OK, some thoughts from the perspective of a BVI charter captain
: Yes, everything is more expensive here, but clearly there is way more stuff available than many charterers realize! And, since our tourism segment is quite high end - many luxury villas in addition to the yachts, of which many of the crewed yachts serve gourmet fare - you just need to know where to look. Heck, the BVI even has an award
winning culinary team, but you probably don't know that!
If you want excellent beef, get Omaha and Angus beef at Riteway. Also Mexican grass fed beef. Don't know about "stringy South American cuts"! Good fruits and vegetables can be had from Riteway, One Mart, and Bobby's on Tortola, and from Buck's, Spanish Town on Virgin Gorda. Beverages can be had from the above mentioned supermarkets, and also from speciality stores: Caribbean
Cellars and Tico's would be the top choices. Lots of yummy things at Deli France
, a short walk from Moorings/Sunsail.
RiteWay's main store is five minutes from Sunsail. One Mart is about fifteen minutes in one direction, and Bobby's is about the same distance, in the other. Riteway has five other stores on Tortola, but they aren't that convenient except the one at Soper's Hole. Buck's Supermarket, in Virgin Gorda Yacht Harbour, is a good sized store and very convenient. They have a smaller branch at Gun Creek at North Sound. It's a free ferry
trip from Bitter End Yacht Club to get there. All the resort stores, such as the ones at Leverick or Bitter End, are much smaller, have fewer choices, and are pretty pricey. None of us who live here shop in those places! RiteWay also has a store in Spanish Town, but it's a cab ride away.
For provisioning, if you want to spend your charter time doing it, take a cab and ask him to wait for you while you shop. They will be happy to do it. Or, shop at the afforementioned stores online and have the provisions delivered to your boat for a small fee. That's what I usually do for my charters. And my plans are usually to get as much as I can in Road Town and then do one "top-up" at Buck's in Spanish Town.
I don't know how good the chefs on HoosierSailor's boat are, but most folks really enjoy some of the restaurants here, both for the food, and also for the ambiance and the chance to avoid having to cook. An incomplete, but reliable, list would include Charley's (right at the Sunsail Base), The Rock Cafe in Spanish Town, The Fat Virgin, in North Sound (small, very homey and reasonable place with excellent food), the Pub at Bitter End (specifically for pizza out of their brick oven), Anegada
, Cow Wreck Beach Bar on Anegada (beach bar food with the best French Fries in the BVI), The Last Resort in Trellis Bay, Myett's in Cane Garden Bay on Tortola, Audriana's in Sea Cow's Bay on Tortola, and Red Rock Restaurant in East End on Tortola. Also, Pirate's Bight, in the Bight at Norman Island, is pretty good...try their lobster salad. Tasty and huge. This is just a short list and doesn't include some great places on the waterfronts and, of course, there are lots of mediocre places as well. Avoid Pusser's, for example.
As for mooring buoys, you can leave your dinghy
, as has been mentioned, but you aren't really supposed to and they sometimes get removed. But, no worries. They don't charge you unless you stay overnight, so why not tell the mooring fee collector that you are leaving for an evening sail and may be returning to another buoy, which you will happily pay for. Or pay when they first come, and when you return, if you have to take another buoy, show them the receipt, which they will have already given you. It includes your name and the boat's name, so you are covered, just maybe on a different buoy. But you said you are coming in July, and things have already started to thin out pretty well so the mooring fields should be far from full.
If you go to St. John, you have to check in and there is only one place and it's NOT Trunk Bay, but Cruz Bay. You could take a cab from Trunk Bay. But it might be easier to just take the boat since the supermarket is in Cruz Bay. Not big, but a nice selection.
Hope this helps and that you have an awesome trip in an awesome place. And enjoy the food! :-)!