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Top 10 Best North America Sailing Trips

Found 756 Sailing Trips activities in North America. Sort by Popularity. - Page 15
 

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

(4.5 of 31 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Start From $60.00
 
Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

  • North America
  • Exellent31 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Start From $60.00
 
 

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

(4.9 of 110 reviews)

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff in this beautiful freshwater paradise. Our years of experience back us up. Qua... More

Free Cancellation
Private Tour
Start From $254.33
 
Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

  • North America
  • Superb110 reviews4.9

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel s....

    Free Cancellation
    Private Tour
    Start From $254.33
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.8 of 20 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Free Cancellation
Private Tour
Start From $91.23
 
Sail on Tall Ship Windy, join us for our Likely to Sell Out

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • North America
  • Superb20 reviews4.8

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Free Cancellation
    Private Tour
    Start From $91.23
 
 

kayaking in Huatulco

(5 of 3 reviews)

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with the most 95% of the time on the tour, so it is highly recommended for biologist... More

Free Cancellation
Private Tour
Start From $76.89
 
kayaking in Huatulco Likely to Sell Out

kayaking in Huatulco

  • North America
  • Superb3 reviews5

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing....

    Free Cancellation
    Private Tour
    Start From $76.89
 
 

Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites

(5 of 6 reviews)

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More

Free Cancellation
Private Tour
Start From $75.00
 
Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites Likely to Sell Out

Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites

  • North America
  • Superb6 reviews5

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 91 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • North America
  • Superb91 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Bacalar Private Sailing Tour : cervezas & Snack with Pickup

(5 of 16 reviews)

Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly unique adventure. Visit hidden, less-explored spots and enjoy the lagoon with skilled captains and crew fluent in Spanish, Englis... More

Free Cancellation
Private Tour
Start From $254.33
 
Bacalar Private Sailing Tour : cervezas & Snack with Pickup Likely to Sell Out

Bacalar Private Sailing Tour : cervezas & Snack with Pickup

  • North America
  • Superb16 reviews5

Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly....

    Free Cancellation
    Private Tour
    Start From $254.33
 
 

New York Harbor Wine and Jazz Sail aboard Clipper City

(4.4 of 21 reviews)

Sail toward the sun setting behind the Statue of Liberty and return with the Manhattan skyline glittering before you—a view that captures New York at its very best. More than a cruise, this is an homage to the owner’s New York... More

Free Cancellation
Private Tour
Start From $150.71
 
New York Harbor Wine and Jazz Sail aboard Clipper City Likely to Sell Out

New York Harbor Wine and Jazz Sail aboard Clipper City

  • North America
  • Exellent21 reviews4.4

Sail toward the sun setting behind the Statue of Liberty and return with the Manhattan skyline glitt....

    Free Cancellation
    Private Tour
    Start From $150.71
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 152 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Free Cancellation
Private Tour
Start From $450.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • North America
  • Superb152 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Reef Snorkeling with ATV, Zipline, Cenote that includes lunch and transportation

(4.3 of 3 reviews)

Welcome to the best experience in the entire Riviera Maya and Cancun, here you will enjoy swimming in a unique underwater world, you will discover the second largest coral reef in the world. Imagine swimming with impressive corals... More

Free Cancellation
Private Tour
Start From $109.65
 
Reef Snorkeling with ATV, Zipline, Cenote that includes lunch and transportation Likely to Sell Out

Reef Snorkeling with ATV, Zipline, Cenote that includes lunch an....

  • North America
  • Exellent3 reviews4.3

Welcome to the best experience in the entire Riviera Maya and Cancun, here you will enjoy swimming i....

    Free Cancellation
    Private Tour
    Start From $109.65
 
 

Luxury Sailing to Isla Mujeres with Lunch and Premium Open Bar

(4.3 of 3 reviews)

Cruise the Caribbean in style on a luxury catamaran, with a maximum capacity of 25 passengers, you will avoid crowds. Upon arrival at the marina, you will enjoy express check-in, the crew will receive you with a welcome drink and... More

Free Cancellation
Private Tour
Start From $129.00
 
Luxury Sailing to Isla Mujeres with Lunch and Premium Open Bar Likely to Sell Out

Luxury Sailing to Isla Mujeres with Lunch and Premium Open Bar

  • North America
  • Exellent3 reviews4.3

Cruise the Caribbean in style on a luxury catamaran, with a maximum capacity of 25 passengers, you w....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch

(4.3 of 3 reviews)

Set sail on an unforgettable day aboard the Star Blue Catamaran from Marina Flamingos in Cancún. Enjoy a premium national open bar while sailing to Isla Mujeres, where you can explore the stunning Playa Norte and spend free time ... More

Free Cancellation
Private Tour
Start From $29.00
 
Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch Likely to Sell Out

Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch

  • North America
  • Exellent3 reviews4.3

Set sail on an unforgettable day aboard the Star Blue Catamaran from Marina Flamingos in Cancún. En....

    Free Cancellation
    Private Tour
    Start From $29.00
 
 

Afternoon Schooner Clearwater Beach Cruise Sailing

(5 of 1 review)

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh l... More

Free Cancellation
Private Tour
Start From $75.00
 
Afternoon Schooner Clearwater Beach Cruise Sailing Likely to Sell Out

Afternoon Schooner Clearwater Beach Cruise Sailing

  • North America
  • Superb1 review5

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable vi....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Okanagan Lake Sailing Tour from Penticton & Naramata BC

(5 of 48 reviews)

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More

Free Cancellation
Private Tour
Start From $186.94
 
Okanagan Lake Sailing Tour from Penticton & Naramata BC Likely to Sell Out

Okanagan Lake Sailing Tour from Penticton & Naramata BC

  • North America
  • Superb48 reviews5

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....

    Free Cancellation
    Private Tour
    Start From $186.94
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 104 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 $100.22
 
Midday Whale Watch: Mā’alaea Harbor Likely to Sell Out

Midday Whale Watch: Mā’alaea Harbor

  • North America
  • Superb104 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $100.22
 
 

Sunset Sail Tour

(4.9 of 90 reviews)

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More

Free Cancellation
Private Tour
Start From $115.00
 
Sunset Sail Tour Likely to Sell Out

Sunset Sail Tour

  • North America
  • Superb90 reviews4.9

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 111 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • North America
  • Superb111 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Schooner Appledore Day Sail with Full Bar in Key West

(4.9 of 113 reviews)

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Private Tour
Start From $49.00
 
Schooner Appledore Day Sail with Full Bar in Key West Likely to Sell Out

Schooner Appledore Day Sail with Full Bar in Key West

  • North America
  • Superb113 reviews4.9

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

Chicago's Fireworks Show aboard Tall Ship Windy!

(4.8 of 14 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Free Cancellation
Private Tour
Start From $113.73
 
Chicago's Fireworks Show aboard Tall Ship Windy! Likely to Sell Out

Chicago's Fireworks Show aboard Tall Ship Windy!

  • North America
  • Superb14 reviews4.8

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Private Tour
    Start From $113.73
 
 

Bacalar : Sailing Tour with Beers & Guacamole and Transportation

(4.9 of 103 reviews)

Let’s go, adventurers! Join a unique shared sailing tour across the Bacalar Lagoon, where we’ll explore the area’s incredible cenotes. Feel the magic of each spot as we sail without engines — just the sound of the wind and... More

Free Cancellation
Private Tour
Start From $50.75
 
Bacalar : Sailing Tour with Beers & Guacamole and Transportation Likely to Sell Out

Bacalar : Sailing Tour with Beers & Guacamole and Transportation

  • North America
  • Superb103 reviews4.9

Let’s go, adventurers! Join a unique shared sailing tour across the Bacalar Lagoon, where we’ll ....

    Free Cancellation
    Private Tour
    Start From $50.75
 
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