I thought a skipper would feel restrictive, but it turned out to be the opposite. A good skipper knows hidden spots, calm anchorages, and local rules. You still sail and make decisions together. If you later want full control, you can go bareboat next time. I compared options through https://12knots.com/en/yacht-charter/destinations/caribbean/bvi/ and liked that they clearly show both bareboat and skippered choices. It helped me pick what matched my confidence level at the time.