What is a checkout skipper on a BVI bareboat charter?

A checkout skipper on a BVI bareboat charter is a licensed captain the charter company puts aboard for the first day to confirm the group can handle the boat before leaving them to it. Think of it as a sea trial for the crew, not the yacht. The skipper watches the group leave the dock, raise sail, pick up a mooring ball and anchor, then signs them off and is collected by the base, usually at the first anchorage. From that point the charter is bareboat. Companies require one when a sailing resume is thin, when the boat is bigger than anything listed on it, or for a first catamaran. Expect $200 to $350 for the day plus meals. If the skipper is not satisfied, the base can insist on a captain for the whole week. Groups that would rather skip the test entirely book a crewed charter in the British Virgin Islands, where the captain stays the full trip.