Sail Jester Sailboat Cruises – Adventure Meets Luxury

Sail Jester’s – One of the world’s leading sailing industry – Sailboat Cruises are a great starting point for a cruise in the Virgin Islands, St. Thomas and St. John.

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“When a man comes to like a sea life, he is not fit to live on land”. Well, who could deny that? Sailing is one of the best sports across the globe. But most importantly: It is simply fun. Sailboat cruises let you discover the world however Sail Jester makes it both unique and peaceful.

Do you remember the last time you went on a vacation? Does your life lack excitement? Are you stressed? Or bored with the monotony? Well then, you are at the perfect place. Sail Jester’s sailboat cruises are the way to go – We offer an unforgettable sailing adventure aboard our top-quality boats.

Traveling alone? Or with friends? Or family? We customize our sailing options to your particulars: The number of people, your overall budget and your hopes and desires for your vacation. What’s more, we do not ask for any previous sailing experience, our professional crew takes care of everything – From your safety to your enjoyment to your comfort.

Exclusive, informal, relaxed – Our five-star luxury sailboat cruises take you across the Virgin Islands – U.S. Caribbean islands popular for their white sandy beaches, verdant hills and reefs – St. Thomas and St. John. Our first-class sailboats do not come with any strict formalities and thus you do not have to worry about anything.

Sail Jester’s Sailboat Cruises: Paradise Awaits You

Begin a voyage for new horizons on a sailboat cruise in the Caribbean! Your flawless journey is our #1 priority and we spare no effort to maximize your pleasure and safety.

We believe that “Wishes do come true in this life” and thus we put forth a personalized approach so you can see, hear, smell, taste and feel the world from a new vantage point. Our sailboat cruises are full of out-of-this-world “surprises” and “delights” – So, browse through our world-class collection of sailboat cruises and current offers now!


But the magic is not over yet – We are recommended by Trip Advisor. What’s more, your satisfaction is our top priority. So, we provide an incredible 24/7 personal service. Our unforgettable sailboat cruises offer stunning island and ocean views, comfortable and mind-blowing sails, staggering wildlife and never-to-be-forgotten experiences.

So, what are you waiting for? Join us on a sailboat cruise today!

Sailboat Cruises Virgin Islands

White-sand beaches, sun-soaked harbors, aquamarine waters, over 25 pristine islands – stretch throughout the Caribbean – famous as the British Virgin Islands (BVI). The British Virgin Islands is a sailor’s heaven – From “supercalifragilistic” seascape to mouth-watering cuisines to contemplating the blue waters from a rustic bar and more. Sounds incredible, right? Luxury sailboat cruises Virgin Islands you will have fun on its peak.

Then you came to the right place. Our mission is to “deliver a personalized experience, 180° from the standard” and thus we believe in “enriching your frame-of-reference via extraordinary voyages”.

We offer everything you are looking for – full & half-day sails, sunset sailing dinner cruises, snorkeling fun, wedding sailing, wedding cruises, private charter and much more.

Sailboat Cruises in St. John

Sunsets on the water, swim and snorkel, discover the life under water, lounging on a beachside bar, pirate tattoos, unlimited cocktails and an open-bar – Are what dreams are made of. And we make your dreams come true. We describe ourselves as a “highly motivated sailing company” that provides economical sailboat cruises so that you can get a buzz out of the beauty of St. John.

We are here to transform your wishes and desires into “the real world” – From “rising and shining” with the gentle sounds of sea water to exploring a hidden beach to seeing wildlife to swimming and snorkeling along the marine life and losing yourself in an exotic culture.

What’s more, all our services are available at competitive rates. So, what’s the wait? Call us now and pack your bags to sail away to the “wonderland” of your dreams.

Sailboat Cruises in St. Thomas

Watch the sunset, explore the coral reefs, stumble on the majestic sea turtles and yellowtail snappers, snap photos, munch on our appetizers, enjoy complimentary beers, cocktails and sodas – Let the warm breeze blow you away aboard our all-inclusive sailboats across the luscious St. Thomas.

We ensure that you have a delightful journey – From our state-of-the-art boats to modern amenities including VHF Radio, dinette converts, double berths, propane stove, fresh water shower, 90 gallons fresh water capacity and much more. We provide additional recreational activities such as skiing, snorkeling, fishing, scuba diving – A whole new package.

We claim that we are “180° from the standard” and so we understand that “it is easy to spend the money, but hard to earn it”. Thus, we provide high-end services at affordable rates. Book our sailboat cruise now and leave everything – From your stresses to tensions to anxieties to work load – behind you. We are your “Utopia” – A great escape: An escape from your stressful daily-life.

Sailboat Cruises: We Are More Than Just A Sail

Destination weddings? Honeymoons? Birthdays? Dinners? We offer everything you could ever think of – Just name it. We believe that “you are our first and foremost priority” and thus, we do everything we can to make your life “memorable” and “fun” for you. We have been in the business for 24 years and have changed and improved our policies and services over the years.

We are proud to have a huge family of satisfied customers across the world. What’s more, we have a professional and skillful staff who is at your service 24/7. We have a simple booking procedure that does not cost a penny. Visit Sail jester and give us a call or e-mail us or just send a text now and begin your journey via our sailboat cruises & sailboat charter today.

Contact us now. Your “Shangri-La” awaits you.

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