For our upcoming trip, I can get by far the best deal on miles flights if I book DEN-SJU round trip with Delta miles and then separately book (on a separate itinerary) roundtrip SJU-EIS on Cape Air.

I assume though, if my Delta flight is delayed on the way down and I miss my Cape Air connection in SJU, I'll forfeit the ticket if they are on separate itineraries? Same going the other direction if my Cape Air flight is delayed and I miss my Delta connection?

Also, what would folks consider to be acceptable connection time between Delta and Cape Air both to and from the BVI?

If we did this, the plan would be to do carry on only.

Thanks.

Sean