The night before we left Racine, Wisconsin for Chicago we had docktails with some other Loopers. Turns out Kim, on Sand Dollar a 43’ Mainship, gets up and runs at dawn. So we got this picture of us leaving Racine harbour – there were already lots of people out fishing for salmon on the break wall:

Our trip to Chicago was pretty good – first couple hours were perfectly smooth, next couple were reasonable with 1 – 2 foot waves, and then the final 2 hours were 3 – 4′ almost directly on the bow so lots of up and down. What was equally annoying about those final couple hours was the City was RIGHT there …. seemed we made no progress at all with the Chicago skyline within reach for 2 hours!


There is an outer break wall that people said watch out for as it’s really close to the water line. It was…. so it provided little or no protection for the harbour. There was a second inner breakwall for marinas, including the one we stayed at – DuSable. They put us in a 70’ slip, we could have fit in sideways! Great location, right downtown with the river beside us, the Chicago Riverwalk right there as we step off the pier, Magnificent Mile 15 minutes away, and the Navy Pier 10 minutes away.

First night we took the Architectural boat tour at dusk – led by a volunteer from the Architectural Society so she knew her stuff. Tour was terrific, lots of history about the buildings – we figured this would make our own trip down the river more meaningful if we knew what we were passing. Great to do it at dusk as the city lit up as the tour progressed:
Next day more sightseeing and another highlight! Catching up with Wayne’s cousin Jennifer and her husband Anthony. They arrived in time for a drink on the boat before dinner bearing traditional boating / Chicago gifts. The champagne was NOT wasted against the hull of our boat…. and the Chicago mix popcorn lasted maybe a day.


We had a dinner reservation at Siena Tavern (Italian Chef Fabio Viviani of tv fame on Top Chef reality cooking show co-owns it), but missed the reservation as Wayne and Jennifer prioritized cocktails over food! So we set out for the alternative and the walk there took us by the Siena Tavern. Wayne and Jennifer walked in on the slim chance we could get a table, and it worked! Dinner was delicious, lived up to the reputation for wonderful salads, pasta, wine and dessert!
But wait, we’re not done yet! Off for a nightcap at the Signature Room on the 95th of the John Hancock building, for one of the best views of the city at night!


And then the quality of the picture taking deteriorated slightly for our walk back to the boat but I did promise to include this Trump tower photo for Jennifer’s sister Julie:
Anyway, wonderful visit with Jennifer and Anthony; especially appreciate their planning for a night on the town that we would otherwise have missed.
Next day Wayne snoozed a fair bit! but more touring around and then a wonderful Labour Day fireworks display Sunday night right at the end of the pier by the lock. A bit of boat prep – had to take down our mast so we could clear the bridges.

We got up early for an 0700 departure for our own river cruise – a bit choppy getting to the lock, and we are locking through with 2 other boaters, both Loopers, both boats called Breakaway, we assumed they were related but nope, just an odd coincidence. First of our river locks, and learn to wear gloves as this lock was simple – hang onto their (slimy) line.



River cruise – fabulous! LOVED Chicago!
Take a trip to Chicago sometime everyone! Illinois River here we come….XO B&W
















































































































