Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 4Small-Group San Diego Sunset Sailing Excursion
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More

Small-Group San Diego Sunset Sailing Excursion
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North America
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Superb548 reviews4.9
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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North America
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Superb100 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Sunset Sip and Sail Key West with Open Bar and Live Music
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Sunset Sip and Sail Key West with Open Bar and Live Music
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North America
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Exellent255 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. ....
Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More

Sunset and Manta Ray Snorkel Adventure
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North America
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Superb744 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
Adults only Sunset Cruise from Key West with Champagne
Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are the house champagne Chandon Brut, 7 premium red and whit... More

Adults only Sunset Cruise from Key West with Champagne
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North America
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Superb872 reviews4.9
Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Ch....
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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Superb47 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
Private Tour
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
Private Tour

Snorkel with Manta Rays Guaranteed
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North America
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Superb660 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
Private Tour
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More
Private Tour

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
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North America
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Superb423 reviews4.6
Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....
Private Tour
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More
Private Tour

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
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North America
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Superb50 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Private Tour

Key West Dolphin and Snorkel Experience
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North America
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Exellent262 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Private Tour
Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More
Private Tour

Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail
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North America
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Exellent346 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More
Private Tour

Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb215 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private Tour
2 hour Tiki Pub Sensational Sunset Cruise (Adults only)
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More
Private Tour

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)
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North America
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Superb53 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More
Private Tour

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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North America
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Superb256 reviews4.8
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
Private Tour

El Cielo Cozumel and Turtle Bay Snorkeling 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
Free Cancellation
Private Tour
(Saving 10% )

El Cielo Cozumel and Turtle Bay Snorkeling by Catamaran
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North America
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Exellent276 reviews4.4
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....
Free Cancellation
Private Tour
(Saving 10% )
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More
Private Tour

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
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North America
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Very Good200 reviews3.7
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....
Private Tour
Private Sailing Charter with Captain, BYOB
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More
Private Tour

Private Sailing Charter with Captain, BYOB
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North America
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Superb45 reviews5
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....
Private Tour
2-Hour Private Sailing Experience in San Diego Bay
Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More
Private Tour

2-Hour Private Sailing Experience in San Diego Bay
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North America
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Superb147 reviews5
Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....
Private Tour
4-Hour Fort Lauderdale Sailing Charter
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More
Private Tour

4-Hour Fort Lauderdale Sailing Charter
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North America
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Superb280 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
Private Tour
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More
Private Tour

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
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North America
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Superb493 reviews5
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....
Private Tour