A Defining Moment – Reaching Chicago!

Gypsies Palace entering Chicago
Gypsies Palace Entering Chicago

As we have gone along on our Great Loop journey a defining moment seemed to be reaching Chicago. We would have completed the Lake Michigan phase our trip and Chicago was the gateway to the inland rivers. Chicago was beckoning us to explore and stay before we would begin the inland river route which we had really not even figured out. We had a long list of things that we wanted to do in Chicago. We docked right by Navy Pier at DuSable Marina. We were close to everything and decided that we needed to stay 6 days especially since the weather was going to be perfect – sunny and in the 70’s. Chicago Navy Pier

Naturally, lots of Looper boats were also there, but everyone was so busy sight seeing that we rarely saw anyone until the end of our stay. What we loved about the city is that people were out jogging, biking and walking – a positive energy. The dogs were fascinated by all the dogs and people. But, it was not a feeling of frenzy like New York City. Chicago just envelopes you in friendliness and a welcoming atmosphere.

We had food at the top of our list – Portillo’s Hot Dogs and Gino’s Pizza. Chicago PizzaWe also had to get to Al’s Italian Beef before we left! I had been yearning for Gino’s Pizza, but we actually found another that we liked even better at Labriola the night we went to a Blues Club.   We just stumbled on the place as we were walking.   We wanted to experience the blues in Chicago and found a club called Blue Chicago. It was just what I pictured in my mind – small, intimate, no food, great band and everyone enjoying the vibe. My only disappointment is that we were pretty pooped from the day and couldn’t stay for a 2nd set.Blue Chicago

Those of you that know me that I tend to cram as much into a day as possible and in Chicago I got my wish. Steve even kept up as he didn’t want to miss out on a thing.   As we pulled into the marina another Looper gave us a good piece of advice to check out Groupon for tourist deals.   They had also taken a Segway Tour with their Groupon and highly recommended it.   They had never done it before and neither had we or One Eye Dog. So, the four of us were in for the adventure. It was the best experience!!   Steve took his Go Pro and put together a cute video of us. We then “paid it forward” by suggesting this to other Loopers as they came in. They also loved it!!Chicago Segway 

When I said that we did a lot we took advantage of the following: Jazzin’ at the Shedd (Aquarium), Hop On Hop Off Bus Tour, Field Museum, Museum of Science & Industry, Navy Pier, Architectural Boat Tour and walked around to see “The Bean”. Boy, we saw it all!   Our favorite was the Museum of Science & Industry. I remember going there as a child and the coal mine ride is still my favorite. I even found time to get the “boys” to the dog park so that they could have some fun.

Chcago Night SkylineOn our last night Steve invited all of the Loopers that were around to our own “boat tour” for a night time ride to see Chicago at night from the water. That was a treat for everyone, plus they had never ridden on a catamaran before. Quite a Doctktail event!




Chicago Lift BridgeMost Loopers leave Chicago through the city traveling under numerous bridges; however, our height would not allow this route.   We had to by-pass downtown through the Cal-Sag canal. Our only “hold your breath” moment was one fixed railroad bridge. We had to clear 19 ft. 7 inches. When you read about the Great Loop this restriction is clearly pointed out before you begin the trip. This obstacle had been on our mind since we left on the Loop as the water table could be up and we might not be able to clear the bridge.   To prepare we knew that we would take down the satellite dish, which got us down to 18 ft. 5 inches. Steve did the measurement several times.   Plus, we made sure that the fuel tanks and water tanks were full.   We had the measuring pole out at the front of the boat. The reality is that even though the Great Lakes were high this year, the rivers have been down, but you never know.   My head was throbbing as we got close and Steve was tense along with The One Eye Dog who were behind us. We approached slowly and lo and behold we had about a foot or more clearance!   I will say that it was quite a release once we got under it. We had no idea what we would have done, but we really thought that we were okay.   And, don’t you know we went under another bridge where the fit was tighter for some reason and cleared by inches not feet! Chicago Bridge

We are now going inland to continue down the Illinois, Mississippi, Ohio, Cumberland and Tennessee Rivers. Who knows what we will experience?   Frankly, we are getting so relaxed about traveling that we haven’t really looked ahead too far.   We just know that Chicago was a blast!

Columbia Yacht Club
Dinner at the Columbia Yacht Club


4 thoughts on “A Defining Moment – Reaching Chicago!

  • October 8, 2017 at 11:37 pm

    I love it when I can sit down for a few minutes and catch up on your blogs 🙂 Miss you guys! XOXO

  • October 8, 2017 at 11:59 pm

    Dear Deb,
    I have been so impressed with your ability to beautifully describe your travels bringing us along with you, feeling as if we were on the Gypsies Palace during this amazing journey.
    Thank You for letting us join you, I wish your days ahead are filled with smooth waters and clear sky’s .


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