A few months ago we went to Fresco ( www.frescomadison.com ), serving contemporary American cuisine on the rooftop of the Museum for Contemporary Art (next to their sculpture garden), and it was wonderful. It would be the perfect place for Valentine's Day, if you can still get a reservation there. Don't miss the beignets for dessert! I posted a detailed report on my meal in the discussion at http://chowhound.chow.com/topics/462929
In addition to that topic, you might also check the other Madison discussions at
However, at this point in time, especially with Valentine's Day on a Saturday night, you may need to take what you can get. Many places are already fully booked, and others are filling up fast!