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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 23
 

San Salvador Spanish Galleon Adventure Day Sail with General Admission

(4.1 of 7 reviews)

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the ... More

Start From $85.00
 
San Salvador Spanish Galleon Adventure Day Sail with General Admission

San Salvador Spanish Galleon Adventure Day Sail with General Admi....

  • North America
  • Exellent7 reviews4.1

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step o....

    Start From $85.00
 
 

Portland Tall Ship Private Charter on Casco Bay

(4.1 of 7 reviews)

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. ... More

Free Cancellation
Private Tour
Start From $1,055.65
 
Portland Tall Ship Private Charter on Casco Bay

Portland Tall Ship Private Charter on Casco Bay

  • North America
  • Exellent7 reviews4.1

What better way to see the delights than in the style of a private charter for you and five friends ....

    Free Cancellation
    Private Tour
    Start From $1,055.65
 
 

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

(4.7 of 7 reviews)

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of the skyline. Our trips are BYOB so bring your favorite bottle of wine for a special e... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable Likely to Sell Out

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

  • North America
  • Superb7 reviews4.7

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun s....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Private Day Sail in San Diego up to 12 guests

(5 of 69 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 $487.50
 
Private Day Sail in San Diego up to 12 guests Likely to Sell Out

Private Day Sail in San Diego up to 12 guests

  • North America
  • Superb69 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 $487.50
 
 

Baltimore Evening Sail on the Summer Wind

(5 of 28 reviews)

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city lights up. Treat ... More

Free Cancellation
Private Tour
Start From $75.00
 
Baltimore Evening Sail on the Summer Wind Likely to Sell Out

Baltimore Evening Sail on the Summer Wind

  • North America
  • Superb28 reviews5

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-ho....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Romantic Dinner Touring the Nichupté Lagoon in Galeón

(5 of 1 review)

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is a unique romance tour in Cancun, as it offers a very special evening, surrounded by ... More

Free Cancellation
Private Tour
Start From $125.00
 
Romantic Dinner Touring the Nichupté Lagoon in Galeón Likely to Sell Out

Romantic Dinner Touring the Nichupté Lagoon in Galeón

  • North America
  • Superb1 review5

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Snorkeling Adventure in Isla Mujeres

(3.8 of 13 reviews)

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world since there is no such thing anywhere. This activity is cataloged as mandatory for all traveler... More

Free Cancellation
Private Tour
Start From $59.00
 
Snorkeling Adventure in Isla Mujeres Likely to Sell Out

Snorkeling Adventure in Isla Mujeres

  • North America
  • Very Good13 reviews3.8

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Los Cabos Sunset Cruise: Iconic Views, Group Joy, Food and Drink

(5 of 1 review)

What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience travelers dream about. You’ll sail right up to the legendary Arch, capturing postcard‑perfect photos as the colors of the sky s... More

Special Offer
Free Cancellation
Private Tour
Start From $89.10
(Saving 10% ) $99.00
 
-10% Los Cabos Sunset Cruise: Iconic Views, Group Joy, Food and Drink Likely to Sell Out

Los Cabos Sunset Cruise: Iconic Views, Group Joy, Food and Drink

  • North America
  • Superb1 review5

What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience t....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $89.10
    (Saving 10% ) $99.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $92.31
(Saving inf% ) $0.00
 
-inf% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $92.31
    (Saving inf% ) $0.00
 
 

2.5 hr Sailboat Tour aboard Orion's Child

(5 of 92 reviews)

TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sail aboard a ... More

Special Offer
Free Cancellation
Private Tour
Start From $130.00
(Saving inf% ) $0.00
 
-inf% 2.5 hr Sailboat Tour aboard Orion's Child Likely to Sell Out

2.5 hr Sailboat Tour aboard Orion's Child

  • North America
  • Superb92 reviews5

TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer t....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $130.00
    (Saving inf% ) $0.00
 
 

Sailboat tour across the seven colors lagoon in Bacalar

(5 of 196 reviews)

Discover the seven colors lagoon and the most iconics points inside (Chanel of the pirates, cenotes and bird sanctuary) . You will sail and swim in cristaline turquoise waters and listen stories and anecdotes uniques from Bacalar.... More

Special Offer
Free Cancellation
Private Tour
Start From $41.20
(Saving inf% ) $0.00
 
-inf% Sailboat tour across the seven colors lagoon in Bacalar Likely to Sell Out

Sailboat tour across the seven colors lagoon in Bacalar

  • North America
  • Superb196 reviews5

Discover the seven colors lagoon and the most iconics points inside (Chanel of the pirates, cenotes ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $41.20
    (Saving inf% ) $0.00
 
 

Isla Mujeres Sailing Adventure from Riviera Maya

(3.6 of 13 reviews)

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel.
Surrounded by all the scale of blue colors, you'll relax and chill, laying in the shade of the big cockpit  or in a comfortable living r... More

Special Offer
Free Cancellation
Private Tour
Start From $149.00
(Saving inf% ) $0.00
 
-inf% Isla Mujeres Sailing Adventure from Riviera Maya Likely to Sell Out

Isla Mujeres Sailing Adventure from Riviera Maya

  • North America
  • Very Good13 reviews3.6

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel.
Surroun....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $149.00
    (Saving inf% ) $0.00
 
 

Key West Sail and Snorkel Day Trip from Fort Lauderdale

(3.1 of 16 reviews)

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More

Special Offer
Free Cancellation
Private Tour
Start From $149.00
(Saving inf% ) $0.00
 
-inf% Key West Sail and Snorkel Day Trip from Fort Lauderdale Likely to Sell Out

Key West Sail and Snorkel Day Trip from Fort Lauderdale

  • North America
  • Good16 reviews3.1

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $149.00
    (Saving inf% ) $0.00
 
 

Sail away! Hobie Cat Tour Bacalar

(5 of 32 reviews)

Discover with us the breathtaking lagoon of the seven colors. We tell you the true stories of the Pirates of the Caribbean. Learn more about cenotes and stomalites and immerse yourself in the mystical world of the Maya.... More

Special Offer
Free Cancellation
Private Tour
Start From $82.40
(Saving inf% ) $0.00
 
-inf% Sail away! Hobie Cat Tour Bacalar Likely to Sell Out

Sail away! Hobie Cat Tour Bacalar

  • North America
  • Superb32 reviews5

Discover with us the breathtaking lagoon of the seven colors. We tell you the true stories of the Pi....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $82.40
    (Saving inf% ) $0.00
 
 

Tall Ship Adventure aboard the Schooner Californian with General Admission

(4.3 of 6 reviews)

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984 Summer Olympic Games in Los Angeles. In July 2003, the Governor signed a bill into law designat... More

Special Offer
Free Cancellation
Private Tour
Start From $85.00
(Saving inf% ) $0.00
 
-inf% Tall Ship Adventure aboard the Schooner Californian with General Admission Likely to Sell Out

Tall Ship Adventure aboard the Schooner Californian with General ....

  • North America
  • Exellent6 reviews4.3

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launch....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $85.00
    (Saving inf% ) $0.00
 
 

Reef Snorkeling with ATV, Zipline, Cenote, lunch & transportation

(4 of 4 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

Special Offer
Free Cancellation
Private Tour
Start From $109.65
(Saving inf% ) $0.00
 
-inf% Reef Snorkeling with ATV, Zipline, Cenote, lunch & transportation Likely to Sell Out

Reef Snorkeling with ATV, Zipline, Cenote, lunch & transportation

  • North America
  • Very Good4 reviews4

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $109.65
    (Saving inf% ) $0.00
 
 

Private Sailing Tour -2 Hour (Up to 12 Passengers)

(4 of 4 reviews)

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval architect Colin Archer (1832-1921), from Larvik, Norway, the Cloudia is... More

Special Offer
Free Cancellation
Private Tour
Start From $1,200.00
(Saving inf% ) $0.00
 
-inf% Private Sailing Tour -2 Hour (Up to 12 Passengers) Likely to Sell Out

Private Sailing Tour -2 Hour (Up to 12 Passengers)

  • North America
  • Very Good4 reviews4

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double en....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,200.00
    (Saving inf% ) $0.00
 
 

Private Luxury Catamaran in Tulum with Snacks and Open Bar

(5 of 239 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

Special Offer
Free Cancellation
Private Tour
Start From $2,700.00
(Saving inf% ) $0.00
 
-inf% Private Luxury Catamaran in Tulum with Snacks and Open Bar Likely to Sell Out

Private Luxury Catamaran in Tulum with Snacks and Open Bar

  • North America
  • Superb239 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $2,700.00
    (Saving inf% ) $0.00
 
 

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

(5 of 3 reviews)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and b... More

Special Offer
Free Cancellation
Private Tour
Start From $70.00
(Saving inf% ) $0.00
 
-inf% 2 Hour Swim, Snorkel & Sail (Kewalo Harbor) Likely to Sell Out

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

  • North America
  • Superb3 reviews5

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolph....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $70.00
    (Saving inf% ) $0.00
 
 

Clear Boat to Cabo Lands End, The Arch and more

(4.6 of 19 reviews)

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take a tour just where the Pacific Ocean meets the Sea of Cortez, the famous Lands End. In our... More

Special Offer
Free Cancellation
Private Tour
Start From $39.00
(Saving inf% ) $0.00
 
-inf% Clear Boat to Cabo Lands End, The Arch and more Likely to Sell Out

Clear Boat to Cabo Lands End, The Arch and more

  • North America
  • Superb19 reviews4.6

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $39.00
    (Saving inf% ) $0.00
 
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