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Rome/Florence/TuscanyWalk/Siena/??

Hello,
In September we have two nights in Rome and two nights in Florence. We then go on a walk through tuscany which starts in San Gimignano and finishes in Siena on a Thursday. We have Friday and Saturday, before we need to be back in Rome on time to catch our evening flight back back home on that Sunday night.
Does anyone have any recommendations on what we should do or where we should go for that weekend? Should we stay in Siena? Head down to Rome? Or travel elsewhere to see a bit more of Italy? We don’t need to be in the hussle and bustle of things, quaint, beautiful with delicious food would be perfect. It will be my birthday on that saturday so we’d love to do something quite special (although just being in Italy is special enough). Any advise will be much appreciated. Thank you

Posted by
174 posts

Siena is a great town and good for at least a day of siteseeing. I loved it and would highly recommend seeing the Duomo complex and Civic Museum, at the very least. It would be a shame if you didn’t have a drink on Il Campo too! As for a good restaurant recommendation, my favorite was Osteria Cice.

Depending on what you do/see on your walk, the local towns near Siena are lovely. Most of them are 45-60 minute drive. I loved Pienza the most but Montepulciano was fun. Montalcino was also quaint. I’ve heard good things about San Quirico too.

If you’re into it, you’re in the heart of wine country and might consider doing a wine tour? My mom and I did that. It felt beautiful and special and might be something fun to do for your birthday.

Not sure if you’re wanting to be back in Rome Saturday night, considering your flight the next day but if you are, I would consider going into the Monti or Trastervere neighborhoods. They are a blast with a lot of good dining. If you chose Monti, you could then see the Colosseum lit at night (I think they even do night tours, if you’d like that.) Trastevere is a lot of fun too and would allow you to wander towards the Vatican to see that area lit.

Posted by
3551 posts

I agree with the Siena poster. It is a wonderful and walkable town. If u wish to venture out from Siena , u cane reach Pienza and Montepulciano by bus from Siena.