I'd wait until the bundle arrives! When he/she is 6 months old + and in good health (and probably easiest if not being nursed), I wouldn't hesitate taking him/her to Turks and Caicos. Have been there several times with my family. There are first class medical facilities on the island (not that I've ever had to use them). We have rented private villas and have also stayed at Beaches. Beaches is pricey, but they really do have a first class "Camp Sesame". Diving is also included and you could go out without stressing about the well-being of your child. It is the norm for the parents to be off resort and diving. There are plenty of resorts in the Caribbean that offer childcare, but Beaches in Turks and Caicos offers both first class childcare and diving. A lot of people on this site turns their noses up at resort-operated diving in general and especially at Beaches (and Sandals) where they include diving in the rates. But if you have no choice but to travel with your kids and you want to go diving, it is among the best choice you can make. I speak here from personal experience! The only downfall, is that you would be leaving the baby from approx 8am until 2pm each diving day. If that's too long for you, somewhere with closer dive sites may be a better option.