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Top 10 Best North America Sailing Trips

Found 754 Sailing Trips activities in North America. Sort by Popularity. - Page 12
 

Los Cabos Catamaran Cruise with Open Bar & Light Snack

(4.8 of 278 reviews)

Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past its most iconic landmarks. Sail along the dazzling Cabo coastline to The Arch (El Arco), Lover’s Beach, and Divorce Beach, where ... More

Free Cancellation
Start From $89.00
 
Los Cabos Catamaran Cruise with Open Bar & Light Snack Likely to Sell Out

Los Cabos Catamaran Cruise with Open Bar & Light Snack

  • North America
  • Superb278 reviews4.8

Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past i....

    Free Cancellation
    Start From $89.00
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 107 reviews)

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More

Free Cancellation
Start From $189.00
 
Waikoloa Catamaran Snorkel Sail Including Lunch Likely to Sell Out

Waikoloa Catamaran Snorkel Sail Including Lunch

  • North America
  • Superb107 reviews4.6

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....

    Free Cancellation
    Start From $189.00
 
 

Waikiki Beach Fireworks Catamaran: Friday Night Open Bar Sail

(4.8 of 56 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Free Cancellation
Start From $90.01
 
Waikiki Beach Fireworks Catamaran: Friday Night Open Bar Sail Likely to Sell Out

Waikiki Beach Fireworks Catamaran: Friday Night Open Bar Sail

  • North America
  • Superb56 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Free Cancellation
    Start From $90.01
 
 

Exclusive Isla Mujeres and Cancun Private Yacht Tour

(4.9 of 36 reviews)

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set the stage for a day of exhilaration and relaxation. Cruise along the mesmerizing Cancun coastlines, dive into vibrant coral reefs du... More

Free Cancellation
Private Tour
Start From $720.00
 
Exclusive Isla Mujeres and Cancun Private Yacht Tour Likely to Sell Out

Exclusive Isla Mujeres and Cancun Private Yacht Tour

  • North America
  • Superb36 reviews4.9

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set th....

    Free Cancellation
    Private Tour
    Start From $720.00
 
 

3 Hours Ultimate Watersports Excursion in Miami

(4.9 of 36 reviews)

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable and stable Catamaran for an unforgettable all-inclusive water experience. Highlights: - Extreme Watersports: Feel the thrill wi... More

Free Cancellation
Private Tour
Start From $139.00
 
3 Hours Ultimate Watersports Excursion in Miami Likely to Sell Out

3 Hours Ultimate Watersports Excursion in Miami

  • North America
  • Superb36 reviews4.9

All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Romantic Sunset Dinner Cruise in Cancun with Open Bar

(4.6 of 11 reviews)

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner. Following you check-in, get aboard the spectacular ship under t... More

Free Cancellation
Private Tour
Start From $112.00
 
Romantic Sunset Dinner Cruise in Cancun with Open Bar Likely to Sell Out

Romantic Sunset Dinner Cruise in Cancun with Open Bar

  • North America
  • Superb11 reviews4.6

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to ....

    Free Cancellation
    Private Tour
    Start From $112.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 468 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Free Cancellation
Private Tour
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb468 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Private Family Catamaran From Isla Mujeres

(5 of 1 review)

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Family Catamaran From Isla Mujeres Likely to Sell Out

Private Family Catamaran From Isla Mujeres

  • North America
  • Superb1 review5

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

(4.9 of 104 reviews)

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical landscapes. You will visit the most beautiful places in the lagoon where yo... More

Free Cancellation
Private Tour
Start From $55.00
 
Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon Likely to Sell Out

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

  • North America
  • Superb104 reviews4.9

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters i....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

(5 of 13 reviews)

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More

Free Cancellation
Private Tour
Start From $53.36
 
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar Likely to Sell Out

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

  • North America
  • Superb13 reviews5

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

(5 of 40 reviews)

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering Likely to Sell Out

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

  • North America
  • Superb40 reviews5

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Sea to Sky Afternoon Sail

(5 of 241 reviews)

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

Free Cancellation
Private Tour
Start From $118.77
 
Sea to Sky Afternoon Sail Likely to Sell Out

Sea to Sky Afternoon Sail

  • North America
  • Superb241 reviews5

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....

    Free Cancellation
    Private Tour
    Start From $118.77
 
 

Mexico City: Xochimilco at sunrise + Breakfast and transportation

(5 of 112 reviews)

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More

Free Cancellation
Private Tour
Start From $171.72
 
Mexico City: Xochimilco at sunrise + Breakfast and transportation Likely to Sell Out

Mexico City: Xochimilco at sunrise + Breakfast and transportation

  • North America
  • Superb112 reviews5

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....

    Free Cancellation
    Private Tour
    Start From $171.72
 
 

Toronto Tall Ship Boat Cruise

(4.3 of 676 reviews)

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, and sit back and relax with a cold drink from the bar or order fr... More

Free Cancellation
Private Tour
Start From $38.41
 
Toronto Tall Ship Boat Cruise Likely to Sell Out

Toronto Tall Ship Boat Cruise

  • North America
  • Exellent676 reviews4.3

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Ta....

    Free Cancellation
    Private Tour
    Start From $38.41
 
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.8 of 41 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Free Cancellation
Private Tour
Start From $57.24
 
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport Likely to Sell Out

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • North America
  • Superb41 reviews4.8

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Sailing on Historic Schooner Yacht in Salem, MA

(4.9 of 172 reviews)

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More

Free Cancellation
Private Tour
Start From $55.00
 
Sailing on Historic Schooner Yacht in Salem, MA Likely to Sell Out

Sailing on Historic Schooner Yacht in Salem, MA

  • North America
  • Superb172 reviews4.9

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

ATV's at Stone Island with Horse Ride, Water Sports, Food & Drink

(3 of 2 reviews)

Welcome to the Beach Club All-Inclusive, where we believe in the power of adventure and the beauty of the beach. We are the ultimate vacation destination, providing the guests with an adrenaline-fueled experience like no other. Ge... More

Free Cancellation
Private Tour
Start From $189.00
 
ATV's at Stone Island with Horse Ride, Water Sports, Food & Drink Likely to Sell Out

ATV's at Stone Island with Horse Ride, Water Sports, Food & Drink

  • North America

Welcome to the Beach Club All-Inclusive, where we believe in the power of adventure and the beauty o....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 317 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Private Tour
Start From $148.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb317 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $148.00
 
 

Private Customizable Sailing Tour in Cancun

(4.7 of 121 reviews)

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More

Free Cancellation
Private Tour
Start From $549.34
 
Private Customizable Sailing Tour in Cancun Likely to Sell Out

Private Customizable Sailing Tour in Cancun

  • North America
  • Superb121 reviews4.7

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....

    Free Cancellation
    Private Tour
    Start From $549.34
 
 

Paragon Lahaina Performance Sail

(5 of 4 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui performance sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infi... More

Free Cancellation
Private Tour
Start From $91.80
 
Paragon Lahaina Performance Sail Likely to Sell Out

Paragon Lahaina Performance Sail

  • North America
  • Superb4 reviews5

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui performance sail f....

    Free Cancellation
    Private Tour
    Start From $91.80
 
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