This story starts eight years ago, with a dream and a plan and a thousand revisions to each of those. However, we won’t start there because things are only now starting to get interesting. Instead, we’ll jump right in to the day I thought we would have to scrap the entire eight years of dreaming and planning, because we could never make it work. Boat buying is hard.

It’s Labor Day Weekend, we’ve packed up our inflatable paddleboards and pointed the car towards Florida. It’s just a quick roadtrip, do a little paddleboarding, visit some breweries, oh, and look at a few catamarans. We’re hoping to purchase in the next six months, so this is a preliminary trip to get an idea of what models we like. Boat buying, step 1!

This is the first thing we’ve done that made the whole dream feel real. We’ve been working towards this for years, but this is the first tangible move we’ve made toward transitioning from a conventional life to a high-risk / high-reward life. Soon after we got on the road, Kyle said, “It feels like we’re both waiting for each other to call each other’s bluff – like, wait, you were serious about this the whole time? As if we want to see who backs down first.” It’s neither of us. This is happening!

We started out with a stop in Jacksonville to look at a 1997 Lagoon 37 at the top of our price range. From the ad online, it looked like a decent boat, except for the cockpit enclosure that had been added. That assessment was spot-on. This boat probably sailed great, but then the owners added a massive weight with the hardtop, essentially turning this boat into a floating condo. We looked at this boat for far longer than we should have.

On top of that, the broker was brand new. I’m certain this was the first sailing cat he’d ever stepped foot on. When I asked him how this catamaran would handle blue water or heavy seas, he told me there was a power cat at his marina that had circumnavigated, so he knew it was possible to take catamarans out on the ocean. Helpful, thanks.

The next catamaran we looked at was in Daytona, and we didn’t even have a broker or owner to show the boat, just a neighbor. It was a 1995 FP Athena 38, also at the very high end of our price range. Based on the ad, it sounded like this boat was ready to sail away as-is so we were excited to see it in person – it checked a lot of the boxes we were looking for.

In the 22 years this boat had been on the water, it had been so heavily modified that it was a motley collection of terrible “upgrades.” The neighbor kept telling us what a smart guy the owner was – an electrical engineer who’d done great work with solar power, wind generator, and LEDs everywhere. They were indeed everywhere, the same way spaghetti sauce is everywhere when you try to feed pasta to a toddler. He’d also built in extra storage in the salon, at the expense of open living space. We spent far too long on this boat too. It was just ugly.

When we got back in the car, I was sure we’d never be able to afford a boat that I loved. The two we looked at, which were barely in our price range, were both ugly. The layouts weren’t the clean, airy living space that I expected, meaning we could cross those models off the list. Driving down the freeway, I was picturing us scrapping the whole catamaran dream and doing something else with our lives. Maybe it’s time to talk about being full-time vanlifers instead. Maybe we should just stay at work, put down a deposit on a house in the suburbs, have our 2.5 kids and call it. It was that bad. Oh, and the AC in the car was intermittent to nonfunctional, we were hot, dehydrated and cranky.

We continued south on 95, but the sky started to look ominous. I pulled up the radar on my phone and confirmed things were about to get ugly. There was no rush, so we found the nearest brewery and stopped in for a pint. We waited out the storm on the porch of Playalinda Brewing Co, where the intense lightning chased everyone else inside (including our poor server, who was not a fan of lightning).

After a long, hot day of traveling, we high-fived for picking an airBNB with a pool we can relax in. It is going to be a long weekend, with a total of seven catamarans to look at. I’m trying to stay positive, maybe the ones we looked at today were wildly overpriced. But at this point it looks like our dream boat might be a unicorn that doesn’t exist in our price range.