Two years ago, a few out of our group took Air Sunshine. You should have no issues with the connection in PR. Note though, it was a little tricky finding the Air Sunshine "counter" and no one in the airport that my family asked had even heard of them (bad signage -- again two years ago so it could have changed). It is a very "island" airline (which is why connecting won't be an issue). My family had booked direct from PR to Tortola -- the pilot actually took them to Virgin Gorda first to "drop off some folks." Overall, it got them where they needed to be and the price and times worked well. Let me know if you want more info on the connection (I can ask family if they remember specific details about the location in the airport). Oh, and to make reservations you actually fax in your request... #oldschool!