Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 687 Sailing Trips activities in North America. Sort by Popularity. - Page 27Sunset Cruise Tequila Tasting
Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought to you by Tequila Cabo Único and Sunrider. You'll get to know the iconic Cabo S... More

Sunset Cruise Tequila Tasting
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North America
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Superb3 reviews5
Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the histo....
Private Sailing Charter and Guided Tour
Our most popular Galveston cruise lets you see the Galveston Channel and the surrounding area including the most popular sights on the northern part of Galveston. These include the Elissa, the Ocean Star museum, Pier 21, the Port ... More
Private Tour

Private Sailing Charter and Guided Tour
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North America
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Superb3 reviews5
Our most popular Galveston cruise lets you see the Galveston Channel and the surrounding area includ....
Private Tour
Private Day Sailing Experience in San Diego up to 12 guests
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we will see the US Midway, Sea port Village, the Rady shell and we might... More
Private Tour

Private Day Sailing Experience in San Diego up to 12 guests
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North America
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Superb49 reviews5
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is be....
Private Tour
Guided Tour of Puerto Morelos Reefs with Snorkeling Experience
Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is for you. We will take you to know the second largest coral reef in the world, the first one... More
Private Tour

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience
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North America
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Very Good3 reviews4
Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....
Private Tour
Cabo San Lucas Sunset Party on the Water - Adult Only
Spend an incredible vacation enjoying an adventure you will never forget, sailing through the blue waters of the Cabo San Lucas Bay, taking in the amazing scenery all while you enjoy the music and dancing. This Party Boat is perfe... More
Private Tour

Cabo San Lucas Sunset Party on the Water - Adult Only
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North America
Spend an incredible vacation enjoying an adventure you will never forget, sailing through the blue w....
Private Tour
Private - Bacalar sailing across the mesmerizing waters
Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon a sailing boat to navigate our way across the mesmerizing waters of 7 different shad... More
Private Tour

Private - Bacalar sailing across the mesmerizing waters
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North America
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Superb8 reviews4.9
Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence o....
Private Tour
Private Key West Sunset Sail
2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More
Private Tour

Private Key West Sunset Sail
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North America
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Superb47 reviews4.7
2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, ....
Private Tour
Whale Watching en San José del Cabo
Experience a Unique Connection with Nature! Our whale-watching tour in San José del Cabo stands out for its personalized service, led by passionate marine life experts who make your journey enriching and unforgettable. You'll sa... More
Private Tour

Whale Watching en San José del Cabo
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North America
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Superb20 reviews5
Experience a Unique Connection with Nature! Our whale-watching tour in San José del Cabo stands ou....
Private Tour
Golden Hour Escape: Private Sunset Sail in Coastal Maine
Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboar... More
Private Tour

Golden Hour Escape: Private Sunset Sail in Coastal Maine
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North America
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Superb9 reviews5
Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the settin....
Private Tour
Whale Watching Amazing Adventure
Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cabos in search of the Cabo’s Whales.” Enjoy listening to the beautiful song of the whales, with the help of our new hydrophones... More
Private Tour

Whale Watching Amazing Adventure
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North America
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Superb9 reviews5
Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....
Private Tour
Isla Mujeres by Private Catamaran
Discover Isla Mujeres, explore a world filled with vibrant colors, fascinating marine life, and crystal-clear waters that will make you feel like you're on another planet. Sail on an exclusive private catamaran, where you'll enjo... More
Private Tour

Isla Mujeres by Private Catamaran
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North America
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Superb9 reviews5
Discover Isla Mujeres, explore a world filled with vibrant colors, fascinating marine life, and crys....
Private Tour
Private Afternoon Harbor Cruise on Kismet for parties up to 15
Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history tours, swim and float on rafts. Kismet does it all! Kismet is a custom-built ... More
Private Tour

Private Afternoon Harbor Cruise on Kismet for parties up to 15
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North America
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Superb16 reviews5
Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise....
Private Tour
Luxury Private Sunset Experience in San Jose
Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 people, the rate offered here is for 8 people, if like to add more pl... More
Private Tour

Luxury Private Sunset Experience in San Jose
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North America
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Superb16 reviews5
Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....
Private Tour
4 Hour Private Sail for up to 6 people
This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a customizable charter. Create your own adventure on a vintage sailing yacht for 4 hours with an experienced captain.... More
Private Tour

4 Hour Private Sail for up to 6 people
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North America
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Superb11 reviews5
This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a c....
Private Tour
Sailing Charter around Vancouver Harbour Private Tour
Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and has all the features of a large cruising Yacht with a rare balance betw... More
Private Tour

Sailing Charter around Vancouver Harbour Private Tour
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North America
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Superb1 review5
Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and....
Private Tour
Bimini Charters - Private 6 Hour catamaran sail & snorkel
We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of time to determine your goals for the day and make them happen. Our guests almost always say that their trip with us was the highlight... More
Private Tour

Bimini Charters - Private 6 Hour catamaran sail & snorkel
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North America
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Superb1 review5
We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of tim....
Private Tour
6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach
Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer to ... More
Private Tour

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach
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North America
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Superb1 review5
Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We a....
Private Tour
Bachelorette Sailing Party on San Diego Bay up to 12 Guests
Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea... More
Private Tour

Bachelorette Sailing Party on San Diego Bay up to 12 Guests
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North America
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Superb1 review5
Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaki....
Private Tour
Cabo's Premier Catamaran Snorkeling: Explore the Waters!
Our snorkeling tour sails towards the beautiful Santa María Bay, where you will swim in tropical waters with abundant marine life, sailing very slowly at each point approximately 20 minutes just to observe the landscape in this w... More
Private Tour

Cabo's Premier Catamaran Snorkeling: Explore the Waters!
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North America
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Superb1 review5
Our snorkeling tour sails towards the beautiful Santa María Bay, where you will swim in tropical wa....
Private Tour
Exclusive Private Sailing Luxury Tour in Los Cabos
Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater world of the Los Cabos area. During the months of December thru March, you can w... More
Private Tour

Exclusive Private Sailing Luxury Tour in Los Cabos
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North America
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Superb1 review5
Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one o....
Private Tour