What do you mean by fairly long trips?
Rent a car and you're no more than an hour drive from the places mentioned.
Thanks for the reply. We are renting a car ; but time to Siena & San Gimingnano seems to be 90 minutes - so that;s at least 3 hours travelling and if we did both in the same day trip - it looks like 4.5- 5 hours
Siena is less than 90 mins more like under an hour and most definitely worth a visit, parking is easy here too. San Gimignano is another 30/40 mins further on beyond Siena and although a very charming place, hugely busy still in September, which might put you off. However, there are so many smaller places locally around Arezzo that are worth exploring and won't require hours of driving. The obvious must-see in my opinion that's right next door is Cortona but little known Castiglion-Fiorentino that you pass en route is worth stopping at too, especially if you're in to local crafts, pottery, etc. Then consider exploring the villages immediately behind Arezzo that don't get much of a mention on this board. If you're interested in art, there are treasures to be found in some of the smaller galleries here (Sansepolcro, for example) and some of the villages are very pretty, Anghiari in particular. Across the Val di Chiana, the historic centre of Monte San Savino hidden away behind it's huge protective doors is a gem, as is next door Lucignano buried behind it's fortified walls. Beyond Monte San Savino you're in the south east corner of the Chianti and that's certainly worth a drive around. A little further south (and only 30/40 mins from Arezzo going cross country via Sinalunga) is Montepulciano with some very beautiful approach roads through the vineyards up from the valley. A similar distance but taking the A1 this time would be the old town of Chiusi. You could visit that first and then head off to Castiglione del Lago on Lago di Trasimeno for lunch, an interesting old town with a castle set on a promontory overlooking the lake. Heading north from Arezzo, Bibbiena, Poppi both have very beautiful old towns (don't be put off by the suburbs) and then there's the monastery at Vallombrosa. Pick up a good guide book and you'll see you don't have to travel far to visit some very lovely places.
Thank you very much. Your recommendations will be very helpful.
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