Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 6Sunset Sail Experience at Kona from Honokohau
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Sunset Sail Experience at Kona from Honokohau
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North America
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Superb143 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....
Private Sailing Tour through the Ten Thousands Islands
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More
Private Tour

Private Sailing Tour through the Ten Thousands Islands
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North America
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Superb137 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
Private Tour
Sunset Sailing Cruise in Monterey Bay
Our most popular and romantic cruise with appetizers! The sunset cruise departs 90 minutes prior to the sunset every day year around. During your hour and a half trip you will enjoy complimentary wine along with a delicious appeti... More
Private Tour

Sunset Sailing Cruise in Monterey Bay
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North America
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Superb10 reviews5
Our most popular and romantic cruise with appetizers! The sunset cruise departs 90 minutes prior to ....
Private Tour
2Hr Private Boat Tour Miami Beach, Captain & Champagne, & Sandbar
Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of friends, bachelorette parties, and anyone looking to celebrate in style. Cruise the sparkling waters of Miami while enjoying your ... More
Private Tour

2Hr Private Boat Tour Miami Beach, Captain & Champagne, & Sandbar
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North America
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Superb264 reviews4.8
Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of f....
Private Tour
Oahu 3pm Whale Watching from Honolulu
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphins, whales and other sea life while getting as close as possible so you c... More
Private Tour

Oahu 3pm Whale Watching from Honolulu
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North America
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Superb225 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
Private Tour
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
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

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
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North America
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Superb48 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles
This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More
Private Tour

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles
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North America
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Superb3 reviews5
This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....
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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Superb406 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
Private Tour
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
Private Tour

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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North America
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Superb19 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Private Tour
Limited Time Weekday Super Promo, 48ft Private Yacht Rental,
Discover the vibrant allure of Miami from the luxurious vantage point of our yacht tours. Embark on a journey where turquoise waters meet golden shores, with panoramic views of iconic landmarks like South Beach and the Miami skyli... More
Private Tour

Limited Time Weekday Super Promo, 48ft Private Yacht Rental,
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North America
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Very Good6 reviews4
Discover the vibrant allure of Miami from the luxurious vantage point of our yacht tours. Embark on ....
Private Tour
Isla Mujeres, Cancún Private Sunset Trip
Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the moment. We are here to bring you the the quality service you so rightly deserve. Our adored crew ensure... More
Private Tour

Isla Mujeres, Cancún Private Sunset Trip
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North America
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Superb70 reviews5
Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the....
Private Tour
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
Private Tour

2.5 Hours of Fun: Catamaran Sunset Sail
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North America
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Superb145 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
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 Good389 reviews4
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
Private Tour
El Cielo Cozumel Snorkeling by Private Boat
TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned r... More
Private Tour

El Cielo Cozumel Snorkeling by Private Boat
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North America
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Superb131 reviews4.8
TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water trea....
Private Tour
Half 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
Private Tour

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
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North America
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Exellent58 reviews4.3
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More
Private Tour

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
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North America
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Superb21 reviews4.9
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....
Private Tour
Sail Splash and Sailing Excursion in Ft. Lauderdale
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More
Private Tour

Sail Splash and Sailing Excursion in Ft. Lauderdale
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North America
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Superb261 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
Private Tour
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
Private Tour

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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North America
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Superb624 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
Private Tour
2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More
Private Tour

2-Hour Oahu Sunset Catamaran Sail
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North America
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Superb99 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
Private Tour
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More
Private Tour

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
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North America
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Superb174 reviews5
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....
Private Tour