This is probably the first real decision you'll make when planning a charter. And it matters — not just for the cost, but for the entire vibe of the trip.
Bareboat: You're In Charge
Bareboat means you take the helm. No captain, no crew — just you, your group, and the boat. You plan the route, handle the anchoring, provision the boat before departure, and cook your own meals (or eat out at every anchorage, which is genuinely a great option in places like the BVI).
You need sailing experience. Most charter companies require a sailing resume and often a certificate (RYA Day Skipper, ASA 104, or equivalent). Some will ask for a "check-out sail" with a local captain before releasing the boat.
The upside: it's meaningfully cheaper, and there's something genuinely satisfying about running your own vessel. The downside: it's work. Real work. Which some people love and others don't.
Crewed: Someone Else Handles It
Crewed charters include at minimum a captain, and often a chef/mate as well. They provision the boat, plan the route (with your input), handle all the sailing, and prepare meals. You just... show up and enjoy it.
This is the right call if: you don't have sailing experience, you have a mixed group (some people want to just relax), or you're celebrating something and don't want to stress about navigation.
The captain's local knowledge also unlocks things you'd never find on your own — the anchorage that's not on any chart, the beach bar that requires knowing exactly where to leave the dinghy.
The In-Between Option
Hire a captain for a bareboat. You rent the boat as a bareboat but add a professional captain (usually $200–$400/day extra). This gives you the cost savings of bareboat with the expertise of a crewed charter. You're responsible for provisioning and the chef situation, but someone else handles the sailing. This is our most underrated recommendation for groups where one or two people have some experience but don't want full responsibility.
The Honest Answer
If you've never chartered before, start crewed. Do it once, learn how it all works, and then decide if bareboat makes sense for your next trip. The learning curve on a crewed charter is basically zero — which means you spend 100% of the trip enjoying it.