I was there 3 weeks ago and posted this in another thread. Milwaukee is awesome!
Some recommendations in the Fiserv area:
-There are a ton of bars in the block east of the arena (old Third Street). Water Street is across the river another block or two east. These bars were all pretty packed and more of the college aged crowd, but a lot of fun and super close.
-Good City Brewing has a location adjacent to Fiserv. They had some excellent beer, and it will probably be a nut house during the games. The Drink Wisconsinably Pub is next door as well.
-Safehouse/Newsroom are a fun pair of bars just off the Riverwalk. Safehouse has a speakeasy theme where you have to play along with the secret password deal to head in. Newsroom is a more normal set up, but cool bar too.
Away from downtown a little
-Brady Street is a cheap cab ride away and I had more fun as a 30 something in this neighborhood. Roman Coin and Wolski's were my favorite bars up here, and the most fun spots we visited that weekend.
-Absolutely do the Lakefront Brewery tour. You could have a great Friday taking the earliest tour of Lakefront, and then walk across the bridge to Brady Street with a nice little buzz. Grab a sandwich for lunch at Glorioso's and bar hop until you're ready to head to the arena.
For Bloody Mary's:
-The Third Ward (just south of downtown) had some really good ones. Cafe Benelux and Wicked Hop (across the street from each other) were my favorites. Both places had very good food too.
-Sobelman's is a little overrated, IMO. Pretty decent bar and worth a stop if it's convenient.
-Steny's was really good, and they had great bar food to boot. Would be an awesome place to watch some of the other games.
Public Market
-Kind of a big indoor market with lots of cool little places. Will be absolutely packed on Saturday AM, so might be a better Friday stop. You can sit at the bar of the St Paul Fish Market and order oysters and Schlitz. I recommend doing this, especially if your wife wants to shop at the little stands in the market.