We land in grand cayman at 12:20pm on the 5th and take off for little cayman at 2:30pm and on the way back (the 12th) we land from little cayman at 11:30am and take off at 1:15pm.
We will have 2 sets of full scuba gear so we will be checking bags...
Any chance that you are flying Cayman Airways through Miami? I ask because they have just started a new program to pre-screen passengers through Cayman immigration at Miami Airport to reduce the lines at GCM, see the link below:
Fast track passengers bypass airport crowds | Cayman Compass
May is a less busy month as compared to the high season of Christmas through Easter, but the airport is currently under construction and Saturday is the busiest day of the week so there could be long lines. However, the new departure lounge is scheduled to open soon, so that may help a bit for your return flight:
Airport’s new departures area to partially open next week | Cayman Compass
As others have said, as long as your planes are on time you should be fine, but if there are delays there could be problems - but that's always a risk with delays - no matter when and where you travel.
On your arrival date, the good news is that you aren't booked on the last plane out to LC; so if you are delayed - you may be able to get seats on the next flight as long as it's not full - but they use small, twin otter planes that book up fast.
On your return date, you have a little less wiggle room, but again, if all goes well you should be fine.
The process of traveling to the sister islands via Grand Cayman is rather complicated. Your plane arrives at GCM and you line up to go through immigration. If there are several other planes landing around the same time, the lines can be very long. Below is a photo of the lines of arriving people waiting outside in the heat to get into the immigration hall, but this was taken on a Saturday in January, a very busy month. It has never been this bad for us, but there have been times when we've been outside waiting to get into the arrival area; make sure to bring a hat with you on the plane.
Plea for patience over airport lines | Cayman Compass
After you get through immigration, you collect your luggage and line up to go through Customs and that usually goes fairly quickly. When you exit Customs you go out the door, turn and come back inside the airport's ticket lounge. You check in with Cayman Airways for your flight to Little Cayman and you check your bags. Then you line up to go through Security and that line may also be long.
In Security, if they try to send you to the exit immigration counter, show them your boarding pass and tell them that you are just flying to Little Cayman and they should waive you through.
When you get to the departure lounge you wait for your plane to be called, then board and head over to LC. It's usually a short flight (half hour) unless your flight makes a stop on Cayman Brac and then it is a little longer. At least that's how it has worked in the past, I hope that they have plans to make it easier to continue on from Grand Cayman when they finish the airport construction.
When you come back from LC, they will probably try to herd you into the incoming immigration line with all the individuals that are newly arrived on Grand Cayman - don't let them do that! Go to the Residents line and tell them that you are doing interisland transport and have just returned from Little Cayman, show them your boarding pass. They should waive you through to go pick up your luggage, check in for your homeward flight, and then line up for Security and Exit Immigration. The Exit Immigration is usually not a big deal, they ask if you have anything to declare and they collect the stub of the immigration card that they gave you on arrival.
Sometimes all of your luggage doesn't make it the same day that you arrive on LC because the planes are small. Missing luggage may show up the same day after the next flight, or not until the next day. We went to LC in November and one of our bags didn't arrive until the next day. Luckily our dive equipment arrived but most of our clothes and personal items did not.
There really isn't much space on the planes, so bags that you might normally think of as carry-ons (like backpacks) have to be checked. I carried a large purse that I could jam under the tiny seat in front of me, and I packed it with a change of undies for both of us, swimsuits, contact lenses, medications, dive computers, C-cards, and a few other essentials. The resort laundered the clothes we were wearing at no charge so we had a change of clothes.
We met another couple that didn't receive their dive equipment until the next afternoon, but the dive shop loaned them rental equipment for free until their missing bag arrived.
So the bottom line is, your flights are a little tight and you are flying on the busiest day of the week at the busiest time of day. But you are flying in May which is not the high season, however the airport is currently under construction so the lines might be long.
If you decide to play it safe and book the Meet & Greet service you should do it soon. There are limited M&G staff and the reservations book up quickly. It is annoying to have to pay more just to fly the flights that you have already booked, but it may give you peace of mind and help you to relax and start your vacation on time:
Meet and Greet Service – CEO’s Welcome
@Candiru had an extremely short connection time for his flight to Brac during the busy month of February, and his domestic flight was 45 minutes late leaving Chicago, but they had booked the M&G service and they made it, see below:
accommodation recommendations for layover in Grand Cayman