Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 692 Sailing Trips activities in North America. Sort by Popularity. - Page 29Private Cancun Sailboat Cruise with Beers and Sodas Included
Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island gem just off the coast of Cancun. Step aboard our fine vessel and embark on a journey of discovery and relaxation in the breathta... More
Private Tour

Private Cancun Sailboat Cruise with Beers and Sodas Included
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North America
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Superb1 review5
Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island....
Private Tour
Private Sailing Experience on Galveston Bay
See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to travel aboard our luxury charter yacht. We offer the perfect blend of comfort and adventure, making it the ... More
Private Tour

Private Sailing Experience on Galveston Bay
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North America
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Superb1 review5
See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and....
Private Tour
Key West Christmas Cruise with Live Band and Drinks
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More
Private Tour

Key West Christmas Cruise with Live Band and Drinks
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North America
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Superb3 reviews5
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christ....
Private Tour
Luxury Catamaran tour to Isla Mujeres with transportation from Playa del Carmen
Because it's an amazing place where you can relax in the beautiful Caribbean Sea, we offer you a personal assistance from our incredible crew that will make you have a great time, you will snorkel in an amazing part of the second ... More
Private Tour

Luxury Catamaran tour to Isla Mujeres with transportation from Pl....
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North America
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Exellent60 reviews4.3
Because it's an amazing place where you can relax in the beautiful Caribbean Sea, we offer you a per....
Private Tour
Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo
Embark on two unforgettable Cancun adventures with this incredible combo package! Day 1: Unleash your inner thrill-seeker on a wild ATV Jungle Tour. Race through the Mayan jungle, soar through the treetops on ziplines, and refres... More
Private Tour

Cancun ATV Jungle Adventure & Isla Mujeres Catamaran Combo
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North America
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Exellent60 reviews4.3
Embark on two unforgettable Cancun adventures with this incredible combo package! Day 1: Unleash yo....
Private Tour

Luxury Camden Sailing Experience
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North America
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Exellent60 reviews4.3
Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....
Private Tour
Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres
A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catamaran tour from Cancun to Isla Mujeres. The day begins with a leisurely sail across the turquoise waters, where you'll enjoy drinks... More
Private Tour

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres
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North America
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Exellent60 reviews4.3
A Caribbean Escape Like No Other! Experience the beauty of the Caribbean on this all-inclusive catam....
Private Tour
2.5 hr Sailboat Tour aboard Orion's Child
TripAdvisor SPECIAL MONDAY ONLY Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sa... More
Private Tour

2.5 hr Sailboat Tour aboard Orion's Child
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North America
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Superb58 reviews5
TripAdvisor SPECIAL MONDAY ONLY Sail. SEE OUR WEBSITE for other options and availability. Since 2009....
Private Tour
Tour in a Catamaran To Isla Mujeres
We are the most complete tour of the Riviera Maya since we offer round transportation from your hotel to the marina, open bar with national drinks on the Catamaran, snorkeling activity, buffet lunch at the beach club and free time... More
Private Tour

Tour in a Catamaran To Isla Mujeres
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North America
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Superb1 review5
We are the most complete tour of the Riviera Maya since we offer round transportation from your hote....
Private Tour
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
Private Tour

Incredible Party in Unlimited Catamaran to Isla Mujeres! + Transp....
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North America
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Superb1 review5
Are you ready for a wonderful day sailing through the Caribbean Sea? aboard a great boat. During the....
Private Tour
Private Sailing Adventure in Bacalar
Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our guides are knowledgeable about the area, each point we visit comes with a detail ex... More
Private Tour

Private Sailing Adventure in Bacalar
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North America
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Superb10 reviews5
Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We....
Private Tour
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
Private Tour

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 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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Superb7 reviews5
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1....
Private Tour
Whale Shark Snorkel Tour in Cancun (Snack Lunch included)
Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whale shark adventure is the most enigmatic activity in Mexico. It is a very docile animal that is just as impressive as any other a... More
Private Tour

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)
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North America
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Superb7 reviews5
Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whal....
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
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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 ....
Free Cancellation
Private Tour
(Saving 10% )
Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres
Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. From there, set sail to the charming Isla Mujeres, a Pueblo Mágico (Magical Town), where you’ll have an hour to explore its vibran... More
Private Tour

Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres
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North America
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Good3 reviews3.3
Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. Fro....
Private Tour
Full-Day Reef Snorkeling in Cozumel from Cancun 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
Private Tour

Full-Day Reef Snorkeling in Cozumel from Cancun with Lunch
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North America
Expore famous Cozumel's top snorkeling locations within the same day on this complete quest featurin....
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
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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Superb74 reviews4.8
We know you’re not just looking for a yacht—you’re looking for an experience. We’re in the ....
Private Tour
Sunset Sailing for Couples and Small Groups
Embark on a magical sunset sailing tour, a luxurious sailboat designed for intimate, small-group experiences. Perfect for couples or small groups looking to share the beauty of a sunset at sea with like-minded sunset and sailing e... More
Private Tour

Sunset Sailing for Couples and Small Groups
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North America
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Superb2 reviews5
Embark on a magical sunset sailing tour, a luxurious sailboat designed for intimate, small-group exp....
Private Tour