I saw the 27 comments in the other post I made and I am really grateful for all the help. Here is my final Italy itinerary. You will notice large sections of my trip to Rome are devoted to just being in the neighborhoods.
August 7th: Milan
Arrive at 10
10-12 Rest, Check-in, Eat.
12-3 Duomo and its museum
4-5 Sforza Castle
5-6 Brera Art Galllery
6-8 Hang out at the Galleria VE
Nightlife: Still don't know about Milan nighlife
August 8th: Florence
10-12 Get situated.
12-2 Wander Florence
2-3 Duomo, and its Museum
4-5 Michaelangelo's House
5-7 Santa Croce
7-12 Walk around, look for a restaurant. Nightlife in Florence suggestions?
August 9th Florence
9-10 Accademia (Reservations made)
10-11 Medici Chapels
11-12 Museum of San Marco
12-2:30 Lunch, Wander, finish what I couldn't from Morning
2:30-4:30 Uffizi (Reservations made)
5-7 Science Museum, Pitti Palace
7-12, See previous day. Really need help with Florence nightlife.
August 10th Rome
12-7 Ancient Rome
7-9 Jewish Ghetto and Tiber Island
9-12 Nightlife: Night Walk Across Rome
August 11th Rome
7-8 Aventine Hill
Nightlife: Monte Testaccio
August 12th Rome
12-1 National Museum
1-3 Wander Campo de Fiori
3-7 Wander Navona, Castel St. Angelo, Pantheon