When choosing a cruising sailboat for a trip to the Caribbean, make sure you remember it's a home first sailboat second.
We enjoyed living on a sailboat for 8 years cruising up and down the Windward's and Leeward's...Virgin Islands to Trinidad and Venezuela. We had a ball cruising on our 35 foot Island Packet sailboat Shadowtime. We chose very well, never wanted any other kind of boat. You can choose well too.