First Sail of the Season: Cold Winds, New Sails, and a Humbling Return

We kicked off our 2025 sailing season on Friday, May 2 — with a chilly but exciting voyage aboard Red Sky. This was our first time back since fall, and as always, the return brought a mix of nerves, muscle memory, and unexpected moments.

We left the house in the early morning hours and arrived at Burnham Harbor in Chicago around noon. The marina was under repair, so Red Sky wasn’t in her usual slip — a small hiccup that turned into a scavenger hunt. We eventually found her, tucked away on the other side of the marina.

Bundled Up and Ready to Go

It was not quite 60°F — cold enough that we had to suit up in our winter coats. Sailing this early in the season feels different: the lake is wide open, but the air still carries winter’s bite. Still, stepping aboard and opening the companionway to find a clean, fresh interior gave us a jolt of excitement. She was ready. So were we. Sort of.

There’s always that early-season apprehension. We’re out of practice. Routines are rusty. But bit-by-bit, it started to come back.

A Surprise Under the Stack Pack

We’ve learned a few lessons over the last couple of years — one of them being: unpack the mainsail before leaving the dock. The stack pack is a type of sail cradle that sits just above the boom. When the sails are doused, they drop neatly into it. Some stack packs are open, but ours zips the full length of the boom — keeping everything snug and tidy.

The catch? The end of the boom is just barely out of my reach. I need the deck to be stable to get it unzipped. Trying to do that underway? No bueno.

This time, when I unzipped the stack pack, Red Sky surprised us — she had new sails! Over the winter, she’d been treated to an upgrade. The stiff, pristine white canvas practically sprang out. (When we hoisted the sails they were beautiful!)

Calm Water, Big Swells, and Role Reversal

At 1 pm, we swapped our usual roles. Kent would take us out of the marina, and I’d bring us back in later. The lake gave us calm 1-foot waves but bigger, rolling swells and light winds (5–10 knots). Under those new sails, Red Sky moved gracefully — but those swells got to me. I felt a touch of seasickness.

Even so, the sail itself was wonderful. Quiet. Restorative. Worth every shiver.

The Return: My Slip-Up in the Slip

Coming back in was my turn at the helm. I used the no-wake zone as a testing ground — easing the throttle, observing our speed along the pier, putting her gently in reverse till we came to a stop. It felt promising. I was building confidence.

But… I didn’t practice going slow enough.

When we entered our slip, I came in too hot. I relied on the bow thrusters way too much and had to back out twice. In the end, I got us in, but it was not pretty. It rattled me. A beautiful sail ended with a rough landing, and I carried that disappointment for a few days.

It wasn’t until our second outing that I could reflect on it with some distance — to see what I learned and how to approach it differently.

Final Thoughts

Not every sail has a picture-perfect arc. This one had cold winds, a few humbling moments, and unexpected joy in the form of new sails. If there’s a lesson here, maybe it’s this: early-season sails are where grace and growth overlap.

Can’t wait to share what happened on outing #2.