Libby, yours is a great question & also a common one, as it mixes together skill-building, boat choosing (& buying) and the aspiration of cruising. Here are a couple of thoughts, some of which contradict others'' comments...
1. There are no mutually-exclusive methods re: learning. You''ll learn tremendous amounts by sailing a boat yourself, and possibly meaningful amounts by sailing with others (depending on what they''ll let you do, how many crew, etc.) Visit yacht clubs (they will not throw you out), marinas, etc. and post your own crew-wanted notices, and then get out on the water.
2. Reading can be especially helpful if you read truly practical, balanced & thoughtful comments from others in your about-to-be shoes. E.g. I can not recommend Latitude 38 enough, because it''s Letters column (many, many pages) and Changes In Latitude column are exclusively written by other sailors (but commented on by the publishing team, which is very experienced). This monthly free mag (as contrasted by the biker-sailor mag of similar title, which is sold) is available at no charge at all West Marine stores; since we began full-time cruising, it is the only subscription I have maintained.
3. Realize that you have set contradictory goals for yourself and so must accept substantial compromise in them. Small boats are less capable of long-term (multiple months) cruising re: seakeeping, food & water stowage, comfort, etc.) tho'' easier to single-hand. Buying a $5-10K boat that you hope to safely cruise just means needing to spend more money to prep it safely (how old is the rigging
? how about that centerboard pin and rudder bearings? how many coats of fresh bottom paint
?) This doesn''t mean you can''t find an old/cheap boat and head out, just that you must accept more compromise in the experience (altering your route to take on water more often; making more repairs
once you''re out there vs. before you leave, and so on). Understand that the Pardeys legitmately but overly emphasize the benefits of small boats, but have only cruised on well-found, new (initially) and custom designed small boats. Eric & Susan Hiscock sailed multiple times around the world on their "30 footer" but, if you saw it, you''d be struck by how big & strong it was (displacement, draft, storage, etc.). The same is true of the Pardeys 2 boats (I''ve seen one, pictures of the other). OTOH we have great friends who''ve sailed many years to and thru-out the South Pacific on a Vancouver 25 (another not so small ''small'' boat), so it can be done.
4. There are some great pocket cruisers tho'' the good ones (aka: strong, thoughtfully designed for cruising; strong enough for the occasional groundings, squalls and such) are probably not in the $5-10K category but - again, with compromise - decent cruisers are out there. I''d strongly recommend considering a Swedish-built Vega 27 built by Albin Marine in the late 60''s thru the late 70''s. This full-keel light but seakindly boat is the best-sailing boat I''ve ever handled, was routinely used to cross the Atlantic since the early 70''s, and should be inexpensive these days. A delightful read - Log of the Mahina by John Neal - is still in print and has an Appendix covering in detail how John set up his used Vega for a 1.5 year cruise to the South Pacific from Washington State.
Good luck with your plans, and please understand that your goals aren''t easily reached but are certainly obtainable: read tons, get on the water, and prowl around boatyards every chance you get, asking any question you can think of. Boatyards are boatshows for the important stuff!
Aboard WHOOSH, lying Port of Spain, Trinidad (but visiting Pensacola to see his son get his Navy wings)