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Top 10 Best North America Sailing Trips

Found 693 Sailing Trips activities in North America. Sort by Popularity. - Page 12
 

Private Day Sailing Experience in San Diego up to 12 guests

(5 of 61 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 $80.00
 
Private Day Sailing Experience in San Diego up to 12 guests

Private Day Sailing Experience in San Diego up to 12 guests

  • North America
  • Superb61 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 $80.00
 
 

Jolly Roger Pirate Ship Cruise & Dinner Show

(5 of 6 reviews)

Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed sunset cruise on the gorgeous Spanish Galleon for the ideal evening out with the whole family. The buccaneers start greeting you a... More

Free Cancellation
Private Tour
Start From $85.72
 
Jolly Roger Pirate Ship Cruise & Dinner Show

Jolly Roger Pirate Ship Cruise & Dinner Show

  • North America
  • Superb6 reviews5

Become a pirate for a night by teaming up with Jolly Roger's cheerful crew! Embark on a fun-packed s....

    Free Cancellation
    Private Tour
    Start From $85.72
 
 

2hr. SUNSET Sailing Experience on San Francisco Bay

(5 of 15 reviews)

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More

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

2hr. SUNSET Sailing Experience on San Francisco Bay

  • North America
  • Superb15 reviews5

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Luxury Catamaran tour to isla mujeres with transportation from Tulum

(3.5 of 62 reviews)

Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More

Free Cancellation
Private Tour
Start From $110.77
 
Luxury Catamaran tour to isla mujeres with transportation from Tulum Likely to Sell Out

Luxury Catamaran tour to isla mujeres with transportation from Tu....

  • North America
  • Good62 reviews3.5

Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....

    Free Cancellation
    Private Tour
    Start From $110.77
 
 

Brunch Cruise with Buffet in Washington

(5 of 4 reviews)

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More

Free Cancellation
Private Tour
Start From $98.21
 
Brunch Cruise with Buffet in Washington Likely to Sell Out

Brunch Cruise with Buffet in Washington

  • North America
  • Superb4 reviews5

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....

    Free Cancellation
    Private Tour
    Start From $98.21
 
 

Small-Group San Diego Sailing Trip

(4.8 of 49 reviews)

Leave the streets behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant waterfront offers expansive views of Downtown, Point Loma, and Coronado Island. Whether you’re looking for an intimate adventure, ... More

Free Cancellation
Private Tour
Start From $130.00
 
Small-Group San Diego Sailing Trip Likely to Sell Out

Small-Group San Diego Sailing Trip

  • North America
  • Superb49 reviews4.8

Leave the streets behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant wa....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.6 of 14 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb14 reviews4.6

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

6-Hour Sailing Charter from Fort Lauderdale

(5 of 3 reviews)

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option to use their time docked or sailing out to sea. Once on the water... More

Free Cancellation
Private Tour
Start From $400.00
 
6-Hour Sailing Charter from Fort Lauderdale Likely to Sell Out

6-Hour Sailing Charter from Fort Lauderdale

  • North America
  • Superb3 reviews5

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

(4.4 of 61 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Private Tour
Start From $149.00
 
Half Day Luxury Sailing Experience in Riviera Maya with Open Bar Likely to Sell Out

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar

  • North America
  • Exellent61 reviews4.4

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

2.5-hour Guided Sailboat Tour

(4.9 of 177 reviews)

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More

Free Cancellation
Private Tour
Start From $118.00
 
2.5-hour Guided Sailboat Tour Likely to Sell Out

2.5-hour Guided Sailboat Tour

  • North America
  • Superb177 reviews4.9

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....

    Free Cancellation
    Private Tour
    Start From $118.00
 
 

4-Hour Sailing Adventure on The Strait of Juan de Fuca

(4.6 of 21 reviews)

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water birds there is always something to see while you are learning the skills to sail one... More

Free Cancellation
Private Tour
Start From $112.78
 
4-Hour Sailing Adventure on The Strait of Juan de Fuca Likely to Sell Out

4-Hour Sailing Adventure on The Strait of Juan de Fuca

  • North America
  • Superb21 reviews4.6

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbac....

    Free Cancellation
    Private Tour
    Start From $112.78
 
 

Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar

(4.7 of 3 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
  • Superb3 reviews4.7

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
 
 

Snorkeling Tour in Los Cabos

(4 of 1 review)

Sail past Lover’s Beach, The Arch, and the Sea Lion Colony on your way to the beautiful Santa Maria Bay, on the Pez Gato, part of Cabo’s premier snorkeling tour. You will swim in the azure waters with colorful tropical fish. O... More

Free Cancellation
Private Tour
Start From $123.00
 
Snorkeling Tour in Los Cabos Likely to Sell Out

Snorkeling Tour in Los Cabos

  • North America
  • Very Good1 review4

Sail past Lover’s Beach, The Arch, and the Sea Lion Colony on your way to the beautiful Santa Mari....

    Free Cancellation
    Private Tour
    Start From $123.00
 
 

South Beach Miami BACHELORETTE Boat Day!

(5 of 1 review)

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good y... More

Free Cancellation
Private Tour
Start From $1,795.00
 
South Beach Miami BACHELORETTE Boat Day! Likely to Sell Out

South Beach Miami BACHELORETTE Boat Day!

  • North America
  • Superb1 review5

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and....

    Free Cancellation
    Private Tour
    Start From $1,795.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 121 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Private Tour
Start From $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb121 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Private Tour
    Start From $250.00
 
 

Polynesian Canoe Day Sail

(4.8 of 26 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Special Offer
Free Cancellation
Private Tour
Start From $180.00
(Saving 10% ) $200.00
 
-10% Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • North America
  • Superb26 reviews4.8

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.00
    (Saving 10% ) $200.00
 
 

The Finest Private Yacht Experience in Cabo

(4.6 of 23 reviews)

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some of the best things to do in Cabo such as whale watching and bathing on soothing crystal waters... More

Free Cancellation
Private Tour
Start From $726.92
 
The Finest Private Yacht Experience in Cabo Likely to Sell Out

The Finest Private Yacht Experience in Cabo

  • North America
  • Superb23 reviews4.6

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30....

    Free Cancellation
    Private Tour
    Start From $726.92
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 230 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb230 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Small Group Sunset Sail in San Diego- Public Sail up to 6 guests

(5 of 45 reviews)

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking to experience the bay from the water without booking a private charter. Relax ... More

Free Cancellation
Private Tour
Start From $119.00
 
Small Group Sunset Sail in San Diego- Public Sail up to 6 guests Likely to Sell Out

Small Group Sunset Sail in San Diego- Public Sail up to 6 guests

  • North America
  • Superb45 reviews5

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perf....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Let’s do a morning sail on San Francisco Bay

(5 of 6 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

Special Offer
Free Cancellation
Private Tour
Start From $160.65
(Saving 15% ) $189.00
 
-15% Let’s do a morning sail on San Francisco Bay Likely to Sell Out

Let’s do a morning sail on San Francisco Bay

  • North America
  • Superb6 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $160.65
    (Saving 15% ) $189.00
 
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