L.S.
We took a great "first" family vacation with our 2-1/2 year old to Milwaukee. Sounds boring at first, but there are actually a lot of fun things to do with a toddler there. We stayed at the Hilton Milwaukee City Center (has an indoor waterpark that's just the right size for younger kids). There is a children's museum (Betty Brinn children's musuem) and lots of playgrounds. If you go when the weather's a bit warmer, there are nice beaches and even a sprinkler/splash park in the area. Do some research ... it was a memorable family trip.