Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 722 Sailing Trips activities in North America. Sort by Popularity. - Page 20Key West: Sunset Sail + Reef Snorkel & Sandbar
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More
Key West: Sunset Sail + Reef Snorkel & Sandbar
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North America
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Superb29 reviews5
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....
Romantic Dinner on a Spanish Galeon in Cancun
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is the perfect opportunity to enjoy a delicious dinner while you fall in love with the liv... More
Likely to Sell Out Romantic Dinner on a Spanish Galeon in Cancun
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North America
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Exellent23 reviews4.3
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner ....
New York City Skyline Lights Sail
Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights from the water and enjoy a peaceful setting as you escape the city and take to a quiet harbor at night. Key points about this activ... More
Likely to Sell Out New York City Skyline Lights Sail
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North America
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Superb13 reviews4.7
Experience New York City from the water on classic Schooner Adirondack. Gaze at the city lights fro....
Captain Steve's Sailing Experience on Long Island
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspecti... More
Private Tour
Likely to Sell Out Captain Steve's Sailing Experience on Long Island
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North America
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Superb10 reviews5
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best ....
Private Tour
Likely to Sell Out
Private 2-Hour Sunset Sailing Tour on Lake Fairview
Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something different to do in Orlando besides theme parks? Escape the crowds and experience the hidden beauty of Central Florida with an unforgettabl... More
Free Cancellation
Private Tour
(Saving 20% )
Likely to Sell Out Private 2-Hour Sunset Sailing Tour on Lake Fairview
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North America
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Superb33 reviews5
Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something differen....
Free Cancellation
Private Tour
(Saving 20% )
Whale Shark Experience Lifetime Memory in Cancun (snack included)
Welcome to the Whale Shark experience, this is an unique activity in the world and is the most enigmatic activity in Mexico. Imagine swimming next to an immense fish like the whale shark. This animal is completely harmless since... More
Private Tour
Likely to Sell Out Whale Shark Experience Lifetime Memory in Cancun (snack included)
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North America
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Very Good17 reviews3.9
Welcome to the Whale Shark experience, this is an unique activity in the world and is the most enigm....
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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Superb82 reviews5
Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....
Private Tour
Likely to Sell Out
Private 2-Hour Day Sailing Experience
As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the joy of sailing with our community and its visitors. From day sailing to sunset cruises or learning the ropes, our private tours off... More
Free Cancellation
Private Tour
(Saving 25% )
Likely to Sell Out Private 2-Hour Day Sailing Experience
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North America
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Superb46 reviews5
As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the j....
Free Cancellation
Private Tour
(Saving 25% )
Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion
Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty of Maine as you glide through the waters of the Saco River and Sa... More
Private Tour
Likely to Sell Out Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion
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North America
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Superb42 reviews4.9
Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sa....
Private Tour
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for gre... More
Private Tour
Likely to Sell Out 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
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North America
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Superb121 reviews5
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....
Private Tour
Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar
Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off the Cancun coast. Cruise on a modern catamaran while sipping a drink or two from the open bar on your way to and from the scenic isl... More
Private Tour
Likely to Sell Out Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar
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North America
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Very Good16 reviews3.8
Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off th....
Private Tour
Private Luxury 42ft Sailing with Snorkeling in Los Cabos
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful white beaches. Your yacht and crew will provide you with all the ameni... More
Private Tour
Likely to Sell Out Private Luxury 42ft Sailing with Snorkeling in Los Cabos
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North America
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Superb123 reviews5
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Sno....
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
Isla Mujeres Plus by Albatros Catamarans
Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise of the Mexican Caribbean, enjoy the delicacies of Mexican food, dance to Latin rhythms and forget a... More
Private Tour
Likely to Sell Out Isla Mujeres Plus by Albatros Catamarans
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North America
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Exellent321 reviews4.2
Delight all your senses aboard a boat that will take you to one of the best islands in the world, sw....
Private Tour
New York City Skyline Night Sailboat Tour
Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New York. See the New York City skyline, the Statue of Liberty and Ellis Island lit up at night. Sit back and relax while enjoying a pe... More
Private Tour
Likely to Sell Out New York City Skyline Night Sailboat Tour
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North America
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Superb13 reviews5
Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New Y....
Private Tour
Brunch Cruise with Buffet in Washington
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More
Private Tour
Likely to Sell Out Brunch Cruise with Buffet in Washington
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North America
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Very Good10 reviews4
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....
Private Tour
Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience where music, drinks and incredible views will never be lacking. ... More
Private Tour
Likely to Sell Out Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
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North America
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Very Good35 reviews3.7
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a sp....
Private Tour
Full-Day Sailing Trip to Mujeres Island from Playa del Carmen
The best way to see Isla Mujeres from Riviera Maya! Set sail for tropical adventure with a luxurious catamaran cruise from Cancun to Isla Mujeres. Includes a guided snorkel tour of the reef and time in downtown Isla Mujeres, open ... More
Private Tour
Likely to Sell Out Full-Day Sailing Trip to Mujeres Island from Playa del Carmen
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North America
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Good23 reviews3.2
The best way to see Isla Mujeres from Riviera Maya! Set sail for tropical adventure with a luxurious....
Private Tour
1 Hour Private Charter in New York Harbor for up to 6 people
This is a private tour which means it is just you and your party on board. You will be sailing on our beautiful classic sailboat named Tara. Tara is a classic sailboat and one of a kind in NYC. You will sail past Elis Island and t... More
Private Tour
Likely to Sell Out 1 Hour Private Charter in New York Harbor for up to 6 people
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North America
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Superb52 reviews4.9
This is a private tour which means it is just you and your party on board. You will be sailing on ou....
Private Tour
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos
Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily at 9:00 a.m. and 2:00 p.m., your journey begins with a... More
Private Tour
Likely to Sell Out Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelo....
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North America
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Very Good10 reviews3.7
Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Ba....
Private Tour