I have been on this site for awhile and missed this particular thread. I keep my boat in Kenosha at Southport. Recommend the following in Ktown, Chops (steak, seafood, live entertainmant) WineKnot good food, wine etc..
Villa Dicarlo italian, Pazzo's for late night new place opening soon Kaiser's pizza,.
You can dock at the Marina they have some transients
Racine love Waves, Saloto's, Chartroom, there is also a bar restaurant at Reefpoint. You can pull into reefpoint, go up the river or pull in the basin near the public launch.
As for places to anchor just soout of Racine is the "boaters beach" inside the breakwall with sandbar.
John S