventure & Free Time
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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,....
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
Likely to Sell Out 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
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
Private Tour
Likely to Sell Out Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....
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North America
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Good4 reviews3.5
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....
Private Tour
Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran
Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sail through the stunning waters of Los Cabos, immerse yourself in breathtaking views at every turn — from the iconic Lover’s Bea... More
Private Tour
Likely to Sell Out Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran
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North America
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Good4 reviews3.5
Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sai....
Private Tour
Chesapeake Bay Private Cruise
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hul... More
Private Tour
Likely to Sell Out Chesapeake Bay Private Cruise
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North America
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Exellent7 reviews4.4
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guy....
Private Tour
Afternoon Kealakekua Snorkel and Sail
Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary of Kealakekua Bay (home of the Captain Cook Monument). Explore the incredible world under the water with its abundance of marine li... More
Private Tour
Likely to Sell Out Afternoon Kealakekua Snorkel and Sail
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North America
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Superb11 reviews5
Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary o....
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
Private Tour
Likely to Sell Out Morning Charleston Harbor Sail Lux Catamaran Shade and Seating
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North America
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Very Good3 reviews3.7
Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the....
Private Tour
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
Private Tour
Likely to Sell Out Private Luxury Yacht for up to 12 people
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North America
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Very Good3 reviews3.7
A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, lu....
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
Private Tour
Likely to Sell Out Private Sunset Sail in Key West Florida
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North America
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Very Good3 reviews3.7
Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just ....
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
Private Tour
Likely to Sell Out JFarwell Private Yacht Wine & Cheese Sunset Sail
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North America
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Superb18 reviews4.9
This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests wil....
Private Tour
Land’s End Sunset Cruise – Open Bar & Tacos Included
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
Private Tour
Likely to Sell Out Land’s End Sunset Cruise – Open Bar & Tacos Included
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North America
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Superb18 reviews4.9
Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....
Private Tour
Private Swim and Sail Charter (Kewalo Harbor)
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). This experience is customization in its duration and activity *Viewing marine life is not guaranteed but we do... More
Private Tour
Likely to Sell Out Private Swim and Sail Charter (Kewalo Harbor)
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North America
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Superb18 reviews4.9
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....
Private Tour