St. Thomas and St. Johns formulate the constituent district of United States Virgin Islands, commonly known as USVI which is supposed to be the unincorporated territory of United States. Spreading over an area of around 83sq. km and 51.8 sq. km.

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St.Thomas and St. Johns respectively, both the islands constitute of many points of interest inclusive of Fort Christian, Cathedral Church of All Saints, Magens Bay, Red Hook, St. Thomas Synagogue, Coral World Ocean Park, Blackbeard’s Castle, Buck Island National Wildlife Refuge, Saints Peter and Paul Cathedral etc.

Definitely, with so much to see and sense, these islands are worth discovering and out of many choices, sails the supreme pleasurable way to make the most of the time and money.  And for that, we welcome you at the legendary jester sailing adventure; 

Sail Jester is the right choice for all those who wish their entire time to be fun-filled and terrific, and also evidently for all those who wish to avoid any kinds of mishaps or even the slightest boredom.

Sailing is often termed as a recreational amusement for people. When you are bored of an everyday tough schedule and you wish to have the best of the times, out of many choices one that is surely going to turn out pleasure able is sailing.

All you need to do is to book your trip, either for a full day or half-day sails and for that the most reliable choice is to book your trip with SAIL JESTER.Yes, when sailing can teach you about resilience, dedication, creativity, and practical thinking.

We are 24/7 available for you What are you waiting for? Make the most of your time, and money and create fun-filled and remarkable memories, book your sailing adventure now.

SAIL JESTER can give you the best of the experience of all the learning. Jester has received the coveted Trip Advisor Certificate of Excellence Winner EVERY YEAR Trip Advisor has given the award!

While onboard with Jester, we welcome our esteemed guests to either learn to sail, experience the smooth flow of water, along with mesmerizing views all around, or they can lie down on the huge foredeck, with cozy cushions to support their backs while they are busy visualizing and feeling the awesome scenery around them, or they can soak themselves in the warm sun. Some might also wish to be in the cockpit the entire time.

Well, whatever preference you may have, you can have it all at SAIL JESTER.


Sailjester boats have been great in size and style with schooner olad. Morning sail is a perfect way to spend your day and create fabulous memories. You either sit or relax onboard, enjoying the drinks, and never-ceasing supply of snacks and coffee and water while basking in the sun, or you can soak yourself in the waters, swim, and snorkel, whatever you may choose.

There’s nothing quite so romantic and magical than a sunset sail!! This late afternoon sailing tour will give time for swimming and snorkeling and then relax and enjoy a glass of wine back onboard watching the sun slip into the sea. Sailing is an experience and a way to discover the unknown and to thank God for creating the best natural sceneries to provide food to our thirsty souls. Undergo the soothing experience of exploring the Caribbean crystal blue waters, and significantly different white sand beaches, feel the essence of cool tropical breezes that will keep you captivated for the entire life and not to forget the colorful coral reefs. Jester sailing adventures will always stay in your mind and you will definitely try to come next time.


Onboard Jester, our crew will give you the necessary information relevant to the trip. At jester sailing, the luxury of the design, amenities, and decoration is sure to satisfy every individual’s needs.

Every boat has a schooner olad which will provide speed and good looks. On boat you will have signature drink which must be mixed in water so none of the guests areto feel drunk. To add to this, Jester is bound to provide you with the best gourmet lunch you have ever tasted. Moreover, the semi-private tour that SAIL JESTER offers is way far better than the overly crowded ones, we have a maximum of six people, so you are neither left all alone to die out of boredom, nor are too much over occupied to find yourself missing the calmness that you have longed for! Similar to full-day sailing excursion, people enjoy swimming, snorkeling, sunset sailing, dinner cruisesailboat cruises and beautiful scenic views.



Jester sailing adventures are always filled with fun so whether it’s a full day sailing trip or a half-day sailing excursion, it is bound to pose a positive and healthy impact on one’s routine.

Sailing with SAIL JESTER is an invigorating sport that offers many rewards; topmost of which is that it can be the best exercise as it is an active endeavor that can involve quite colossal of physical work.

Learning how to sail does not have to be complicated if you invest with SAIL JESTER. When you learn how to sail, you’ll not only become intimately familiar with all aspects of your boat but also how your boat relates to its environment in terms of everything from the weather to wind. This is why learning how to sail can be so fulfilling and can foster such a sense of accomplishment. Also, this is why it is often said that sailing is not an adventure, it’s a lifestyle. SAIL JESTER makes sailing your dream lifestyle, even if it is just for a day or half a day.

You can always book your favorite virgin island destination with SAIL JESTER.

Sail Jester virgin island

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Jester Sailing Adventures

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