Embarking on Season Three with SailTime Chicago

Ahoy, fellow sailing enthusiasts!

We’re thrilled to announce our return to the helm! Kent and I have signed on for our third season with SailTime Chicago! Once again, we will be sailing aboard the sweet sailing vessel, Red Sky!

For those new to our journey, Red Sky is a Jeanneau Sun Odyssey 349 configured as the owner’s version with a V-berth, one aft cabin, and a single head with a shower. She has a double helm, twin rudders, electric winch, and bow thrusters, and has become our trusted companion on Lake Michigan.

I first met Red Sky when in November 2023 when I took the opportunity to participate in a boat delivery. As SailTime shifts their fleet from Chicago’s Burnham Harbor to Waukegan for winter storage, they rely on members to help. When the call went out, I eagerly volunteered. The trip was doubly rewarding, checking off a bucket-list item (boat delivery), and introducing me to Red Sky!

In 2024, our first full season, we signed up for Red Sky. I remember the learning curve of our first check sail, and the ultimate reward of mastering the landing. Learning to use the electric winch and the bow thrusters, handling the mainsail with its reefing system, all important steps forward in our sailing education, hands-on skills we are keen to master. Maneuvering Red Sky in and out of the Burnham Harbor marina has become a familiar (albeit stressful!) ritual and each successful outing builds our confidence and solidifies our growing skills.

Red Sky was the stage for some truly memorable moments in 2024. We had the privilege of hosting Kent’s family – including his mom, his sister and niece, and brother-in-law, a former Air Force pilot – for the spectacular Chicago Air and Water Show. Despite the dynamic conditions on Lake Michigan that day, with waves reaching 5 to 7 feet and winds blowing at 20 to 25 knots, Red Sky handled beautifully, with Kent skillfully at the helm. Sharing that spectacle from the water was an experience we hope to repeat.

Beyond the thrills, Red Sky has also provided a comfortable and welcoming space for quieter adventures.  I recall a lovely Thursday in mid-May when we spent the night aboard in Burnham Harbor, followed by a serene sail on a calm and foggy Lake Michigan. Later that weekend, it was incredibly rewarding to welcome our son, daughter-in-law, and grandson aboard for a delightful day on the water, a true “proof of concept” for sharing our sailing dreams with loved ones.

Our favorite memory of 2024? Our first Lake Michigan crossing. This three-day passage, from Burnham Harbor to Michigan City, IN, then to New Buffalo, MI for a family visit, and finally back to Chicago, marked a significant milestone in our sailing adventures. Admittedly, the anticipation of being out of sight of land was tinged with apprehension, but the reality was nothing short of exhilarating. And witnessing the Chicago skyline emerge on the horizon was a breathtaking moment, far exceeding our expectations. We are still basking in the afterglow of this milestone passage.

Now, as we embark on our third season with SailTime Chicago, the excitement is palpable. Returning to Red Sky feels like coming home to a familiar friend. We have a history with her, a shared logbook of learning, laughter, and the sheer joy of harnessing the wind on Lake Michigan. We eagerly anticipate many more spectacular days and new memories aboard our trusty Red Sky!

Stay tuned for updates from the 2025 sailing season!

Fair winds and following seas!