I wish this forum had been around for my first charter. In February of 1978 I chartered a Pearson 365 from St. Tropez Charters on St. Thomas for a cost of $994. We (2 couples) knew nothing about provisioning but learned there was a food market a few blocks from the harbor. We filled two shopping carts there and as we exited the market there was a young man whose job was to help load groceries into customer's cars. We gave him a very nice tip and he walked the carts with us right onto the pier and handed the groceries onto the boat. I had purchased some actual charts (from the original Lands End, which at that time was a small chandlery with a side room of nautical clothes located on the North Branch of the Chicago River) but at the chart briefing he had two place-map sized laminated charts of the USVI and BVI and that is what we used the entire trip - think about that as we now use our GPS based chart plotters, etc.
We cleared into BVI at West End and that receipt shows $.92 for Clearing, $2.06 for Overtime, $5 for Harbour Dues and $.60 Misc. We made it to BEYC and STILL have the T-shirt. On the run from North Sound to JVD the other guy wanted to nap and as we were making too much noise he decided to try to nap in the dinghy we were towing. He actually fell asleep so I tied ALL the dock lines end to end then to the dinghy and let it go probably 100 feet behind us. When he woke up he looked around and thought he was adrift in the ocean. That night we ate, drank and danced at Foxy's. It was one of those nights when everybody was dancing with everybody and a local gentleman had several dances with my wife. At the end of the evening he approached me and made it clear he expected me to tip him - for dancing with my wife! During the party my friend needed another nap and used a hammock outside Foxy's. The next day he was covered with red bites from the bugs living in that hammock.
After numerous charters in the BVI, USVI/Spanish VI, Grenadines, St. Martin, Belize (which I highly recommend), long distance trips on Jeannius, etc., I developed my own lists for provisioning, packing, boat inspection, chart briefing, etc.
Now all my sailing is vicarious. After 60 years of racing and cruising my doctor not-too-gently advised me to stay on dry land. So, this forum is greatly appreciated as one way of the ways to stay connected.