I got the bug in a big way a few years ago. Thought of buying a boat very seriously. With a new baby and house still being renovated, we chose not to.
Instead, though, we signed on with a "lease share" company called
Pinnacle Yachts for a 1/8th share for a season of a new Jeanneau 37 in Boston Harbor. At about $7,000 for the year, everything included, it turned out to be a wonderful deal for us. All maintenance, gas, insurance included on a $180,000 boat that we had rights to use 30 times that season. I honestly sailed 24+ times that year. I really, really enjoyed skippering the boat and taking friends and colleagues out. It was a fantastic craft.
I didn't necessarily enjoy the limitations of the lease: you must pre-schedule, and if weather sucks, you're hosed and simply lose that slot. If weather is ideal, someone else is likely using the boat and you can't. (They promise free, unscheduled availability, but it
never happens.) And occasionally another lessee will leave the boat a mess - a strictly agreed responsibility. Still, all-in-all, a
great value.
Another firm that does this is called
Sailtime. Cheaper than Pinnacle, but a lower-end boat (Hunter), more lessees per boat, and shoddier maintenance. We chose Pinnacle are were very satisfied with all aspects save those mentioned above. There are other firms that do this, too, as well as many sailing clubs.
We dropped the lease after that season and I really feel like I scratched that itch. Sometime later in life, we may own another boat or do the lease share again. Right now, though, I'm busy with many other things.
Your location isn't shown, but perhaps the lease share will work for you. As Mark suggested, and as the adages go, a boat is a hole in the water where you throw your money. The happiest 2 days of a boat owners life? The day he buys and the day he sells.
Lastly, I personally greatly prefer a boat with a wheel instead of a tiller. Just feels more serious to me.
Happy boating!