Oh, no. We celebrated Thanksgiving with a 9 month old in Montego Bay. He never had a birthday in the US until he was about 9 years old. With one child it's easy.

Hotels can arrange baby sitters. Parents are much less trusting than they were 40 years ago (can my son really be 40?).

We basically went to beach resorts. This was really early in my traveling career so I wasn't too astute. We went to St. Barths for years. The hotel we stayed at had lots of children. We played on the beach, went swimming. The staff doted on my son.

I'm not so sure about trying to go to a city. With a resort, when the child gets cranky, you can just go up to the room. In a city, you might be a long way from the hotel. Also with a resort, you can sit on your balcony and enjoy the time even though you have to be close to a sleeping child.