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It's a nice day trip. A number of good river front restaurant options. My favorite is Water Buffalo.
McKinley Marina on the north side and South Milwaukee Yacht Club are both viable launch options. Note: SMYC ramp is not protected from breakers if wind is out of south or southeast (unusual conditions but a real bitch to recover if you get caught in it - ask me how I know ) http://county.milwaukee.gov/BoatingampMcKinleyMa9139.htm http://www.smyc.net
The Milwaukee harbor inside the break walls is quite large. I believe there are some activity restrictions, can't remember for sure, check rules before you get out there. Harbor is patrolled.
Many days you can go out in the big lake, wave conditions vary greatly - from glass to perilous, so check forecasts and use your judgment. Note: Lake Michigan conditions can change quickly...use caution if you don't have experience on it (and use caution if you do ).
You can make a great day of it. If you come during Summerfest you can catch a concert from the water, also! http://www.summerfest.com