We brought our son (2.5 yo) home seven months ago and this week we were able to take our first family vacation. We were having some trouble with his citizenship/passport so we stayed in the country and went to Puerto Rico. We had a wonderful experience! Flight is 4 hours direct from NYC, we rented a car and stayed on Condado Beach. Puerto Ricans love ninos and everyone was so, so friendly to us and we found most everything to be accommodating to families. We brought a puddle jumper and LO had lots of fun swimming in the resort pools and even tried the ocean.
We went to El Yunque rainforest, Luquillo Beach and Old San Juan.
We weren't worried about the flight since he had already done a 14 hour flight but that went smoothly as well thanks to kids gear headphones. We stayed in a suite with two rooms so he slept in one room and we were able to hang out on the balcony and in the bedroom at night. We got the Shrunks inflatable toddler bed and he loved it. The kitchen was helpful for storing snacks and drinks and heating things up.
I think my LO is an exceptionally easygoing traveler but if anyone is looking for a family friendly vacation, I would definitely recommend PR!