Flying with a 16 Month Old:
Much more of a challenge than when he was non-mobile that's for sure! We took two flights each way, one to Houston (little over an hour) and then Houston to Grand Cayman (2.5 hours). It really wasn't too much travel time, but when the little one is going non-stop it can get a little bit harder. Cole didn't want to sleep at all on the flights. So he had no nap the day we went down there and was able to get a morning nap before we left, but was up until 11:30+ at night! Luckily, he was pleasant and just wanted to play. No meltdowns.
We chose a condo complex called The Anchorage on Seven Mile Beach. We had a 2 bedroom condo with a kitchen, 2 bathrooms, living room, and tv room. It was nice to have lots of space for all our stuff and for the little man to have his own room. We usually ate breakfast and lunch at the condo and went out for dinners. Our condo was right on the beach and had a pool. We loved staying here and would again for sure! The only annoying thing that happened was 3 of the power generators on the island blew or something on our last day. We didn't have any power from 6:30 am until the time we went to the airport. Of course the airport had power, but not much else did unless they had a back-up generator! Good thing we didn't have much food left in our refrigerator and we could just go to the beach!
First pic is looking back at the condo from the beach: