Your obligation is to have skipper adequate meals aboard vessel. If skipper decides to eat ashore, it is not your responsibility.
Having said that, giving skipper a "per diem"(or "per meal") option is very generous of you and I am sure it would be appreciated.

In regards to dinners ashore, I would recommend discussing your plans with skipper so he can plan.... For instance, we are planning to eat ashore at Cooper Monday and Leveick Bay Tuesday, and we want you to join us. We planning another dinner ashore Wednesday with family on Virgin Gorda so if you would like to make plans for Wednesday night, but of course there is food aboard (which could be with friends or it could be a relaxing alone on the boat).

I would have boat menu of meals listed so that captain doesn't accidentally use any essential ingredients. Also, most professionals will not hit alcohol hard, but may outline expectations of "We have your first 2 cocktails on our tab"..

If you will do a search, you will find a few (the exceptions) to skippers taking advantage of generosity (bar tabs etc) and likewise a few charterers who left skipper will little to eat.


With what you have laid out, I would concur with Manpot that the skipper will be happy with your royal plans.