Sail Jester’s “All-Inclusive & All About You” Sailing Holidays

We, human beings, need a little something to escape our day-to-day frustrations and if you are one of those adventure seeking individuals with a love of the ocean, crystal-clear waters, sandy beaches, then what is better than an all-inclusive sailing holiday?


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However, if you have been doing your home work for top-notch sailing companies and popular locations across the globe, then you must be aware of the fact that such holidays can prove to be expensive and might leave you broke. But fret not! Sail Jester is here to save you. We understand that “it is easy to spend the money, but hard to earn it” and the sacrifices you make to earn in this competitive era. So, we have kept our high-end amenities and other packages all-inclusive, and that too, at economical prices.

We provide all-inclusive sailing adventures such as full-day and half-day sails, snorkeling and sail excursions, dinner cruisessunset cruises, honeymoon cruises and wedding sails to the Virgin Islands, St. Thomas and St. John.

Try Sailing on Your Next Holiday. Come and Join Us on A Sail to The Virgin Islands, St. Thomas And St. John. For Bookings.

All-Inclusive Sailing Holiday in The Virgin Islands

Sailing in the Virgin Islands is one of the experiences that everyone wants to have at least once in a lifetime, the scenic views of the Virgin Islands attract everyone. Sail Jester provides you the facility to spend some quality time with your loved ones.

We enable you to sail to a destination where every anchorage opens the door to something new and each minute on board is exciting and unforgettable. Our all-inclusive sailboat and cruise charters are available across the Caribbean including the Virgin Islands.

A Holiday for Everyone

The Virgin Islands are home to alluring aqua-blue waters, stunning white sand beaches and exotic marine creatures. We bet you will find this destination truly fascinating. Join hands with Sail Jester now and sail away from the monotonous routine of your everyday life.

We welcome you to join our all-inclusive activities, or just soak yourself in the waters and sand across the Virgin Islands. Full-day, half-day and sunset sails; snorkeling and cruising excursions; wedding and honeymoon packages; gourmet dinner and champagnes and much more – It is all-inclusive and all included, just take a pick.

Our state-of-the-art boats are ready and ensure that you have a pleasant journey across the crystal-clear waters of the Caribbean. We offer the best deals and thus, we believe that we are the perfect choice for you – from sailing excursions to boat rentals and much more – We are everything you have been searching for.

So, What Are You Waiting For? Discuss Your Questions and Requirements with Our Agents Today!

All-Inclusive Sailing Holiday in St. Thomas

St. Thomas is another beautiful destination to sail with many incredible points of interest. All-inclusive sailing in St. Thomas is now being introduced with the highest standard by Sail Jester. Unspoiled islands, wonderful coastlines, picturesque beaches and beautiful turquoise waters are waiting for you to be discovered.

Sailing across the crystal-clear waters of St. Thomas, snorkeling, swimming and sunbathing at luscious white sandy beaches, discovering fascinating unspoiled sites and dining in first-class restaurants serving mouth-watering local cuisines are among the many all-inclusive services and pleasures offered by Sail Jester. Sail Jester has been operating in St. Thomas for approximately 24 years and has been recommended by Trip Advisor – Award Winner Travel Agency. We have come a long way from our beginnings and thus, can prove to be the ideal choice for your sailing in St Thomas honeymoon packages.

Sail Away to Unspoiled Shores on A Private Yacht

We are fond of the crystal-clear waters, luscious white sand beaches and pretty harbors of St. Thomas. The history of the island as a “hidden gem of nature” is absorbing. The local cuisines, champagnes and wines are excellent. And we would love to share this stunning destination with you.

By day-time, look out for hidden beaches and bays easily accessible from the clear turquoise waters, swim along with the aquatic creatures or just get lost in the beauty of the island on a sun-kissed deck. And as the sun sets, walk across the local streets and discover a charming local brasserie, taverna or pizzeria for supper.

Get in Touch to Book Your St. Thomas Sailing Adventure Now!

All-Inclusive Sailing Holiday in   St. John

A journey to St. John provides you plenty of time to relax on board your comfortable and luxurious yacht, while also enabling you to enjoy the fascinating shore excursions and delicious local food and wine – all-inclusive! Your sailboat takes you to the most popular places across St. John.

No matter what you choose, your preferences, from snorkeling to gourmet dinners to day-to-day sail excursions to wedding and honeymoon packages, are always our #1 priority.

This excursion is an all-inclusive, exclusive and immersive journey that will not only help you connect with your loved ones but will enable you to get to the heart of St. John as you go on exploring the place. Just make sure to make the most of our high-end services.

A Tailored Dream Adventure

We blend the spirit of holidays with comfort, luxury and reliability to tailor an all-inclusive vacation for you. Our top-notch and modern boats provide accommodation for your whole group and we plan an unforgettable journey for you. We love a good adventure and so, we do not forget to share our passion for unspoiled luscious beaches with you. 

We enable you to create lasting memories that you will cherish forever. During our all-inclusive sailing vacation, you will enjoy the opportunity to visit local ports and harbors to take in the exotic traditions and culture of St. John – All in the glory of a majestic ocean, warm breeze and sunshine.

How to Book

To book a sailing journey across the Caribbean, do not hesitate to contact us. Our professionals and support team have extensive knowledge about our top-notch sailing excursions and local destinations and are always glad to help you.

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Jester Sailing Adventures

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