[Jhooley]

I am a begginning sailor, and I am looking to buy a used boat by the end of this summer. I am looking to get as much advice as I can beforehand to better my search.
I know that I will need a fairly rugged boat for the type of sailing I wish to do. It must be seaworthy. My fiance has family in Jamaica, and Cuba. We are both born and raised in the US. I have family in Florida.
I work in Massachusetts, Landscaping from March until late october. So between the months of October and March, I would like to sail with my wife in the carribean, leaving from Florida.
I am not picky about anything. I just want a seaworthy boat that will allow me to island hop.Sailing for a week and then staying in port for a few weeks at a time. Correct me if I am wrong, but sailing to Cuba isnt that diffucult. 90 miles, and then from their on in you can cruise the coast until you make the turn around the eastern tip of Cuba and set off for Jamaica, which is no more than 150 miles soutwest of Cuba. None of those sailing trips seem too extensive...I am not crossing the atlantic or anything. So I figure I can get away with a boat from 27-30 feet, with a decent ballast. There are boats out there in my price range, under $12,000 dollars that fit that description. The question that I am asking is, what kind of boat can I get away with for this type of cruising? Blue water boats are usually more than I can afford. But there are alot of boats, branded ''coastal cruisers'' that are seaworthy enough to make the trips I want to make. Like the Catalina 27, Hunter 27, and Morgan 30. There are alot of these boats on the market from the late 70s to the early 80s. That are under $12,000. Those are the kind of boats I can afford. If there is anyone out there who can give me advice on the seaworthiness of these boats, I would appreciate it. My impression is that these boats can make these types of trips. I dont think that they are seaworthy enough for crossing the atlantic, but I figure that they can make trips in the open ocean no more than 100-150 miles from land at any one time. I am currently looking at a 1977 Morgan 30. 1977 Catalina 27, and a 1983 Luger 30. Any advice is very appreciated. Sincerly. JIM