Do not assume you are. This is the single most under-discussed risk in freelance skippering, and the clearest warning comes from the underwriters themselves.
From a specialist marine insurer: "The boat you operate may be insured but may not cover you. Most owners believe their insurance covers anyone who operates it, but we have seen many claims where the operator was not covered."
And more specifically: "Charter Skippers, particularly Bareboat or non-crewed/demise charter skippers and crew are especially at risk."
Why bareboat is the awkward case
When guests charter a boat bareboat and hire you separately, the boat's policy is typically written on a private pleasure use basis. Whether the insurer treats a paid professional at the helm as a material change of risk is not something we could find any insurer addressing publicly.
That gap is the problem. Not a rule against you, just an absence of anyone having decided.
What to actually do
Ask in writing whether the vessel's policy covers a paid skipper, and keep the answer.
Consider standalone skipper liability cover. Products exist for exactly this gap. Note that some are contingent cover, described by one insurer as the yachting equivalent of a driving-other-cars extension: they respond when the boat's own policy does not. They generally do not cover damage to the boat you are skippering.
Check the commercial use question. Paid work is usually rated differently from private use, and cover bought for leisure sailing may not respond.
One thing to ignore: we found no professional indemnity product marketed to freelance charter skippers and no source saying PI is required. If someone tries to sell you one as mandatory, ask them to show you the requirement.
Sources
Last reviewed 16 August 2026. This is general information, not insurance advice. Speak to a broker about your own situation.