Originally Posted by
websterlewis
From Caribbean; you can do a bit of island hopping with BA and AA but will need to get to Havana to get to Cancun to get to Santiago.
San Juan Puerto Rico will get you to lots of islands (direct flights with Iberia from Spain) but not sure who stamps the passport!
San Juan is most definitely out as well. For immigration purposes, San Juan is no different from any city in the US - you get the full "felon" treatment. (fingerprints and mugshots) The same thing applies at Guam, by the way.