I fly from Ottawa and the day begins with a 6AM or so flight to one of the US hubs (Newark for United, Philly for US Air, etc). I recall a similar timeline for boat crew coming from Toronto one year. The arrival time at the hub allows you to be on a 9:30-10:00AM flight to St Thomas arriving at 2:30-3:00PM which gives you enough time to make the last ferry of the day. The ferry ride over is a great way to kick start the trip as it is a bit of party with everyone hitting the Pump Room (bar at the ferry dock) before departure. The ferry is not as much fun at the end of the trip.

Air Canada use to do a weekly (Saturday) flight to St Thomas from Toronto. You may want to check their schedule to see if they are running it this winter. However as stated, it is often cheaper even with the drive, to go to a U.S. border city/town and start your flight there. I've never flown West Jet but it would be a good idea to see if STT is on their destination list.

With an early start, ferry wait time, crossing to Tortola and then growing old in the Roadtown customs line up, you don't arrive at your boat until 6:30-7:00 PM which makes for a long travel day. On my last two trips I decided to go down a day before the boat is available and stay a night at the Village Cay Marina.

I've never done the drive & fly from a US airport (living in Ottawa, we would drive to Syracuse, not Buffalo). It saves money though a winter storm could play havoc with a drive at the start or end of the trip.

cs