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Top 10 Best North America Sailing Trips

Found 690 Sailing Trips activities in North America. Sort by Popularity. - Page 5
 

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

(3.7 of 202 reviews)

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

Free Cancellation
Start From $69.99
 
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar

  • North America
  • Very Good202 reviews3.7

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....

    Free Cancellation
    Start From $69.99
 
 

2-Hour Private Luxury Boat Tour in New York City

(5 of 73 reviews)

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More

Free Cancellation
Private Tour
Start From $499.99
 
2-Hour Private Luxury Boat Tour in New York City

2-Hour Private Luxury Boat Tour in New York City

  • North America
  • Superb73 reviews5

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Sailing Charters in Wilmington

(5 of 156 reviews)

After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More

Free Cancellation
Private Tour
Start From $89.00
 
Sailing Charters in Wilmington

Sailing Charters in Wilmington

  • North America
  • Superb156 reviews5

After a successful first season I am happy to be here for back to back seasons. Sail in style on the....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Southwest Florida Sunset Sail

(4.9 of 432 reviews)

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Free Cancellation
Private Tour
Start From $70.00
 
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

  • North America
  • Superb432 reviews4.9

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 26 reviews)

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

Free Cancellation
Private Tour
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • North America
  • Superb26 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(5 of 63 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 $676.31
 
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb63 reviews5

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

    Free Cancellation
    Private Tour
    Start From $676.31
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 702 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Private Tour
Start From $141.57
 
Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

  • North America
  • Superb702 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Private Tour
    Start From $141.57
 
 

Pau Hana Sunset Cocktail Cruise

(4.8 of 55 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Private Tour
Start From $165.00
 
Pau Hana Sunset Cocktail Cruise

Pau Hana Sunset Cocktail Cruise

  • North America
  • Superb55 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

(4.9 of 729 reviews)

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

Free Cancellation
Private Tour
Start From $116.10
 
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres Likely to Sell Out

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

  • North America
  • Superb729 reviews4.9

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....

    Free Cancellation
    Private Tour
    Start From $116.10
 
 

Sunset Sail Experience at Kona from Honokohau

(4.8 of 157 reviews)

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

Free Cancellation
Private Tour
Start From $152.55
 
Sunset Sail Experience at Kona from Honokohau Likely to Sell Out

Sunset Sail Experience at Kona from Honokohau

  • North America
  • Superb157 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Private Tour
    Start From $152.55
 
 

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

(4.9 of 221 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
Private Tour
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
  • Superb221 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $72.96
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.8 of 29 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
Private Tour
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
  • Superb29 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

San Francisco Bay Cruise

(4.4 of 268 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

Free Cancellation
Private Tour
Start From $38.00
 
San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • North America
  • Exellent268 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Free Cancellation
    Private Tour
    Start From $38.00
 
 

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
Private Tour
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
    Private Tour
    Start From $95.00
 
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 153 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
Private Tour
Start From $79.00
 
BYOB Waikiki Sunset Swim and Diamond Head Sailing Likely to Sell Out

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • North America
  • Superb153 reviews5

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

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

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
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 458 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Private Tour
Start From $52.95
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb458 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Private Tour
    Start From $52.95
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 242 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
  • Exellent242 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
 
 

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat

(5 of 28 reviews)

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More

Free Cancellation
Private Tour
Start From $899.00
 
Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat Likely to Sell Out

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat

  • North America
  • Superb28 reviews5

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....

    Free Cancellation
    Private Tour
    Start From $899.00
 
 

Sail and Turtle Snorkeling Tour in Waikiki

(4.8 of 247 reviews)

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

Free Cancellation
Private Tour
Start From $99.00
 
Sail and Turtle Snorkeling Tour in Waikiki Likely to Sell Out

Sail and Turtle Snorkeling Tour in Waikiki

  • North America
  • Superb247 reviews4.8

Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....

    Free Cancellation
    Private Tour
    Start From $99.00
 
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