Keep in mind when going to the Caribbean, you dont necessaily have a choice of the day that you fly on. All the charters usually offer weekly stays, that can be extended to 2 weeks, 3 weeks etc, but they will all leave on a pre-determined day and return on a pre-determined day. So, if you have your mind made up on a certain destination, your choices will be limited as to when you leave and return.
The beaches etc on the west coast are not nice, you might have surfing, but the beaches and weather dont compare to the east Caribbean side. We did Cozumel for 2 weeks, you can do everything except surfing. We stayed at the Fiesta Americana, not the hotel, but the sort of condos at the back. It is right on the beach, offers 3 pools as well. We had the breakfast or brunch whatever you want to call it included, it was very substantial and you could have custom made dishes too. Then we did our own thing the rest of the day. All inclusives can be a good price, but they tie you down as well and depending on the food offered, are not necessarily such a great deal. Also, doing your own thing leaves you the freedom to try out the local fare. On the island of Cozumel, in the main center of San Miguel, Poncho's and the Mission are musts to eat at. The Mission has the best seafood on the island and the salsa is the best!!! There is another good place, certainly not much for atmosphere but was referred by a local working at the hotel, and they made the greatest conch chowder!!!
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