Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 674 Sailing Trips activities in North America. Sort by Popularity. - Page 26Whale 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

Whale Watching Amazing Adventure
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North America
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Exellent31 reviews4.4
Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....
Golden Gate Sail on San Francisco Bay
Welcome aboard for a family friendly 1 hour 45 minute San Francisco Bay sailing tour aboard USA 76, an International America’s Cup Class racing yacht that challenged in 2003 for sporting’s oldest active trophy, the America’s... More

Golden Gate Sail on San Francisco Bay
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North America
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Superb7 reviews5
Welcome aboard for a family friendly 1 hour 45 minute San Francisco Bay sailing tour aboard USA 76, ....
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
Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas
Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of children and adults alike. Our pirates dance, sing, climb the ropes, while you enjoy the beautiful sunset and li... More
Private Tour

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas
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North America
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Superb1 review5
Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show whi....
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
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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Good2 reviews3.5
Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....
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
2 Hour Sailing Adventure in Lake Michigan (up to 6 people)
Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking views of the city of Racine and on clear day views of Milwaukee and Kenosha You can lay back and relax to the sounds of the wave... More
Private Tour

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)
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North America
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Superb5 reviews5
Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....
Private Tour
Sailing Tour around the Bacalar Lagoon
Embark on the adventure of knowing the Bacalar lagoon. Aboard our ranger 26, the Taan'ik (facing the wind in the Mayan language), we are at your disposal to offer you a unique experience. Visiting the lagoon of the 7 colors by sai... More
Private Tour

Sailing Tour around the Bacalar Lagoon
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North America
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Superb12 reviews4.8
Embark on the adventure of knowing the Bacalar lagoon. Aboard our ranger 26, the Taan'ik (facing the....
Private Tour

Wrightsville Beach Day Sail Private Catamaran Charter
On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew will dinghy you around wherever you'd like to go! The boat is fully equipped with ai... More
Free Cancellation
Private Tour
(Saving 20% )

Wrightsville Beach Day Sail Private Catamaran Charter
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North America
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Superb12 reviews4.8
On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islan....
Free Cancellation
Private Tour
(Saving 20% )
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
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
Private Sailboat Guided Tour of New York City
Distinctively combine luxury, relaxation, adventure and education aboard a professionally guided private sailboat tour of the Hudson River & New York Harbor. Instead of a walking tour, sit and relax, as we serve you anything you b... More
Private Tour

Private Sailboat Guided Tour of New York City
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North America
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Superb4 reviews5
Distinctively combine luxury, relaxation, adventure and education aboard a professionally guided pri....
Private Tour
The Hamptons Date Night Dining Hot Spots
This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single excursion hassle-free, maximizing their time and providing a convenient way to explore the Hamptons. Guests won't have to worry abo... More
Private Tour

The Hamptons Date Night Dining Hot Spots
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North America
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Superb1 review5
This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single e....
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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Superb1 review5
Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....
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
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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Superb13 reviews5
Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise....
Private Tour
1 hour Private Navigation in Transparent Boat Arco de Los Cabos
Get to know the famous Arch of Los Cabos in private mode, where only you and your loved ones will be on the boat, together with the guide and captain, you will be able to enjoy incredible rock formations, tropical fish, reefs, the... More
Private Tour

1 hour Private Navigation in Transparent Boat Arco de Los Cabos
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North America
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Exellent31 reviews4.4
Get to know the famous Arch of Los Cabos in private mode, where only you and your loved ones will be....
Private Tour