A Sister, a Regatta, and the Sea 

We went sailing again last Sunday and it turned into one of the most special outings we’ve had all season.

The plan was simple:

We’d drive to Chicago Saturday night, sleep on the boat, and head out Sunday morning with my sister aboard for her first-ever monohull sail. But if sailing teaches you anything, it’s to expect the unexpected.

When we arrived at the marina, the folks who had just finished using Red Sky were still trying to wrestle the new sails back into the stack pack — a struggle we know well. We debated offering help, but ultimately decided to let them have space, so we walked to the bar for cocktails instead.

Between the blaring music from the Beyond Wonderland festival on Northerly Island, a live band at the marina bar, and the shock of an unusually cold evening, we made a game-time decision: skip the boat bed and book a hotel.

We found a nearby room and grabbed dinner at Boleo, a Peruvian rooftop spot just around the corner. When we walked in, a flamenco dancer was mid-performance. The night felt cinematic. We sipped white sangria with apples and passionfruit, devoured ceviche mixto, and shared Lomo Saltado — a gorgeous stir-fry of beef, red onions, tomatoes, and French fries! A total treat.

Go Time!

The next morning, we woke up early (earlier than I’d like for a “leisurely” morning), and I was buzzing with anticipation: my sister Maria would be joining us for her first monohull sail!

I was also nervous. Lately, Kent and I have been switching roles so I can get more confident at the helm — especially docking. I really wanted Maria to have a great first experience, but I also knew I’d be the one bringing us back in. Part of me wanted to hand the hard part back to Kent, but the bigger part of me knew this was the only way I’d grow.

After a full safety briefing for Maria, Kent took us out of the marina, and I committed to bringing us back in.

The weather was exactly as forecast: sunny skies in the 70s, steady wind up to 10 knots, and one-foot waves. Rain was predicted for later in the day, and it held off long enough for a perfect outing.

With space to spare, we turned upwind, hoisted the sails and turned off the engine. Headed north and east on a close reach, we were hitting up to 6 knots under sail. Maria kept saying how relaxing it was. I was so relieved — it really was the perfect day to show someone what sailing can be.

That same day, the Helly Hansen Sailing World Regatta Series was underway, and through the haze we could see clusters of sails poking up far on the horizon. We steered our way north, weaving gently past the committee boats, the crib, and just beyond Navy Pier.

The entire out-and-back was smooth and beautiful — until we got back, about a half mile out from the marina. When the wind suddenly picked up to 10–15 knots, we made the call to douse the sails and motor in.

Performance Anxiety

It was my time to take the helm. Kent and I always talk through our strategy before docking, and we did that again here. But today came with a twist: Carol Ann III, our slip neighbor who’s usually out, was home! And her crew was lounging on deck, drinks in hand, watching us come in. No pressure! 😩🤢

I ran through everything I’ve learned: account for wind, use gentle nudges from the engine, and remember: “slow is pro.”

Oh! Did I nail it!!

No drama. A clean entrance. A textbook landing. Carol Ann herself said, “You looked so calm!”  — which made me laugh. I was not calm. But I was proud.

We ran through our end-of-day checklist, tied in tight, and walked back to the bar for celebratory cocktails. A day for the books, for sure.

One last note before we called it a day.

As we neared the marina, the wind picked up fast — probably 15 to 20 knots — and for a moment, we caught more of it than we meant to. We didn’t get knocked down, but we definitely got knocked around.

And yet, I wasn’t rattled. Kent was at the helm and handled it smoothly. I helped furl in the jib, and we dropped the mainsail quickly. It felt… manageable.

The contrast hit me later. Last fall, during a broach, I was terrified — truly shaken. (You can read about that here). This time? I felt something closer to confidence. Not overconfidence. Just the quiet awareness that we’d been here before — and that we knew what to do.

That feeling — of growing into experience — might have been the best part of the whole day.

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