Dreams of Sunsets, Rum & Island Life
I think you will want to learn how to sail first on a small boat like 25 feet or so. Keep that boat for a couple of years and learn on that one. Then, you will better know what you want and don''t want in a cruising sailboat and not have alot of money invested.
If you decide that cruising is not for you then you have not put all you eggs in one basket. Give yourself a few years to become familiar with sailing and cruising. Don''t rush into it. Take your time and check out all your options along the way. Sailing is a wonderful way to spend a life!
Just my two cents.