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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 37
 

Bacalar Seven Colors Lagoon Adventure with Boat Ride and Lunch

(5 of 1 review)

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
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
  • Superb1 review5

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

    Free Cancellation
    Start From $189.00
 
 

Magic Night Boat Dinner with Show & Speedboat Experience at Cancun (1 day tour)

(5 of 1 review)

Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are looking for an exciting activity, experience an intrepid adventure in our guided speed boat and snorkeling tour. Our speed boats ar... More

Free Cancellation
Start From $180.00
 
Magic Night Boat Dinner with Show & Speedboat Experience at Cancun (1 day tour)

Magic Night Boat Dinner with Show & Speedboat Experience at Cancu....

  • North America
  • Superb1 review5

Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are l....

    Free Cancellation
    Start From $180.00
 
 

Beyond Bacalar: Pirate Route Exploration + River Float + Lunch

(4.9 of 7 reviews)

The Hidden Gem Tour! Explore Bacalar’s secret lagoons and the historic Pirate Route, float gently in peaceful currents, spot wildlife, and enjoy fresh snacks and authentic ceviche on a private 5-hour boat tour away from the crow... More

Free Cancellation
Private Tour
Start From $318.13
 
Beyond Bacalar: Pirate Route Exploration + River Float + Lunch

Beyond Bacalar: Pirate Route Exploration + River Float + Lunch

  • North America
  • Superb7 reviews4.9

The Hidden Gem Tour! Explore Bacalar’s secret lagoons and the historic Pirate Route, float gently ....

    Free Cancellation
    Private Tour
    Start From $318.13
 
 

Epic 34 Catamaran Sailing and Snorkeling Adventure

(4.9 of 7 reviews)

Epic 34' catamaran sailing and snorkeling in Waikiki Bay. With Diamond as the back drop you lay back and enjoy the amazing views.... More

Free Cancellation
Private Tour
Start From $299.00
 
Epic 34 Catamaran Sailing and Snorkeling Adventure

Epic 34 Catamaran Sailing and Snorkeling Adventure

  • North America
  • Superb7 reviews4.9

Epic 34' catamaran sailing and snorkeling in Waikiki Bay. With Diamond as the back drop you lay back....

    Free Cancellation
    Private Tour
    Start From $299.00
 
 

Private Dolphin Catamaran Sail In Cocoa Beach

(4.9 of 7 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Dolphin Catamaran Sail In Cocoa Beach Likely to Sell Out

Private Dolphin Catamaran Sail In Cocoa Beach

  • North America
  • Superb7 reviews4.9

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

Private Sailing Charters on La Vie Dansante

(4.9 of 7 reviews)

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht "La Vie Dansante" through Florida’s stunning Intracoastal Waterway.... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Sailing Charters on La Vie Dansante Likely to Sell Out

Private Sailing Charters on La Vie Dansante

  • North America
  • Superb7 reviews4.9

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your fa....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

3.5 hour Sailing Adventure in Nanoose Bay

(5 of 3 reviews)

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mountain vistas and island shorelines. Sea Lions are often seen, and sightings of Humpback Whales and Orcas are common in Georgia Str... More

Special Offer
Free Cancellation
Private Tour
Start From $104.55
(Saving 20% ) $130.68
 
-20% 3.5 hour Sailing Adventure in Nanoose Bay Likely to Sell Out

3.5 hour Sailing Adventure in Nanoose Bay

  • North America
  • Superb3 reviews5

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mou....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $104.55
    (Saving 20% ) $130.68
 
 

Bertram Yacht 58 Feet Up to 25 People 4 hrs

(5 of 3 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $2,250.00
(Saving inf% ) $0.00
 
-inf% 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
  • Superb3 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $2,250.00
    (Saving inf% ) $0.00
 
 

Sausalito Shared Sailing Tour 4 Day Voyage

(5 of 3 reviews)

Set sail on a transformative multi-day adventure aboard the tall ship Matthew Turner, navigating the stunning coastal waters of Northern California. Under the guidance of a skilled crew, learn essential sailing techniques from lin... More

Special Offer
Free Cancellation
Private Tour
Start From $1,595.00
(Saving inf% ) $0.00
 
-inf% Sausalito Shared Sailing Tour 4 Day Voyage Likely to Sell Out

Sausalito Shared Sailing Tour 4 Day Voyage

  • North America
  • Superb3 reviews5

Set sail on a transformative multi-day adventure aboard the tall ship Matthew Turner, navigating the....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,595.00
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $599.00
(Saving inf% ) $0.00
 
-inf% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $599.00
    (Saving inf% ) $0.00
 
 

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

(5 of 2 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

Special Offer
Free Cancellation
Private Tour
Start From $135.00
(Saving inf% ) $0.00
 
-inf% Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran Likely to Sell Out

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

  • North America
  • Superb2 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $135.00
    (Saving inf% ) $0.00
 
 

Private Catamaran Charter for Exclusive Celebrations

(5 of 2 reviews)

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with family and friends, this rental offers total freedom to create memorable experie... More

Special Offer
Free Cancellation
Private Tour
Start From $1,500.00
(Saving inf% ) $0.00
 
-inf% Private Catamaran Charter for Exclusive Celebrations Likely to Sell Out

Private Catamaran Charter for Exclusive Celebrations

  • North America
  • Superb2 reviews5

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Per....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,500.00
    (Saving inf% ) $0.00
 
 

Hobie Cat rental or sailing lessons

(5 of 2 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

Special Offer
Free Cancellation
Private Tour
Start From $68.05
(Saving inf% ) $0.00
 
-inf% Hobie Cat rental or sailing lessons Likely to Sell Out

Hobie Cat rental or sailing lessons

  • North America
  • Superb2 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $68.05
    (Saving inf% ) $0.00
 
 

Private Sailing for up to 10 people 4 hrs

(5 of 2 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 charming classic-style sailboat, where you can enjoy the pleasure of sailing thro... More

Special Offer
Free Cancellation
Private Tour
Start From $1,216.00
(Saving inf% ) $0.00
 
-inf% Private Sailing for up to 10 people 4 hrs Likely to Sell Out

Private Sailing for up to 10 people 4 hrs

  • North America
  • Superb2 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,216.00
    (Saving inf% ) $0.00
 
 

Private Luxury Yacht Charter aboard Tu Enamorado

(3 of 6 reviews)

Pamper yourself, your friends and family to an unforgettable sailing cruise around scenic Cabo San Lucas Bay aboard the beautifully crafted Tu Enamorado. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and bre... More

Special Offer
Free Cancellation
Private Tour
Start From $5,572.00
(Saving inf% ) $0.00
 
-inf% Private Luxury Yacht Charter aboard Tu Enamorado Likely to Sell Out

Private Luxury Yacht Charter aboard Tu Enamorado

  • North America

Pamper yourself, your friends and family to an unforgettable sailing cruise around scenic Cabo San L....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $5,572.00
    (Saving inf% ) $0.00
 
 

Cancun Premium Shared Yacht and Catamaran Experience

(3 of 6 reviews)

This is not a typical catamaran tour in Cancun. It’s a premium shared yacht experience designed to combine luxury, gastronomy, and a social atmosphere in the heart of the Caribbean. Unlike standard boat tours, this experience o... More

Special Offer
Free Cancellation
Private Tour
Start From $220.00
(Saving inf% ) $0.00
 
-inf% Cancun Premium Shared Yacht and Catamaran Experience Likely to Sell Out

Cancun Premium Shared Yacht and Catamaran Experience

  • North America

This is not a typical catamaran tour in Cancun. It’s a premium shared yacht experience designed to....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $220.00
    (Saving inf% ) $0.00
 
 

Exciting Public Afternoon Sail on our Newest Sailboat

(3 of 6 reviews)

Looking for a more personal sailing experience without the cost of a private charter? Our Afternoon Public Sail is the perfect balance. With a maximum of just 6 guests onboard, you’ll enjoy an intimate, relaxed atmosphere. Aboar... More

Special Offer
Free Cancellation
Private Tour
Start From $153.85
(Saving inf% ) $0.00
 
-inf% Exciting Public Afternoon Sail on our Newest Sailboat Likely to Sell Out

Exciting Public Afternoon Sail on our Newest Sailboat

  • North America

Looking for a more personal sailing experience without the cost of a private charter? Our Afternoon ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $153.85
    (Saving inf% ) $0.00
 
 

Romantic Luxury Sunset Sail with Premium Drinks & Appetizers

(3 of 6 reviews)

Set sail from the vibrant, world-class Marina of Cabo San Lucas for an evening of pure elegance and relaxation. Escape the crowds on this intimate, small-group excursion aboard a premium French-made sailing boat, designed for trav... More

Special Offer
Free Cancellation
Private Tour
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Romantic Luxury Sunset Sail with Premium Drinks & Appetizers Likely to Sell Out

Romantic Luxury Sunset Sail with Premium Drinks & Appetizers

  • North America

Set sail from the vibrant, world-class Marina of Cabo San Lucas for an evening of pure elegance and ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Catamaran Cruise to Isla Mujeres with Snorkeling and Lunch

(3 of 6 reviews)

Set sail across the turquoise waters of the Mexican Caribbean aboard a spacious catamaran designed for both comfort and fun. Feel the ocean breeze as music, refreshing drinks, and a lively onboard atmosphere transform your journey... More

Special Offer
Free Cancellation
Private Tour
Start From $139.00
(Saving inf% ) $0.00
 
-inf% Catamaran Cruise to Isla Mujeres with Snorkeling and Lunch Likely to Sell Out

Catamaran Cruise to Isla Mujeres with Snorkeling and Lunch

  • North America

Set sail across the turquoise waters of the Mexican Caribbean aboard a spacious catamaran designed f....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $139.00
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $145.00
(Saving inf% ) $0.00
 
-inf% Sailboat on the Mayan Riviera at sunset Likely to Sell Out

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $145.00
    (Saving inf% ) $0.00
 
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