Your skipper will be your best source by far knowing the conditions on your arrival. Again, I would have taken the ferry from West End/ Charlotte Amalie both ways rather than taxi to from redhook an embark and return on the sailboat from there. But it's all good.
We just returned from spending the month of February. We had dead calm and 30 kt winds. Calm seas at times and 10 ft swells with some wind chop at others. We had an afternoon and night with strong winds from the South. We were on Anegada and coming back when the wind switched to due South. We had a period where the wind was from due west, with some squalls. Winds due west and due South are very unusual and will change your approach. A couple days of North and northwest winds and the rest of the time East or South of East or North of East as is usual course. There were days on beaches affected by the swell it would be unsafe to land a dinghy. Several days that it would have been unwise to anchor at say mountain point or pond bay on virgin Gorda.
Most sailing prefer to do a counter clockwise trip. So I would imagine you will clear in at West End Tortola unless you spend a night on St. John. You don't have to check out of USVI. Now remember you are on a sailboat going neither direct or fast. So if going to West End and get started at 9 am, I'd guess about noon to West end. Pick up a ball and Captain will clear you in. (Btw some who prefer the USVI charter start make way too big a deal about the inconvenience of going through customs in the BVI arriving by ferry or air) it usually takes much longer to get the boat on a ball, launch the dink, Captain go to dock, to C&I window, clear in. Go back to dink, to boat put it back on davits, get underway. Of course would be a good time for rest to have lunch.
Then let's say it's about 1 PM out of Sopers...be a short trip to Indians and or caves to snorkel. Then let's say it's 3:30 ..can go to Norman a short distance for the night or up the channel to Peter.
Tuesday depending on conditions they may want to pick up a ball at the baths or go to Spanishtown and taxi to baths. They could go straight on to North sound with a stop at the dogs to snorkel.
Assuming one way or the other you end up in North Sound Tuesday night.
Wednesday if didn't do the baths I would rent a car at Leverick and do so..maybe enjoy a stop at my favorite beach Savannah bay..go back via Hog Heaven for a snack and great photo ops. If stayed at Leverick Tuesday night Id probably move the boat to Saba area for Wednesday night. Ideally I'd snorkel Eustacia, look at cannons. Lots of turtles down by oil nut but lots of boat traffic.
Thursday head for Jost
stop at Monkeys point for a snorkel. I really like a stop at Diamond Cay Foxies Taboo a great lunch spot can go to bubbly pool if north swell turtles are common.
Your Captain may prefer not to anchor in white bay or be able too depending on conditions ..so will move to Great Harbor.
Friday ..enjoy white bay, check out of BVI, go check in at St. John in afternoon. Captain might want to go to Christmas cove so can unload you quicker on Saturday. Could go to one of the north shore anchorages on St. John and enjoy a morning snorkel. Then head back to REDHOOK.
So itineraries are like battle plans, they are great until the battle starts.
. This week with big winds and big seas things will be problematic at many locations. Have fun.