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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 9
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 393 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb393 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Start From $99.00
 
 

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

(4.8 of 393 reviews)

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan that can accommodate up to 25 passengers. It's decked out with a kitchen, bedroom, bathroom, and even water sports gear like kayak... More

Free Cancellation
Private Tour
Start From $1,250.00
 
Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience Likely to Sell Out

Ultimate Bay Tours -Private 25 Travelers- Trimaran Experience

  • North America
  • Superb393 reviews4.8

Hey there! Just wanted to share this amazing find with you - a private 43 feet Trimaran in Mazatlan ....

    Free Cancellation
    Private Tour
    Start From $1,250.00
 
 

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu.

(4.4 of 7 reviews)

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. In Cancun you have an incredible opportunity to ... More

Free Cancellation
Private Tour
Start From $95.00
 
Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster & Beef menu. Likely to Sell Out

Romantic Dinner in the Spanish Galeon with Sax in Cancun. Lobster....

  • North America
  • Exellent7 reviews4.4

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out o....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Sunset Cruise with the Whales on our Sailing Catamaran

(4.8 of 49 reviews)

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More

Free Cancellation
Private Tour
Start From $165.00
 
Sunset Cruise with the Whales on our Sailing Catamaran Likely to Sell Out

Sunset Cruise with the Whales on our Sailing Catamaran

  • North America
  • Superb49 reviews4.8

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Dolphin Adventure Sail in Cocoa Beach

(4.9 of 170 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More

Free Cancellation
Private Tour
Start From $50.85
 
Dolphin Adventure Sail in Cocoa Beach Likely to Sell Out

Dolphin Adventure Sail in Cocoa Beach

  • North America
  • Superb170 reviews4.9

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....

    Free Cancellation
    Private Tour
    Start From $50.85
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 937 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Special Offer
Free Cancellation
Private Tour
Start From $76.49
(Saving 10% ) $84.99
 
-10% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • North America
  • Superb937 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $76.49
    (Saving 10% ) $84.99
 
 

Sailing Tour through the Laguna de los Siete Colores

(5 of 1,539 reviews)

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More

Free Cancellation
Private Tour
Start From $40.00
 
Sailing Tour through the Laguna de los Siete Colores Likely to Sell Out

Sailing Tour through the Laguna de los Siete Colores

  • North America
  • Superb1,539 reviews5

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....

    Free Cancellation
    Private Tour
    Start From $40.00
 
 

Key West Dolphin Watch and Sunset Sail on Catamaran

(4.7 of 36 reviews)

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unob... More

Free Cancellation
Private Tour
Start From $117.17
 
Key West Dolphin Watch and Sunset Sail on Catamaran Likely to Sell Out

Key West Dolphin Watch and Sunset Sail on Catamaran

  • North America
  • Superb36 reviews4.7

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lig....

    Free Cancellation
    Private Tour
    Start From $117.17
 
 

Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks

(4.8 of 268 reviews)

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k reviews. Connect your phone & be your own DJ—bring your own food, drinks & alcohol. Our boat is fully equipped with a Bluetooth sound... More

Free Cancellation
Private Tour
Start From $150.00
 
Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks Likely to Sell Out

Snorkel & Millionaire Row - Private Miami Boat Rental w/ Drinks

  • North America
  • Superb268 reviews4.8

Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k revie....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Los Cabos Catamaran Cruise with Open Bar & Light Snack

(4.8 of 260 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
Private Tour
Start From $75.00
 
Los Cabos Catamaran Cruise with Open Bar & Light Snack Likely to Sell Out

Los Cabos Catamaran Cruise with Open Bar & Light Snack

  • North America
  • Superb260 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Vancouver Sailing Experience on a 50 foot Sailboat

(5 of 100 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Private Tour
Start From $112.11
 
Vancouver Sailing Experience on a 50 foot Sailboat Likely to Sell Out

Vancouver Sailing Experience on a 50 foot Sailboat

  • North America
  • Superb100 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Private Tour
    Start From $112.11
 
 

Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar

(4 of 5 reviews)

Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your picture at The Arch, one of Cabo’s main landmarks, and get a glimpse of Lover’s Beach and the Sea Lion Colony. Known as the a... More

Free Cancellation
Private Tour
Start From $89.00
 
Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar Likely to Sell Out

Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar

  • North America
  • Very Good5 reviews4

Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Bacalar Lagoon Tour Open Bar With Pick Up

(4.9 of 92 reviews)

Bilingual captain (English, Spanish and French) who shares local stories in a fun way. • Pickup right from your hotel so you can just relax and enjoy. • Cold drinks and Mexican snacks throughout the tour. • Snorkeling and... More

Free Cancellation
Private Tour
Start From $50.22
 
Bacalar Lagoon Tour Open Bar With Pick Up Likely to Sell Out

Bacalar Lagoon Tour Open Bar With Pick Up

  • North America
  • Superb92 reviews4.9

Bilingual captain (English, Spanish and French) who shares local stories in a fun way. • Pickup r....

    Free Cancellation
    Private Tour
    Start From $50.22
 
 

Private Charleston Harbor Catamaran Sail

(5 of 28 reviews)

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Charleston Harbor Catamaran Sail Likely to Sell Out

Private Charleston Harbor Catamaran Sail

  • North America
  • Superb28 reviews5

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Sunset Catamaran Sail in Cocoa Beach

(4.9 of 177 reviews)

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Floridaâ... More

Free Cancellation
Private Tour
Start From $56.49
 
Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Sunset Catamaran Sail in Cocoa Beach

  • North America
  • Superb177 reviews4.9

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....

    Free Cancellation
    Private Tour
    Start From $56.49
 
 

One Hour Cruise Around Marina del Rey

(4 of 32 reviews)

Explore Los Angeles' best-kept secret on a classic boat tour of Marina del Rey. See the city, admire the yachts of the rich and famous, enjoy the fresh air, and look for wildlife like sea lions.... More

Free Cancellation
Private Tour
Start From $90.00
 
One Hour Cruise Around Marina del Rey Likely to Sell Out

One Hour Cruise Around Marina del Rey

  • North America
  • Very Good32 reviews4

Explore Los Angeles' best-kept secret on a classic boat tour of Marina del Rey. See the city, admire....

    Free Cancellation
    Private Tour
    Start From $90.00
 
 

Statue of Liberty Sunset Cruise and New York City Sky Line

(3.2 of 45 reviews)

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More

Free Cancellation
Private Tour
Start From $35.99
 
Statue of Liberty Sunset Cruise and New York City Sky Line Likely to Sell Out

Statue of Liberty Sunset Cruise and New York City Sky Line

  • North America
  • Good45 reviews3.2

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....

    Free Cancellation
    Private Tour
    Start From $35.99
 
 

Classic Tall Ship Cruise in Boston Harbor

(4.7 of 615 reviews)

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeata... More

Free Cancellation
Private Tour
Start From $39.55
 
Classic Tall Ship Cruise in Boston Harbor Likely to Sell Out

Classic Tall Ship Cruise in Boston Harbor

  • North America
  • Superb615 reviews4.7

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liber....

    Free Cancellation
    Private Tour
    Start From $39.55
 
 

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

(4.9 of 373 reviews)

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous Arch, Land's end, and Sea Lion Colony before you head out of the bay.  Visit a secl... More

Free Cancellation
Private Tour
Start From $2,299.00
 
Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Likely to Sell Out

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Ba....

  • North America
  • Superb373 reviews4.9

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great ph....

    Free Cancellation
    Private Tour
    Start From $2,299.00
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 35 reviews)

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More

Free Cancellation
Private Tour
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • North America
  • Superb35 reviews4.8

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....

    Free Cancellation
    Private Tour
    Start From $95.00
 
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