We’ve all heard it. While talking boats with your friends or shooting the breeze with a stranger at the docks, someone usually throws the familiar saying out there: The two best days for a boater are the day they buy and the day they sell.

Having bought and sold my fair share of boats, and having just sold my most recent boat (a 1995 Cigarette 38 Top Gun), this old adage got me thinking. Now I realize we’re all different, but for me, buying a boat is stressful. Don’t get me wrong, the hunt is fun but the purchase is anything but. Did you buy the right boat? Will it meet your expectations? Is it a good price? Then there’s moving money around, shipping and all the little details, etc.

Then there’s the first run. Not the sea trial mind you, that is anything but stressful. A sea trial is basically a vacation to the location of the boat. Besides dropping some cash for fuel or a small amount to show you’re serious, the sea trial is usually pretty relaxed. Not to mention if anything goes wrong, you don’t have to worry—heck, it’s not your boat!

However, the first time you actually run your new boat alone is nowhere close to relaxing. Getting assimilated to your new ride, watching all the gauges to ensure everything is correct, listening to the motors, getting the attitude of the boat right and so on. It can seem more like work than play.

Selling a boat can be equally as nerve-racking as buying. There’s all the listings needed to advertise your boat. All the phone calls, tire kickers and scammers. Then there’s the sea trial where, even if your boat is in tip-top shape, in the back of your mind you’re still hoping nothing goes wrong—as we all know things tend to do at times with boats.

If all goes well, you receive the money and your boat is gone to its new happy owner. I think the best way to sum it up is with one word—bittersweet. Unless of course you were in dire need to get rid of your boat.

I can think of countless “best days” I’ve had on the water in a boat I’ve owned. So many in fact that I couldn’t possibly narrow it down to only two. There’s another old boating adage that rings true: Better a bad day of boating than a good day of no boating. Even when I lost a motor, it wasn’t a horrible day. It was actually a great boating day, up to that point. My point is, nothing beats a warm day on the water with good friends in a great location.

Although the “two best days for a boater” saying is always met with a hardy laugh, I don’t think it’s quite accurate. Buying and selling can be tough. But as I said, the hunt is the fun part. So onto the fun part … what’s next for me? Guess it’s time to peruse the classifieds!