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Top 10 Best North America Sailing Trips

Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 35
 

Sunset Fiesta Cruise: Open Bar, Dancing & El Arco Views

(5 of 4 reviews)

Dance, drink, and sail into the sunset on Cabo’s original party cruise! The Pez Gato offers the perfect mix of sightseeing and non-stop fun, cruising past iconic landmarks like the Arch, Lover’s Beach, and sea lion colony befo... More

Start From $108.00
 
Sunset Fiesta Cruise: Open Bar, Dancing & El Arco Views

Sunset Fiesta Cruise: Open Bar, Dancing & El Arco Views

  • North America
  • Superb4 reviews5

Dance, drink, and sail into the sunset on Cabo’s original party cruise! The Pez Gato offers the pe....

    Start From $108.00
 
 

Sailboat on the Mayan Riviera at sunset

(5 of 1 review)

Ready to set sail on a catamaran at sunset? The Riviera Maya is the ideal place to do it. This incredible coastal region is home to some of the calmest waters in the world and the most picturesque landscapes. Board one of our full... More

Start From $145.00
 
Sailboat on the Mayan Riviera at sunset

Sailboat on the Mayan Riviera at sunset

  • North America
  • Superb1 review5

Ready to set sail on a catamaran at sunset? The Riviera Maya is the ideal place to do it. This incre....

    Start From $145.00
 
 

Super ATVs and Romantic Dinner Combo, with transport & dinner

(3.3 of 3 reviews)

Would you like to give your partner the best birthday or anniversary gift during the holidays? Join us in this great adventure that takes you to experience the Caribbean jungle during the day and the best dinner in Cancun at night... More

Free Cancellation
Start From $184.00
 
Super ATVs and Romantic Dinner Combo, with transport & dinner

Super ATVs and Romantic Dinner Combo, with transport & dinner

  • North America
  • Good3 reviews3.3

Would you like to give your partner the best birthday or anniversary gift during the holidays? Join ....

    Free Cancellation
    Start From $184.00
 
 

Private Catamaran Sailboat 4hrs 15Pax

(3.3 of 3 reviews)

Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelor party or alone enjoy a private sunset with your friends.... More

Free Cancellation
Private Tour
Start From $3,058.00
 
Private Catamaran Sailboat 4hrs 15Pax

Private Catamaran Sailboat 4hrs 15Pax

  • North America
  • Good3 reviews3.3

Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelo....

    Free Cancellation
    Private Tour
    Start From $3,058.00
 
 

Bacalar Seven Colors Lagoon Adventure with Boat Ride and Lunch

(3.3 of 3 reviews)

What truly sets this experience apart is the perfect blend of nature, history, and comfort in one seamless adventure. You won’t just visit Bacalar — you’ll fully experience it. Sail across the breathtaking Seven Colors Lago... More

Free Cancellation
Private Tour
Start From $189.00
 
Bacalar Seven Colors Lagoon Adventure with Boat Ride and Lunch

Bacalar Seven Colors Lagoon Adventure with Boat Ride and Lunch

  • North America
  • Good3 reviews3.3

What truly sets this experience apart is the perfect blend of nature, history, and comfort in one se....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

75ft Sailboat Courses in Isla Mujeres

(3.3 of 3 reviews)

Gain sailing skills and confidence on a 75-foot ocean sailboat equipped with the latest navigation technology. Two course options are available: the Basic day course, perfect for beginners or those seeking practice, and the compre... More

Free Cancellation
Private Tour
Start From $150.00
 
75ft Sailboat Courses in Isla Mujeres

75ft Sailboat Courses in Isla Mujeres

  • North America
  • Good3 reviews3.3

Gain sailing skills and confidence on a 75-foot ocean sailboat equipped with the latest navigation t....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

JFarwell Sip & Sail aboard the Reverie

(5 of 19 reviews)

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More

Free Cancellation
Private Tour
Start From $843.69
 
JFarwell Sip & Sail aboard the Reverie Likely to Sell Out

JFarwell Sip & Sail aboard the Reverie

  • North America
  • Superb19 reviews5

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....

    Free Cancellation
    Private Tour
    Start From $843.69
 
 

Oyster Bay Three Hour Sailing Experience

(5 of 19 reviews)

Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard WINDSWEPT, a Jeanneau 36i. This charter offers flexible departure times, allowing you to choose a start time that suits your sche... More

Free Cancellation
Private Tour
Start From $825.00
 
Oyster Bay Three Hour Sailing Experience Likely to Sell Out

Oyster Bay Three Hour Sailing Experience

  • North America
  • Superb19 reviews5

Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard....

    Free Cancellation
    Private Tour
    Start From $825.00
 
 

Private Luxury Sailboat for 12 people 4 hrs

(5 of 19 reviews)

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to have fun with your friends in private. It is a beautiful sailboat, comfortable, spacious, and excellently equipped. Interior: Sp... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Luxury Sailboat for 12 people 4 hrs Likely to Sell Out

Private Luxury Sailboat for 12 people 4 hrs

  • North America
  • Superb19 reviews5

Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Spend the Day on Buzzards Bay - Powerboat Cruises

(5 of 1 review)

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are welcome aboard. Whether you crave adventure, relaxation, or both, our charters prom... More

Free Cancellation
Private Tour
Start From $540.00
 
Spend the Day on Buzzards Bay - Powerboat Cruises Likely to Sell Out

Spend the Day on Buzzards Bay - Powerboat Cruises

  • North America
  • Superb1 review5

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per ho....

    Free Cancellation
    Private Tour
    Start From $540.00
 
 

4 Hours Private Yacht in Puerto Vallarta with Snorkeling and Beach

(5 of 1 review)

Enjoy an exclusive getaway on a private yacht in Puerto Vallarta, where adventure and relaxation meet. On this 4-hour tour, sail to the stunning Arches of Mismaloya and explore the natural beauty of Playa Paredón. With snorkeling... More

Free Cancellation
Private Tour
Start From $1,087.54
 
4 Hours Private Yacht in Puerto Vallarta with Snorkeling and Beach Likely to Sell Out

4 Hours Private Yacht in Puerto Vallarta with Snorkeling and Beac....

  • North America
  • Superb1 review5

Enjoy an exclusive getaway on a private yacht in Puerto Vallarta, where adventure and relaxation mee....

    Free Cancellation
    Private Tour
    Start From $1,087.54
 
 

4th Of July Fireworks Cruise Experience in Lake Chatuge

(5 of 1 review)

Celebrate Independence Day with a festive 4th of July fireworks boat experience on Lake Chatuge. Travelers are collected from the pickup location to cruise past scenic lake houses and neighborhood celebrations, concluding the even... More

Free Cancellation
Private Tour
Start From $620.00
 
4th Of July Fireworks Cruise Experience in Lake Chatuge Likely to Sell Out

4th Of July Fireworks Cruise Experience in Lake Chatuge

  • North America
  • Superb1 review5

Celebrate Independence Day with a festive 4th of July fireworks boat experience on Lake Chatuge. Tra....

    Free Cancellation
    Private Tour
    Start From $620.00
 
 

Bertram Yacht 58 Feet Up to 25 People 4 hrs

(5 of 1 review)

This is a beautiful and comfortable Yacht, ideal for planning an excellent vacation and having a fun and spectacular party. The magnificent 58-foot-long boat has the capacity to simultaneously accommodate up to 25 people. Renting ... More

Free Cancellation
Private Tour
Start From $2,250.00
 
Bertram Yacht 58 Feet Up to 25 People 4 hrs Likely to Sell Out

Bertram Yacht 58 Feet Up to 25 People 4 hrs

  • North America
  • Superb1 review5

This is a beautiful and comfortable Yacht, ideal for planning an excellent vacation and having a fun....

    Free Cancellation
    Private Tour
    Start From $2,250.00
 
 

Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

(5 of 2 reviews)

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything you need, and bring the party with custom curated playlists, Tiki-Oki, a... More

Free Cancellation
Private Tour
Start From $599.00
 
Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise Likely to Sell Out

Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

  • North America
  • Superb2 reviews5

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Yo....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

6-Night Private Charter in Lake Clark National Park

(5 of 1 review)

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group of up to six guests. Settle into three queen guest cabins, each with ... More

Free Cancellation
Private Tour
Start From $30,769.24
 
6-Night Private Charter in Lake Clark National Park Likely to Sell Out

6-Night Private Charter in Lake Clark National Park

  • North America
  • Superb1 review5

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot saili....

    Free Cancellation
    Private Tour
    Start From $30,769.24
 
 

Private Daytime Sailing Cruise on Lake Champlain 12 Passengers

(5 of 5 reviews)

Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adirondack and Green Mountains await. This private two-hour cruise accommodates groups of 2 to 12, allowing you to share the experience wi... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Daytime Sailing Cruise on Lake Champlain 12 Passengers Likely to Sell Out

Private Daytime Sailing Cruise on Lake Champlain 12 Passengers

  • North America
  • Superb5 reviews5

Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adironda....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

(5 of 5 reviews)

Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sail through the stunning waters of Los Cabos, immerse yourself in breathtaking views at every turn — from the iconic Lover’s Bea... More

Free Cancellation
Private Tour
Start From $135.00
 
Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran Likely to Sell Out

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

  • North America
  • Superb5 reviews5

Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sai....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Private Afternoon Snorkel with Sunset Sail in Key West

(5 of 4 reviews)

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Afternoon Snorkel with Sunset Sail in Key West Likely to Sell Out

Private Afternoon Snorkel with Sunset Sail in Key West

  • North America
  • Superb4 reviews5

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

Hobie Cat rental or sailing lessons

(5 of 4 reviews)

Rent a Hobie Cat and experience the Bacalar lagoon in a fun, fast and adventure-filled way. This lightweight and agile sailboat is perfect for both experienced boaters and beginners who want to learn about the water. In rental mo... More

Free Cancellation
Private Tour
Start From $63.12
 
Hobie Cat rental or sailing lessons Likely to Sell Out

Hobie Cat rental or sailing lessons

  • North America
  • Superb4 reviews5

Rent a Hobie Cat and experience the Bacalar lagoon in a fun, fast and adventure-filled way. This lig....

    Free Cancellation
    Private Tour
    Start From $63.12
 
 

Private Couples Sunset Sailing Tour in San Diego

(5 of 4 reviews)

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Your sunset saili... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Couples Sunset Sailing Tour in San Diego Likely to Sell Out

Private Couples Sunset Sailing Tour in San Diego

  • North America
  • Superb4 reviews5

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....

    Free Cancellation
    Private Tour
    Start From $800.00
 
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