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Top 10 Best North America Sailing Trips

Found 720 Sailing Trips activities in North America. Sort by Popularity. - Page 28
 

Private Luxurious Sailing Cruise in San Diego Bay

(5 of 12 reviews)

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll make sure your time on the sailing vessel RIVIERA is the highlight of your visit.... More

Free Cancellation
Private Tour
Start From $2,700.00
 
Private Luxurious Sailing Cruise in San Diego Bay Likely to Sell Out

Private Luxurious Sailing Cruise in San Diego Bay

  • North America
  • Superb12 reviews5

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, an....

    Free Cancellation
    Private Tour
    Start From $2,700.00
 
 

Private Afternoon Harbor Cruise on Kismet for parties up to 15

(5 of 26 reviews)

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history tours, swim and float on rafts. Kismet does it all! Kismet is a custom-built ... More

Free Cancellation
Private Tour
Start From $1,549.00
 
Private Afternoon Harbor Cruise on Kismet for parties up to 15 Likely to Sell Out

Private Afternoon Harbor Cruise on Kismet for parties up to 15

  • North America
  • Superb26 reviews5

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise....

    Free Cancellation
    Private Tour
    Start From $1,549.00
 
 

Snorkel in the beautiful reef of Puerto Morelos with transport

(3 of 1 review)

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reefs in Puerto Morelos. Sail through the turquoise clear water of the Caribbean Sea and arrive to the Mesoamerican reef. Our captain... More

Free Cancellation
Private Tour
Start From $59.00
 
Snorkel in the beautiful reef of Puerto Morelos with transport Likely to Sell Out

Snorkel in the beautiful reef of Puerto Morelos with transport

  • North America

The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reef....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

2 Hours Private Guided Sailing Adventure in Pensacola Beach

(5 of 4 reviews)

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of ... More

Free Cancellation
Private Tour
Start From $375.00
 
2 Hours Private Guided Sailing Adventure in Pensacola Beach Likely to Sell Out

2 Hours Private Guided Sailing Adventure in Pensacola Beach

  • North America
  • Superb4 reviews5

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, De....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Dinner and show pirate night Hook in Cancun

(5 of 4 reviews)

Captain Hook’s Cancun tour offers an immersive experience unlike any in the area. More than just a cruise, it’s a dinner-show aboard an authentic 18th century pirate galleon, where travelers become part of an exciting adventur... More

Free Cancellation
Private Tour
Start From $136.00
 
Dinner and show pirate night Hook in Cancun Likely to Sell Out

Dinner and show pirate night Hook in Cancun

  • North America
  • Superb4 reviews5

Captain Hook’s Cancun tour offers an immersive experience unlike any in the area. More than just a....

    Free Cancellation
    Private Tour
    Start From $136.00
 
 

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch

(5 of 1 review)

Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect for couples, families, or small groups, this 2-hour cruise offers front-row views of El Arco, Lover’s Beach, and local sea lion... More

Free Cancellation
Private Tour
Start From $999.00
 
Private Yacht Charter in Cabo San Lucas – Cruise to The Arch Likely to Sell Out

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch

  • North America
  • Superb1 review5

Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

Private Paddle Tour at Sunrise

(5 of 215 reviews)

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity to be complete. We are an ecologically responsible company that promotes... More

Free Cancellation
Private Tour
Start From $71.16
 
Private Paddle Tour at Sunrise Likely to Sell Out

Private Paddle Tour at Sunrise

  • North America
  • Superb215 reviews5

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hou....

    Free Cancellation
    Private Tour
    Start From $71.16
 
 

Whale Watching Amazing Adventure

(5 of 215 reviews)

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cabos in search of the Cabo’s Whales.” Enjoy listening to the beautiful song of the whales, with the help of our new hydrophones... More

Free Cancellation
Private Tour
Start From $97.00
 
Whale Watching Amazing Adventure Likely to Sell Out

Whale Watching Amazing Adventure

  • North America
  • Superb215 reviews5

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....

    Free Cancellation
    Private Tour
    Start From $97.00
 
 

Private Transparent Boat Tour in the Sea of Cozumel

(5 of 215 reviews)

Incredible experience in a 100% transparent boat, we are also the only tour currently that offers snorkeling, sunken ships, there is more probability of finding marine life on this tour since we are on the second largest reef in t... More

Special Offer
Free Cancellation
Private Tour
Start From $519.69
(Saving 20% ) $649.61
 
-20% Private Transparent Boat Tour in the Sea of Cozumel Likely to Sell Out

Private Transparent Boat Tour in the Sea of Cozumel

  • North America
  • Superb215 reviews5

Incredible experience in a 100% transparent boat, we are also the only tour currently that offers sn....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $519.69
    (Saving 20% ) $649.61
 
 

Private Sailing and Swim Tour in Waikiki

(5 of 215 reviews)

Join our friendly crew for a beautiful coastal sail on a 40ft Beneteau sailboat up the south shore of Oahu! Cruise by the iconic Waikiki coastline and up past our famous Diamond Head State Monument as our crew shares their local k... More

Free Cancellation
Private Tour
Start From $899.00
 
Private Sailing and Swim Tour in Waikiki Likely to Sell Out

Private Sailing and Swim Tour in Waikiki

  • North America
  • Superb215 reviews5

Join our friendly crew for a beautiful coastal sail on a 40ft Beneteau sailboat up the south shore o....

    Free Cancellation
    Private Tour
    Start From $899.00
 
 

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 $750.00
 
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 $750.00
 
 

San Francisco City Lights Sail

(5 of 6 reviews)

The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us for a city-front cruise to enjoy the majestic sites of San Francisco in the night sky. See the Bay Bridge lit in all its glory, alo... More

Free Cancellation
Private Tour
Start From $85.00
 
San Francisco City Lights Sail Likely to Sell Out

San Francisco City Lights Sail

  • North America
  • Superb6 reviews5

The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us f....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Marina Del Rey Luxury Yacht Experience

(3 of 2 reviews)

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly and knowledgeable captains. Whether you’re seeking a laid-back day cruising... More

Free Cancellation
Private Tour
Start From $99.00
 
Marina Del Rey Luxury Yacht Experience Likely to Sell Out

Marina Del Rey Luxury Yacht Experience

  • North America

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Mar....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Sunset Sailing

(5 of 1 review)

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premium Open Bar and a Cheese and Cold Cuts table as snacks. Go in style and go Private. Since Covid-19 additional measures and precauti... More

Free Cancellation
Private Tour
Start From $999.00
 
Private Sunset Sailing Likely to Sell Out

Private Sunset Sailing

  • North America
  • Superb1 review5

A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premiu....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 of 1 review)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran for 7-12 People

  • North America
  • Superb1 review5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
 

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)

(5 of 1 review)

Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whale shark adventure is the most enigmatic activity in Mexico. It is a very docile animal that is just as impressive as any other a... More

Free Cancellation
Private Tour
Start From $189.00
 
Whale Shark Snorkel Tour in Cancun (Snack Lunch included) Likely to Sell Out

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)

  • North America
  • Superb1 review5

Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whal....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Discover Hobie-Cat Sailing and Fish your own Lunch

(5 of 6 reviews)

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freedom that only the ocean can give. You'll realize that you will be able to get to some of the most beautiful places on the planet wi... More

Free Cancellation
Private Tour
Start From $225.00
 
Discover Hobie-Cat Sailing and Fish your own Lunch Likely to Sell Out

Discover Hobie-Cat Sailing and Fish your own Lunch

  • North America
  • Superb6 reviews5

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freed....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran

(5 of 4 reviews)

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More

Free Cancellation
Private Tour
Start From $76.00
 
Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran Likely to Sell Out

Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran

  • North America
  • Superb4 reviews5

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....

    Free Cancellation
    Private Tour
    Start From $76.00
 
 

Friday Night Waikiki Fireworks Sail

(3 of 1 review)

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More

Free Cancellation
Private Tour
Start From $699.00
 
Friday Night Waikiki Fireworks Sail Likely to Sell Out

Friday Night Waikiki Fireworks Sail

  • North America

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Whale Watching with Lunch and transportation included

(4.4 of 19 reviews)

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of whales in their natural habitat. Setting sail from the Marina, you... More

Free Cancellation
Private Tour
Start From $99.00
 
Whale Watching with Lunch and transportation included Likely to Sell Out

Whale Watching with Lunch and transportation included

  • North America
  • Exellent19 reviews4.4

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll hav....

    Free Cancellation
    Private Tour
    Start From $99.00
 
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