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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Episode Dialogue

We are gettin’ ready to leave Chicago. We just spent the last five days here and it’s been absolutely wonderful. We got to hang out with family and friends. They wished us bon voyage and now we’re loadin’ up the boat with all of our stuff. We got a bunch of food, that’s only half of it, all of our computers, and cameras, and clothes. Clean clothes thanks to Jon and Katherine because they so wonderfully let us use their apartment for the weekend while they were away. Thank you so much. Um, yeah, so now we got a quick trip south to Calumet River. It’s just 12 miles south of here. And that’s where we’re gonna have our mast unstepped. Um, yeah. The trip seems to have really be beginning today.

[Kirk] See ya, Landslide.

Damn! So what did we just do?

We decided we’re gonna spend the night in the Playpen.

[Kirk] On anchor.

On anchor. And the Playpen is this little area behind the breakwater. It’s right in front of downtown Chicago just off of Oak Street Beach.

[Kirk] Our favorite beach when we lived here.


Well, that was one of our shortest trips ever. We left Belmont Harbor about an hour and 20 minutes ago. We were gonna sail on the outside of Chicago Harbor. We had 25, 26 knots gusting and we were just motoring because our genoa is just so dang big. Our only headsail is 155% genoa. We reach hull speed at about 13 knots of wind and are quickly overpowered. Heading upwind is even worse. Reefing the genoa is pointless. Once furled, it looses all shape. So if the winds are up and on our nose, for now, we’re motoring. So we decided, well, let’s just go on the inside harbor and we’ll zoom in close to Navy Pier and be able to see all the old places we used to be at on shore, and, well shoot, let’s go stop at Oak Street Beach and we haven’t tested our anchor yet, so now here we are. We’re gonna anchor out right in the heart of downtown Chicago tonight, on a whim, to test out our anchor. I wanted to make sure we could test it in decent conditions so we know what we were doing when we were on the river and we needed to anchor and we’ve got four knots of current pulling us backwards and we’re struggling to figure it out. And it was good ’cause using our anchor bridle, I screwed it up like three times in a row. Hopefully now we’ve kind of worked out the kinks. So, we have the million-dollar Chicago view right now, right in the heart of downtown. ♪ I need a sign or a signal ♪ ♪ I’ve overthought everything ♪ ♪ I can think of ♪ ♪ I need the coat and your jacket ♪ ♪ And the remnants of your cigarette packet ♪ ♪ Yeah, yeah, yeah ♪ ♪ Yeah, yeah, yeah ♪ ♪ Yeah, yeah ♪

[Lauren] What, tonight?

[Kirk] Yeah.

Cruisin’ in to the beach. Kirk thinks we’re gonna sink. Actually, I do too. Look at this dinghy.

[Kirk] All right, right there.

[Lauren] It’s our pier.

[Kirk] Grab it.

[Lauren] Mmm. Look at this thing. Looks like a fork for a giant. Kirk, it’s our last meal.

[Kirk] It’s our last meal? Why?

Our last downtown Chicago, fancy, juice bar, everything’s, you know, foo-foo organic meal.

[Kirk] That may be true.

I mean, who knows. I think we’re being a little bit fatalistic.

[Kirk] Hopefully.

I’m hoping our bar is set so low and we’ll be surprised.

Quite the view this morning, huh?

[Lauren] Mmm.

Wow, it’s pretty nice.

All right, good enough.

[Kirk] Probably gonna get sprayed again. All right, you ready? I hope this is really what we want to do.

We only had 12 miles left before leaving the Great Lakes for the river. We desperately wanted to sail one last time. Unfortunately, the winds had not faded overnight, we still had 20 to 25 knots almost on the nose, and after seeing how badly the genoa performed upwind the day before, we decided we definitely need a new headsail soon.

[Lauren] Okay.

[Kirk] All right, I’m ready. Are you?

[Lauren] Yeah.

[Kirk] All right. Here it comes.

Are we?


[Lauren] Is it really?

Yeah. I think. I think it said 125 feet. Okay, so that was train one. There’s a barge coming through. Oh, we’re gonna do we’re gonna gonna start to understand radio speak better, I hope. ♪ I need a sign or a signal ♪ ♪ The remnants of your cigarette packet ♪

[Lauren] How the whole house is lifting up, too. ♪ Yeah, yeah, yeah ♪

[Lauren] Yeah.

[Kirk] Skyway Yacht Works.

[Lauren] So that’s the end of our time in the Great Lakes. Now we start a new adventure as we ready our boat for a 1,300-mile journey down the river to the Gulf of Mexico. Test, rolling. All right, what are we talking about? We originally planned to talk about finances in the video you just watched, like how much our boat really cost and how much we spent making upgrades before leaving the dock to go cruising. We realized we had way too much we wanted to tell you for a short segment, so it’s all coming up in our next episode.