For those interested in SJU>EIS options:

Just booked six SJU>EIS RT tickets for early/mid December. Originally booked with Silver but ended up cancelling because the arrival at SJU on the return only left about 2 1/2 hours to make our connection and Silver's on-time record is not great. Ended up re-booking with InterCaribbean with an earlier arrival which will give us about 5 hours. Both airlines came in around $250-300 round trip. The ticket price for the InterCaribbean was on the higher side of that spectrum, but it included one piece of checked luggage per person whereas Silver was going to charge $39 per piece each way. After factoring that in InterCaribbean was the less expensive option as we will have at least one checked bag per person. I looked at Cape Air as well but they were over twice as much - maybe for a reason but multiply that by six and it adds up to a significant amount. I get a little nervous with the reliability of some of these regional airlines but I make sure to get travel insurance that will cover missed connections or cancelled flights.

We are flying JetBlue into San Juan (from Portland, OR) and then spending a few days there before heading to the BVIs as it's pretty much impossible to get to Tortola in one day. We are doing the return home all in one day though since we get an extra three hours of travel with the time change. I asked JetBlue about booking the return from EIS on the same ticket since Silver shows as a partner, but they couldn't do it. The only airline they could book on the same ticket is Cape Air - but at a higher price. I could have linked tickets on Silver purchased separately with my JetBlue tickets and then had my Jet Blue boarding passes printed at the Silver counter at EIS and my luggage checked through. However, JetBlue would not have been responsible for a missed connection since the Silver ticket was purchased separately.

I got the six of us round trip SJU>EIS for what I consider a reasonable price at just over $1,700 but it wasn't easy to coordinate everything. And I still have to be on the ball and keep an eye on schedule changes and cancellations. Not like the "old" days when you booked all the way through with American and they'd even let you layover in Puerto Rico for a couple days.