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Sailing the Caribbean is easier than you might think! Our Virgin Island sailing school location, based in St. Thomas, USVI, is the perfect “jumping off” point for an incredible sailing vacation. You will find us cruising the US, British, and Spanish Virgin Islands every winter! Check out the available sailing experiences and learn more below.



Our Caribbean sailing vacations are insanely fun and informative. We have been teaching sailing and providing captained charters in these waters since 1995!

The Virgin Islands are truly a sailing mecca. Steady trade winds, crystal clear waters, hundreds of secluded harbors to explore, reefs to snorkel, white sand beaches to enjoy, famous beach bars, excellent restaurants, happy people, and gorgeous scenery are some of the reasons why these islands are the charter boat capital of the world.

We have watched these islands grow in popularity over the past two decades, but fortunately, we know the waters 1,000 times better than the average charterer, and can easily avoid the charter boat “herd” and show our students the many secluded spots that the islands have to offer those in the know.

Sadly, the Caribbean is littered with sailing schools that offer “fast track to cruising” and “instant bareboater” schemes. These schools attempt to cram three or four certifications into a one week crash course, and these “accelerated” courses do a MAJOR disservice to their students by skipping entire sections of the curriculum, eliminating any repetition built into the curriculum, and basically producing graduates who know just enough to be dangerous. Shame on them!

Add to this the fact that many of these schools have high student to instructor ratios, teach aboard poorly maintained vessels, and hire random dudes who think it would be cool to sail around the islands “teaching” people how to sail while they visit a girlfriend in every port, and it becomes pretty obvious that you want to do some serious homework before choosing a sailing school in the Caribbean. What we see day to day while down there, and the stories we hear from graduates of certain Caribbean sailing schools are quite incredible!

If you are serious about learning how to cruise and/or bareboat charter, we strongly recommend avoiding schools that offer “fast track to cruising” or “instant bareboater” schemes. There are a few schools who choose to slow things down in order to teach their students properly (and safely).

We at Black Rock are confident in saying that we are also the Virgin Island’s Foremost Sailing School! We perform more thorough lectures and sailing drills than ANY other sailing school in the Caribbean, aboard some of the nicest training boats available – guaranteed!

We offer NO MORE than two ASA certifications within an eight day period – and our combination courses truly complement each other, reinforcing your knowledge/skills instead of overwhelming them. We do not cram, skim, or skip critical sections of the curriculum! Our days are long, but OUR students will fully understand key concepts, feel safer, and be better prepared.  OUR students will master more practical skills, and become much better sailors by taking the time to learn the proper way.

We specialize in monohull and multihull cruising and bareboat charter courses! We offer ASA 101/103 & ASA 103/104 combination courses over an eight-day period, and ASA 104 or 104/114 courses over a seven-day period – and our results will blow ANY “fast track” school away!


We chose St. Thomas as our base for plenty of reasons – but they all have to do with minimizing cost and maximizing convenience for our customers! Here are a few reasons:

1) Inexpensive, and frequently direct flights are available aboard many major carriers from points all around the US. Round trip tickets from Boston have ranged from $300 – $900 peak season!

Flying into Beef Island, Tortola, BVI is extremely expensive and can be a hassle. Flying into St. Thomas and then trying to catch ferries over to the BVI is quite a hassle too – and frequently cancels out any savings you may have from your less expensive flight!

2) Our fleet is only a 30-minute cab ride from the airport so you quickly feel like you are on vacation and/or can get settled into your new “home” for the week before we head out the following morning.

3) The British Virgin Islands are only 15 miles to the east and the Spanish Virgin Islands are only 15 miles to the west!

4) Checking a boat and crew into a foreign country is part of the ASA curriculum, so why not sail over to customs and immigration in the British or Spanish VIs instead of clearing in at the airport!