Thoughts on our yet another Tuscan itinerary?


New member
I will be traveling with another lady in October. We've both been to Rome, Florence, Siena, Venice and the Cinque Terre before. This time we want to concentrate on Tuscany. I've already gained much from reading here, but appreciate any suggestion for improvement on our plan.
Day one our flight arrives in Rome at 0730 from the US. We'll catch trains to Rome Termini, and from there to Siena. In Siena, will rent a car near the station and go about 35 min. up SS222 to our apartment near Castellina in Chianti. Knowing how jet lagged we'll be, our drive will probably suffice for sightseeing that day, other than dinner in Castellina after a nap.
We will be based in the apartment 7 nights. We have so many places we'd like to day trip to, it's hard to prioritize. We tend to choose day to day when we travel, and are trying to avoid rigid schedules to be able to enjoy the peace of Tuscany, but I would hate to miss anything fabulous.
I think for sure we will go north in Chianti to Greve and Panzino one day, and perhaps to Radda and Gaiole if time allows. Another day we expect to visit Volterra and San Gimignano. I thought we'd take one day off from driving and catch a train in Poggibonsi to Pisa and Lucca if the train schedules cooperate. The last day we will likely stay close to home to do laundry (we only take carryon luggage) and pack.
So, there are so many other places to see in our other few days. Would anyone like to recommend what is best to see, or comment on our choices? Our goal is to get out after breakfast and,without feeling rushed, try to be back before it's very dark to avoid much night driving. When we leave we'll return the rental to Siena and catch a train to Verona for the night before leaving for Venice to join a cruise. I know we could drop the car in Florence, but prefer the bit longer train ride to trying to find where to drop it in the city.
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The Tuscan Expert ;-)
Staff member
lots to see, your days won't be enough ;)

Ciao Gstrick,

:D No problems on providing feedback on another itinerary, I know each one has their own preferences and can get ideas from sharing their proposed travel plans.

Day 1 sounds fine, you definitely don't want to do too much and the train/ride will already be enough. Go to bed early so you can try to get over the jet lag sooner.

I completely agree that the best way to see Tuscany and anywhere else in Italy is to have a list of places to see but to remain flexible and see day to day where to head off to... or sometimes just stay in and relax. Since you're in the heart of Chianti, you'll also definitely want to visit the surroundings, take your time and you'll feel like you'll get to know the area.
Greve and Panzano on one day sound fine, Radda and Gaiole on another as well.
I'd dedicate a whole day to Volterra and another to San Gimignano.

How much time did you spend in Siena? It is definitely worth a visit back, there are so many sights generally not visited by those that just walk around and see the Piazza del Campo, cathedral from the outside and then leave. I'd recommend buying a Siena SI pass to see the inside of the Siena Duomo and other monuments around the cathedral if you didn't do that before.

Other options to add:
Monteriggioni, a medieval castle just outside of Siena and not far from Castellina
San Donato in Poggio - another medieval hilltop town near Castellina - the drive there between the vineyards is beautiful (from Castellina).
Colle Val d'Elsa - on your way to Volterra, make a stop!
Abbey of San Galgano - a little further out of the way but visit on your way to Massa Marittima.. or on a day you head toward the coast?
Along the coast - Bolgheri, Castagneto Carducci (Etruscan Coast)
Opposite direction ---> Arezzo and Cortona
south of Siena - the Val d'Orcia area includes Pienza, Montalcino, San Quirico and Montepulciano... lots to see!

Need more ideas?? ;)


New member
Re: lots to see, your days won't be enough ;)

Grazie Lourdes! I'm excited to research all your recommendations and work with them in our itinerary. I think a month wouldn't be enough to see all we'd like, but this is a wonderful start to sort through the options. I hoped to find at least one Abbey, so appreciate that suggestion as well. I'd always appreciate any more ideas, but this should keep me plenty busy for now :)


The Tuscan Expert ;-)
Staff member
you're welcome! :)

If you head to Montalcino, head a little further south and go visit the Abbey of Sant'Antimo too, it is a beauty :) You can read more about it here.