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Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 16
 

Catamaran Sailing Cruise in Monterey

(4.8 of 30 reviews)

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More

Free Cancellation
Start From $65.00
 
Catamaran Sailing Cruise in Monterey

Catamaran Sailing Cruise in Monterey

  • North America
  • Superb30 reviews4.8

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....

    Free Cancellation
    Start From $65.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 720 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 a... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb720 reviews4.9

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

    Free Cancellation
    Start From $136.19
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 246 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
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb246 reviews4.9

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

    Free Cancellation
    Start From $136.19
 
 

4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres

(4.9 of 246 reviews)

Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catamaran, with room for up to 60 guests, and enjoy a premium experience from start to finish. Our team is dedicated to providing except... More

Free Cancellation
Private Tour
Start From $2,400.00
 
4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres Likely to Sell Out

4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres

  • North America
  • Superb246 reviews4.9

Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catama....

    Free Cancellation
    Private Tour
    Start From $2,400.00
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 156 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Private Tour
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun Likely to Sell Out

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • North America
  • Superb156 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Private Tour
    Start From $120.69
 
 

2-Hour Private Sailboat Charter in the San Francisco Bay

(4.9 of 20 reviews)

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the romance of sail. Private sailboat charters are a great way to celebrate you... More

Free Cancellation
Private Tour
Start From $695.00
 
2-Hour Private Sailboat Charter in the San Francisco Bay Likely to Sell Out

2-Hour Private Sailboat Charter in the San Francisco Bay

  • North America
  • Superb20 reviews4.9

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

(5 of 180 reviews)

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More

Free Cancellation
Private Tour
Start From $750.00
 
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling Likely to Sell Out

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

  • North America
  • Superb180 reviews5

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks

(5 of 12 reviews)

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and enjoy this adventure aboard our luxurious French-made sailboats and cat... More

Free Cancellation
Private Tour
Start From $180.00
 
Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks Likely to Sell Out

Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Dr....

  • North America
  • Superb12 reviews5

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel a....

    Free Cancellation
    Private Tour
    Start From $180.00
 
 

Visit Private Beaches around Puerto Vallarta in a Private Yacht

(5 of 106 reviews)

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More

Free Cancellation
Private Tour
Start From $1,500.00
 
Visit Private Beaches around Puerto Vallarta in a Private Yacht Likely to Sell Out

Visit Private Beaches around Puerto Vallarta in a Private Yacht

  • North America
  • Superb106 reviews5

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 236 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Private Tour
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • North America
  • Superb236 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Private Tour
    Start From $49.99
 
 

Crystal Boat Tour with Snorkeling and Drinks in Cozumel

(4.6 of 5 reviews)

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first port gate, the diver's monument, sunken ships and natural landscapes. Marv... More

Free Cancellation
Private Tour
Start From $58.11
 
Crystal Boat Tour with Snorkeling and Drinks in Cozumel Likely to Sell Out

Crystal Boat Tour with Snorkeling and Drinks in Cozumel

  • North America
  • Superb5 reviews4.6

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and dis....

    Free Cancellation
    Private Tour
    Start From $58.11
 
 

Ultimate Party in Miami : Boat Party, Party Bus & Nightclub

(3.1 of 16 reviews)

This is not just another night out, it’s Miami’s nightlife on the water. Step aboard a spacious double-decker boat transformed into a moving nightclub with a live DJ, dazzling lights, and a vibrant atmosphere. As the sun sets,... More

Free Cancellation
Private Tour
Start From $189.00
 
Ultimate Party in Miami : Boat Party, Party Bus & Nightclub Likely to Sell Out

Ultimate Party in Miami : Boat Party, Party Bus & Nightclub

  • North America
  • Good16 reviews3.1

This is not just another night out, it’s Miami’s nightlife on the water. Step aboard a spacious ....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Deluxe private Sunset & Day Sail

(5 of 2 reviews)

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More

Free Cancellation
Private Tour
Start From $714.00
 
Deluxe private Sunset & Day Sail Likely to Sell Out

Deluxe private Sunset & Day Sail

  • North America
  • Superb2 reviews5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Free Cancellation
    Private Tour
    Start From $714.00
 
 

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

(5 of 27 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

  • North America
  • Superb27 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Clear Boat to Cabo Lands End, The Arch and more

(4.4 of 14 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 $35.10
(Saving 10% ) $39.00
 
-10% 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
  • Exellent14 reviews4.4

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 $35.10
    (Saving 10% ) $39.00
 
 

Private Sunset Sail for Two

(5 of 5 reviews)

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More

Free Cancellation
Private Tour
Start From $462.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • North America
  • Superb5 reviews5

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....

    Free Cancellation
    Private Tour
    Start From $462.00
 
 

Private Family Catamaran From Isla Mujeres

(5 of 1 review)

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Family Catamaran From Isla Mujeres Likely to Sell Out

Private Family Catamaran From Isla Mujeres

  • North America
  • Superb1 review5

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Diamond Head Sunset Sail

(4.7 of 15 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • North America
  • Superb15 reviews4.7

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

(5 of 87 reviews)

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical landscapes. You will visit the most beautiful places in the lagoon where yo... More

Free Cancellation
Private Tour
Start From $55.00
 
Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon Likely to Sell Out

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

  • North America
  • Superb87 reviews5

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters i....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Party On Sailing Cruise to Isla Mujeres from Cancun

(3.9 of 19 reviews)

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our national drinks onboard the catamaran. You will snorkel at one of the best reefs and see beautiful tropical fish, then eat lunch ... More

Free Cancellation
Private Tour
Start From $49.99
 
Party On Sailing Cruise to Isla Mujeres from Cancun Likely to Sell Out

Party On Sailing Cruise to Isla Mujeres from Cancun

  • North America
  • Very Good19 reviews3.9

Come join the party in our adults-only catamaran from Cancun to Isla Mujeres. Start the day with our....

    Free Cancellation
    Private Tour
    Start From $49.99
 
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