So the time is starting to go quickly and now we're working out the details of the trip. So far, we've got Rome & Tuscany figured out:

Arrive in Rome mid-day on Friday, check into the hotel and freshen up a bit.
We'll head off to see the Colosseum, Roman Forum, Palatine Hill before settling down for some dinner with a walk by the Trevi Fountain on the way back to the hotel for the night (and don't tell EDP, but there will be several gelato breaks along the way)
Saturday, we're getting up nice & early to go to the Vatican where we will be see the best sights, compliments of a tour guide (thanks for the tip, Katy.)
After that, we're going to fit in the Pantheon and the Capuchin crypt and maybe the Spanish Steps
Sunday, we'll see anything we didn't manage to fit in or discovered while we were there before boarding a train and heading to our Tuscan villa
Once there, we'll be enjoying a four-course dinner and wandering around the vineyard and Monday will include a winery tour!

After that, it's off to Florence!