Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 4Two Hour Coastal Sailing Cruise
What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. Unlike crowded tour boats, our open-deck layout offers plenty of room... More
Two Hour Coastal Sailing Cruise
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North America
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Superb26 reviews5
What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one....
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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North America
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Superb958 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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North America
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Superb45 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Key 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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Superb186 reviews4.8
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Molokini Snorkel and Performance Sail: Mā’alaea Harbor
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More
Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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North America
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Superb214 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Deluxe Sunset & Day Sail Small Group
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More
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Deluxe Sunset & Day Sail Small Group
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North America
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Superb247 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
Free Cancellation
(Saving 15% )
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More
Likely to Sell Out Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
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North America
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Superb107 reviews4.6
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More
Likely to Sell Out Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
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North America
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Superb445 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unforgettable journey to the famous El Cielo sandbar! Just 5–10 minutes by taxi from any cruise terminal or downtown, enjoy award-wi... More
Private Tour
Likely to Sell Out Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
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North America
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Superb20 reviews4.8
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unfo....
Private Tour
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Private Tour
Likely to Sell Out Waikiki Sunset Boat Cruise
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North America
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Superb104 reviews4.9
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Private Tour
Key West Reef Snorkel & Sail 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
Private Tour
Likely to Sell Out Key West Reef Snorkel & Sail Adventure
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North America
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Superb541 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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
Likely to Sell Out Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
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North America
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Exellent372 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Private Tour
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 ... More
Private Tour
Likely to Sell Out Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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North America
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Superb173 reviews4.8
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Private Tour
2 hour Tiki Pub Sensational Dolphin 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
Likely to Sell Out 2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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North America
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Superb111 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
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
Likely to Sell Out Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
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North America
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Very Good206 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
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour
Likely to Sell Out Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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North America
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Superb166 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Tour
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, 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 pals on ou... More
Private Tour
Likely to Sell Out Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
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North America
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Superb30 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
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
Likely to Sell Out El Cielo Cozumel Snorkeling trip by Catamaran
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North America
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Exellent279 reviews4.4
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....
Private Tour
Akialoa Mā’alaea Sunset Sail
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More
Private Tour
Likely to Sell Out Akialoa Mā’alaea Sunset Sail
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North America
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Exellent8 reviews4.5
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....
Private Tour
Private Sailboat tour in Cabo San Lucas with Papillon Yachts
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More
Private Tour
Likely to Sell Out Private Sailboat tour in Cabo San Lucas with Papillon Yachts
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North America
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Superb199 reviews5
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....
Private Tour