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Top 10 Best North America Sailing Trips

Found 754 Sailing Trips activities in North America. Sort by Popularity. - Page 29
 

Cancun Private Classic Sailboat Cruise with Beers and Sodas

(5 of 1 review)

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island gem just off the coast of Cancun. Step aboard our fine vessel and embark on a journey of discovery and relaxation in the breathta... More

Free Cancellation
Private Tour
Start From $579.00
 
Cancun Private Classic Sailboat Cruise with Beers and Sodas

Cancun Private Classic Sailboat Cruise with Beers and Sodas

  • North America
  • Superb1 review5

Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island....

    Free Cancellation
    Private Tour
    Start From $579.00
 
 

SUNSET CRUISE in Key Largo,FL.

(5 of 3 reviews)

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personab... More

Free Cancellation
Private Tour
Start From $389.00
 
SUNSET CRUISE in Key Largo,FL. Likely to Sell Out

SUNSET CRUISE in Key Largo,FL.

  • North America
  • Superb3 reviews5

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need t....

    Free Cancellation
    Private Tour
    Start From $389.00
 
 

2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar

(4.3 of 6 reviews)

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single day—Isla Contoy, a protected ecological reserve with limited daily visitors, and t... More

Free Cancellation
Private Tour
Start From $80.00
 
2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar Likely to Sell Out

2 Island Adventure: Contoy & Mujeres with Snorkeling & open bar

  • North America
  • Exellent6 reviews4.3

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you ....

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

Luxury Sailboat at Sunset in Cancun

(3 of 4 reviews)

To cross the calm waters of the Caribbean, there is no better means of transportation than a catamaran. These specialized sailboats have multiple hulls so that sailing in them is the most pleasant. They are ideal for those looking... More

Free Cancellation
Private Tour
Start From $150.00
 
Luxury Sailboat at Sunset in Cancun Likely to Sell Out

Luxury Sailboat at Sunset in Cancun

  • North America

To cross the calm waters of the Caribbean, there is no better means of transportation than a catamar....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Key West Christmas Cruise with Live Band and Drinks

(5 of 5 reviews)

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More

Free Cancellation
Private Tour
Start From $97.61
 
Key West Christmas Cruise with Live Band and Drinks Likely to Sell Out

Key West Christmas Cruise with Live Band and Drinks

  • North America
  • Superb5 reviews5

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christ....

    Free Cancellation
    Private Tour
    Start From $97.61
 
 

Private - Bacalar sailing across the mesmerizing waters

(4.9 of 10 reviews)

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon a sailing boat to navigate our way across the mesmerizing waters of 7 different shad... More

Free Cancellation
Private Tour
Start From $499.00
 
Private - Bacalar sailing across the mesmerizing waters Likely to Sell Out

Private - Bacalar sailing across the mesmerizing waters

  • North America
  • Superb10 reviews4.9

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence o....

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Whale Watching Amazing Adventure

(4.9 of 10 reviews)

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cabos in search of the Cabo’s Whales.” Enjoy listening to the beautiful song of the whales, with the help of our new hydrophones... More

Free Cancellation
Private Tour
Start From $97.00
 
Whale Watching Amazing Adventure Likely to Sell Out

Whale Watching Amazing Adventure

  • North America
  • Superb10 reviews4.9

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....

    Free Cancellation
    Private Tour
    Start From $97.00
 
 

Private Key West Sunset Sail

(4.7 of 51 reviews)

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Key West Sunset Sail Likely to Sell Out

Private Key West Sunset Sail

  • North America
  • Superb51 reviews4.7

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

The Best Catamaran Tour to Isla Mujeres from Cancún

(4.8 of 5 reviews)

Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran equipped with all the comforts! Enjoy with your family and your friends a quiet ride catamaran sailing on the crystal clear waters... More

Free Cancellation
Private Tour
Start From $75.00
 
The Best Catamaran Tour to Isla Mujeres from Cancún Likely to Sell Out

The Best Catamaran Tour to Isla Mujeres from Cancún

  • North America
  • Superb5 reviews4.8

Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran ....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 1 review)

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More

Free Cancellation
Private Tour
Start From $50.00
 
Waikiki Sunset Cruise and Iconic Views with Swimming Likely to Sell Out

Waikiki Sunset Cruise and Iconic Views with Swimming

  • North America
  • Superb1 review5

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Isla Mujeres by Private Catamaran

(5 of 1 review)

Discover Isla Mujeres on an unforgettable journey that combines adventure, relaxation, and Caribbean beauty. Sail aboard an exclusive private catamaran, feeling the sea breeze and admiring panoramic views of the turquoise Caribbe... More

Free Cancellation
Private Tour
Start From $1,350.00
 
Isla Mujeres by Private Catamaran Likely to Sell Out

Isla Mujeres by Private Catamaran

  • North America
  • Superb1 review5

Discover Isla Mujeres on an unforgettable journey that combines adventure, relaxation, and Caribbean....

    Free Cancellation
    Private Tour
    Start From $1,350.00
 
 

Sailing Charter around Vancouver Harbour Private Tour

(5 of 2 reviews)

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and has all the features of a large cruising Yacht with a rare balance betw... More

Free Cancellation
Private Tour
Start From $2,392.86
 
Sailing Charter around Vancouver Harbour Private Tour Likely to Sell Out

Sailing Charter around Vancouver Harbour Private Tour

  • North America
  • Superb2 reviews5

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and....

    Free Cancellation
    Private Tour
    Start From $2,392.86
 
 

South Beach Miami BACHELORETTE Boat Day!

(5 of 1 review)

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good y... More

Free Cancellation
Private Tour
Start From $1,795.00
 
South Beach Miami BACHELORETTE Boat Day! Likely to Sell Out

South Beach Miami BACHELORETTE Boat Day!

  • North America
  • Superb1 review5

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and....

    Free Cancellation
    Private Tour
    Start From $1,795.00
 
 

Private Luxury Sunset Sail in San Jose del Cabo Marina

(5 of 1 review)

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 people, the rate offered here is for 8 people, if like to add more pl... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Private Luxury Sunset Sail in San Jose del Cabo Marina Likely to Sell Out

Private Luxury Sunset Sail in San Jose del Cabo Marina

  • North America
  • Superb1 review5

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp

(4.3 of 72 reviews)

Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres or just sail on the bay. Snorkel and discover the natural beauty of the great reefs of Cancun. Private... More

Free Cancellation
Private Tour
Start From $2,231.00
 
Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp Likely to Sell Out

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp

  • North America
  • Exellent72 reviews4.3

Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go....

    Free Cancellation
    Private Tour
    Start From $2,231.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail Likely to Sell Out

Luxury Diamond Head Sunset Sail

  • North America
  • Superb3 reviews5

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $1,398.00
 
 

Private Afternoon Harbor Cruise on Kismet for parties up to 20

(5 of 27 reviews)

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history tours, swim and float on rafts. Kismet does it all! Kismet is a custom-built ... More

Free Cancellation
Private Tour
Start From $1,549.00
 
Private Afternoon Harbor Cruise on Kismet for parties up to 20 Likely to Sell Out

Private Afternoon Harbor Cruise on Kismet for parties up to 20

  • North America
  • Superb27 reviews5

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise....

    Free Cancellation
    Private Tour
    Start From $1,549.00
 
 

Private Luxury Yacht Charter with Snorkeling in Los Cabos

(5 of 27 reviews)

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater world of the Los Cabos area. During the months of December thru March, you can w... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Private Luxury Yacht Charter with Snorkeling in Los Cabos Likely to Sell Out

Private Luxury Yacht Charter with Snorkeling in Los Cabos

  • North America
  • Superb27 reviews5

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one o....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

4th of July Sunset Sail on the Black Pearl

(5 of 27 reviews)

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across the water as we find our most perfect spot for viewing the fireworks while watching the suns... More

Free Cancellation
Private Tour
Start From $1,195.00
 
4th of July Sunset Sail on the Black Pearl Likely to Sell Out

4th of July Sunset Sail on the Black Pearl

  • North America
  • Superb27 reviews5

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The ....

    Free Cancellation
    Private Tour
    Start From $1,195.00
 
 

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

(4.5 of 4 reviews)

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun.... More

Free Cancellation
Private Tour
Start From $1,199.00
 
Explore Turtle Canyons Waikiki Snorkel and Sail Adventure Likely to Sell Out

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

  • North America
  • Exellent4 reviews4.5

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....

    Free Cancellation
    Private Tour
    Start From $1,199.00
 
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