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Rome to Tuscany to Florence itineary

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First time travelers to Italy in our 50’s. Been reading the forums diligently and feeling a bit concerned about our current itinerary, specifically how feasible is it logistically. If anyone has suggestions to improve please let me know. TIA

We booked this trip only last week because we saw a cheap flight available with points. We will be there early October. Plane is booked to and from Rome.
Hotels are booked but we may be able to change if we can find alternates in rather short notice

Current itinerary below
- Day 1 Arrive early AM, secure bags at our hotel near the Pantheon and walk about on our own. May try to get colosseum or other site tix for that afternoon.
- Day 2 Wed Locate a guide to do a lightning round tour of the well known stops
- Day 3 rent a car in Rome or perhaps train to Chiusi to pick up car. Drive to agriturismo in Pienza with stops in Orvito or other towns en route.
- Day 4 stay in Pienza, drive to nearby towns and explore followed by cooking class at agriturismo.
- Day 5 stay in Pienza, explore Tuscany in rental car or possibly book wine tour guide
- Day 6 orig plan was to drive to Florence, enjoy the drive and stop at Siena or other towns en route and drop off car at approx 3-5pm. After reading the threads on this forum, Now thinking to return car at Chiusi and take the train to Florence. This is a Sunday so we need to consider which locations will be open
- Day 7 Florence - walking tour and cooking class
- Day 7 Florence - explore
- Day 8 Florence - possibly day trip via train to Lucca or Bologna
- Day 9 early Train from Florence to Rome - return flight at 3pm.

Thank you.

Posted by
16815 posts

It works. However I would prefer to leave Rome (return flight) for last. So in your case you could do Florence first, by taking a train upon landing (about 2 hours+ from the airport train station) then go to Pienza after your stay in Florence. Finally spend your last nights before the flight in Rome.

You could rent a car in Florence and drive from Florence to Pienza of course (about 1.5 hours), or you could rent the car in Chiusi after taking a train from Florence to Chiusi. However only a small Avis-Budget franchise agency is present in Chiusi, and they are open Monday-Saturday only (Saturday open in the AM only) and they close a few hours for lunch every day. If the times of the rental agency work for you, after return in the car at Chiusi you could take the train to Rome for the last few days. The train also stops in Orvieto, which is between Chiusi and Rome, and there is a luggage storage available at the Orvieto station run by the coffee bar there.

Posted by
6600 posts

We were just in Tuscany spring, 2025. Parking at the various hills towns is a challenge, and is often on the outskirts, so you still need to spend time walking/taxiing getting into/out of town. Finding parking is best in the mornings, and gets worse as the day goes on, especially on the weekends.
Just wanted to give you an idea of realistic time blocking, so you can have a fantastic time in this beautiful area. Enjoy!

Posted by
1357 posts

I would not be comfortable being in Florence the morning I'm flying home from Rome. If you switch days 7 & 8 then you do your day trip on day 7, spend day 8 out and about in Florence (your hotel can hold your bags) and take a train that afternoon or evening to Rome, sleeping in Rome the nite before your flight home.

Posted by
8306 posts

Take Roberto’s advice and head to Florence on arrival
End in Rome-even if flight is 3 it’s too risky staying in Florence night before

Gives you better options for car availability and hours in Florence (or at FLR)

There should be plenty of availability for hotels in Florence and Rome
Also gives you better time in Rome
As you have it now you only have 1 full day, first day is jet lag-don’t expect to accomplish much
Rome needs way more than that

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