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Top 10 Best North America Sailing Trips

Found 684 Sailing Trips activities in North America. Sort by Popularity. - Page 30
 

Private Experience in Punta Mosquito Holbox

(3.3 of 3 reviews)

If you come to Holbox you cannot miss a visit to Punta Mosquito, one of the most beautiful beaches on the entire Holbox Island, visit the flamingos and enjoy the beaches, the water and the beautiful sand banks of Punta Mosquito on... More

Free Cancellation
Private Tour
Start From $140.39
 
Private Experience in Punta Mosquito Holbox

Private Experience in Punta Mosquito Holbox

  • North America
  • Good3 reviews3.3

If you come to Holbox you cannot miss a visit to Punta Mosquito, one of the most beautiful beaches o....

    Free Cancellation
    Private Tour
    Start From $140.39
 
 

2-hour Customizable Private Day Sail in Key West

(1 of 1 review)

This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon one of our historic schooners. This trip has a capacity of up to 26 people, and a selection of sodas, beer, and wine are included... More

Free Cancellation
Private Tour
Start From $2,100.00
 
2-hour Customizable Private Day Sail in Key West

2-hour Customizable Private Day Sail in Key West

  • North America

This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres

(1 of 1 review)

Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catamaran, with room for up to 60 guests, and enjoy a premium experience from start to finish. Our team is dedicated to providing except... More

Free Cancellation
Private Tour
Start From $2,400.00
 
4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres Likely to Sell Out

4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres

  • North America

Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catama....

    Free Cancellation
    Private Tour
    Start From $2,400.00
 
 

Ft Myers Beach Tiki Pub Tropical Beach Getaway Cruise

(5 of 13 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach Tiki Pub Tropical Beach Getaway Cruise Likely to Sell Out

Ft Myers Beach Tiki Pub Tropical Beach Getaway Cruise

  • North America
  • Superb13 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 13 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • North America
  • Superb13 reviews5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,595.00
 
 

Isla Mujeres Private Dream Getaway

(4.9 of 12 reviews)

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with a transfer to the dock, where your guide will take you out by boat to the island of Is... More

Free Cancellation
Private Tour
Start From $545.00
 
Isla Mujeres Private Dream Getaway Likely to Sell Out

Isla Mujeres Private Dream Getaway

  • North America
  • Superb12 reviews4.9

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres,....

    Free Cancellation
    Private Tour
    Start From $545.00
 
 

Private Luxury Yacht for up to 12 people

(4.9 of 12 reviews)

A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, luxurious and sophisticated, it is specially designed to satisfy the demands of the best tastes and turn moments into memories that ... More

Free Cancellation
Private Tour
Start From $3,250.00
 
Private Luxury Yacht for up to 12 people Likely to Sell Out

Private Luxury Yacht for up to 12 people

  • North America
  • Superb12 reviews4.9

A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, lu....

    Free Cancellation
    Private Tour
    Start From $3,250.00
 
 

Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

(4.9 of 12 reviews)

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting nautical activities! If you are looking to live a unique and unforgettable experience with family or friends, this is the perfect plac... More

Free Cancellation
Private Tour
Start From $3,708.00
 
Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs Likely to Sell Out

Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

  • North America
  • Superb12 reviews4.9

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting naut....

    Free Cancellation
    Private Tour
    Start From $3,708.00
 
 

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

(4.9 of 12 reviews)

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic of the Mexican Caribbean, snorkeling in Isla Mujeres and Cancun's ... More

Free Cancellation
Private Tour
Start From $5,900.00
 
Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers Likely to Sell Out

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....

  • North America
  • Superb12 reviews4.9

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....

    Free Cancellation
    Private Tour
    Start From $5,900.00
 
 

Discover Catamaran CaboMar: Authentic Mexican Flavor!

(4.9 of 12 reviews)

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, with approximately 40 minutes spent at each captivating point along the route. As you glide through the stunning landscapes of Cab... More

Free Cancellation
Private Tour
Start From $140.00
 
Discover Catamaran CaboMar: Authentic Mexican Flavor! Likely to Sell Out

Discover Catamaran CaboMar: Authentic Mexican Flavor!

  • North America
  • Superb12 reviews4.9

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....

    Free Cancellation
    Private Tour
    Start From $140.00
 
 

All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs

(5 of 2 reviews)

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and delicious dishes and our host will serve you 'refreshing cocktails.... More

Free Cancellation
Private Tour
Start From $3,150.00
 
All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs Likely to Sell Out

All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs

  • North America
  • Superb2 reviews5

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and....

    Free Cancellation
    Private Tour
    Start From $3,150.00
 
 

JFarwell Private Yacht Wine & Cheese Sunset Sail

(4.9 of 14 reviews)

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine upon boarding, and then set sail. With the engines off and fully under wind power,... More

Free Cancellation
Private Tour
Start From $147.74
 
JFarwell Private Yacht Wine & Cheese Sunset Sail Likely to Sell Out

JFarwell Private Yacht Wine & Cheese Sunset Sail

  • North America
  • Superb14 reviews4.9

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests wil....

    Free Cancellation
    Private Tour
    Start From $147.74
 
 

Romantic Sunset Sailing in Cabo

(4.9 of 14 reviews)

Designed with couples in mind, the tour provides a romantic setting aboard a sailboat, where you can enjoy the gentle breeze of Los Cabos while savoring a glass of wine and a gourmet picnic basket. Unlike other tours, this experie... More

Free Cancellation
Private Tour
Start From $120.00
 
Romantic Sunset Sailing in Cabo Likely to Sell Out

Romantic Sunset Sailing in Cabo

  • North America
  • Superb14 reviews4.9

Designed with couples in mind, the tour provides a romantic setting aboard a sailboat, where you can....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

(1 of 1 review)

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in the South's picturesque setting, this 2-hour sail gives yo... More

Free Cancellation
Private Tour
Start From $38.00
 
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating Likely to Sell Out

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

  • North America

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the....

    Free Cancellation
    Private Tour
    Start From $38.00
 
 

Snorkeling and Sailing Adventure In the Riviera Maya

(1 of 1 review)

Our tour isn’t just an adventure—it’s a one-of-a-kind experience designed to immerse you in the natural beauty and vibrant culture of the Riviera Maya. Here’s what sets us apart: 1️⃣ Exclusive Snorkeling Spot: Swim in... More

Free Cancellation
Private Tour
Start From $199.00
 
Snorkeling and Sailing Adventure In the Riviera Maya Likely to Sell Out

Snorkeling and Sailing Adventure In the Riviera Maya

  • North America

Our tour isn’t just an adventure—it’s a one-of-a-kind experience designed to immerse you in th....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Themed and Special Event Cruise in Chesapeake Bay

(5 of 1 review)

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversa... More

Free Cancellation
Private Tour
Start From $699.00
 
Themed and Special Event Cruise in Chesapeake Bay Likely to Sell Out

Themed and Special Event Cruise in Chesapeake Bay

  • North America
  • Superb1 review5

This cruise is a unique way to celebrate that special event in your life while cruising on your very....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Full-Day Sailing Adventure to Isla Mujeres

(3.5 of 4 reviews)

This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun to Isla Mujeres aboard a wind-powered catamaran with an experienced and friendly captain and crew. Lounge, swim, eat, and drink at ... More

Free Cancellation
Private Tour
Start From $69.99
 
Full-Day Sailing Adventure to Isla Mujeres Likely to Sell Out

Full-Day Sailing Adventure to Isla Mujeres

  • North America
  • Good4 reviews3.5

This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun t....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Early Sail with the Whales from Ma'alaea Harbor

(3.3 of 3 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $91.89
 
Early Sail with the Whales from Ma'alaea Harbor Likely to Sell Out

Early Sail with the Whales from Ma'alaea Harbor

  • North America
  • Good3 reviews3.3

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $91.89
 
 

4 Day Alaskan Excursion

(3.3 of 3 reviews)

This is a Tour that no other Company in the World offers. You will be sailing and enjoying the Alaskan wilderness. Each day is unknown because the climate here is so unpredictable. But we always make the best with what we have got... More

Free Cancellation
Private Tour
Start From $6,000.00
 
4 Day Alaskan Excursion Likely to Sell Out

4 Day Alaskan Excursion

  • North America
  • Good3 reviews3.3

This is a Tour that no other Company in the World offers. You will be sailing and enjoying the Alask....

    Free Cancellation
    Private Tour
    Start From $6,000.00
 
 

Sailing Charter

(3.3 of 3 reviews)

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Free Cancellation
Private Tour
Start From $195.00
 
Sailing Charter Likely to Sell Out

Sailing Charter

  • North America
  • Good3 reviews3.3

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....

    Free Cancellation
    Private Tour
    Start From $195.00
 
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