Anniversary Trip to Tuscany

Get the Rick Steves Florence and Tuscany guidebook. It will be very helpful.

Hello Silvia,

If you really want to see many small towns in Tuscany renting a car is probably a necessity. May of the smaller towns are not well served by public transportation so it is harder to visit many of them without a car. You might look and see what you're interested in and maybe do a "train" half of your trip - Lucca, Pisa, Siena, Arezzo are all reasonable by train and then a car half where places like Pienza, Volterra, Montepulciano and Montalcino are on the plan.

I would suggest choosing two or three bases and exploring the area around each one. Search the many "best towns in Tuscany" guides and decide what your tolerance for daily driving is and see what's close enough to string together several cities and choose some bases at which to stay. I spent a week outside Castellina in Chianti which is between Siena, San Gimignano and Florence and many smaller towns were within reach for this area. If you really want nonstop small Tuscan towns I would suggest one more northern and one more southern.

If you plan to rent a car brush up on ZTLs and when approaching towns take the suggested "Park Here" outside the towns and don't assume you'll do better closer to or inside the town. And get an international drivers license.

Pisa and Florence are the closest airports but Rome and Milan - the big international ones - can work just leave some time on the ends for airport logistics. You can rent a car many places but popular choices are from the Florence airport (just outside the city) or from Orvieto or Chuisi training up from Rome in the south.

Check on festivals and sagras that might happening and plan accordingly. Also be sure to schedule enough down time and get into the easy flow of Tuscan countryside life. It is as beautiful as advertised so be sure you're soaking it in and not scheduling every day.

Have an amazing trip,
=Tod

If you have 15 days to spend in Tuscany, you should have lot of choice about how to use those. To pick which airport to fly to, I would check Google Flights and see what the difference in price/schedule is for various airport in the area. As mentioned already, Florence airport is the closest but not always the cheapest to fly into. You can also look at Pisa, which is in the area, but also Milan and Rome and see if they're worth saving money to use. Trains are fast and easy to use from both cities to get you to where you want to start.

I'd give a few days each to Florence and Lucca, using them as a base with trains to explore other towns (Pisa, Arezzo, etc). The exact number of days depends on how you like to travel. In 2021 I picked up a rental car at the Pisa airport and spent about 9 days driving around Tuscany. You really need a car to see Tuscany properly, since a lot of the most beautiful parts are the drives between towns. I made my bases in Volterra (day trip to San Gimignano), Siena (did RS Tuscany drive) and Montepulciano (did day trips to Pienza, Montalcino, Bagno Vignoli). It was not hard to find places to stay that were outside or very close to the edge of the ZTL so I didn't have to worry about getting fines. I was continuing on farther south from there, but if that was the end of your trip you could return your car at whichever airport you wanted to fly out of (Florence, Rome, Pisa, etc).