Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 696 Sailing Trips activities in North America. Sort by Popularity. - Page 21Nights of Lights Sailboat Tour at St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More

Nights of Lights Sailboat Tour at St Augustine Sailing
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North America
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Superb9 reviews5
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....

Sailing Snorkel Adventure
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North America
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Exellent6 reviews4.5
Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....

Private Sunset Sail for Two
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North America
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Superb6 reviews5
A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Sky....
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

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....
Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.
Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to ... More

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster....
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North America
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Exellent7 reviews4.4
Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out o....
Sailing Charter
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Sailing Charter
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North America
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Superb2 reviews5
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....
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

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail
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North America
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Superb117 reviews4.9
This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....
Private Tour
Rosé Brunch Under Sail
Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning waters of Hilton Head while enjoying complimentary mimosas and light brunch bites. This relaxing 2-hour sail is the perfect blend ... More
Private Tour

Rosé Brunch Under Sail
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North America
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Very Good1 review4
Wake up with our daily Brunch Under Sail aboard a luxury catamaran. Cruise through the calm morning ....
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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Very Good1 review4
Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....
Private Tour
Sunset Sail on the Black Pearl
Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point Amusement Park from the water, sail past the Marblehead Lighthouse, and... More
Private Tour

Sunset Sail on the Black Pearl
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North America
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Exellent6 reviews4.3
Come experience the tranquility of gliding through the water under sail on the Black Pearl while app....
Private Tour
Private Sailboat + Captain for a Day Experience
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More
Private Tour

Private Sailboat + Captain for a Day Experience
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North America
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Superb558 reviews5
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....
Private Tour
Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar
Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous Arch, Land's end, and Sea Lion Colony before you head out of the bay. Visit a secl... More
Private Tour

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Ba....
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North America
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Superb292 reviews4.9
Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great ph....
Private Tour
San Diego Bay Sailing Tour
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 group sail is li... More
Private Tour

San Diego Bay Sailing Tour
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North America
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Superb16 reviews5
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
Private Tour
Sailing Adventures 3-Hour Activity in Destin
There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stiletto Catamaran. Harnessing the power of the wind as we sail along these beautiful waters is magical. You might even get to experie... More
Private Tour

Sailing Adventures 3-Hour Activity in Destin
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North America
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Superb4 reviews5
There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stil....
Private Tour
3 Hour Luxury Private Sailing Catamaran for 7-12 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour

3 Hour Luxury Private Sailing Catamaran for 7-12 People
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North America
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Superb4 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Afternoon Sail
Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More
Private Tour

Afternoon Sail
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North America
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Superb28 reviews5
Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....
Private Tour
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More
Private Tour

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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North America
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Superb13 reviews4.6
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
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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Superb6 reviews5
Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....
Private Tour
Sunset Sail from Ma'alaea Harbor
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More
Private Tour

Sunset Sail from Ma'alaea Harbor
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North America
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Superb211 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Private Tour
Sunset Boat Tour 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 Includes Open Bar and Dinner
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North America
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Superb211 reviews4.6
No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boa....
Private Tour