Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 721 Sailing Trips activities in North America. Sort by Popularity. - Page 9Key West Sailing & Snorkeling: A Reef Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Key West Sailing & Snorkeling: A Reef Adventure
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North America
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Superb157 reviews4.8
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Snorkel with Manta Rays Guaranteed
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North America
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Superb733 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
Key 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

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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North America
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Superb730 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
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North America
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Superb67 reviews4.7
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport
Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport
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North America
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Superb39 reviews4.8
Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....
Waikoloa Catamaran Snorkel Sail Including Lunch
Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snorkeling cruise. As you head out across the clear Pacific waters, enjoy panoramic views of volcanic mountains, golden coastline, and ... More

Waikoloa Catamaran Snorkel Sail Including Lunch
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North America
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Superb98 reviews4.6
Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snork....
El Cielo Cozumel Snorkeling tour by Private Boat
TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned r... More
Private Tour

El Cielo Cozumel Snorkeling tour by Private Boat
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North America
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Superb134 reviews4.8
TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water trea....
Private Tour
Deluxe private Sunset & Day Sail
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More
Private Tour

Deluxe private Sunset & Day Sail
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North America
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Superb2 reviews5
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....
Private Tour
Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience
Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan that can accommodate up to 25 passengers. It's decked out with a kitchen, bedroom, bathroom, and even water sports gear like kayak... More
Private Tour

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience
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North America
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Superb2 reviews5
Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan ....
Private Tour
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore pristine beaches and beautiful sights while savoring fresh guacamole and a selection of delicious snacks. This pe... More
Private Tour

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb60 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
Private Tour
Seattle Sunset Sail BYOB
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More
Private Tour

Seattle Sunset Sail BYOB
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North America
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Superb187 reviews4.9
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....
Private Tour
Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB
Sail the Charleston Harbor, see dolphins, amazing sunsets 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

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB
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North America
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Superb54 reviews4.9
Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....
Private Tour
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
Private Tour

HipHop Catamaran Party from Cancun to Isla Mujeres
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North America
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Very Good9 reviews3.8
Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....
Private Tour
Luxury Snorkel Adventure in Cabo
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More
Private Tour

Luxury Snorkel Adventure in Cabo
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North America
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Superb46 reviews4.8
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....
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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Exellent4 reviews4.5
Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatab....
Private Tour

Polynesian Canoe Morning 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% )

Polynesian Canoe Morning Sail
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North America
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Superb17 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
Private Tour
(Saving 10% )
Chicago's Fireworks Show aboard Tall Ship Windy!
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More
Private Tour

Chicago's Fireworks Show aboard Tall Ship Windy!
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North America
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Superb14 reviews4.8
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....
Private Tour
Shallow Water Snorkeling and Dolphin Watching in Key West
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More
Private Tour

Shallow Water Snorkeling and Dolphin Watching in Key West
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North America
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Superb460 reviews4.6
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....
Private Tour
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More
Private Tour

Half-Day Deluxe Molokini Snorkel Excursion in Maui
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North America
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Superb91 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
Private Tour
El Cielo Cozumel Snorkeling trip by Catamaran
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More
Private Tour

El Cielo Cozumel Snorkeling trip by Catamaran
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North America
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Exellent275 reviews4.4
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....
Private Tour