Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 687 Sailing Trips activities in North America. Sort by Popularity. - Page 6Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
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North America
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Exellent60 reviews4.4
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
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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Superb20 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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North America
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Superb23 reviews4.8
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
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

4-Hour Fort Lauderdale Sailing Charter
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North America
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Superb287 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
2.5 Hours of Fun: Catamaran Sunset Sail
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More

2.5 Hours of Fun: Catamaran Sunset Sail
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North America
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Superb148 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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North America
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Superb10 reviews4.9
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
9am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

9am Turtle Canyon Snorkel Adventure
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North America
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Superb243 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Portland Tall Ship Cruise on Casco Bay
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More

Portland Tall Ship Cruise on Casco Bay
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North America
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Exellent222 reviews4.5
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb433 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
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

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)
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North America
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Superb62 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Dagger and set sail in search of treasure! But wait it's not... More

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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North America
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Superb634 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
Monterey Bay Whale Watching
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Monterey Bay Whale Watching
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North America
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Superb276 reviews4.7
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More
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FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
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North America
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Very Good9 reviews3.9
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....
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Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More

Dolphin Adventure Sail in Cocoa Beach
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North America
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Superb131 reviews5
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....
Sail and Turtle Snorkeling Tour in Waikiki
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More

Sail and Turtle Snorkeling Tour in Waikiki
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North America
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Superb235 reviews4.9
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....
6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches
Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make... More
Private Tour

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beac....
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North America
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Superb11 reviews5
Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure ....
Private Tour
Sail Biscayne Bay: An Intimate Eco-Adventure
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
Private Tour

Sail Biscayne Bay: An Intimate Eco-Adventure
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North America
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Superb412 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
Private Tour
Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard
• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish and rich marine life that inhabit the colorful reefs of the island. • Paddleboard a... More
Private Tour

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboa....
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North America
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Superb217 reviews4.8
• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel a....
Private Tour
Private Guided Sunset and Dolphin Cruise up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Private Tour

Private Guided Sunset and Dolphin Cruise up to 6 Passengers
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North America
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Superb57 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
2-Hour Windjammer Sailing Trip in Maine with Licensed Captain
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More
Private Tour

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain
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North America
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Very Good390 reviews4
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
Private Tour