Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 725 Sailing Trips activities in North America. Sort by Popularity. - Page 192hr 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

2hr Luxury Private Sailing Catamaran for 7-12 People
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North America
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Superb1 review5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks
Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff in this beautiful freshwater paradise. Our years of experience back us up. Qua... More
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Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks
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North America
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Superb98 reviews4.9
Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel s....
Free Cancellation
Private Tour
(Saving 10% )
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More
Private Tour

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
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North America
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Superb12 reviews4.9
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....
Private Tour
52' Yacht Rental in Miami Beach with Experienced Captain
Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 reviews on Google with a 4.9 score guarantee our quality. Our Yacht & Captains are certified & licensed by the USCG, giving you a... More
Private Tour

52' Yacht Rental in Miami Beach with Experienced Captain
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North America
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Very Good7 reviews3.6
Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +950 ....
Private Tour
San Diego Sunset or Afternoon Sail on Classic Yacht
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of a 1904 gaff-rigged Friendship sloop. Our boat features highly-finished woodwork, bronze fixtures, and gaff rigging that showcase ... More
Private Tour

San Diego Sunset or Afternoon Sail on Classic Yacht
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North America
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Superb77 reviews5
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....
Private Tour
Excursion to Reefs in a transparent boat from Cancun
It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine life, in addition, the colors of the blanquizal of Cancun are something spectacular and there is a great diversity of marine life... More
Private Tour

Excursion to Reefs in a transparent boat from Cancun
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North America
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Exellent7 reviews4.3
It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine l....
Private Tour
Private New Orleans 2-Hour Sail Aboard a Luxury Yacht
Escape the ordinary, just 8 miles from the French Quarter! Relax and leave your cares behind while you explore the lake side of New Orleans on a private 2 hour sail. Hop aboard a 47' luxury Beneteau sailboat called "Roux Stir", na... More
Private Tour

Private New Orleans 2-Hour Sail Aboard a Luxury Yacht
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North America
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Superb44 reviews5
Escape the ordinary, just 8 miles from the French Quarter! Relax and leave your cares behind while y....
Private Tour
Private Sail Around New York City and The Statue of Liberty
Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are breath taking. See the Statue of Liberty up close like you can almost touch it. Sit ba... More
Private Tour

Private Sail Around New York City and The Statue of Liberty
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North America
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Superb7 reviews5
Discover NYC from a completely different perspective on a private sailboat charter. You and your gro....
Private Tour
Private Sailing Charter: Up to 24 Passengers
Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting... More
Private Tour

Private Sailing Charter: Up to 24 Passengers
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North America
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Superb1 review5
Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....
Private Tour
Sunset Sail from Ma'alaea Harbor in Maui
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 in Maui
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North America
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Superb214 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Private Tour
Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks
Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of friends, bachelorette parties, and anyone looking to celebrate in style. Cruise the sparkling waters of Miami while enjoying your ... More
Private Tour

Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks
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North America
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Superb267 reviews4.8
Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of f....
Private Tour
Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More
Private Tour

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb110 reviews4.9
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....
Private Tour
Sail & Splash Excursion in Ft. Lauderdale
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More
Private Tour

Sail & Splash Excursion in Ft. Lauderdale
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North America
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Superb270 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
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

Private Sunset and Eco Tour in Destin-Up to 16 Guests
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North America
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Superb41 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
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More
Private Tour

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago
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North America
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Superb27 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Private Sailboat tour in Cabo San Lucas with Papillon Yachts
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More
Private Tour

Private Sailboat tour in Cabo San Lucas with Papillon Yachts
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North America
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Superb197 reviews5
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....
Private Tour
Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More
Private Tour

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
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North America
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Superb31 reviews5
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....
Private Tour
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
Private Tour

Polynesian Canoe Sunset Sail
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North America
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Superb124 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
Sea to Sky Afternoon Sail
Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More
Private Tour

Sea to Sky Afternoon Sail
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North America
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Superb241 reviews5
Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....
Private Tour
America's Cup Day Sailing Adventure on San Francisco Bay
Welcome aboard for a thrilling 2.5 hour sailing adventure aboard USA 76, an International America’s Cup Class racing yacht that challenged in 2003 for sporting’s oldest active trophy, the America’s Cup. Feel the adrenaline a... More
Private Tour

America's Cup Day Sailing Adventure on San Francisco Bay
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North America
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Superb101 reviews4.9
Welcome aboard for a thrilling 2.5 hour sailing adventure aboard USA 76, an International America’....
Private Tour