Sail Your Dreams with A Full-Service Luxury Sailboat Charter

Hello, and welcome to Jester Sailing Adventures–One of the world’s leading sailboat charter companies. We are proud to announce that we hold an unsurpassed record of achievement whenever it comes to ‘dream’ destinations and customer satisfaction.

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Founded in [Year], Jester Sailing Adventures is committed to the provision of top-notch sailboat charter. We truly believe that“Travel is necessary” not only for your physical but your mental health as well. And whether you are stressed out, bored or just need a break – We encourage you to take one of our best sailboat charters and spend quality time at our top destinations: Virgin Island, St. Thomas and/or St. John.

We provide an ideal way for you to travel and explore the destinations you have always longed to visit. Whether you are traveling alone, with a bunch of friends or family, we have the best, unique deals and packages for you. Our one-of-a-kind sailboat charter and dream destinations join together to create a beautiful vacation for you.

Exquisite and Wonderful Sailboat Charter Destinations

At Jester Sailing Adventures, we know exactly “what dreams are made of”, and so, we provide the best sailboat charter vacations to luxurious and diverse destinations such as Virgin Island, St. Thomas and/or St. John.

Whether you are an adventurous “travel freak” or a simple “quiet type”, we tailor our sailboat charter to suit your preferences, wants and needs. If it is for a special moment, such as a St Thomas bachelorette party, proposal or a surprise birthday party, trust to make your special day memorable for you.

What’s more, we have a huge family of distinctive customers who have tried us and are satisfied with our work and services. 

Sailboat Charter in Virgin Island

The Virgin Islands include hundreds of small sandy yet out-of-this-world sort of beaches – and is well-known for its beautiful and breathtaking sceneries, clear blue waters and luscious surroundings – which makes it a perfect dream destination not only for vacation but Virgin Islands bachelorette party, weddings, engagements, birthday parties etc.

What’s more, Virgin Islands is a best-example of a fun culture – with activities such as water-sports to delicious foods etc. And who wouldn’t like that?

Well, if you do, look no further. We invite you to explore the wonders of the Virgin Island with our sailboat charter – customized to your particulars and desires. We provide modern boats with all the modern, state-of-the-art amenities to ensure that you have a perfect ride.

We understand how difficult it is to earn today, and so, we strive hard to make your wishes come true in this life by the provision of our first-class services at competitive yet affordable rates.

Sailboat Charter in St. Thomas

St. Thomas – one of the islands of the Virgin Island – is known for its scenic beauty. We started our services in St. Thomas in [Year] but we have come a long way from our beginnings.

We specialize in various recreational activities and are available 24/7. If you are looking for jet skiing, scuba diving, snorkeling, fishing etc. then we are the perfect option for you.

Contact us today and explore the hidden gem of nature with us. Just make sure to make the most of your trip whenever you arrive at St. Thomas.

Sailboat Charter in St. John

The scenic and awe-inspiring beauty of Virgin Island is one of the major reasons why almost everyone across the world considers it a perfect vacation destination.

And if you are looking for a first-class yet affordable sailboat charter & sailboat cruises company at St. John, then you ought to be aware of the expenses of a vacation. You may even go broke. But who could blame you?

Fret no more! Since we are here to save you. With us, you will experience the best and the most memorable trip of your life. So, pack your bags and witness the exotic creatures you have always wished to see.


If you are planning a vacation, a wedding, a honeymoon, a birthday party etc. Join us now and let us help you – from the basic groundwork to actually visiting the Caribbean and making the most of your trip – we are here to help you and guide you accordingly.

Additional Services and Facilities: Fun-time with our sailboat charter

Jester Sailing Adventures offers everything you are looking for. Let the breeze sail you away with our “Full Day Sail” where we provide you with an opportunity to make the most of your day with facilities such as open bar and full-lunch. On the other hand, you may opt for a “Half Day Sail” under the sun and just swim around and snorkel with snacks and open bar.

And who doesn’t wish to sail into a 2-hour long “Sunset Sail” with appetizers? Appealing, isn’t it? We promise to make everyday a memorable day for you while you are with us.


Believe us when we say that “You are the center of our universe” and we are nothing without you.So, we let you walk into a new future with our special “Virgin Islands Bachelorette Party”services.

If you are an employer, then we invite you to boost the morale of your team by spending a stress-free day with us. You can visit the islands, enjoy a sail, swim around with turtles, play a sport-game and much more. We even offer tasty dinner cuisines and dishes from Thailand, India, America, Italy, France etc.

Why Choose Us

We believe that “Our customers come first”. You are our #1 priority. And we strive hard to ensure that you are satisfied not only with the standard of our services but with our overall conduct. This is why we have put together a highly professional yet friendly team of experts from across the globe to make sure that you experience the best.


So, what are you waiting for? Don’t even think twice. Contact Jester Sailing Adventures and order your custom sailboat charter now. We are available 24/7 to answer your queries and respond to your problems – and that too – without any additional costs.

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Jester Sailing Adventures

Jester Sailing Adventures in St. Thomas, US Virgin Islands at Secret Harbour Resort – eastend