Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 17Sunset Sail Experience by Catamaran in Waikiki
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More
Sunset Sail Experience by Catamaran in Waikiki
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North America
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Superb6 reviews4.8
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
Sunday Brunch Sail in Greenport
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More
Sunday Brunch Sail in Greenport
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North America
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Superb9 reviews5
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included
Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included
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North America
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Superb8 reviews5
Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....
Boat Fishing Tour, Puerto Morelos CIPREA, 25'
We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welcome. Come and enjoy the beauties of the Caribbean Sea, the setting where we fish We have the best boats in Puerto Morelos. Come an... More
Private Tour
Boat Fishing Tour, Puerto Morelos CIPREA, 25'
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North America
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Superb2 reviews5
We are a team with 20 years of experience in sport fishing tour only. Newbies and experts are welco....
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
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North America
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Superb27 reviews4.7
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Private Sailboat Charter from San Pedro: Port of Los Angeles
Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis (39ft) sailing yacht, perfect for couples or small groups looking for a memorable out... More
Private Tour
Private Sailboat Charter from San Pedro: Port of Los Angeles
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North America
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Superb27 reviews4.7
Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a su....
Private Tour
All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks
Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two exciting activities. Whether you want to ride ho... More
Private Tour
All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks
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North America
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Very Good15 reviews3.8
Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatab....
Private Tour
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More
Private Tour
Likely to Sell Out Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
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North America
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Superb73 reviews4.9
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....
Private Tour
Detroit Sunset Sail on the River
Our sunset sail is designed to feel effortless, intimate, and elevated from the moment you step aboard. This is not a crowded cruise. It’s a small group sailing experience where guests can truly relax, connect, and take in Detro... More
Private Tour
Likely to Sell Out Detroit Sunset Sail on the River
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North America
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Superb73 reviews4.9
Our sunset sail is designed to feel effortless, intimate, and elevated from the moment you step aboa....
Private Tour
6 Hour Private Fishing Charter in the Riviera Maya
Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully private experience, not a shared tour. The itinerary is flexible ... More
Private Tour
Likely to Sell Out 6 Hour Private Fishing Charter in the Riviera Maya
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North America
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Superb13 reviews4.9
Unlike many destinations, your fishing time starts within minutes of departure—no long boat ridesâ....
Private Tour
Luxury Catamaran Whale Watch
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More
Private Tour
Likely to Sell Out Luxury Catamaran Whale Watch
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North America
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Superb89 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Private Tour
4-Hour Sailing Adventure on The Strait of Juan de Fuca
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More
Private Tour
Likely to Sell Out 4-Hour Sailing Adventure on The Strait of Juan de Fuca
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North America
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Superb27 reviews4.7
Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....
Private Tour
Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Private Tour
Likely to Sell Out Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
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North America
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Exellent75 reviews4.4
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
Afternoon Schooner Clearwater Beach Cruise Sailing
Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh l... More
Private Tour
Likely to Sell Out Afternoon Schooner Clearwater Beach Cruise Sailing
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North America
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Superb2 reviews5
Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable vi....
Private Tour
Likely to Sell Out
Polynesian Canoe Day 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
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out Polynesian Canoe Day Sail
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North America
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Superb29 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out
Whale Shark Experience Lifetime Memory in Cancun (snack included)
Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explore the Caribbean Sea aboard a small-group boat for a more exclusive adventure. Experience a memorable whale shark encounter featuri... More
Free Cancellation
Private Tour
(Saving inf% )
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
Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explor....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
90 Minute Sailing Tour of Portland
Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate channel on Portland's own "Jungle Cruise" to the spectacular city riverfront wh... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out 90 Minute Sailing Tour of Portland
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North America
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Very Good5 reviews3.8
Our tour begins with a cruise across the river to the most expensive floating homes on the Willamet....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Experience Maalaea Harbor Sailing Snorkeling Adventure
Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Maui, where your adventure takes you to the stunning waters of Molokini or a secret turtle sanctuary. Enjoy hand-shaken Mai Tais and ... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Experience Maalaea Harbor Sailing Snorkeling Adventure
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North America
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Very Good5 reviews3.8
Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Mau....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
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
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks
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North America
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Superb112 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 inf% )
Likely to Sell Out
Seattle Golden Gardens Sunset Sail 70ft Boat Tour
Experience a beautiful Seattle evening on this 2-hour sunset sailing cruise departing from Shilshole Bay Marina near the iconic Golden Gardens Park. Step aboard a classic 70-foot former ocean racing yacht and head out onto Puget S... More
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out Seattle Golden Gardens Sunset Sail 70ft Boat Tour
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North America
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Superb2 reviews5
Experience a beautiful Seattle evening on this 2-hour sunset sailing cruise departing from Shilshole....
Free Cancellation
Private Tour
(Saving inf% )