Cayman Air?

[AggieDiver]

I must be a daredevil or something, Because we have done the ~1 hour connection multiple times and never had a problem. Now with that said, we were usually doing it with a United flight getting in at 3:55 and a Cayman Express Flight leaving at 4:55 or 5:10. So going through very late in the day may in fact make a big difference. However, I can't imagine that Wednesday traffic is anywhere near as crowded as a Saturday. The safe play is to book the later flight, then try to get bumped to the earlier flight when you get there. In my case, there isn't a later flight available when we fly in on United from Houston, so we either have to take the short layover or plan to stay a night on GC. As was said, you can always head upstairs and hang out in the Hungry Horse for a few hours. Or drop your bags at Cayman Express and head into town for a late lunch somewhere like Georgetown Yacht Club. They supposedly have a shuttle that will take you to and from the airport.

 

[Doctorfish]

I've tried the one hour race as well several times. Sometimes you win and sometimes you lose. I had a heck of a time getting on a later flight.
Not sure that Cayman Airways Express will take your bags early. You might have to schlep them with to Georgetown Yacht club. That's why I suggested the Hungry Hippo.

 

[kerrycorcoran]

I'm hoping to make this trip in the near future - good information about flights and connections!

 

[BDSC]

Make the trip. You won't be disappointed because the end result is well worth it.