Sailing

Lots of looking on yacht sales websites like yachtworld.com. Get out and inspect lots of boats. I saw many that just didn't have a 'good energy', but the one we finally got just felt 'happy'.

Depends on what you consider "smaller" and "decent". Also what your overall budget is for purchase and maintenance, your ability to do the maintenance, and what your expectations are. Very important to determine even before starting to look.

You don't specify what you consider "small" trips either, or the comfort you expect on those trips, which would be key points in expectation. Plenty of great overnight trips you can have in a sailing dingy depending on the location and your tolerance for roughing it. Heck, depending on your tolerance, people have sailed around the world in little 4 meter boats, open canoes and all sorts of wacky things.

Also consider what resources you have for storing it. The cost of mooring, and consider a swing keel or otherwise trailerable if that is not a cost you want to continually incur (and also consider the additional maintenance of a boat left in water).

Cost of purchase can be all over the map, usually tethered to the sense of urgency the owner has to sell more than the actual value of the boat (see cost of mooring/maintenance).

You may even find a lot of boats that drop to free, or might as well be free. But be very wary of a very inexpensive sailboat (at least one that is larger than a dingy). I've had a free boat that only cost a can of resin and a can of flat black paint in its life with me. I sailed it for many years and many miles until the keel literally fell off. But I've also had a free boat that ended up costing $16,000 over a few years, then another $4000 to crush and responsibly dispose of it, without sailing it once.

Regardless of budget or expectations, start visiting your local docks. Sailors are often looking for others to infect, you'll gain lots of information whether you wanted it or not, and often leads on boats. Though I feel a word of caution is warranted here: listen to everything a sailor has to tell you, trust none of it. Not to say it isn't going to be reliable information, but take what you gather from the docks and use it as a reference point for your own research. A lot of it can be unreliable.

As noted in other comments, get familiar with maintenance, it is essential to survival. But you can also easily fall into the trap of being a boat builder first, sailor very distant second if you purchase a boat based on what you think you can make of it. There are many trite jokes about the money pit sailing can be. This is true as evidenced by vast majority of boats rotting at docks. As a fully committed lifestyle however, it really isn't expensive. The key is to be living the lifestyle. Adjust your expectations to the constraints of your current life to maximize the amount of time actually sailing. There will always be another good deal on the potential "ideal" boat with a "little" work when have the capacity and experience to take such a thing on.

From someone that has spent zero to well over 200K and counting on boats, my advice would be to maximize your budget for condition of the boat. As in, if you have a small budget, get a very small boat in very good condition. If you want a larger boat, wait until you have the budget for one in very good condition. It will always be more work and more money than you expect. You'd be shocked how many thousands you can spend on something as simple as stainless bolts.

Don't know your budget or starting expectations, but personally, if I lost it all and had to start again, I'd get $5K together and buy the nicest trailerable sailing/rowing dingy I could find; buy a tent; find a nice sheltered area with a couple of islands to explore. And just sail non-stop while squirreling away money for your dream. You'll gain more experience through pleasure over pain that way.

If you are a social type, there are often folks looking for crew. I was never one for that myself, but I suspect it is a far more sensible way to learn than "I wonder what would happen if I did this?".

The larger dream of living on the hook is totally rad. I encourage anyone that is committed to the idea.