On a weekday when the wind is out of the southwest, trailer to Lloyd Park Launch in Winnetka. Cruise from there down the lake shore to the area of Navy Pier. Find a place to leave your boat secure for a couple of hours. Take the guided architectural tour of Chicago by river. Great experience. Take time to walk and enjoy Navy Pier. Back to your boat and head north. Hang out in the breakwater areas of Ohio or Oak Street beaches. Then cruise back up to Winnetka. Trailer the boat and head home from a full day on Lake Michigan.