One of the best vacations I ever went on was when my son was not even a year old. We went to Musha Cay. A group of islands in the Bahamas that had been recently bought by David Copperfield. He's an old family friend and invited us to his exclusive paradise that really only the fabulously wealthy can afford! It is truly heaven on earth. You stay in these bungalows and there aren't that many. And you can basically have anything you want, any time. It even has an outdoor movie theatre. The white sand beaches are beautiful and you might be the only people for miles and miles.
Another, more down to earth travel experience I loved was going to Harbour Island this past year. The Ocean View Club is like a big charming house and its a great place to rent out entirely for a birthday. Next door is the local hang out Sip Sip which has the best margaritas and lobster quesadillas. Oh and the sand on the beach is pink. Really pink.