Somewhere warm to wear shorts -- do you mean any time of year or just during a particular season?
Puerta Vallarta is still my favorite destination in Mexico -- it doesn't have the overbuilt touristy feeling of Cancun, there are some lovely restaurants and shops, and plenty of warm weather activities.
St Maarten -- half French, half Dutch, wholly captivating. From the Burger King truck to the 150+ foot yachts that moor in the harbors, the island is truly unique. If you want a two hour lunch followed by a trip to the nude beach, then head for the French side, if you want to gamble there are casinos on the Dutch side.
Turks and Caicos is supposed to be another fantastic trip, and neither that or SMX are too far from you being Caribbean.
My goal next year is to branch out westward, beyond Hawaii -- I think I want to do a bareboat sailing passage around the South Pacific - the Marquesas, Fiji, Tahiti, that neighborhood.
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