This historic town is a must see on any Tuscan trip. Sienna is most well known for Palio, a horse race held in the main square twice a year in July and August; however, there is so much more to do. Many of the roads in Old Sienna are only open to pedestrians so it is ideal for window shopping. I personally wish I had bought more hand painted ceramics while in Siena. Pick up some gelato and head to the Palazzo Publico to sunbathe and watch the clock tower's shadow creep along the palazzo like a gigantic sundial.
This little town will afford you the BEST views in Tuscany. It is located on top of a hill and surrounded by vineyards and farms. Go here on a clear day and you can see all of Tuscany while sipping a cappuccino.
Lucca is a hidden gem of Tuscany. It is was an ancient walled city with a rich history. I recommend renting a bike and ride along the top of the wall all the way around the city. It only takes about 30 minutes to circumvent the town so feel free to stop along the way and take in the sights. Be sure to climb one of the many towers to get an even better view of the surrounding countryside. Rest your legs and get some gelato at Piazza dell'Anfiteatro, a bizarre circular square (I know) where the buildings are perfectly curved and seamless.
Okay, so Bologna isn't technically in Tuscany but it is definitely worth a short visit while you're in the area. I recommend taking a cooking class as they are known for their delicious wild meat and stuffed pasta. If your didn't come to Italy to cook, be sure to sample some spaghetti bolognese from the source. However, order Tagliatelle Bolognese if you don't want to look like a tourist. More adventurous eaters will find a restaurant that makes their rage with wild rabbit. If visiting in colder months, you will love another regional specialty, Tortellini in Brodo. Also be sure to stop in the San Petronio Basilica in the main square as it is the largest brick church in the world. It isn't Italy's most beautiful church but there is something powerful about being in a space that huge.
If you are like me, you can't stop thinking about your next trip for months before your flight. Give in to your obsession with Italy by watching Under the Tuscan Sun. Basically, Diane Lane moves to Cortona and has the best life! It will get you so excited about your visit to Tuscany, even if you can't make it to Cortona. But it's worth a visit! Discover the wonderful world of agriturismo where you can stay at a villa or working olive orchard. Pick a place with meals included, thank me later.
While Perugia has been in the news lately for sinister reasons, don't let Amanda Knox scare you away from this beautiful town in Tuscany. We visited for the annual Chocolate Festival during October. It was amazing to see so many people from all over Italy congregate in Perugia to try some truly delicious chocolate. There were tons of free samples and local artisans to talk to.
If you are in Tuscany in September, you MUST attend the Chianti Classico Wine Festival in Greve. This was one of the more perfect days I had in Italy, and that's a high bar. You buy a €10 wine glass and walk around to each of the 100-some vinyard stalls and sample all the best chianti wines. Test out your Italian with the vendors and you'll find they become generous pourers. I bought 4 bottles to take back to friends and family because they were all so good. You can soak up the wine with some yummy foccacia then take a walk around town. I found some beautiful vintage earrings in a shop down the street from the expo.
And finally, the capital and artistic soul of Tuscany, Firenze. I lived here for 5 months and I still have more to discover about this beautiful city. There's amazing food, beautiful scenery, rich history, and, of course, enough art to make your head spin! If you are planning a visit to Florence, you have to check out my Art Historian's Guide to Florence. There you'll learn all the hidden secrets Florence has to offer.
Whatever you do, you can't go wrong in Tuscany!
Let me know if you have any questions before you book.
Go confidently travelers!