If you're new to sailing, I think the above suggestions are awesome. Just wanted to add our perspective to round things out.
We live in a HCOL area on the west coast of Canada--boats can be bought in the US MUCH more cheaply, especially on the East coast.
We bought our first sailboat, an Alberg 23, for $6500 and moored it locally at a run down marina (cheapest we could find in our area) for about $230/mo. We spent probably $1000 in maintenance for the 3 years we owned it, and spent $2000 on a new outboard motor. DH did all the maintenance and upgrades and kept it in excellent condition. When we were ready to move on, we sold it to a friend (after months of trying to sell--echo that it is hard to sell and easy to buy) for $5500. So total, about $4000/year.
We moved on to a larger boat, a 30' Alberg, which we bought as an estate sale WAY under book value for $7500. We have had the boat about 5 years now, and pay $275/mo for moorage. Hauling/maintenance her costs about $1000-1500 year, and we probably put $2000 into her in the first couple of years to bring her out of her neglect after her owner passed. So lets say she has cost us about $5000/year.
It's a lot in some ways. But the key for us is that we LOVE to sail; it's DH's major hobby. So we consider this our travel/holiday budget, DH's entertainment budget (we never go to movies, rarely to concerts, etc), and it's a major social outlet too--a way that we build friendships and community. It's SUPER cheap weekend trips, as the sailboat burns hardly any gas, and it has a kitchenette. We don't usually stay at marinas when we go on trips, so all we pay for is groceries. It a major stress reliever, esp for DH, and in our area we can sail almost all year round. Old boat owners are also generally penny pinchers, so there's a natural mustachian peer group built in, which is fun.
So we figure, *many* people spend $5000/year on travel and entertainment; we feel like this is a very reasonable hobby that we get a lot of reward out of. We are also clear with ourselves that this is a luxury. We carry some liability insurance (which the marina requires), but if the boat sinks, we are clear that it is not a necessity that needs to be replaced immediately. It will need a new motor at some point, which could run us around $10K, but we're going to run the current one until it dies and if we need to slap a $2000 outboard on her after that, we will for a while.
BUT! We are not typical. Marinas are FULL of boats that never get sailed, or get sailed once a year. Boats are also exponentially more expensive to moor, maintain, and repair according to length. Even the difference between parts for the 23' vs the 30' was noticeable. Once you have some experience, get the smallest boat that suits your needs. As with cars, buy boats whose value is already depreciated and you'll get out more or less what you bought the boat for, if well maintained. Maintain a DIY, desire to learn attitude; having other people do the work for you is expensive, but there are a million youtube videos that will tell you everything you need to know, and old timey boat owners love to share knowledge.
Lastly, once you're ready to own your own boat, consider sharing ownership with a few other like-minded people. There are a lot of boatshare arrangements that are possible, where the initial purchase price is shared, moorage and repair costs are shared, and then there's ample time to rotate use through the various owners.
We love being sailboat owners! But it's important to go in with your eyes open. And don't blow all your cash at the marina pub! (easier said than done, lol).
