My guess would be no on the open jaw option with a reward ticket but don't know the answer honestly. Totally understand regarding not rushing on arrival, especially with already having to make one connection.

In that scenario, I think STT is your best option. There is very little difference in timing from Houston with the connections through Atlanta. You get in a little later but that means less waiting for the ferry, if you choose that option.

You would still have the option for booking a private puddle jumper from STT to EIS (20 minute flight) if you want to splurge on the luxury. Also have the option of a private ferry or regular ferry and it solves the issue of return for your son in case open jaw is not available with reward tickets.

Just my two cents! <img src="http://www.traveltalkonline.com/forums/images/graemlins/Grin.gif" alt="" />