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How to use 3 nights in Tuscany, late March 2026

My spouse and I, travelling with our two first-year college students and subject to their spring break schedules, will be in Italy for ten nights in late March. The current plan is four nights in Rome, three nights in Tuscany with a car, and three nights in Florence.

On the day we leave Rome, we will rent a car and drive north, stopping en route to one or two towns. On the fourth day in Tuscany, we head into Florence and return the car. (We would return it at the Florence train station, and lodge nearby so that three days later we could easily walk to catch the train and the connection to the Milan airport.)

Here are some options we're considering for the time in Tuscany, and we would appreciate thoughts on these ideas and/or suggestions for other possibilities.

Option 1: Spend three nights in Siena with two day trips. If so, what day trips? This seems more relaxing, but maybe there would be too much backtracking?
Option 2: Similar to #1, but in a town other than Siena. If so, what town?
Option 2: Change locations each night in Tuscany. If so, what towns?

The four of us, variously, have been to cities in Italy (Rome, Florence, Venice, Milan, and Bologna) but not smaller places. Hence, carving out time in Tuscany. Another reason for that: even though my spouse and I are art historians (but in fields far from Italian medieval and Renaissance art), we find looking at buildings (and the paintings and sculptures within them) and urban spaces less taxing and more exciting than non-stop museum time.

I welcome thoughts, suggestions, and the collective intelligence of this forum's hive mind!

Posted by
1902 posts

Off the top of my head - do not stay near the Florence train station because you're flying out in 3 days. Choose your hotel based on seeing what you want in town - Florence veterans will tell you to check out Oltrano. Florence is small so worst you're going to pay a small cab fare or take the bus to stay in a more interesting/convenient area or accommodations. Staying near the train station is a one night stay behavior not several nights.

Stayed in Siena for 3 nights and plenty to see in the city itself. Keep in mind that 3 nights means 2 full days so if you stay in Siena plan one full day for Siena and one day trip. The San Gimignano, Volterra loop is popular although I find SG too touristy. In March maybe it will be quiet enough that the beauty of the tiny town will be more evident. Honestly if this is the plan I'd take the fast train from Rome to Florence and train to Siena. Stay a couple of nights - rent the car for one day for a day trip - and then return by train or bus to Florence for several nights. Or return the car in Florence if the drop off charge isn't bad. If you are not touring rural Tuscany the car is an expensive burden.

Or coming north from Rome choose southern Tuscany and check out the Pienza, Montalcino, Montepulciano area - staying one town for all three nights and explore by car. This area demands a car but will reward you with sweeping beauty and tiny towns - maybe sleepy in March which is really pretty early.

Usual warnings:
- If you're flying out of Milan most people will sensibly advise you stay in the city of your departure the night before you leave to prevent potential travel issues.
- Be sure to read up on ZTLs before you go and check each town before driving there, every driver needs an IDP before leaving the states, add at least 25% to Google drive times for rural driving. You will get lost - that's part of the experience.

Have a great trip,
=Tod

Posted by
5146 posts

I have not taken his tours, but Tours by Roberto out of Siena are often recommended by RS fans.

Posted by
8865 posts

Siena is lovely and deserves a night or 2- but- it is a pain to drive in and out of and parking is always an issue.
If you can find lodging with easy access and parking it's a great place to stay.

If you want to explore Tuscany you might be better off staying in the Val d'Orcia area- Montepulciano, Pienza. Much easier with a car.

Agree with Todd- no need to stay right at the station in Florence. It is so compact you can walk most anywhere.