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Embark on an unforgettable maritime journey in the stunning Virgin Islands with our premier sailing school, private charter, and bareboat charter services. Whether you're a beginner eager to learn the art of sailing or an experienced sailor seeking to explore these azure waters, our expert instructors offer comprehensive lessons tailored to your skill level. Set sail aboard our well-equipped charters, guided by experienced captains who'll navigate you to hidden coves, vibrant coral reefs, and pristine beaches. For those with a knack for adventure, our top-notch bareboat sailboat charters provide the freedom to create your own nautical odyssey. Discover the magic of the Virgin Islands from a sailor's perspective – where every gust of wind becomes a new horizon, and every wave carries the promise of an extraordinary journey.

Virgin Islands Winter Sailing

Captained Charters

 Let our experienced captains take care of the sailing and navigation! Whether you're seeking a romantic getaway, a family adventure, or a friends retreat, our captained sailboat charter promises an unforgettable and carefree escape into the tranquil beauty of the Caribbean.

Starting at $9,599.00

ASA Certification Courses

Attain your American Sailing certifications while sailing the unbelievable waters of the Virgin Islands. We offer single course weeks and combination course weeks where you can achieve two ASA certifications in the same week! Feel free to bring along a significant other or friend to share your cabin for a deeply discounted rate!

Starting at $3,599.00 per person

Bareboat Charters

Exclusive to SailTime Boston Members and qualified First Reef Sailing graduates, sailors can bareboat charter our 2022 Beneteau Oceanis 40.1, "SV Serenity" and take command of their own vacation! The potential sailing area includes US, Spanish and British Virgin Islands and the incredible anchorages therein.

Starting at $6,999.00

The Boat

2022 Beneteau Oceanis 40.1 

Beneteau's latest cruising model that combines a stiff rig and high performance with maximum interior volume and luxury

Beneteau 40.1 Exterior.jpg

Upcoming Courses and Charters

Our Marina

The trip will begin and end at our dock at American Yacht Harbor, in Red Hook on St. Thomas. 


American Yacht Harbor is a full service marina with on-shore showers and bathrooms, Wi-Fi, and 24/7 Security staff. It is located in the center of Red Hook, the easternmost town on St. Thomas, making it the logical departure point for charters in the USVI and the British Virgin Islands.


Red Hook itself boasts plenty of dining and shopping opportunities within a 5 minute walk of the marina. There is a gourmet supermarket across the street from the marina as well as a full service laundromat.



American Yacht Harbor

6100 Red Hook Quarters #2

St. Thomas, USVI 00802

Get in touch to book!

(617) 466 3317

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