Sailing is awesome. I friend runs a business where they take care of other people’s boats and make a market for people to buy a boat share. Basically, you pay way less and use the boat when you want it. He took me out on a beautiful boat a while ago, probably cost about 300k. I’m not sure what the pricing is like, but unless you think you’ll use the boat every weekend it may be worth looking into.
I grew up with a similar sized boat on the sound and absolutely loved it. We “sold” it a few years back, and I quote sold because I’m pretty sure it was worth USD$0 at the time. A couple things I’d note: 1) do you sail? Cuz if not I’d say motorboat > sailboat by a mile. 2) If your answer to 1 was yes, I’d say you should look into going into it with someone else who sails. Not only can you split the carrying costs (10-12k/ year I believe) but you’d also have a competent sailor who could routinely join you. Having to “teach” the people you bring everytime to help you out could get old real fast.