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Cortona (of Under the Tuscan Sun fame) is about a 25-30 minute drive away, and it really is a lovely town. Parking is very limited there and it fills up fast (especially on Saturday market day), so try to arrive and park by 10:00 am. Cortona's annual steak festival in August is not to be missed!
The city of Arezzo is about a 30 minute drive away. It is the “city of gold”, so called because of the gold jewelry manufacturing there. Arezzo is also famous for Piero della Francesca’s Legend of the True Cross fresco cycle in the basilica of San Francesco, and as the setting for the first half of Roberto Begnini’s movie Life is Beautiful. The lovely Café Costanza, which featured in the film, is just across the piazza from the church of San Francesco.
The famous Arezzo monthly antiques fair (the biggest in Italy) is the first Sunday of every month and the Saturday before that Sunday (essentially the first weekend of the month). It offers real antiques, including some beautiful pieces of furniture, as well as vintage jewelry mixed in with lots of junk and knick-knacks. We like to do the antiques fair in the morning and then have a long Sunday lunch at La Lancia d’Oro in the Piazza Grande before driving home. Saturdays are also Arezzo’s market day, so Saturdays in the city are more crowded than Sundays. Even without the monthly antique fair, Arezzo has many antique stores, jewelry shops, nice clothing stores, and churches and museums worth exploring.
The province of Arezzo has a tourism website (for the English version, click on the British flag in the upper right hand corner of the homepage) that lists events and festivals throughout the province, as well as museums and other sites and sights: http://www.apt.arezzo.it/
In Arezzo province, in our Chiana valley, Civitella in Val di Chiana, Foiano della Chiana, and Castiglion Fiorentino are also worth a visit, as is the very tiny village of Gargonza. If you happen to be here in February before Lent begins, Foiano della Chiana has one of the oldest Carnevales in Italy.
In neighboring Siena province (just to the west), the city of Siena itself is maybe a 30 minute drive, with another 15 minutes needed to figure out how to approach the city and find a place to park. Follow the signs for “Siena ovest” and then towards the “centro”; park in one of the large lots outside the walls. The province of Siena’s tourism website (for English, click the British flag in the upper right hand corner of the homepage) is: http://www.terresiena.it/ You can find several brochures for museums and interesting walks in Siena in our house basket. Despite the crowds of tourists and college students at all times of the year, I love Siena, and its colors and light and beautiful buildings. Spend some time admiring the piazza, walk up and down the steep streets, see the museums, relax over lunch in one of Siena’s great restaurants, then find your way back to your car.
Buonconvento, San Quirico d’Orcia, the lovely town of Pienza, Monte Oliveto Maggiore (a Benedictine monastery with famous frescoes, and the wonderful restaurant Locanda dell’Amoroso nearby), Castelnuovo Berardenga (famous for its wines and for what Wine Spectator has named one of the best seafood restaurants in Italy), Montalcino, Montepulciano, the Abbey of Sant’Antimo, Bagno Vignoni, Cetona, San Casciano dei Bagni, Chiusi (with its Etruscan tombs), and Sarteano are all charming towns with interesting sights and museums. These are easy day trips (some of the smaller towns you can cover two or even three by lunchtime if you start early). Leave an entire day and evening for Montalcino: Brunello shopping and a wonderful, unforgettable dinner at Poggio Antico or Castello Banfi. Drive home carefully.
Several mineral springs and spas are in the area – some impressively fancy, some less so. You can get a day pass and treatments at most, even if you are not staying the night.
The region of Umbria is to the east. Assisi and Perugia can each be a day trip, or spend a day at Lake Trasimeno.
About roads and driving: looking on a good map, you will see that there are multiple roads – some large, some small – to get to most towns. This explains why you may see two signs pointing in opposite directions for the same place name. Other than navigating the outskirts and parking lots of Florence, Perugia, Siena, and Arezzo – and Cortona (if you get there after 10:00 am) – the driving around here is not too scary. If you make a wrong turn, you can usually reconnect to the right road within a short distance. Relax – you’re on vacation.
For drives into Florence (a little over an hour if there is not much traffic on the autostrada), we suggest taking the Firenze Certosa exit and following the signs toward the centro all the way to Porta Romana, where there is a parking lot just inside the gates. In the summer that lot fills up fast with tourists, so try to get to town by 9:30 am or so. There are more expensive lots closer to the river and near the train station.
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