Rome. Tuscany. Florence. Venice.
Still in Planning:
Approximately 12+ Days. Not too sure about airfare just yet as I'll be using my AAmiles (30k each way): Flying into Rome, Leaving from Venice airport.
Rome: Collosseum, Vatican City
Tuscany: Food, Old Architecture
Venice: Lido Beach (Temperature is around the 60s)
This will be a budget friendly trip so $/night will be close to $50 for hotels. Travel via mass transit.