Like TWT, we are Orlando people. For the purposes of travel to the BVI, I think we have it easier than most. We have tried just about every option at one point or another. The last 4-5 trips, we have found JetBlue to be the best intersection of convenience & value. They have several direct flights a day to SJU, and they codeshare with Silver. We are usually able to get round trip for around $600 pp. Yes, you have to deal with SJU and Silver, but our luck has been pretty good overall.

For our upcoming trip next month, we purchased the new AA route EIS-MIA-MCO on the way home. We booked the tickets the day after they released them, and got them for $320 pp one-way. They are now showing $1400+ one-way for our same flight. I am hopeful that the rates will come down something closer to what we paid months ago. If not, we will stick with the JetBlue/Silver codeshares.

Southwest also flies direct to SJU from Orlando, but it necessitates a separate Silver ticket. We have never found the rate savings to justify the risk of having separate tickets, and all that entails in the way of connections & baggage.