Bareboat & Captained charters. If you have sailing experience, you can be the master of your own sailing vacation. Bareboating offers the utmost freedom and privacy. Set sail from Pikes Bay and head for any of the easy-to-reach island anchorages for the vacation of a lifetime. No sailing experience? Captained charters enable you to escape the mainland. Sit back, relax and enjoy the ride or sail the boat yourself, with a US Coast Guard licensed captain not far away to provide guidance. Overnight at the marina or anchor out - it's your choice.