Re: Captain for charter?
Keep in mind you have to feed the captain and provide a place for him to stay aboard. I have a lot of charter experience, but used a captain in Greece because I wasn't familiar with the area. It was great. When we arrived in a crowded harbor, he called his friend, the dockmaster, and a space appeared miraculously. We got water at the local rate, not the tourist rate, and he sent us to some great restaurants off the tourist path.
Something you should consider is combining a captain with charter instruction. Most of the sailing schools offer either ASA or US Sailing certification during a one-week charter. You're already paying for a captain: you might as well add a few hundred dollars to get a certificate that will be acceptable to charter companies in the future. Remember that a captained charter doesn't count for sailing experience with most of them, but a certificate does.