Finally Casting Off

Up until this point, we’d only managed a few little “mini sails” with Agra2 on Lake Michigan. Nothing too ambitious…mostly because the weather had other plans and our “new-to-us sailboat learning curve” was steep enough without adding big waves and scary wind. Tom did spend plenty of time practicing backing into the slip though. Let’s just say there was a lot of circling…and a few times he had to stop because I felt a lot seasick. 😆

The Day We Really Sailed

With no extra time to spare in our prep timeline, June 6th, 2024 became the day. Destination: Kenosha. Our first real sail—and our unofficial “sea trial.”

Unfortunately, we had been denied a proper sea trial by the marina. The previous owner had made endless promises to take us out sailing and teach us the ropes…but cancelled every single time. Meanwhile, the marina was pressuring us to finalize paperwork and sign off on the trial. We had already moved our departure date up by a week and would be leaving Racine in just over a week, so we needed this.

There was a lot riding on this first sail.

I honestly can’t even describe the emotions I felt as we headed out down Lake Michigan. It was calm, gentle, and welcoming in a way I desperately needed. Even with three years of sailing behind us, this was completely different from the Ottawa River. Agra2 is bigger, stronger, far more capable, and comes with grown-up gear: complicated navigation systems, a true helm, better rigging, and WAY more comfort than our sweet little Agra. On Lake Michigan the world feels massive…with endless possibility.

Lake Michigan must have known we were newbies. The waves sat around 1 ft, the wind was perfect, and before long we had full sails and the most beautiful sense of peace.

Tom was officially living his dream.

Captain mode: fully activated.

But wow…did it wipe him out! The man was exhausted and totally crashed for a nap on route. Meanwhile, the Admiral (yup that’s me 😉) suddenly had to step up. On Agra, we had tiller steering and I honestly hated sailing her alone. Agra2 though? A wheel. A real helm. MUCH more manageable…even if the learning curve still felt enormous and overwhelming. I reminded myself we were doing this ...really doing this.

Arriving in Kenosha

Sliding into Kenosha went shockingly smoothly. Docking felt calm and controlled, and I could actually see our confidence growing with every maneuver, it didn't hurt that we just had to glide into the space. We treated ourselves to dinner at the Kenosha marina, soaking in the quiet victory of our first real passage.

The Not-So-Fun Part: Stable Fly War

The sail back was…less peaceful.

Enter: STABLE FLIES.

And not friendly ones. These monsters bit through clothing and showed absolutely zero mercy. We didn’t get the enclosure zipped in time, so we basically spent the entire sail swatting, yelping, and dancing around like lunatics while trying to pretend we were still “seasoned sailors.”

Romantic sailing life, right? 😂

But even with sore, bleeding, itchy legs and a cockpit full of squashed battlefield casualties, we made it safely back to Racine.

What This Sail Meant

This first real sail wasn’t just about mileage on the water; it was proof that we could do this. That all the frustration, repairs, learning, and second-guessing were leading somewhere meaningful. Tom truly was Captain now. And me? I was slowly, shakily, but 'bravely' becoming the Admiral I needed to be for him.

It wasn’t perfect. It wasn’t glamorous. But it was ours and it was the beginning of everything that came next. ⚓💙

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Racine, WI ➜ Kenosha, WI ➜ Racine, WI 21.3 Nautical Miles