For those going to Tortola, flying to St. Thomas and taking the ferry works. It often doesn't for those heading further east, including Virgin Gorda.

In our case, the earliest flight into STT arrives at 2:16. I believe that would put us on the 5pm ferry, and through Customs in Road Town at maybe 6:30pm. No way to get to Trellis Bay and across before dark. So we would have to add a night in a hotel.

Expense wise, with four checked bags and two carry-ons, you have an extra $60 in baggage fees on the ferry, plus in the taxi. By the time one adds it all up, if going to STT, it's little more to fly Cape Air or Island Birds, plus one gets in before dark and avoids the extra night in a hotel. Anegada can be even more difficult.

So, in our case it's three flights through STT or SJU. And very often SJU is cheaper, and avoids the extra taxi and ferry fees.