Icroberts,
1 & 2. we have always flown into STT, taxi from airport (used Alvin from Islander Taxi but will try Kevin based on awesome TTOL recommendations!)to Compass Point Marina/Benner
Bay. Taxi driver drops me and one crew member off at Food Center which is a few miles before Red Hook - you will pass right by Food Center from airport on the way to Red Hook. The Marina Market grocery store that used to be in Red Hook is closed. I get groceries at Food Center while others unload at the dock. Taxi driver returns 30 mins later and picks me and groceries up, takes me back to boat at marina. Check with a medical doctor or nurse friend of yours, get them to save you one of the large styrofoam coolers that drugs are shipped in. These coolers hold about 50 lbs weight which is standard weight limit on most airlines w/o surcharge. Buy meat in advance and freeze meat. Use a few of the freezer packs that are shipped in the coolers with the drug shipments. I always take one whole beef tenderloin which when cut will make 8-10 very nice size filets mignon. Be sure that the butcher does not take it out of the original cryovac (sp?) packaging. Frozen, I throw this in with my suitcase with clothes, etc. On my 6 hour trip from South Carolina to STT, it is still frozen in my suitcase when I arrive in STT. Kept in a cooler (it will not leak if still in original cryovac packaging) it will hold for at least 3 - 4 days. I plan my menu to include some type boneless chicken breasts, which I slice in tenderloin "chicken strip" lengths, season with olive oil, greek, mexican or whatever seasoning you prefer, seal in ziplock type bag, freeze and pack in the styrofoam cooler. Buy flat package sandwich meats - my wife doesn't like oscar mayer or other package sandwich meats because of preservatives but for BVI trip preservatives are good. Get brand that is packaged in flat and not boxy type container. Flat packs well in cooler and uses less space than boxy square type containers.
Freeze sandwich meat. Get flat packaged cheese as well, but no need to freeze. Make hamburger patties, wrap with saran wrap, freeze flat in ziplock for cheseburgers in paradise night - we usually have those at Cooper Isl. Buy a flat or two of the precooked bacon. Pack all of these meat and cheese items in medical styrofoam cooler; the frozen items will function as ice and keep cheese, etc. cool. Seal cooler well with duct taqpe (but before sealing, I put a partial roll of the duct tape inside cooler, on top, with note: Dear US Customs: If you inspect this cooler, will you kindly use the extra roll of duct tape and re-tape the cooler after your inspection. Thank you for the great work you do." They have never inspected my cooler even though they have often gone through my suitcase. Find a cardboard box that the cooler will fit tightly into. Check it just as you would a suitcase. I have each of the other 7 in my group pack a few spices, etc. in their luggage - no need to buy 8 or 9 full size spices in BIV when you will only use a small amount. No problems with taking food into BVI. It will be on your boat and you will go ashore once in BVI to clear customs. BVI customs does not ask about items aboard your vessel. Th Food Center in STT will have everything else you need. You can trash the free styrofoam cooler or give it to one of the guys on the dock. Re-supply bread, eggs, veggies, bottled water half way on cruise, at Bobby's CGB or at Trellis Bay.
3. Restaurant in Cruz BAy - several, but Cruz Bay is always our last stop (we do the circle backwards I guess. We sail from STT to JVD for first night, clearing customs at JVD. Go clockwise around the circle, last night on St. John anchoring at Caneel Bay for short taxi or dinghy to Cruz). We always like Cafe Roma - food is very good; it may not be fancy or the best restaurant in Cruz Bay, but we love it, especially last night when we are worn out). We have tried others Rhumb Line, Banana ____ something or another...but have always liked Cafe Roma the best for our last night. Will see what others have to say about snorkeling on St John as nowhere in the USVI is near the top of my list. We have seen many sea turtles in Hawksnest Bay, snorkeling at Trunk bay is supposed to be good but a lot better in BVI at Monkey Point, Loblolly, Norman Isl., etc. Trunk Bay reminds me too much of US - way too many signs, do this, don't do that, etc. Everything in BVI seems to work perfectly well without US Park Service posting signs everywhere.
4. We clear customs going into BVI at JVD but do paperwork ahead of time - your charter company in STT should have blank BVI customs forms for you ahead of time. Otherwise plan on spending an hour or so clearing. WE then clear back into US at Cruz Bay - easy.
I've probably gone on for too long here but we have always done exactly as you are planning to do on this trip. Yo0u may pm me if you want more details. My next trip this June will be from Moorings in Tortola so I will posting for restaurant tips, provisioning, etc in Tortola early next year.