With all the above information, how would you design a trip? My plan was to spend about 5 nights in an agriturismo just outside of Florence (maybe max 30-50 minutes). During the days we would spend 2 days visiting Florence, 1 day Siena, 1 day Lucca, 1 day Volterra/San Gimignano.
Two years ago my wife and I did just what you are thinking about. We were also celebrating an anniversary. We were celebrating our first kiss which we shared in Florence, in 1966! 50 years later we shared another kiss in Florence.
Here's our itinerary, given as an example:
We flew into Rome FCO because we could get the best airline ticket prices. We picked up our Hertz rental at the airport. I bought a card for my Garmin that has maps of Italy and Greece. Before we went, I saved a number of addresses, including the address of our agriturismo. As soon as we picked up the rental car, we set up the Garmin, pulled up the saved address and were taken on a wonderful drive to our destination.
We stayed at Castello di Verrazzano, which is 5 minutes north of Greve and 35 minutes south of Florence. It is a great winery and there is a farmhouse complex just down the hill from the castle and winery that they use for their agriturismo. After checking in, we rode down to the charming town of Greve, looked at the Christmas fair (we went in December) and had a great dinner at La Cantina.
We figured we'd be tired, so for our first full day on the ground we took a tour of the winery of Castello di Verrazzano, along with a food and wine tasting. Our tour started at 11:00 and we sat down for the tasting at 12:30. We didn't leave until 4:00! It was an amazing meal. Luckily we were staying on the property because they were generous with their wine!
Day 2 we drove down to Greve and parked in the free public lot. We caught the 6:45 bus to Florence, which is a 35-40 minute ride. Everyone else on the bus were locals commuting to work. Once in Florence, we took the Walks of Italy Best of Florence tour. We saw the Duomo and David in the morning, along with a great walking tour of the heart of Florence. In the afternoon we took a Walks of Italy tour of the Uffizi. We took a late bus back to Greve.
Day 3 was a Tuscan ramble south of Greve, including the charming towns of Radda and Gaiole. We ended up at the Abbey of Monte Oliveto mid afternoon. After taking a tour of the Abbey, we had dinner at the adjoining restaurant. Our host spoke no English, but by using our extremely limited Italian and pointing at the menu, we were able to order a wonderful dinner. We returned to the Abbey for Vespers celebrating in Gregorian Chant. There were the monks, one woman from a nearby village and us. We were invited to sit with the monks and were shown the responses where we could participate. It was a very moving experience!
Day 4 had us head southwest to Siena, passing through Castellina on the way. Siena is very different from Florence and we had a wonderful time!
Day 5 was a great drive to San Gimignano and Volterra. We started with San Gimignano in the morning and spent the afternoon and evening in Volterra. We had planned to leave late afternoon, but we went outside the walls to the town's promenade. The sunset on the town was spectacular and we stayed to watch it. I photographed until dark and came back with one of best photos from the trip.
Day 6 had us say goodbye to Tuscany and drive back to Rome. We had and early flight and decided to stay at the FCO Hilton. We checked in and I returned the rental car. We then took the free hotel shuttle into Rome. We took the Walks of Italy evening stroll and had a wonderful time. It was the last Saturday before Christmas and all the locals were out shopping. It was crowded, but everyone was in a festive mood!