With that number of people, anything "reasonable" on the East end isn't likely to be possible Sugar Bay and the Ritz are the only options. I'd suggest you overnight closer to town where you have more options with the Best Western Emerald Beach Resort on the airport road and the Windward Passage on the waterfront. You'll be paying taxi fare anyway so book one for early in the morning to take you out to Red Hook which will probably take you only 15-20 minutes. Have fun!

If I can bother you just a little more :):)
We are flying in on the 12th and will be taking 8am ferry to JVD on the 13th. We are landing at 330pm on the 12th and each of us are going to bring one cooler on wheels along with a suitcase on wheels. It is our plan to stay at a hotel on st Thomas on the 12th, stock our coolers on the 12th, and then go to JVD the next morning at 8am for 3 days. How would you suggest we go bout doing that on St Thomas. IE...hotel, groceries, cab, etc

FYI - on the way back we are staying at St. John for 3 days but we have that covered

First of all, have you checked the ferry schedule from Charlotte Amalie to Tortola and from Tortola to JVD? You may find this to be way more flexible than the very limited schedule between STT and JVD.

And have you checked the restrictions on importing foodstuffs to the BVI from the USVI? You might also check Bobby's Market Place on Tortola and do your provisioning there. The prices there are comparable, you'll save the additional ferry charges for baggage and it'll be easier all around to shop there rather than here. As far as logistics are concerned if you carry out what you've planned, you'll need to hook up with a taxi driver which won't be a problem. You'll all fit into the standard taxi van and can work it out with the driver as far as pick-up times and stops are concerned.

You'll have to pay customs duty on any foodstuff brought into the BVI.
My niece lived in Tortola and would come to STT to shop every now and then.
She said it was worth it to pay the duty for the selection and the prices as higher in Tortola.
JVD has some small markets but not any large grocery stores that I know of.

Why don't you ask the villa or property manager/owner about what is available on JVD and the best way to get there with your schedule.

For only a 3 day stay on JVD (they're going to STJ afterwards) it just doesn't seem feasible to go to all that trouble to shop on STT. 😀

I bring a rolling cooler of food to the BVI all the time. NEVER in three decades ever a problem or custom duty. Might be different if your bringing big boxes of bulk items. One small rolly cooler per person for a few days shouldn't be a big deal. But to be on the safe side you may to have your orginal grocery reciept.

ShoPping in STT is good idea. Are you trying to provision for your group? or just pick up some idividual stuff to fill inbetween meals out? For provisioning you may want to send one or two folks up to Costuless (the VI's verison of costco--small less organized not as well stocked).

Ethier way, I would strongly suggest that you bring your own meats from home. Freeze chicken and steaks and ground turkey (beef) and cold cuts. Meats in the VI cost 2x as much and have 1/2 the quality and selection. Seal in air tight zip locks. Wrap in paper. Lable. Pack tightly in one or two rolly coolers. Air lines won't allow ice. I your checking bags. Freeze some shampoo or lotion. Seal in zip locks. you can replace froozen shampoo with ice when you arrive in STT.

also if you do stay closer to the airport (emerald bay, blue beards, bolongo) allow at LEAST one hour to arrive at ferry. So if you are trying to catch an 8 am ferry from redhook you should be seated in your taxi before 7. 8 am is very busy time in red hook.

Why don't you just bring the foodstuff from the states since you are lugging the coolers anyway.
Just freeze everything very well and wrap in plastic bags or saran wrap (No Foil) and then you have what you want and it will save you $$ and time, shopping. You can probably get fresh produce in JVD (ask the property owner) and also in STJ at Starfish and the other markets.
The meat selections/cost will be higher in STT, JVD (if available) and STJ or just plan on eating out.
Bring your seasonings is small ziplocks as costs pretty high and you won't use an entire container.
You can do this with coffee, cereals, rice, etc.
You can bring most of what you will need so why spend more and waste time when there's lot's of "fun" stuff to do?
Grocery shopping is not on my list of "fun."

Good Luck and let us know how it turns out?