I’m in California and did the American Sailing Association ASA courses. First one ASA 101 is a weekend and was like $300 ten years ago. You need to read the book and it’s 100 question test then the weekend is for hands on sailing. That gets you inland waterways, bays, lakes etc up to 27 ft.

Then rent from local club on those sized boats. I joined a sailing club for a few hundred a year and get discounts. then take your ASA 103 coastal cruising & 104 bareboat courses which were like 700 combined. then you are bare boat certified and can rent up to 50 feet. Rent up to that size for a while then consider to buy.

I still just rent and charter as I don’t have the time to maintain a boat and slip fees are pretty expensive here. The cheaper way is to keep your boat on a mooring ball and have a dingy to get to shore. Wait lists can be long for both slips (dock) and moorings. You could do a small boat there can be put on a trailer too.

There’s additional courses for further developing your skills. I went on to do the catamaran 114 and the pure navigation 105. Then did some endorsement courses for customs/international and night time. I’ve charted boats in Mexico, SE Asia, and Greece as captain with my friends. Great trips. Especially if you are also scuba certified. I bring my gear and do dives in the trips.

If not in US, look up your sailing association. The British one is most respected worldwide I hear.