Welcome to CYOA.

You are probably going to want to do this in a different order.

I would start by heading east towards St John. Christmas Cove or the North Shore the first full day. Do a figure eight around St John and St Thomas. Spend a day in town at Cruz Bay. It is the coolest town in the Virgins both British and US. Then a night in Maho/Francis. (You could spend days on the North Shore of St John and around the small barrier islands).

From there head around St John, snorkeling at Leinster. Possibly an overnight in Coral Bay. Then Salt Pond or Lameshur's. From there take a nice long down wind sail to Magen's on the next to last night. From Magen's head around the west end of St Thomas also down wind and spend your last night at Brewers, Lindbergh or Water Island.

As for places on shore. Things are changing quickly over here. There is now a beach bar at Honeymoon on St John. There is a food cart/bar at Maho Bay that opened this week. Some concessions are back open at Trunk Bay. The owners of Lime Inn are opening a floating food truck/bar in Hansen Bay right inside Coral Bay any day. It is called the Lime Out. Several Coral Bay favorites are open including Skinny Leggs. You also can get a slip or anchor in Red Hook if you want a town day. Back here is St Thomas Megan's has a bar and food during the day. At Christmas Cove you have Pizza Pi which might be the best floating food truck on the planet. Then back at Water Island you have Dinghy's Beach Bar and Heidi's Honeymoon Grill. In Lindbergh you have access to the beach bar and restaurant at Emerald Beach Resort.

Here is a link to the National Park Marine Resources Guide. ST JOHN MARINE RESOURCE GUIDE