Originally Answered: Want to buy a sail boat but need help?
Was reading your question and had some thoughts. The following is NOT advice. It is just informal web chat, completely at your own sole risk.
Good move on the sailing experience. If you are serious about sailing you might do well to get all the crewing experience and training you possibly can with very experienced captains on their boats. The more experience you get the better. Speaking for myself only. I like to show up at sailing races, make friends with experienced, careful and sober captains and crew with them, I get all the experience I can. Even though I already have my own boat, I still deliberately sail with more experienced captains and I learn much that way, as well as sail my own boat I have had for several years..
Sailing is a little like flying an airplane, you don't (at least not wisely) just get on a plane one one day and take off and fly cross country! Many small steps, and much training lead to a thorough understanding of your plane, how to operate it in a wide variety of conditions, deal with equipment failures, weather problems, operator failures, navigation issues and etc.
Same in sailing, there is much training, much paractice, and etc. , then gradually you build confidance to move from a few hours of sailing at a time always in fairly mild lake conditions, to maybe a weekend out on a lake in varied conditions, very, very gradually you build...
After a year of two of very frequent weekend protected waters sailing, proving your skills, building your understanding, maybe you take some additional costal sail training and if your boat is capable AND you are well skilled and equipped then maybe you get to the point whare you eventually try a short near costal or protected bay day sail, probably along side with a friend shadowing you on his boat.
After much, much practice at that sort of thing maybe you eventually get to the point where you can maybe one day take a trip of 50 or a hundred miles from one near costal harbor to another one but ONLY after a very carefully planned trip and ONLY embarked upon under a excellent weather window, and etc.
My point is this: sailing is done in incremental steps, much learning under skilled captain's training, much paractice under mild conditions & building on from that...
Although a few folks have up and bought a small boat and set out inexperienced on an ocean sail and lived to tell it, many have most decidedly not...frankly, from my perspective its a very likely way to get "yer self" killed!
Most 20 to 25 foot sailboats are NOT made to cross oceans, most 20 to 25 foot boats are for protected waters or at best near costal sailing. There are a very few exceptions...and they are expensive heavy boats (20 ft Flicka, Contessa 26).
These are full keel boats and not ones easily pulled behind cars or light trucks.
There are however many, many 15 to 25 foot sailboats that are loads of fun to sail on lakes and in protected waters, or for a few of the more selected ones perhaps (maybe) eventually in protected near costal waters, but YOU have to be ready..
as well as your boat.
For me, a small very affordable used cruiser, that I have slowly learned to sail under controled conditions (protected waters) has been the ticket to a lot of fun. More than I can say.
The adventure factor of a weekend sail on a beautiful inland lake., river, protected waters is HUGE. Boring it is not, at least if there is any wind up.
MY ticket to sailing has been to start with a small affordable cruiser, and sail frequently in protected conditions, a lot of fun.
Happy sails, but also be wise & careful...
Here is a URL to a Sailing chat group for Folks who like small over-nightable Pocket Cruisers: