3 choices
As I see it you are going to end up in Port Washington, Milwaukee, or Racine. If I were you, I would do Port W. Good marina - reasonable rates - great town! You can easily walk to many restaurants and bars though groceries is another matter. Groceries are even harder to come by in Mil and Racine when on foot. If you decide Racine , go to the yacht club in the north area of the harbor. Enter the club from the channel. DO NOT approach the docks from the north. If you draw over 6 ft go to Reefpoint in Racine.Milwaukee is actually 2 ports. McKinley Marina is on the north end and is next door to MYC. If you belong to a YC, then MYC has some things to offer. The other choice is South Shore YC. Great place w/ restaraunts and bars in walking distance. The actual club house has good food and a very nice bar. You need to be a YC member to dock. Rates at SSYC are VERY reasonable. Sheboygan would be a longer trip for you, but certainly in the realm of poosibilities. Again, groceries are not easily available. Two places to stay. SYC docks are not the best, but the club is one of the best on the lake (only behind Racine YC) Skipper Bud runs a huge marina. If you want a pool, hot tub, floating docks, etc. do Harbor Point Marina (Skipper Bud). It ain't cheap. My 34 cost me $55 for one night.