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Top 10 Best North America Sailing Trips

Found 686 Sailing Trips activities in North America. Sort by Popularity. - Page 6
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 154 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Start From $79.00
 
BYOB Waikiki Sunset Swim and Diamond Head Sailing

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • North America
  • Superb154 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Start From $79.00
 
 

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

(4.6 of 91 reviews)

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

Free Cancellation
Start From $95.00
 
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music Likely to Sell Out

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

  • North America
  • Superb91 reviews4.6

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....

    Free Cancellation
    Start From $95.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 382 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb382 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Start From $99.00
 
 

New York City Sunset Jazz Sail aboard Clipper City

(4.4 of 102 reviews)

Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantage point of the harbor. Order a drink from our full bar as we raise canvas and leave Manhattan behind as the melodies of live jazz ... More

Free Cancellation
Start From $112.00
 
New York City Sunset Jazz Sail aboard Clipper City Likely to Sell Out

New York City Sunset Jazz Sail aboard Clipper City

  • North America
  • Exellent102 reviews4.4

Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantag....

    Free Cancellation
    Start From $112.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 342 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb342 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Start From $64.95
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 222 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • North America
  • Superb222 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.8 of 30 reviews)

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

Free Cancellation
Start From $49.00
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast Likely to Sell Out

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • North America
  • Superb30 reviews4.8

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Start From $49.00
 
 

Day Sail from Traverse City with Food, Wine, & Cocktails

(4.9 of 129 reviews)

For a full description please visit our website at https://www.winddancertc.com/ where you can learn about the vessel, crew, local history and make your bookings!... More

Free Cancellation
Start From $169.00
 
Day Sail from Traverse City with Food, Wine, & Cocktails Likely to Sell Out

Day Sail from Traverse City with Food, Wine, & Cocktails

  • North America
  • Superb129 reviews4.9

For a full description please visit our website at https://www.winddancertc.com/ where you can learn....

    Free Cancellation
    Start From $169.00
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 650 reviews)

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

Free Cancellation
Start From $41.99
 
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger Likely to Sell Out

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

  • North America
  • Superb650 reviews4.9

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....

    Free Cancellation
    Start From $41.99
 
 

Wrightsville Beach Sunset Cocktail Sail

(5 of 5 reviews)

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while you cruise our local waterways and watch the sunset. Wind permitting, we'll turn off the engines and enjoy the beauty of sailing!... More

Free Cancellation
Start From $150.00
 
Wrightsville Beach Sunset Cocktail Sail Likely to Sell Out

Wrightsville Beach Sunset Cocktail Sail

  • North America
  • Superb5 reviews5

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while....

    Free Cancellation
    Start From $150.00
 
 

Newport Sunset Sail on Schooner Adirondack

(4.9 of 40 reviews)

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailbo... More

Free Cancellation
Start From $67.84
 
Newport Sunset Sail on Schooner Adirondack Likely to Sell Out

Newport Sunset Sail on Schooner Adirondack

  • North America
  • Superb40 reviews4.9

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....

    Free Cancellation
    Start From $67.84
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 515 reviews)

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

Free Cancellation
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • North America
  • Superb515 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Start From $79.00
 
 

Sailing Experience on a 50’ sailboat

(5 of 72 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Start From $111.85
 
Sailing Experience on a 50’ sailboat Likely to Sell Out

Sailing Experience on a 50’ sailboat

  • North America
  • Superb72 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Start From $111.85
 
 

Sunset Catamaran Sail in Cocoa Beach

(5 of 146 reviews)

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Florida�... More

Free Cancellation
Start From $55.37
 
Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb146 reviews5

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Start From $55.37
 
 

Private Yacht Tour Miami

(4 of 6 reviews)

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

Free Cancellation
Private Tour
Start From $286.00
 
Private Yacht Tour Miami Likely to Sell Out

Private Yacht Tour Miami

  • North America
  • Very Good6 reviews4

Discover the vibrant allure of Miami from the luxurious vantage point of our yacht tours. Embark on ....

    Free Cancellation
    Private Tour
    Start From $286.00
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(5 of 128 reviews)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Free Cancellation
Private Tour
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • North America
  • Superb128 reviews5

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Tall Ship Silva Sailing Cruise Ft. a Live Musician

(4.1 of 205 reviews)

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More

Free Cancellation
Private Tour
Start From $40.59
 
Tall Ship Silva Sailing Cruise Ft. a Live Musician Likely to Sell Out

Tall Ship Silva Sailing Cruise Ft. a Live Musician

  • North America
  • Exellent205 reviews4.1

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....

    Free Cancellation
    Private Tour
    Start From $40.59
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 80 reviews)

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More

Free Cancellation
Private Tour
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • North America
  • Superb80 reviews4.9

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(5 of 64 reviews)

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

Free Cancellation
Private Tour
Start From $671.68
 
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling Likely to Sell Out

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb64 reviews5

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....

    Free Cancellation
    Private Tour
    Start From $671.68
 
 

Private Guided Sunset and Dolphin Cruise up to 6 Passengers

(5 of 64 reviews)

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

Free Cancellation
Private Tour
Start From $249.99
 
Private Guided Sunset and Dolphin Cruise up to 6 Passengers Likely to Sell Out

Private Guided Sunset and Dolphin Cruise up to 6 Passengers

  • North America
  • Superb64 reviews5

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....

    Free Cancellation
    Private Tour
    Start From $249.99
 
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