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Top 10 Best North America Sailing Trips

Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 15
 

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

(5 of 84 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
Start From $55.00
 
Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

  • North America
  • Superb84 reviews5

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

    Free Cancellation
    Start From $55.00
 
 

Party On Sailing Cruise to Isla Mujeres from Cancun

(3.9 of 19 reviews)

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our national drinks onboard the catamaran. You will snorkel at one of the best reefs and see beautiful tropical fish, then eat lunch ... More

Free Cancellation
Start From $49.99
 
Party On Sailing Cruise to Isla Mujeres from Cancun

Party On Sailing Cruise to Isla Mujeres from Cancun

  • North America
  • Very Good19 reviews3.9

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our....

    Free Cancellation
    Start From $49.99
 
 

Cabo San Lucas Snorkel Adventure with Photos Included

(5 of 2 reviews)

Cruise out of the Marina of Cabo San Lucas on an unforgettable snorkeling journey. Your adventure begins with a photo stop at the stunning Arch of Cabo San Lucas and a glimpse of the lively Sea Lion colony. Afterward, dive into th... More

Free Cancellation
Start From $70.00
 
Cabo San Lucas Snorkel Adventure with Photos Included

Cabo San Lucas Snorkel Adventure with Photos Included

  • North America
  • Superb2 reviews5

Cruise out of the Marina of Cabo San Lucas on an unforgettable snorkeling journey. Your adventure be....

    Free Cancellation
    Start From $70.00
 
 

Newport Sunset Sail on Classic Sailboat

(4.8 of 42 reviews)

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More

Free Cancellation
Start From $67.84
 
Newport Sunset Sail on Classic Sailboat Likely to Sell Out

Newport Sunset Sail on Classic Sailboat

  • North America
  • Superb42 reviews4.8

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....

    Free Cancellation
    Start From $67.84
 
 

The Best Catamaran Tour to Isla Mujeres from Cancún

(4.8 of 5 reviews)

Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran equipped with all the comforts! Enjoy with your family and your friends a quiet ride catamaran sailing on the crystal clear waters... More

Free Cancellation
Start From $68.00
 
The Best Catamaran Tour to Isla Mujeres from Cancún Likely to Sell Out

The Best Catamaran Tour to Isla Mujeres from Cancún

  • North America
  • Superb5 reviews4.8

Discover Isla Mujeres and visit one of the beutiful beaches in the world, from incredible catamaran ....

    Free Cancellation
    Start From $68.00
 
 

Squamish Afternoon Sailing Experience

(4.8 of 5 reviews)

Set sail for a tranquil evening on Howe Sound with our enchanting afternoon sailing experience! Our certified instructors are dedicated to providing a safe, comfortable, and unforgettable outing. Guests are welcome to be as hands... More

Free Cancellation
Start From $109.91
 
Squamish Afternoon Sailing Experience Likely to Sell Out

Squamish Afternoon Sailing Experience

  • North America
  • Superb5 reviews4.8

Set sail for a tranquil evening on Howe Sound with our enchanting afternoon sailing experience! Our....

    Free Cancellation
    Start From $109.91
 
 

Sunset Sail Experience by Catamaran in Waikiki

(4.8 of 6 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • North America
  • Superb6 reviews4.8

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Start From $92.31
 
 

Tour to The Arch and Lover's Beach (optional) from Cabo

(4.8 of 9 reviews)

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, and through the Marina. See it all in one tour! During this awesome experience, you will be able to see a great variety of tropical... More

Free Cancellation
Start From $30.00
 
Tour to The Arch and Lover's Beach (optional) from Cabo Likely to Sell Out

Tour to The Arch and Lover's Beach (optional) from Cabo

  • North America
  • Superb9 reviews4.8

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, a....

    Free Cancellation
    Start From $30.00
 
 

Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun

(4 of 54 reviews)

Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectacular day in the crystal-clear waters of the Mexican Caribbean, sailing from Cancun to Isla Mujeres on a boat full of fun, explorin... More

Free Cancellation
Start From $49.99
 
Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun Likely to Sell Out

Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun

  • North America
  • Very Good54 reviews4

Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectac....

    Free Cancellation
    Start From $49.99
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 168 reviews)

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More

Free Cancellation
Private Tour
Start From $625.00
 
2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb168 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Private 40' Bali Catamaran – Drinks & Food Included

(5 of 347 reviews)

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredible sailing catamaran, with a host and a chef at your disposal, the captain will take you to sail in the most beautiful waters of ... More

Free Cancellation
Private Tour
Start From $2,100.00
 
Private 40' Bali Catamaran – Drinks & Food Included Likely to Sell Out

Private 40' Bali Catamaran – Drinks & Food Included

  • North America
  • Superb347 reviews5

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredi....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 20 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb20 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Luxury Sailing to Isla Mujeres with Lunch and Premium Open Bar

(5 of 20 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
  • Superb20 reviews5

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
 
 

Champagne Dolphin Sail and Reef Snorkel

(5 of 5 reviews)

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the ... More

Free Cancellation
Private Tour
Start From $108.91
 
Champagne Dolphin Sail and Reef Snorkel Likely to Sell Out

Champagne Dolphin Sail and Reef Snorkel

  • North America
  • Superb5 reviews5

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now l....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch

(5 of 5 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 $39.00
 
Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch Likely to Sell Out

Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch

  • North America
  • Superb5 reviews5

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

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

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 $31.46
 
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 $31.46
 
 

Let’s do a morning sail on San Francisco Bay (semi private)

(5 of 7 reviews)

Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boat? Come sail with me, Captain John. Let me share my passion for sailing with you. I’m a U.S. certified sailing instructor and li... More

Free Cancellation
Private Tour
Start From $189.00
 
Let’s do a morning sail on San Francisco Bay (semi private) Likely to Sell Out

Let’s do a morning sail on San Francisco Bay (semi private)

  • North America
  • Superb7 reviews5

Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Afternoon Charleston Historic Harbor Sail - Lux Catamatan

(4.5 of 6 reviews)

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 50-foot catamaran offers the perfect vantage point to experience the city’s charm from the water, away from the ... More

Free Cancellation
Private Tour
Start From $50.00
 
Afternoon Charleston Historic Harbor Sail - Lux Catamatan Likely to Sell Out

Afternoon Charleston Historic Harbor Sail - Lux Catamatan

  • North America
  • Exellent6 reviews4.5

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s histor....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Key West Dolphin Watch and Sunset Sail on Catamaran

(4.7 of 28 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
  • Superb28 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
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 822 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Private Tour
Start From $145.41
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • North America
  • Superb822 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Private Tour
    Start From $145.41
 
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