Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 768 Sailing Trips activities in North America. Sort by Popularity. - Page 13Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More
Likely to Sell Out Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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North America
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Superb893 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
Public Daytime Sailing Cruise
Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests, this intimate sailing adventure is perfect for anyone looking to escape th... More
Likely to Sell Out Public Daytime Sailing Cruise
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North America
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Superb11 reviews5
Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, ....
2hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
Likely to Sell Out 2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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North America
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Superb98 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
2.5-hour Guided Sailboat Tour
2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More
Likely to Sell Out 2.5-hour Guided Sailboat Tour
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North America
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Superb184 reviews5
2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....
Halifax Summer Breeze Sail
This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's Island, Pier 21, Point Pleasant Park, and more. This laid-back sail is designed for you to en... More
Likely to Sell Out Halifax Summer Breeze Sail
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North America
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Superb25 reviews5
This two-hour sail allows you to soak in the sights along the coastline so close to our urban center....
HipHop Catamaran Party from Cancun to Isla Mujeres
Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant marine life. Then, head to a secluded sandbank—a hidden gem pe... More
Likely to Sell Out HipHop Catamaran Party from Cancun to Isla Mujeres
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North America
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Very Good20 reviews3.9
Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate
Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More
Private Tour
Likely to Sell Out Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate
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North America
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Superb51 reviews5
Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht ....
Private Tour
Private Sailing Charter on San Diego Bay
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This private charterÂ... More
Private Tour
Likely to Sell Out Private Sailing Charter on San Diego Bay
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North America
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Superb47 reviews4.9
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
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
Likely to Sell Out 2 Hour Sailing Adventure in Lake Michigan (up to 6 people)
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North America
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Superb12 reviews5
Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....
Private Tour
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More
Private Tour
Likely to Sell Out Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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North America
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Superb19 reviews4.7
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (LÄ“â€....
Private Tour
Private Classic Sailboat Tour in New York City
This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More
Private Tour
Likely to Sell Out Private Classic Sailboat Tour in New York City
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North America
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Superb1 review5
This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....
Private Tour
Daytime Charleston Harbor Sail - Lux Catamatan w/Bar
Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to experience the city’s charm from the water, away from the ... More
Private Tour
Likely to Sell Out Daytime Charleston Harbor Sail - Lux Catamatan w/Bar
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North America
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Superb9 reviews4.7
Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s histor....
Private Tour
Likely to Sell Out Monday Night Concert Series: Blues and Views Aboard Tall Ship
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North America
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Superb1 review5
Book early, as these tend to sellout! you are free to move about the ship, while the music plays, ev....
Private Tour
San Diego Sailing Cruise Small Group 6 Guests Classic Yacht
Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More
Private Tour
Likely to Sell Out San Diego Sailing Cruise Small Group 6 Guests Classic Yacht
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North America
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Superb84 reviews5
Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....
Private Tour
The Finest Private Yacht Experience in Cabo
This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some of the best things to do in Cabo such as whale watching and bathing on soothing crystal waters... More
Private Tour
Likely to Sell Out The Finest Private Yacht Experience in Cabo
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North America
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Superb23 reviews4.6
This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30....
Private Tour
2hr Shared Sailing Experience in Toronto
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More
Private Tour
Likely to Sell Out 2hr Shared Sailing Experience in Toronto
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North America
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Superb25 reviews5
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....
Private Tour
Private Sunset Sailing Cruise in Puerto Vallarta
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains and the prettiest areas of Down Town Puerto Vallarta. While on tour we provide 2 cour... More
Private Tour
Likely to Sell Out Private Sunset Sailing Cruise in Puerto Vallarta
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North America
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Superb25 reviews5
On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on ....
Private Tour
Sailing Tour through the Laguna de los Siete Colores
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More
Private Tour
Likely to Sell Out Sailing Tour through the Laguna de los Siete Colores
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North America
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Superb1,636 reviews5
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....
Private Tour
Private Sunset and Eco Tour in Destin-Up to 16 Guests
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More
Private Tour
Likely to Sell Out Private Sunset and Eco Tour in Destin-Up to 16 Guests
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North America
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Superb44 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
Guided Seattle Sailing Adventure from Bainbridge Island
Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we could see a nuclear submarine, inbound container ships, or century-old schooners... More
Private Tour
Likely to Sell Out Guided Seattle Sailing Adventure from Bainbridge Island
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North America
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Superb83 reviews5
Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....
Private Tour