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Top 10 Best North America Sailing Trips

Found 687 Sailing Trips activities in North America. Sort by Popularity. - Page 27
 

Sunset Cruise Tequila Tasting

(5 of 3 reviews)

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought to you by Tequila Cabo Único and Sunrider. You'll get to know the iconic Cabo S... More

Free Cancellation
Start From $110.00
 
Sunset Cruise Tequila Tasting

Sunset Cruise Tequila Tasting

  • North America
  • Superb3 reviews5

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the histo....

    Free Cancellation
    Start From $110.00
 
 

Private Sailing Charter and Guided Tour

(5 of 3 reviews)

Our most popular Galveston cruise lets you see the Galveston Channel and the surrounding area including the most popular sights on the northern part of Galveston. These include the Elissa, the Ocean Star museum, Pier 21, the Port ... More

Free Cancellation
Private Tour
Start From $550.00
 
Private Sailing Charter and Guided Tour

Private Sailing Charter and Guided Tour

  • North America
  • Superb3 reviews5

Our most popular Galveston cruise lets you see the Galveston Channel and the surrounding area includ....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

Private Day Sailing Experience in San Diego up to 12 guests

(5 of 49 reviews)

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we will see the US Midway, Sea port Village, the Rady shell and we might... More

Free Cancellation
Private Tour
Start From $212.50
 
Private Day Sailing Experience in San Diego up to 12 guests

Private Day Sailing Experience in San Diego up to 12 guests

  • North America
  • Superb49 reviews5

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is be....

    Free Cancellation
    Private Tour
    Start From $212.50
 
 

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

(4 of 3 reviews)

Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is for you. We will take you to know the second largest coral reef in the world, the first one... More

Free Cancellation
Private Tour
Start From $55.00
 
Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

  • North America
  • Very Good3 reviews4

Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Cabo San Lucas Sunset Party on the Water - Adult Only

(3 of 2 reviews)

Spend an incredible vacation enjoying an adventure you will never forget, sailing through the blue waters of the Cabo San Lucas Bay, taking in the amazing scenery all while you enjoy the music and dancing. This Party Boat is perfe... More

Free Cancellation
Private Tour
Start From $97.00
 
Cabo San Lucas Sunset Party on the Water - Adult Only Likely to Sell Out

Cabo San Lucas Sunset Party on the Water - Adult Only

  • North America

Spend an incredible vacation enjoying an adventure you will never forget, sailing through the blue w....

    Free Cancellation
    Private Tour
    Start From $97.00
 
 

Private - Bacalar sailing across the mesmerizing waters

(4.9 of 8 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 $500.00
 
Private - Bacalar sailing across the mesmerizing waters Likely to Sell Out

Private - Bacalar sailing across the mesmerizing waters

  • North America
  • Superb8 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 $500.00
 
 

Private Key West Sunset Sail

(4.7 of 47 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
  • Superb47 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
 
 

Whale Watching en San José del Cabo

(5 of 20 reviews)

Experience a Unique Connection with Nature! Our whale-watching tour in San José del Cabo stands out for its personalized service, led by passionate marine life experts who make your journey enriching and unforgettable. You'll sa... More

Free Cancellation
Private Tour
Start From $95.00
 
Whale Watching en San José del Cabo Likely to Sell Out

Whale Watching en San José del Cabo

  • North America
  • Superb20 reviews5

Experience a Unique Connection with Nature! Our whale-watching tour in San José del Cabo stands ou....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Golden Hour Escape: Private Sunset Sail in Coastal Maine

(5 of 9 reviews)

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboar... More

Free Cancellation
Private Tour
Start From $1,020.00
 
Golden Hour Escape: Private Sunset Sail in Coastal Maine Likely to Sell Out

Golden Hour Escape: Private Sunset Sail in Coastal Maine

  • North America
  • Superb9 reviews5

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the settin....

    Free Cancellation
    Private Tour
    Start From $1,020.00
 
 

Whale Watching Amazing Adventure

(5 of 9 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
  • Superb9 reviews5

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
 
 

Isla Mujeres by Private Catamaran

(5 of 9 reviews)

Discover Isla Mujeres, explore a world filled with vibrant colors, fascinating marine life, and crystal-clear waters that will make you feel like you're on another planet. Sail on an exclusive private catamaran, where you'll enjo... More

Free Cancellation
Private Tour
Start From $1,100.00
 
Isla Mujeres by Private Catamaran Likely to Sell Out

Isla Mujeres by Private Catamaran

  • North America
  • Superb9 reviews5

Discover Isla Mujeres, explore a world filled with vibrant colors, fascinating marine life, and crys....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

Private Afternoon Harbor Cruise on Kismet for parties up to 15

(5 of 16 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 15 Likely to Sell Out

Private Afternoon Harbor Cruise on Kismet for parties up to 15

  • North America
  • Superb16 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
 
 

Luxury Private Sunset Experience in San Jose

(5 of 16 reviews)

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
 
Luxury Private Sunset Experience in San Jose Likely to Sell Out

Luxury Private Sunset Experience in San Jose

  • North America
  • Superb16 reviews5

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

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

4 Hour Private Sail for up to 6 people

(5 of 11 reviews)

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a customizable charter. Create your own adventure on a vintage sailing yacht for 4 hours with an experienced captain.... More

Free Cancellation
Private Tour
Start From $1,100.00
 
4 Hour Private Sail for up to 6 people Likely to Sell Out

4 Hour Private Sail for up to 6 people

  • North America
  • Superb11 reviews5

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a c....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

Sailing Charter around Vancouver Harbour Private Tour

(5 of 1 review)

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 $2,358.83
 
Sailing Charter around Vancouver Harbour Private Tour Likely to Sell Out

Sailing Charter around Vancouver Harbour Private Tour

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $2,358.83
 
 

Bimini Charters - Private 6 Hour catamaran sail & snorkel

(5 of 1 review)

We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of time to determine your goals for the day and make them happen. Our guests almost always say that their trip with us was the highlight... More

Free Cancellation
Private Tour
Start From $1,400.00
 
Bimini Charters - Private 6 Hour catamaran sail & snorkel Likely to Sell Out

Bimini Charters - Private 6 Hour catamaran sail & snorkel

  • North America
  • Superb1 review5

We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of tim....

    Free Cancellation
    Private Tour
    Start From $1,400.00
 
 

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach

(5 of 1 review)

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer to ... More

Free Cancellation
Private Tour
Start From $1,432.99
 
6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach Likely to Sell Out

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach

  • North America
  • Superb1 review5

Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We a....

    Free Cancellation
    Private Tour
    Start From $1,432.99
 
 

Bachelorette Sailing Party on San Diego Bay up to 12 Guests

(5 of 1 review)

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea... More

Free Cancellation
Private Tour
Start From $1,500.00
 
Bachelorette Sailing Party on San Diego Bay up to 12 Guests Likely to Sell Out

Bachelorette Sailing Party on San Diego Bay up to 12 Guests

  • North America
  • Superb1 review5

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaki....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Cabo's Premier Catamaran Snorkeling: Explore the Waters!

(5 of 1 review)

Our snorkeling tour sails towards the beautiful Santa María Bay, where you will swim in tropical waters with abundant marine life, sailing very slowly at each point approximately 20 minutes just to observe the landscape in this w... More

Free Cancellation
Private Tour
Start From $129.00
 
Cabo's Premier Catamaran Snorkeling: Explore the Waters! Likely to Sell Out

Cabo's Premier Catamaran Snorkeling: Explore the Waters!

  • North America
  • Superb1 review5

Our snorkeling tour sails towards the beautiful Santa María Bay, where you will swim in tropical wa....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Exclusive Private Sailing Luxury Tour in Los Cabos

(5 of 1 review)

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
 
Exclusive Private Sailing Luxury Tour in Los Cabos Likely to Sell Out

Exclusive Private Sailing Luxury Tour in Los Cabos

  • North America
  • Superb1 review5

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