Very interesting thread - My experience with charter captains has been through onboard sailing courses - once in the BVIs and once in Grenada - Grenadines. When we ate out we always took care of the captain and this was the expectation - but If I recall most places offered the charter captain a free meal if there were 4 paying guests. Is this not done anymore in the BVIs? And there was definitely no rule about not drinking once anchored - o'l captain got hammered at Willy T's and Cain Garden bay - all had a great time! Don't recall this being the rule at Grenada - But the captain introduced us to a wonderful restaurant in Carriacou (the Slipway restaurant - I can highly recommend) and we paid his tab as was expected given the situation. One night we stayed anchored off of Petit Saint Vincent and ate at the Resort restaurant (also another great meal!). The Captain stayed onboard and played candy crush or some such game smoking his weed. Great guy - loved his ganja!

With a full or half charter it is different though I agree - no way should the OP be expected to pay all meals ashore. I would of course extend an invite to at least one dinner (probably the last) to celebrate a good trip!