12 day itinerary
Buongiorno,
looks like a well planned circular itinerary.
Remember to book your tickets for Pisa in advance if you want to climb to the tower.
Lucca is a lovely town to spend a day in, and you may even want to see about fitting in the Villa Reale, which in may comes alive with one of the most famous flower gardens in Tuscany.
https://www.discovertuscany.com/lucca/villa-reale-marlia-near-lucca.html
When you pick up your car in Florence, plan on a leisurely drive down to
Arezzo before heading over to your accommodations in Cortona. I suggest you take this itinerary along the via Setteponti, which will give you some lovely scenery, light on the traffic, no toll roads and great places to stop along the way.
https://www.discovertuscany.com/itineraries-in-tuscany/setteponti-in-valdarno.html
This itin ends in Arezzo which is becoming more and more popular with Italian and foreign tourists looking for an important piece of history and monuments as well as a real slice of Tuscany.
Cortona will definitely merit a full day of exploration (see our
quick guide) and then there are a few other places nearby which you can entertain for a day trip. Check out this link for a few suggestions in Val di Chiana near Cortona:
https://www.discovertuscany.com/val-di-chiana/
Siena is great - a beautiful contrast to Florence which is busy and jam-packed with something from all epochs of time from the Etruscans to today. In fact, Siena, is a little easy on the tourist, especially at night when the city seems to empty out just a bit. Definitely make a point of visiting the
Duomo and the Museum in front of the Duomo. Closeby you could even join a lovely
wine experience which I did, both the scenery and the wine were incredible.
Volterra is another one of those fabulous little towns that are amazing to visit yet still manages to maintain a distinctly Tuscan feel about it.
Buon viaggio,
Donna Denise