We are going on our first trip in January, flying to San Juan on United, landing at 4pm. Looking to take the intercaribbean flight from San Juan to Tortola, which leaves San Juan at 6pm. Is intercaribbean reliable? What do you think would be the earliest flight out of San Juan that would be safe to make? Thanks

Are you checking a bag? You will need to collect your bag from your United flight and then go out and back through security after checking in for your Intercaribbean flight. Intercaribbean’s counter opens 1.5 hrs prior to departure, maybe less - 2 hours should be okay if your UA flights lands on time.

I have flown them a few times now with no problems. Make sure you know what their policies are around COVID.....

Last year I flew that route about 25 times. With carry-on, I could make an InterCaribbean flight with about 45-60 minutes of layover but that assumed I was sitting up front. They do not even open the gate agent desk until 30 minutes before the flight.

If you are checking bags, you need most of that 2 hours because you have to exit security, find your bags and check in with bags 60 minutes before the flight. 90 minutes might be doable but it would be tight.

I think they are pretty reliable. Sometimes they cancel the mid-afternoon flight and make everyone fly on the 6pm flight. I suspect that is all about filling planes even though they don't say that.

Enjoy!

I flew with IC a few years ago and one thing I recall is where many airlines say "one carry on bag AND one personal item", IC allowed one item to carry on in total. I ended checking my day pack so I could carry on a travel guitar. It might have been related to plane size but the major airlines allow me to carry on both.
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We've flown them and found them to be reliable.