My response may be a little late given summer is almost here so you may have already found a charter company. Our boat is with CYOA Yacht Charters in St. Thomas, USVI. We have our boat with CYOA because they are meticulous in maintaining our boat. Part of any reputable charter company is to do a thorough vetting process for potential charterers. Without having a bareboat
charter under your belt you may expect reputable companies to offer a captain
for the first day or two as they evaluate your skills and orient you to the boat and sailing area. Depending on where you charter, some crewed or captained boats may depart for the night by dinghy
after you are moored or anchored to allow you some privacy. Doing your first charter with a knowledgeable captain
is really a good strategy, IMHO.