There are not a lot of boat accessible restaurants,bars,groceries compared to the BVI - it is better to stock the boat while at CYOA with the majority of your provisions.
leaving there and heading West - Honeymoon beach on Water Island has 2 beach bars, Brewers Bay has 2 food trucks. After that rounding the West End and heading up the North Side, Hull bay has a restaurant and Magens has a beach bar and are really the only 2 viable overnight anchorages - and that depends on the N. Swell 100%.
Heading East a day stop at some of the small Cays has merit and anchoring in Water Bay or Red Hook are possible options. restaurants and groceries are available in Red Hook - continuing to Great St James Christmas Cove - a floating pizza boat, some moorings possible and the STYC is a fair dinghy ride away.
St John is a very different story, many bays have NPS moorings and the peace and quiet anchorages are truly stunning.Cruz Bay is accessible by dinghy from the Caneel Bay mooring field and has restaurants aplenty and some groceries. Taking a taxi into town from some of the other N.Shore bays is possible for shopping if need be.
The south side of STJ has more peaceful mooring fields, a day stop at Reef Bay would be a treat - the Lameshurs and Salt Pond are fine deserted spots.
Coral Bay is a small village with restaurants and groceries.
There are a few bays NOT in NPS waters where anchoring is allowed, Rendezvous,Hansen,Newfound,Brown, -- all weather dependent.
Staying in the USVI is a sharp contrast to the barhopping crowded mooring fields of the BVI and a much quieter boat oriented vacation - great snorkeling opportunities abound, a kayak or SUP carried aboard will get used daily for exploring, sharing food and drink aboard is much more relaxing and affordable. The NPS moorings are generally plentiful and the honor system prices are a bargain.
I include the STJ NPS link:
https://www.nps.gov/viis/planyourvisit/virgin-islands-marine-visitor-use-information.htmA great way to avoid the steep BVI fees, the crowds and race for moorings,any C&I visits, overpriced shore spots with intoxicated sailors and to kick back and enjoy boating life with friends and family. Much different than a BVI trip so being prepared before departing CYOA is more important, the staff there is very good and Very Helpful for your planning.
