Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 688 Sailing Trips activities in North America. Sort by Popularity. - Page 22Whale Shark Experience Lifetime Memory in Cancun (snack included)
Welcome to the Whale Shark experience, this is an unique activity in the world and is the most enigmatic activity in Mexico. Imagine swimming next to an immense fish like the whale shark. This animal is completely harmless since... More

Whale Shark Experience Lifetime Memory in Cancun (snack included)
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North America
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Very Good17 reviews3.9
Welcome to the Whale Shark experience, this is an unique activity in the world and is the most enigm....
Private Luxury 42ft Sailing with Snorkeling in Los Cabos
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful white beaches. Your yacht and crew will provide you with all the ameni... More
Private Tour

Private Luxury 42ft Sailing with Snorkeling in Los Cabos
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North America
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Superb122 reviews5
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Sno....
Private Tour
Whale Shark Encounter Experience in Cancun (Snack Lunch included)
If you like awesome and unique activities, then this activity is for you. Welcome to the Whale Shark experience, this is a unique activity in the world and is the most enigmatic activity in Mexico. Imagine swimming next to an imme... More
Private Tour

Whale Shark Encounter Experience in Cancun (Snack Lunch included)
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North America
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Exellent4 reviews4.3
If you like awesome and unique activities, then this activity is for you. Welcome to the Whale Shark....
Private Tour
New York City Live Jazz Sail
Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around New York Harbor. Sit back and relax while enjoying live Jazz music played throughout this s... More
Private Tour

New York City Live Jazz Sail
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North America
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Superb12 reviews4.9
Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's....
Private Tour
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 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 in Waikiki for 1-6 People
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North America
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Superb14 reviews4.8
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Full-Day Sailing Trip to Mujeres Island from Playa del Carmen
The best way to see Isla Mujeres from Riviera Maya! Set sail for tropical adventure with a luxurious catamaran cruise from Cancun to Isla Mujeres. Includes a guided snorkel tour of the reef and time in downtown Isla Mujeres, open ... More
Free Cancellation
Private Tour
(Saving 25% )

Full-Day Sailing Trip to Mujeres Island from Playa del Carmen
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North America
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Good23 reviews3.2
The best way to see Isla Mujeres from Riviera Maya! Set sail for tropical adventure with a luxurious....
Free Cancellation
Private Tour
(Saving 25% )
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More
Private Tour

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
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North America
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Superb27 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Jolly Roger Pirate Show and Dinner Cruise with Open Bar
Spend you vacations' funniest evening along with Jolly Roger's flamboyant priate crew. Cruise along the Cancun coast while singing, drinking, dancing and participating in a variety of hilarious games and contests. The little pirat... More
Private Tour

Jolly Roger Pirate Show and Dinner Cruise with Open Bar
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North America
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Superb8 reviews4.6
Spend you vacations' funniest evening along with Jolly Roger's flamboyant priate crew. Cruise along ....
Private Tour
Isla Mujeres Plus by Albatros Catamarans
Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise of the Mexican Caribbean, enjoy the delicacies of Mexican food, dance to Latin rhythms and forget a... More
Private Tour

Isla Mujeres Plus by Albatros Catamarans
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North America
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Exellent310 reviews4.3
Delight all your senses aboard a boat that will take you to one of the best islands in the world, sw....
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
Private Tour

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....
Private Tour
Private Catamaran Tour
Our starting point is the iconic Casa China with incredible views of the lagoon from its 360° lookout tower. Our friendly bilingual staff enlivens the tour with stories of the place and important facts about the local ecosystem. ... More
Private Tour

Private Catamaran Tour
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North America
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Superb137 reviews4.9
Our starting point is the iconic Casa China with incredible views of the lagoon from its 360° looko....
Private Tour
San Diego Half-Day Marine Wildlife Tour with Lunch
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the Pacific Ocean and catch a chance to see local marine wildlife in its natural habitat, including sea lions, pelicans, and migrator... More
Private Tour

San Diego Half-Day Marine Wildlife Tour with Lunch
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North America
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Superb27 reviews4.8
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the P....
Private Tour
Hidden Beach - Marietas Islands
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursion, departing from Puerto Vallarta. Even those without experience can feel comfortable participating in guided snorkeling excursion... More
Private Tour

Hidden Beach - Marietas Islands
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North America
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Exellent42 reviews4.4
Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursio....
Private Tour
Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres or just sail on the bay. Snorkel and discover the natural beauty of the great reefs of Cancun. Private... More
Private Tour

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp
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North America
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Exellent61 reviews4.2
Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go....
Private Tour

Private Sailing Tour of Bodega Bay
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North America
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Superb81 reviews4.8
This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be i....
Private Tour
Private sailing excursions, nice spacious sailboats.
We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfortable, 2 canopy’s to keep you protected from the elements and a 5 star crew. We provide an atmosphere for you to take over and T... More
Private Tour

Private sailing excursions, nice spacious sailboats.
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North America
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Superb24 reviews4.9
We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfor....
Private Tour

Private Chica SAILING Adventure Puerto Vallarta ALL INCLUSIVE
Explore the stunning Bay of Banderas aboard the 41-foot Chica Sailing Adventure. Customize your tour to suit your desires—whether you’re after a romantic sunset cruise, adrenaline-pumping sailing, or a tranquil journey to a se... More
Free Cancellation
Private Tour
(Saving 15% )

Private Chica SAILING Adventure Puerto Vallarta ALL INCLUSIVE
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North America
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Superb43 reviews4.9
Explore the stunning Bay of Banderas aboard the 41-foot Chica Sailing Adventure. Customize your tour....
Free Cancellation
Private Tour
(Saving 15% )
2 hours - Private Day Sail along Historic St Augustine Bayfront
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More
Private Tour

2 hours - Private Day Sail along Historic St Augustine Bayfront
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North America
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Superb18 reviews5
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....
Private Tour
All Inclusive Caribbean adventure, reef snorkeling, Food & Drinks
Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience. Explore Isla Mujeres impressive sites are waiting for you. You will visit one of ... More
Skip The Line
Private Tour

All Inclusive Caribbean adventure, reef snorkeling, Food & Drinks
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North America
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Very Good33 reviews3.7
Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sail....
Skip The Line
Private Tour
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos
Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoamerican Barrier Reef System, the second-largest coral reef in the world! Departing daily at 9 AM and 2 PM, our adventure begins wit... More
Skip The Line
Private Tour

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelo....
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North America
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Very Good10 reviews3.7
Join us for an unforgettable sailboat tour to the stunning Puerto Morelos Reef, a part of the Mesoam....
Skip The Line
Private Tour