I always figure when one of those serendipitous airline tickets falls in my lap, I should do something I normally might not have considered. Chile would be a great choice; you could do the Caribbean anytime! Santiago is quite fine, in fact, everything I saw in Chile I enjoyed, altho I did not go north of Santiago. Travelling by myself, I had a little rental car &poked around the Lake District &went down to Puerto Montt &met interesting people every day. LP was helpful to me in both things to see &do &reasonable B &B's. I found I really didn't need much else. As a vegetarian, however, the further south I went, the more challenging dining became. They really do like meat!
Another wonderful AA destination is Quito, Ecuador (service from Miami). What a great city! Besides the Inca history at nearby locations (you don't have to go all the way to Macchu Pichu to experience fine sites), around the city are lots of interesting markets, volcanoes, hiking, dining and resorts. Again, it's not necessary to go down to the Galapagos to enjoy Ecuador. LP can give you good advice here. You can also check out Metropolitan Touring at http://www.equadorable.com for good info on the country &tours.
Spanish is helpful in both countries.
Gail in Eugene