Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 28Full-Day Reef Snorkeling in Cozumel from Cancún with Lunch
Expore famous Cozumel's top snorkeling locations within the same day on this complete quest featuring the island's most spectacular reefs. Discover the stunning marine flora and fauna of the Dzul-Ha, Casa Blanca and Dalila Reefs,... More

Full-Day Reef Snorkeling in Cozumel from Cancún with Lunch
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North America
Expore famous Cozumel's top snorkeling locations within the same day on this complete quest featurin....
Incredible Party in Unlimited Catamaran to Isla Mujeres! + Transportation
Are you ready for a wonderful day sailing through the Caribbean Sea? aboard a great boat. During the tour you can feel the sun and the breeze while sailing towards a reef, where you will have the opportunity to snorkel and admire ... More

Incredible Party in Unlimited Catamaran to Isla Mujeres! + Transp....
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North America
Are you ready for a wonderful day sailing through the Caribbean Sea? aboard a great boat. During the....
Romantic Experience Sunset Dinner Columbus in Cancun (2x1 price)
Love will surrender to the most cherished secrets of Nichupte Lagoon aboard Columbus Lobster Dinner Cruise. This is one of a kind romance tour in Cancun offering a special evening surrounded by breathtaking views, live saxophone m... More

Romantic Experience Sunset Dinner Columbus in Cancun (2x1 price)
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North America
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Exellent5 reviews4.2
Love will surrender to the most cherished secrets of Nichupte Lagoon aboard Columbus Lobster Dinner ....
Private Afternoon Boat Ride and Beach Excursion 3 hours
Enjoy a half day cruising the harbor on a private center console captained by a professional yacht captain. Stop at secluded island beaches for shark tooth hunting, shelling or just lay out on the beach. We pass by all the histo... More
Private Tour

Private Afternoon Boat Ride and Beach Excursion 3 hours
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North America
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Superb8 reviews5
Enjoy a half day cruising the harbor on a private center console captained by a professional yacht c....
Private Tour
Key West Nighttime Full Moon Sail
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moo... More
Private Tour

Key West Nighttime Full Moon Sail
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North America
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Superb6 reviews5
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1....
Private Tour
Schooner Bloody Mary Day Sail with Full Open Bar in Key West
Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water’s surface or circling in the blue sky above you. P... More
Private Tour

Schooner Bloody Mary Day Sail with Full Open Bar in Key West
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North America
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Superb6 reviews5
Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in pa....
Private Tour
2 Hours Cocktail Sail Aboard Bella
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the water. Spot dolphins, seabirds, and other wildlife as you pass by islands and marshlands. The boat is fully equipped with air con... More
Private Tour

2 Hours Cocktail Sail Aboard Bella
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North America
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Superb6 reviews5
Our experienced captains will sail you to the most beautiful local spots to watch the sunset on the ....
Private Tour
2-Hour Private Morning Charter on Heart's Desire in Casco Bay
Sail aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in ... More
Private Tour

2-Hour Private Morning Charter on Heart's Desire in Casco Bay
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North America
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Superb6 reviews5
Sail aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and fea....
Private Tour
Isla Mujeres Catamaran Day Trip with Snorkel Open Bar and Buffet
Discover the Magic of Isla Mujeres on a Catamaran Adventure! Sail across the turquoise Caribbean waters from Cancun to Isla Mujeres on this unforgettable catamaran tour. Perfect for adventure seekers and families alike, this expe... More
Private Tour

Isla Mujeres Catamaran Day Trip with Snorkel Open Bar and Buffet
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North America
Discover the Magic of Isla Mujeres on a Catamaran Adventure! Sail across the turquoise Caribbean wa....
Private Tour
Morning Pali Coast Snorkel and Performance Sail
The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Gardens which boasts a unique blend of coral and sea life tucked into the cliffs near the West Maui Mountains. Enjoy the best conditions... More
Private Tour

Morning Pali Coast Snorkel and Performance Sail
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North America
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Superb4 reviews4.8
The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Garden....
Private Tour
Condor Sailing Public Dolphin and 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

Condor Sailing Public Dolphin and Sightseeing Cruise
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North America
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Superb4 reviews5
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....
Private Tour
Private Tour Isla Mujeres excursion in Transparent Boat
We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our 100% transparent boat. It will be a unique activity for you, where you will be given a guided tour of different reefs to apprecia... More
Private Tour

Private Tour Isla Mujeres excursion in Transparent Boat
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North America
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Good3 reviews3.3
We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our ....
Private Tour
Catamaran Sailboat Bacalar Excursions
Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike traditional catamarans, the Stiletto combines the thrill of speed with exceptional stability, ensuring a smooth and exciting ride,... More
Private Tour

Catamaran Sailboat Bacalar Excursions
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North America
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Superb1 review5
Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike ....
Private Tour
Private South Shore Sail Charter
Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More
Private Tour

Private South Shore Sail Charter
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North America
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Superb2 reviews5
Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....
Private Tour
Spend the Day on Buzzards Bay - Sailing Trips
Skip the Newport bridge traffic and toursit traps and come spend the day in picturesque Mattapoisett Harbor, a quaint New England coastal village. Whether you want to go for a sail or cruise the shoreline, we're happy to make sug... More
Private Tour

Spend the Day on Buzzards Bay - Sailing Trips
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North America
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Superb6 reviews5
Skip the Newport bridge traffic and toursit traps and come spend the day in picturesque Mattapoisett....
Private Tour
3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya
We know you’re not just looking for a yacht—you’re looking for an experience. We’re in the business of making dreams come true! Our new yacht is the hottest new addition to our fleet. The Canadian built Neptunus is truly ... More
Private Tour

3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya
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North America
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Superb56 reviews4.7
We know you’re not just looking for a yacht—you’re looking for an experience. We’re in the ....
Private Tour

Jolly Roger Pirate Ship Cruise & Dinner Show
Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed sunset cruise on the gorgeous Spanish Galleon for the ideal evening out with the whole family. The buccaneers start greeting you a... More
Free Cancellation
Private Tour
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Jolly Roger Pirate Ship Cruise & Dinner Show
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North America
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Superb56 reviews4.7
Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed s....
Free Cancellation
Private Tour
(Saving 10% )
The Ultimate Catamaran Party Cruise Experience!
Experience the Ultimate Catamaran Party Cruise! Step aboard the renowned Pez Gato for Los Cabos' original and most exhilarating sunset party cruise. Groove to the beats of today's hits and timeless classics with our curated play... More
Private Tour

The Ultimate Catamaran Party Cruise Experience!
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North America
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Superb56 reviews4.7
Experience the Ultimate Catamaran Party Cruise! Step aboard the renowned Pez Gato for Los Cabos' or....
Private Tour
SUNSET CRUISE in Key Largo,FL.
KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personab... More
Private Tour

SUNSET CRUISE in Key Largo,FL.
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North America
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Superb3 reviews5
KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need t....
Private Tour
Los Cabos Amazing Resort Day Pass (Snorkel, Jet Ski, SUP, Surf)
Los Cabos is known for its beautiful beach areas, amazing views, astonishing beach locations but only a few are safe for swimming. If you are looking for a unforgettable day full of Fun, Sun, Amazing Beach Area and a wide variety ... More
Private Tour

Los Cabos Amazing Resort Day Pass (Snorkel, Jet Ski, SUP, Surf)
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North America
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Superb3 reviews5
Los Cabos is known for its beautiful beach areas, amazing views, astonishing beach locations but onl....
Private Tour