To Chicago and Back

On Friday, my brother and I sailed from Waukegan to Chicago. We had to motor for about 2/3rds of the way since the wind was right on the “nose”. We were able to sail the last 3rd of the trip on our way to Belmont Harbor.
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(Motoring into the wind and waves)

Even motoring it took about 8 hours to go 27.5 miles because the wind and waves were against us.

(Hello Chicago)

I had called to make a slip reservation on the Monday before we left, but when we arrived (about 7:15 pm) there was a motor boat in the slip that was assigned to us (D08) so I pulled into the next empty slip. I went to the Harbor Master to let them know about the issue and after a half hour of checking this and checking that and confirming D08 was my slip, but no one was onboard the boat in D08 to move it, they assigned me to slip E29. When we got to E29….yep there was another boat in that slip. They were onboard and said that E29 was theirs and they have been there all season. So we pulled into the next empty slip (E26). Another trip to the Harbor Master found the office closed (by now it was after 8:00pm), but I found one of the staff who brought me into the office. The girl who reassigned me to slip E29 must be dyslexic, because she wrote E29, but meant E26.

On Saturday, my wife, brother, and a friend and I sailed the Chicago lake front and got to see the Chicago to Mackinac racers start the race. It was pretty cool seeing a forest of sails as hundreds of sailboats where across the horizon. Shortly after putting the sails up and turning the motor off we had to turn the motor back on to maneuver out of the way of the racers. They all turned west right out of the “gate” to head up the west coast right passed Belmont Harbor.

(Chicago to Mackinac Racers)


(more Chicago to Mackinac Racers)

Sailing the Chicago lake front inside the breakwater is always enjoyable and picturesque, if not crowed with a lot of wave action and little wind. Once we got south of the breakwater the wind picked up nicely and were able to sail ~ 4 knots.




I had planned to sail as far south as the new 31st street harbor, but as we got close and I had gone below to get a drink, I smelled fuel. Checking the engine compartment I saw a fuel line slowly dripping fuel. It was a simple and fast fix to tighten the fitting, but when I came back on deck and looked overboard I could see the bottom of the lake. We had gone a bit further south than planned and were in very shallow and rocky water (Morgan Shoal). We immediately came about to head back the way we came in and did touch bottom briefly during the turn.

(We sailed a little too far south)

After that little excitement we sailed back inside the breakwater area where the wind died down again. We enjoyed the view some more and then tacked to head outside the breakwater to find some wind. Once outside the breakwater the wind picked back up and we sailed back to Belmont Harbor.


It was a very nice day.

One Sunday my brother and I sailed back to Waukegan with much more favorable winds that the trip down. We were on a beam reach for the first 1/3rd of the trip and a broad reach the rest of the trip (except for the last 2 miles when the wind was at our backs and we sailed wing and wing). The return trip only took about 6 hours.

Along the way we did a couple small projects including installing the new lifeline covers I bought on eBay. They are designed to go over a “pool noodle” and provide much needed comfort when leaning against the lifelines.

(Goodbye Chicago)


(Sailing comfortably on a broad reach)


(Bro relaxing on the foredeck)


(Sailing wing and wing)