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Considering its reputation as a working-class city in the Midwest, Milwaukee is not what I expected. The downtown area is surprisingly walkable...more so than most comparable sized cities. The first few times I came to Milwaukee I stayed downtown. If you stay downtown, you do not need a car. There are a lot of nice hotels downtown and a great gym too. The YMCA downtown is FILLED with hot college guys (Marquette University is downtown in Milwaukee) and the equipment is very nice as well. It is one of the nicer YMCA facilities I have been to. In the complex with the YMCA there are also a lot of meal options as well (including one of my favorite sandwich shops - Potbelly Sandwich Works).
The last few times I have been to Milwaukee I have stayed about 8 minutes north of downtown. I prefer this location now because it is close to Bayshore Mall. Bayshore Mall is an outdoor mall with a lot of great food options. This is also the location of the Milwaukee LA Fitness. Although this gym is never packed, it has great equipment and the facility is very nice as well. There are also a lot of very hot straight guys at this gym....so the eye candy is great as well. There is also a bd's Mongolian BBQ, CPK, and a Cheesecake Factory at this mall....so food options are plentiful.
Now for the picture at the top of this post. The Milwaukee Art Museum sits on Lake Michigan. It is architecturally stunning. It is definitely not what you would expect in this working-class Midwestern town.