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Top 10 Best North America Sailing Trips

Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 695 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Start From $129.00
 
Sunset Catamaran Cruise in Ft. Lauderdale

Sunset Catamaran Cruise in Ft. Lauderdale

  • North America
  • Superb695 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Start From $129.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 77 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $159.00
 
Day's End Cocktail Sunset Sail

Day's End Cocktail Sunset Sail

  • North America
  • Superb77 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $159.00
 
 

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(4.6 of 727 reviews)

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More

Free Cancellation
Start From $89.00
 
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

  • North America
  • Superb727 reviews4.6

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....

    Free Cancellation
    Start From $89.00
 
 

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

(4.9 of 678 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 Sparrow and set sail in search of treasure! But wait it's no... More

Free Cancellation
Start From $47.99
 
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
  • Superb678 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 $47.99
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 402 reviews)

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Luxury Yacht Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Yacht Charters, BYOB & Dolphins

  • North America
  • Superb402 reviews5

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.4 of 435 reviews)

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

Free Cancellation
Private Tour
Start From $59.95
 
Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

Key West Afternoon Reef Snorkeling with Open Bar

  • North America
  • Exellent435 reviews4.4

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Key West Sunset Sail Aboard Legendary Schooner Appledore

(5 of 321 reviews)

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Private Tour
Start From $89.00
 
Key West Sunset Sail Aboard Legendary Schooner Appledore Likely to Sell Out

Key West Sunset Sail Aboard Legendary Schooner Appledore

  • North America
  • Superb321 reviews5

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 616 reviews)

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Free Cancellation
Private Tour
Start From $99.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • North America
  • Superb616 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 829 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Private Tour
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • North America
  • Superb829 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Private Tour
    Start From $202.59
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 255 reviews)

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

Free Cancellation
Private Tour
Start From $149.00
 
Half-Day Luxury Sailing Experience in Tulum with Open Bar Likely to Sell Out

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent255 reviews4.2

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,117 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Private Tour
Start From $149.95
 
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • North America
  • Superb2,117 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Private Tour
    Start From $149.95
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 594 reviews)

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More

Free Cancellation
Private Tour
Start From $59.00
 
Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • North America
  • Superb594 reviews4.8

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 349 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Free Cancellation
Private Tour
Start From $69.95
 
Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • North America
  • Exellent349 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 401 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Free Cancellation
Private Tour
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • North America
  • Superb401 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

(4.5 of 299 reviews)

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More

Free Cancellation
Private Tour
Start From $199.00
 
Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef Likely to Sell Out

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

  • North America
  • Exellent299 reviews4.5

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Bimini or Grand Bahama Island by Ferry

(3.5 of 18 reviews)

Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Florida! Picture this: pristine white beaches, crystal-clear turquoise waters, and tons of fun activities waiting for you. We'll pick... More

Free Cancellation
Private Tour
Start From $225.00
 
Bimini or Grand Bahama Island by Ferry Likely to Sell Out

Bimini or Grand Bahama Island by Ferry

  • North America
  • Good18 reviews3.5

Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.8 of 399 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Private Tour
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • North America
  • Superb399 reviews4.8

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

(4.6 of 438 reviews)

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More

Free Cancellation
Private Tour
Start From $109.00
 
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar Likely to Sell Out

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

  • North America
  • Superb438 reviews4.6

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

(4.8 of 2,317 reviews)

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More

Free Cancellation
Private Tour
Start From $109.00
 
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Likely to Sell Out

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

  • North America
  • Superb2,317 reviews4.8

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 732 reviews)

A three hour tour you won't want to miss! 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 a... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb732 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Private Tour
    Start From $136.19
 
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