Welcome to the world’s most professional and trained platform of renting out the super luxurious sail boats for your perfect yacht trip!

United States Virgin Islands are the most popular destination for many individuals willing to spend their spare time leisurely.

SAILBOAT JESTER is more than happy to welcome its guests aboard with jester sailing’s well-equipped and comfortable yachts and with the crew which is 24/7 available at your service!

With SAIL JESTER Sailboat rentals you will find the best set up for spending your time with minimum expenditures. You can view our customers’ reviews for our sailboat rentals and you are sure to be more than satisfied.

Dream And Believe! You Are At The Virgin Islands!

The idea of choosing the USVI as your sailing destination is itself wonderful if you are a native or if you have travelled from far beyond some corner of the world: Because the United States Virgin Islands are one of the most attractive and charming destinations, rather the actually mesmerizing part of natural beauty with three large islands of St. Croix, St. Thomas and St. Johns and various small islets with crystal clear waters and coral reefs and ample amount of opportunities for various water sports largely snorkeling, scuba diving and fishing etc.

Sailboat Rentals At The Virgin Islands:

Expediate a Brief Sojourn In Usvi - Have a Funfilled Sailboat Rental

Our specifically designed sailboats are made for activities and fun adding ease, comfort and luxury to your trip so you can have the most memorable times of lives. Of course when you have invested your money and time, we make sure that you go back home with zero regrets. This is the reason that we keep on reminding you to book your time with us so that you can make most of your time and money!


We provide you with most modernized snorkeling gears, coolers and Ice, Swim noodles and rafts, custom stereo system and much more- not to mentioned food and drinks!

SAIL JESTER makes sure that we are the best customer care providers throughout your entire trip so you feel happy, contended and satisfied when you go back!

And definitely you would come again and again!

Offering Different Ventures!

Of course when we are offering several amenities we will provide you opportunities for different activities to have entertainment and fun. Sail jester feels proud to announce that you would have your plates full of land and beach excursions, fishing, snorkeling and free diving, scuba diving etc.

If you are in search of the yacht adventure that you would be able to explore all the mainstream three islands of USVI or separately visit each thoroughly, and you wish to glide through the waters, Sail Jester is the best sailboat rental service that you can imagine. We make sure to provide what you haven’t even thought about!

We are the best service provider for your next sailboat adventure! Enjoy the freedom of planning your own way or you can simply decide from one of our guided excursions that can be amended as per your need.

With noiseless motors and stereo according to your own taste, you can set the mood for your entire travel. Moreover our extensive seating arrangements make for an extra soothing and comforting ride.

We Have An Exceptionally Efficient Crew!

One of the biggest reason that most people choose SAIL JESTER over others is that we have an extensive research and knowledge over the entire USVI, so our captain and the team is best able to guide you through the entire excursion and can take you easily to the best snorkeling and dive spots.

Also because the islands are non-native to most visitors, your safety is our utmost priority!

No matter how much experience you have in sailing trips, it is always a good idea to go through the safety measures, and common safety practices before you go for sailing.

Remember sailing is a fun past time but it comes with its own hazards! And the relaxing and exhilarating trip can turn sour if the crew is unable to handle any emergency situation which can turn to fatal casualties! Therefore it is advisable to book your sailboat rental to the earthly paradise of USVI with SAIL JESTER!

Contact and book NOW!