Sailing into Chicago was pretty surreal for us. We first began hatching cruising plans while living in the city ten years ago. Now, looking back at the shoreline we used to walk along, a sailboat floating only in our imaginations, it feels like we’ve come full circle, our dream now a very real 20,000-pound vessel underfoot, carrying us past the same Chicago shoreline — and beyond, wherever we desire to go.

After our family and friends gathered in Chicago to send us off in our previous episode, we depart Belmont Harbor with a plan to reach Skyway Yacht Works at the Calumet River mouth (where our mast will be unstepped). But the wind is whipping 20-25 just off the bow, much too strong for our 155% genoa, and we’re forced to turn on the engine. Instead of motoring all the way to the river, we decide to duck into the Playpen, an anchorage right next to downtown, with the most incredible view of the Chicago skyline.

The next morning even though the winds haven’t abated, we can’t delay any longer. We put up a double reefed main and a heavily furled headsail. The going is tough, but we really want to sail one last time before our 1300-mile journey down the river as a motorboat. We even sail backwards (on purpose!), which is the last step of the boat renaming ceremony, intended to be performed during your first sail back on the water.

We enter the Calumet River, and are immediately confronted with our new cruising environment: bridges, barges and commercial industry abound. It’s a whole new world with a new set of rules. The journey is just beginning.

Hope you enjoy!
Lauren & Kirk

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WE’RE LOOKING FOR MUSIC! If you or someone you know makes good tunes, give us a shout at


Back Again – MÆSON
Odesza – Say My Name (Mulle Remix) – Mulle
Adventures – A Himitsu

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