Here's How You Buy A $500 Sailboat And Finally Start Living

Sailing is generally thought of as being for rich people. When I say “sailboat owner” you think of an asshole who knows how to tie several kinds of knots. That’s not you, but that doesn’t mean you — yes, you — can’t go out and enjoy a nice breeze on your very own boat. You can, and you should.

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This is going to sound like bad advice, and I get it. You’ve probably heard all the classic kernels of boating wisdom, “The day you get your boat is the second best day of boat ownership after the day you sell it.” “Boat stands for Break Out Another Thousand.” “A boat is a hole in the water you’re always trying to fill with money.” In general, that’s all true. It’s very easy to spend tens, if not hundreds of thousands on sailing, and that has kept a lot of people away from trying it. Which is a shame, because it’s just as easy to spend $500 on sailing and have way more fun with a boat you don’t have to worry about scratching.

Getting a boat ready to sail is a potentially a little more work than just going for a drive. But as far as the actual act of sailing, sailing a small boat is easier than driving a car. It’s not some “rich people-only” skill that gets passed down through the generations, you can watch YouTube for a few minutes and figure it out. And as someone who likes driving more than most things, it’s just as much if not more fun than driving. Plus, you don’t have to feel bad about burning a bunch of gas, which is nice.

Cheat codes often don’t work when it comes to buying old stuff — a cheap project car car will often find a way to get you in the end, making you sad, broke or both. Boats that rely on gas motors are similarly risky, you can absolutely ruin your summer with a finicky boat motor, I have.

But, a sailboat…with a sailboat you can get away with buying and operating a cheap one if you follow some simple rules:

1. Aim Small, Miss Small

Screenshot: Jalopnik via Craigslist

Finding a big boat that’ll take you around the world on the cheap is theoretically doable, but that’s really playing on expert mode. What you want is something to get you out on the water with minimal maintenance costs, storage considerations and setup time. I’d look for something smaller than 18 feet with no more than two sails. The simplest end of the spectrum would be something like an old Sunfish, which should get two people out in a lake or bay for less than $500 without any difficulty. There are currently thirteen Sunfish on my local craigslist ranging in price from $325 to $1750 for one of the nicest ones I’ve seen. The best thing about a boat like a Sunfish is that you can just throw it on the roof of your car, no trailer required. When you’re done, lean the hull against the garage wall or hoist it up like a canoe.

For more space, there are a lot of Daysailer options that are plenty roomy for at least two couples, like this one from O’Day.

Screenshot: Craigslist

A Melges Scow or Hobie Cat will get you a lot more speed/excitement, but they’re more complicated to rig, which means more lines, more hardware and, more stuff to break. There’s also more to learn as far as the actual sailing goes and the experience is more “wet Caterham” than cruiser.

2. There is no reason to buy a project, ever.

Screenshot: Craigslist

As you’ve seen, you can buy a working sailboat for less than the average American car payment. If you encounter a leaky boat, wonky trailer, spongey fiberglass or anything that looks like it’ll cost more than a couple hours and a couple hundred bucks to fix, just walk. Again, you can buy the best example of most small boats in your state for nothing. Do not make another project for yourself. Note that this doesn’t apply to cosmetics. If you want to spend a Saturday morning polishing, you can usually restore a sun-faded hull to like new with a bottle of toilet bowl cleaner and wax.

3. Don’t gamble More Than You Can Afford To Lose

You must understand, that despite your best efforts to carefully inspect a boat, it may not work out in the end. Restrict your budget to a number that won’t have you despondent if it were to disappear.

4. Know when To Cut Your Losses

Part of the reason you want to keep your budget small is that you don’t want to get into a situation where you have a good amount of money into a boat that you can’t sell or use without fixing some new issue. If you have $500 into a boat that suddenly develops a big crack, you can walk away. If you have $5000 into it, that’s a more difficult calculus.

5. Just buy a normal-ass boat

If you see something that catches your eye, do a minute of research to make sure you can find parts for it. When sailing was really popular, there were a lot of weirdos building often cool/good boats that just never managed to develop a following. Unless you have a good source for weird boat parts, stick with more common boats.

As far as I’m concerned, that’s about all there is to it. You may have additional advice, or if you’ve ruined your life chasing the cheap sailboat dream, feel free to drop it in the comments.