10 Days in Rome, Tuscany and Cinque Terre

Hello everybody,

This is my first posting in this amazing website and I would really like your opinions to the following itinerary, which I am planning between 28/09 and 07/10:

Rome (3 nights)

Day 1: Arrival in Rome late morning

Day 2: Rome

Day 3: Rome

Florence (2 nights)

Day 4: Arrival in Florence early afternoon by train from Rome

Day 5: Florence

Siena (2 nights)

Day 6: Renting a car in Florence and driving through Chianti (and maybe San Gimignano if there's enough time) before arriving in Siena late in the evening.

Day 7: Siena and visit Val d'Orcia by car.

Pisa (2 nights)

Day 8: Siena in the morning (or San Gimignano if not 2 days before) and drive to Pisa late afternoon where visiting the leaning tower area until 7pm when it closes.

Day 9: Train from Pisa to Cinque Terre until late evening when returning back to Pisa to spend the night.

Day 10: Fly back from Pisa airport early in the morning.

I know that the above itinerary is quite hard and tight but I would really appreciate your help in making it as feasible as possible. I would also like to ask you if using Siena as a base in order to visit the Tuscan countryside makes sense or I should pick another small town as a base.

Thank you very very much and I look forward to your help!!


The Tuscan Expert ;-)
Staff member
Ciao Elessar,

I think your itinerary is actually looking pretty good actually. You are trying to fit a good amount of things, so I'd just suggest these small changes:

Day 6 - go straight to Siena and spend that day there so that you can dedicate all of day 7 to the Val d'Orcia.

Day 8 - visit San Gimignano on the way to Pisa as soon as you leave Siena, that way you fit it in and is on route.... you'll love driving the countryside through here for the views, even if it takes longer to get to Pisa.

I think that will just better optimize the time you have in Siena, which I love! Be sure to visit the cathedral as the pavement will be completely uncovered when you're there!

Siena works great as your base for those 2 nights - just make sure to look for a place that either offers parking for your car or that it isn't too far into the center so that you can you park (at either one the main garages or outside the walls) and walk in easily to your hotel.
Take a look here: http://www.tuscanyaccommodation.com/siena-city/
We actually stayed at Chiostro del Carmine last summer and we chose it because it was really central but it was also pretty close to the gate at Via San Marco - while they have parking right behind the cloister, it costs 15 euro per day. We chose to park on the Strada Comunale Giuggiolo right outside the gate, where the per hour rate made it come out to 12 euro per day. There is another garage right inside the gate too.

We've also stayed at the Locanda San Martino in a previous visit and also liked it, was really close to Piazza del Campo - but they didn't offer any parking and walking in to them from the closest parking was a little further. You can drive in to drop off luggage and then drive out to park, just make sure to follow the directions they send really well so that you won't have any problems with the ZTL.

If you have any other doubts, just ask! In the meantime, enjoy the planning!