Personally, this being your first charter, I wouldn't pick up the boat in St Thomas. Of your six day trip, you just wasted a day considering sailing time and customs. I haven't experienced or heard of any ferry problems this year so landing in St Thomas at 3:30 would get you on the 5 PM Fast Ferry. Sleep on the boat that night and you're set up for what ever islands you want to visit. Starting in St Thomas with limited time, I wouldn't even consider Anegada on this trip.