There is much to address here, however, since this the How to Go Cruising…NOW! blog, safety and cost come first. In order to go cruising now, you do the best you can with what you have right now. A good cruising boat should first and foremost be seaworthy. That means it should be able to perform in adverse conditions, as well as those perfect sailing days we all dream of. You’re going to look for the integrity of construction. Whether the hull is fiberglass, aluminum, steel, wood, or ferrocement, it must have been constructed with quality in mind. You can get a survey done of the boat before you buy it. If that is not in your budget, then get a book on how to survey a boat and attempt to do it yourself. If you have a mechanically minded friend, bring them along to help spot deficiencies. Fiberglass hulls are easy to repair and simple to care for. I would recommend a fiberglass hull for a beginner. Now, the books about buying a new boat are going to tell you all sorts of guidelines that you must follow or risk getting burned. I’m here to tell you that if you have a limited budget, you’re not going to be able to follow all of their advice. As long as you’re prepared to work, learn and do things yourself then you are ready to buy your boat. The more learning, work and hands on projects you do, the better cruiser you will be anyway. I have had friends with towboat companies and the Coast Guard say that they rescue more people with really expensive boats and all the high tech, top dollar equipment than people who are on more low key, simple, even smaller boats. Boating really levels the playing field economically. A bigger and more expensive boat isn’t going to help you survive an ocean passage, only your personal skill level can do that. My point is, a lot of people pay others to do everything for them, survey the boat, repair the boat, maintain the boat. Unless you’re going to hire professional crew to operate the boat, it is best you begin doing what you can for yourself now. Real cruising is about self-sufficiency to me. Of course, if you feel you need an expert and you can afford one, go for it. I’m just trying to promote what I see as an essential trait of a successful, safe and happy cruiser. In addition to quality construction, you’ll want to take a look at what kind of rig the boat has, how many sails, and do a bit of research into the history of the performance of the type of boat. It’s a very personal choice, and nothing is more personal that the boats’s overall looks. Many people fall in love with a boats lines, but think about function, safety, and performance. Evaluate your personal needs. Just doing coastal cruising? Then you don’t need the capacity to store a ton of fuel, food and water. If you’re planning extensive offshore passages, you’ll need extra storage. If you’re single and you really want to escape, you have the most options. There are lots of quality boats for sale in the Caribbean that are cheap enough to pay cash for, relatively simple to work on, and plenty of room for one person. If you have a partner or a family, it’s a joint decision because everyone is going to have to live with this. Again, being stubborn about waiting until you can afford your dream boat is a pitfall. If you want to cruise now, be flexible, make doing it your top priority. Do it now, the best you can, with what you have. Compromise and promise yourself you will move up to your dreamboat someday. After all, once you get some real cruising experience, all of your priorities will change anyway. You might hate it and be glad you didn’t waste more money. You might change your mind about the way you want to do things… leave yourself some growing room.