St. John Sailing Charters

St. John Sailing Charters – Explore the Wonders of the Caribbean Sea Like Never Before


Known for its pristine beaches, crystal clear waters, and lush tropical landscapes, St. Johns is a paradise waiting to be explored!

At Summerwind Sailing Adventures, we offer USVI boat charters where you can discover the hidden gems of this beautiful island. Luxurious amenities, exquisite meals, expert crew, advanced yacht tech, and more—we go above and beyond to provide an unforgettable journey through the stunning waters. Our St. John Sailing Charters offer the perfect blend of indulgence, adventure, and relaxation, providing you with a once-in-a-lifetime sailing experience that will leave you with cherished memories for years to come.

As one of the largest private sailing yachts available in St. Thomas, the Summerwind ensures a delightful and memorable journey for you and your guests. It’s a luxurious Jeanneau DS 50-foot sailing vessel providing comfortable and safe USVI boat charters.

You can enjoy boat charters for St. John from November to April and make the most of the weather conditions and serene waters. Whether you seek a bachelorette escape, a romantic gateway, a family adventure, or a corporate retreat, our St. John boat charters offer an unparalleled experience.

Summerwind – a luxury private yacht ready for a sailing trip

What Our Yacht Has to Offer

Summerwind, a stunning Jeanneau DS 50-foot sailing vessel, is one of the most exquisite private boat charters in St. John, USVI. With its advanced features and top-notch amenities, the Summerwind ensures that your guests enjoy unparalleled comfort and relaxation while exploring the captivating waters of the Virgin Islands. Here are some of its features:

Entertainment Options

As you sail on Summerwind, you’ll have access to various entertainment options that will keep you engaged throughout your journey. Stream your favorite shows or movies on TV or listen to your favorite music on a surround sound stereo system, there’s something for every guest to enjoy. Whether you’re here with your partner, kids, business partners, friends, or anyone else, our advanced entertainment ensures everyone has a great time.

Fine Dining

Savor gourmet meals prepared by our talented chefs onboard and enjoy unforgettable dining experiences aboard the Summerwind yacht. Moreover, the fully equipped galley boasts all the amenities you need, from a refrigerator and freezer to a coffee station and microwave. Not to forget our fully stocked bar featuring various wines, champagne, beers, and more.

Unforgettable Adventures for Everyone

Every moment of your journey will be filled with excitement and exploration at Summerwind. Dive into the crystal-clear waters of the Caribbean from our circular swimming platform, perfect for ocean swimming and refreshing dips. Go kayaking with your partner in our tandem kayaks. Explore underwater beauty with our snorkeling equipment or just chill by the sea.

We also offer sunset sailing adventures featuring breathtaking sunset views and encounters with marine life. So regardless of your preference or age, our Boat charters in St. John have something for everyone.

Comfort and Relaxation

Indulge in the ultimate comfort and relaxation aboard the Summerwind yacht. With three luxurious staterooms, including a spacious owner’s stateroom and two VIP staterooms, as well as a roomy salon accommodating up to six guests, you’ll feel right at home on the water.

Sink into plush seating, bask in the natural light streaming through large windows, and unwind in style on the luxurious cockpit as you sail the serene waters of St. John.


We understand that we sailing aboard one of the major concerns people have is their safety. This is why, our yacht is equipped with all essential safety measures including medical kits, fire extinguishers, an eight-persons Winslow auto-inflate life-raft, VHF radios, flares, strobes, and EPIRBS.

Other Facilities

In addition to its luxurious accommodations and state-of-the-art navigation equipment, the Summerwind yacht offers a range of other facilities to enhance your sailing experience. Freshen up in style with two electric flush bathroom facilities and private showers onboard, ensuring convenience and comfort throughout your journey.

Our boat charters in the US Virgin Islands are designed to provide you with a safe, comfortable, and enjoyable experience. From the moment you step aboard, you’ll experience a unique journey that you won’t soon forget.

We offer last-minute bookings with a 48-hour prior notice for those spontaneous trips! Don’t miss out on the adventure of a lifetime. Contact us today to learn more about our boat charters and rentals in St. John.

Book Your Virgin Islands Sailing Yacht Charter Adventure Today

Ready to embark on your St. Thomas adventure with SummerWind? Contact us today to book your charter boat during the months of November through April. We can’t wait to welcome you aboard!

Serving St Thomas, U.S. Virgin Islands (Nov-April) &
St. Augustine, Florida (May-Oct)

3219 Harbor Dr.
St. Augustine, FL 32084

American Yacht Harbor
6100 Redhook Quarters C 3–6
St. Thomas, VI 00802

get in touch

Contact Us

Looking to book a sailing charter on Summerwind?
Get in touch, either via the form below or calling us directly at (404) 229-0507. Someone from our team will address your needs and answer any questions you may have. We are happy to help and look forward to getting to know you!