Our point of departure would be either Chesapeake Bay, MD or Neuse River, NC. Because of the appreciable boating congestion in the northeast, we were contemplating South America. Being an American citizen may pose some problems, but if the weather patterns of Venezuela, Columbia and Mexico, at that time of the year are comfortable, those destinations would be possible considerations.
It's been a long time since we've cruised the Caribbean, so a fair amount of this information is based on hearsay. A quick suggestion. We have belonged to the Seven Seas Cruising Association for many years, and have found that the information provided by their Commodore's bulletins to be valuable. There is a great deal of information about the Atlantic cruising grounds since the majority of members are Americans. If you choose to join (http://www.ssca.org) you can buy their CD of the past 8 years of bulletins. You can then search for those destinations you are interested in.
Back in the 80s Venezuela was a very popular destination for Caribbean cruisers trying to get out of the hurricane zone. It was then, and probably still is, very cheap. I loved the time we spent in Venezuela. We spent a lot of time at Margarita Island, then went to the marina in Cumana when we did some inland traveling (to Merida, Angel Falls, Caracas). Venezuela has had so many political ups and downs that I think that current information can only be obtained by cruising down the Caribbean and listening to the various ham and SSB radio nets for current conditions. Crime is worse than it used to be, I understand (though that seems to be true throughout the Caribbean).
Back in the 80s, thanks in part to Donald Street's influence, Trinidad was considered too dangerous then to visit. (it wasn't, and we spent many a pleasant month or more there. http://www.cruiser.co.za/hostmelon3.asp
is, in my opinion, the neglected jewel of the Caribbean. Few people visit, and they are missing a wonderful experience. Another wonderful, and under-visited island (at least by Americans) is Martinique
We know lots of people who stopped for a visit to Cartagena, Colombia, and loved it. It's a tough place to get out of, however. Going East back to the windward or leeward Islands is such a terrible slog to windward (for whatever reason, the winds seem to blow much harder from about Curacao west to panama, making for big seas and rough going the other way.) We had friends who tried 3 times to sail from Cartagena north to Florida, and gave up and returned each time. They finally made it, but not without some drama.
Although there is some
"anti-American" behavior, in my opinion it's exaggerated. For all the missteps of these past few years, the US has a fairly sizeable good-will credit in most places (plus, compared to the French, the other dominant cruisers of the Caribbean, Americans are wonderful).
I hope this is helpful.