A Stay in Chicago

A Stay in Chicago

October 13–15, 2022: Do It Now‘s Great Loop Adventure begins with a 2-night stay in Chicago.


(continued from Do It Now Gets On the Loop.)

I’m very far behind in writing up my trip so far, but I’ll do my best to catch up over the next few days. (I’m not sure if I’ll ever be able to catch up on the trip I took with Captain John this past spring, but who knows?)

We spent two nights at DuSable Marina in downtown Chicago — just enough to give my crewmate Janet a taste of a tiny portion of that city, including, of course, pizza.

Day 1: Arrival Day

We left the boat right after arrival, heading into the city on something called Riverwalk. As the name suggests, it hugs the side of the Chicago river, with a series of paved walkways and small parks and a handful of what may have been shops. Trouble is, just about anything that had food — which is what we were in search of — was closed. I think my pups enjoyed the walk a heck of a lot more than we did.


Here are Janet and Rosie on the Michigan Avenue Bridge. My pups were really weirded out (at first) by the number of people and cars in the city.

Eventually, we gave up on Riverwalk and climbed up to the Michigan Avenue bridge, which crosses the Chicago River. I really longed to go for a walk up the Avenue to at least as far as Water Tower, which I glimpsed in the distance. In the beginning of my second career, where I wrote how-to books and articles and did computer training, I’d been flown out to Chicago a bunch of times on training gigs and stayed in the hotel across the street from Water Tower. It held fond memories for me and I wanted to see how much of it I remembered after 20+ years. But Janet had confessed to a sort of distain for cities and we were both hungry so I passed up the opportunity in our continued search for food. We wound up at a trendy little deli kind of place called Foxtrot that had a handful of sandwich or salad meals they prepared to go. We ordered crazy expensive sandwiches and ate them outside in a dining area. It was chilly, so we didn’t stay long. At least the food was interesting and good. A little bird sat on the table with us, hoping for crumbs.

Afterwards, we tried to walk back to the boat on the opposite side of the river as Riverwalk, just for a change of scenery. It was a mistake that got us into dead ends twice. We eventually backtracked and crossed the river at the Columbus Drive bridge, descended down to Riverwalk, and made our way back.


While I don’t need a dinghy imported from Australia, I do like the dingy davits mounted on Pony‘s swim platform.

Sometime either before or after we’d left the boat, we’d met the folks in the Ranger Tug R-31 next to mine, Kim and Ted in Pony. I was especially impressed with their dingy setup, which I took a photo of for reference. I had invited them for docktails — their first ever and my first on my own boat. I left the time open, which may have been a mistake. They arrived about 20 minutes before our Instant Pot dinner was done. We crowded around the table, which I hadn’t had time to properly clear, and Janet, Ted, and I split a bottle of champagne that I’d brought along to celebrate getting on the Loop. We learned a lot about each other and hit it off. We even exchanged boat cards — the first time I’d given one out.

We ate dinner after they left. The Instant Pot had finished cooking and kept our dinner warm for 45 minutes.

Day 2: Full Day in Chicago

The only full day of our stay in Chicago was spent mostly at the Navy Pier, which I’d never been to. It’s a tourist attraction with restaurants, bars, and shops, all indoors. We went to Giordano’s for pizza, ordered our food, left my number, and wandered around the shops until they called that our table was ready. We didn’t buy anything. We went to lunch; it came quickly — we’d ordered it 40 minutes before — and was delicious. We even had some leftovers to take back to the boat.


Now this is a Chicago pizza.

We felt as if we were done with the place so we walked back to the boat. It was extremely windy and the walk wasn’t particularly pleasant. Crossing over the bridge, I got a chance to take a photo back out toward the lake and the lock we’d drive through the next day. (It wasn’t until much later that I learned we’d only seen about one quarter of what the Navy Pier had to offer. Duh-oh!)


Here’s a shot from the Lakeshore Drive Bridge, looking out toward Lake Michigan and the Chicago River Lock. There were a lot of tour boats out that Friday afternoon.


Here’s the first mark for 25 feet of anchor chain. I took this photo when the paint was dry.

We spent the afternoon marking my anchor chain and rode. I’d decided on a color-code for the marks: red, white, blue, gold, with markings every 25 feet. So the 25 foot mark would be red, the 50 foot mark would be white, the 75 foot mark would be blue, and the 100 foot mark would be gold, with the colors cycling through every 100 feet. The idea is to be able to tell as you release the anchor chain/rode how much is out. (It matters more than a lot of non-boaters think.) I had already bought the cans of oil-based spray paint with the idea of doing it myself back in Olympia, but it is definitely a two-person job.

The trick is getting all the anchor chain and rode laid out on a dock surface — that’s what takes two people. One has to operate the windlass while the other walks off with the anchor, dragging the chain behind. Guess what part I did? No, the anchor. The marina was huge but mostly deserted that time of the year and we were able to lay it all out without bothering anyone. We then applied the appropriate spray paints, protecting the dock beneath them with bags or boxes from the trash. It took quite a while. And then we had to keep it all out until the paint dried.

While the paint dried, we went up to hose out the now empty anchor locker. The trouble is, the water wouldn’t drain out — the drain hole was clogged with tiny pine needles that the previous owner had managed to drag in. We tried all kinds of things to clear it and did not succeed. A neighbor came by and asked if we’d tried a high pressure hose; I told him we had using the spray nozzle. He came back a while later with a special high-pressure attachment. I put it on the hose, put it against the drain, turned on the water, and wham! The debris shot out and the locker drained. I cleaned up what was left with a rag.

Much later, we put everything away. The paint was “dry enough.” The windlass gave us some trouble pulling in the rode, but had no trouble with the chain. I know that replacing the 50-foot length of chain with 150 feet is in my future. The total, by the way, of chain and rode is nearly 300 feet.


Here’s an after sunset view down our pier at DuSable Harbor. Pony is the first boat on the right; Do It Now is right beyond it. Short walk!

Day 3: Departure Day

We were kind of surprised to notice that Kim and Ted had not left the marina on Saturday as they’d originally planned. They told us they’d decided to stay an extra day and asked whether we wanted to buddy boat with them down to the town wall in Joilet. I was game for that so we planned on a departure time. I told them I needed to pump out my waste tank before departing and would leave 30 minutes before them to get to the pompous dock.

That was the plan we made on Saturday. On Sunday morning, Janet and I were up early and decided to take a walk to a Mariano’s Market, which was near the marina. It was about a half mile away. It was a nice supermarket, slightly upscale, with two floors and giant elevators to take your shopping cart up and down. We bought a few food items although we were unable to buy the alcoholic beverages we’d put in our cart because neither of us had ID. (Seriously, Illinois? Anyone who mistakes me for someone under 21 needs eye surgery.)

Back at the boat, we filled the water tank and prepared to leave. Kim and Ted stood by to help us push off; there was some wind but not nearly as much as the two previous days. I backed out into the fairway without incident and made my way to the pump-out dock deeper into the marina. I turned around in the channel and pulled up next to the pump-out. Janet handled the starboard tie.

We were the only ones there and parked in the middle of the dock, closest to the hose. Of course someone came before we were done. It was a huge sailboat and although we moved up for him, I really thought he’d hit us with his bow. I finished up as quickly as I could, seeing Pony up in the channel ahead of us.

And then, we were done and casting off and heading out of the marina to catch up with Pony for our trip down the Chicago River, Sanitary Canal, and Illinois River to Joliet.

But that’s for another blog post.

(continued in Chicago to Joliet, IL.)

2 Comments

    • I left Washington the day after Thanksgiving. We’ve been cruising since Monday. 153 miles so far. Started in Alton near St. Louis. We’re now in an anchorage near Cape Girardeau, MO. We’ll have another anchorage tomorrow before we finally get to a marina with fuel on Friday.

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