Flying from the west coast (SFO) St Thomas is always a lot cheaper. Provided you get to STT by early afternoon ferries should not a be a problem..water taxis always seem very expensive to me. As for post sailing lodgings it really depends on your budget. You can stay on the beach at "Rhymer's" or down the road at " Sunset" for around $100 a night or stay in maybe the best boutique hotel in the Caribbean, The Sugar Mill, for about $400 a night. There are also rental villas...we are hoping out large beachfront studio will be back and rentable by then for about $160 a night..