The bareboat charter company will provide you with maps, instructions on what to watch out for, and information on where to stay while sailing bareboat. But really, why would they care where you are?
The answer: because there are some surprising dangers if you venture outside the prescribed waters of the British Virgin Islands. Storms, pirates, and reefs pose dangers that can do more than ruin your vacation.
Perhaps the most common danger is overestimating your own sailing skills. Even if you have a boating license accepted by the rental company, do you really know what you are doing? Can you handle the sails with your own crew or do they need more seasonings? If in doubt, a day or two with an unmanned captain to train everyone could be the right decision.
Storms are a concern, especially during hurricane season. For the most part, the British Virgin Islands are free of sudden gusts, although you can expect afternoon showers to be common during the summer. If you rent your boat bareboat in advance during hurricane season, be sure to purchase vacation insurance as well. It is rare for a hurricane to hit this area without warning, but it does happen occasionally. If you’re worried about the sky or the wind, turn on the radio or head for the coast. The charter company should be available to tell you what to do. Never try to get out of the storm yourself; While it is true that boats close to shore can be broken by wave action, ideally you should not be on the boat during a hurricane. If so, stay in constant contact with the rental company so they can send you help.
Reefs are another hazard, but if you stay within the boundaries of the map your rental company provided, you shouldn’t find them a problem. If you are at sea during a storm they can become a problem, and you will want to drive well far and leeward / downstream of them. Otherwise, follow their maps.
Pirates are part of the history of the British Virgin Islands and pirates still exist all over the world. They’re just boat thieves, after all. If you are on a ship alone at sea, you are in an exceptionally vulnerable position. The good news is that the British Virgin Islands are well monitored by the United States Coast Guard and the British Virgin Islands Coast Guard, and pirates rarely venture into such busy areas. As long as you stay within the area prescribed by your charter company, you must be safe. Venture outside and you may find some nasty surprises.
Most of the piracy in the Caribbean takes place near continental coasts: Venezuela, Guatemala, Colombia, Brazil (where at least one wealthy yacht owner died), and other poverty-prone areas are more likely to have pirates operating in high sea. On the islands, you are more likely to find them near Trinidad. However, it is a bad idea to pick up strangers without first radioing to shore. Pirates sometimes pose as castaways or migrant workers. Also, picking up a stranger can get you in trouble with the British Virgin Islands as they have a problem with illegal immigration and therefore have very strict laws. To protect yourself, always check first before picking up strangers and do so only at docks recommended by your rental company.
Avoid problems in general. You’re on vacation; don’t let it be ruined by setbacks.