Thanks for all the input guys. I got this response directly from Digicel:

[color:"blue"]We do not offer the devices for sale online however, you can provide us with your FeDex/DHL account where it can be shipped. Or if you are sailing with a charter company from the BVI, we can have it delivered there. We would not advise that you have the plan activated until you get to the BVI as the plans are valid for 30 days and do not roam.[/color]

I asked a few follow up questions and I'll post the answers when I get them.