WOW!! Thank you for the detailed and helpful responses, what a great resource of info!
Looks like the Caribbean is hands down less expensive and most likely a gentler way to ease into the cruising life.
Looks like the Bahamas is a pretty popular destination, do you get the persistent tradewinds at the Bahamas?
TQA: Where is a good place to find the boats in Trinidad, I tried Yachtworld but only came up with about 60. Is there a better site?
Killarney: Good site, OnAinia.blogspot.com
Thanks again for all the posters, probably give me a few more weeks of research!