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TUSCANY

The region of Tuscany, known for its beautiful landscapes, wineries, and historical towns, has 279 towns, each with their own distinctive personality. While I have visited quite a few, I’d love to try to visit them all, but that would mean I’d probably need to spend almost a year in Tuscany. While I’m TOTALLY on board for that, I don’t think my husband, or our bank account would be down for that. However, about 10 years ago, after a couple glasses of wine, my husband agreed that after we retire, we could live in Italy for a year. Needless to say, I’ve never let him forget it, so not all is lost. Perhaps I will be able to visit every Tuscan town one day!

If you’re planning a trip and are unsure which towns to visit, here’s a bit of information on my five favorites Tuscan towns:

CORTONA

Cortona is a beautiful hill town with a charming and lively atmosphere. Cortona gained a lot of popularity after the book “Under the Tuscan Sun” was published. Then, after they made it into a movie, I, like millions of other women, became enamored with the dreamy romance of Cortona.

The atmosphere in Cortona is warm and welcoming. Its old town is filled with little shops and eateries, many with outdoor seating. One evening, as we were having dinner, an orchestra gathered on the steps of Town Hall in the main square and began playing. It was so surreal and magical that it felt like perhaps we were going to witness an engagement or the filming of a movie scene. It made what was already an amazing summer evening, a night to remember.

If you have the opportunity to enjoy an evening in Cortona, book a dinner reservations at Ristorante La Loggetta or La Bucaccia, both excellent. As for accommodations, Cortona is a great place to base yourself if you plan to explore Tuscany. There are many options ranging from studio apartments to castle-like villas that sleep 20 people. If you’re traveling with a group, then I’d highly recommend Villa Caprile, a beautiful villa in the hills not far from Cortona. You can read my review here.

If you’re just planning to visit on a day trip, Cortona’s old town is not too big and can be visited in several of hours. Be sure to see the Duomo, museum, and Church of San Francesco.

SIENA

Siena, my favorite Tuscan town (Cortona is a close second), is brimming with charm. As you enter the historic center, a UNESCO World Heritage site, it feels as though you’re walking into the Middle Ages.

My husband and I spent 4 nights in Siena, using it as a base to explore Tuscany. We stayed at The Grand Continental, which is a luxury 5-stary hotel that is not only beautiful, but ideally located in the heart of the historic center.

Unbeknownst to us, our stay was during the festivals of the 17 Contrade (neighborhoods). During this event, the streets are filled with decorations and the contrada’s flags hang from the buildings. Each district is dressed to the nines in their contrada’s colors and costumes, as they march through the streets flipping their flags and drumming, drawing attention to their neighborhood pride and representation. The 17 Contrade celebrations are a lead up to Siena’s most popular annual event, the Palio. The contrada’s are represented in the Palio, a horse race, which takes place once in July and once in August. Amazingly, the race takes place right in the heart of the historic center, in the Piazza del Campo, Siena’s main square. The Palio is a hugely popular event in Siena, so if you’d like to attend, be sure to book your accommodations and purchase tickets many months in advance.

Siena has many boutiques, galleries, and great restaurants. There is a fairly good size historic center that is a great place to shop, if that’s your thing. If you’re feeling energized, climb the 300 steps to the top of the Torre del Mangia, and enjoy sweeping views of the landscapes around Siena. Also, be sure to visit Siena’s underground aqueducts, as well as the Santa Maria della Scala museum.

Should you have time, consider taking a cooking class in Siena. My husband still talks about the Pici carbonara he had in Siena as one of the best pasta dishes he’s ever had (Pici is a thick pasta noodle and is typically served with a boar or pork ragù).

If you can spend at least one night in Siena’s old town center, it’s definitely worth it, but if not plan to spend at least 5 or 6 hours exploring this amazing Tuscan town. Conveniently, there is a direct train that goes from Florence to Siena, making day trips easy if you’ve based yourself in Florence. The ride takes about 1.5 hours and costs $10-15.

SAN GIMIGNANO

If there ever was a medieval storybook town, San Gimignano is that town. As you approach the hilltop town, it’s impossible not to notice the 14 towers standing prominently in the distance (at one time there were 72). Have your camera ready, because I guarantee you’ll want some photos of this beautiful little town.

San G is small, but definitely worth a visit. It is brimming with character, with its terracotta rooftops, quaint buildings and curvy cobbled streets. Just be warned that the town gets very busy during the day, but don’t let that stop you.

Brian and I spent two nights here, and while it was busy and energetic during the day, it is sleepy and quiet at night. We stayed at Il Nido di Anna, a small B&B that is simple yet makes for a lovely stay in this little village. Plus, the owner Renata was wonderful, and our room had AC, which is a non-negotiable of my hubby.

If you’re planning how much time you’ll need for a day trip, San G can be seen in 2 or 3 hours. If you’d really like to get a feel for the town, consider spending a night here.

I cannot wrap up without mentioning Cum Quibus restaurant. The service is excellent, atmosphere is intimate, and the wild boar paradelle ragu with truffles is out of this world! Brian and I both agree that our meal here is in our top three EVER!!! We were blown away by this restaurant, so much so, that we cancelled our dinner reservation for the following night so that we could come back to Cum Quibus again.

PIENZA

Even smaller than San Gimignano, Pienza, a UNESCO World Heritage Site, is located between Montepulciano and Montalcino, so these three towns are geographically suited to see in one day trip. It is renowned for its stunning landscapes, Renaissance architecture, and pecorino cheese.

Explore Corso il Rossellino, the main street that runs all the way through Pienza. Make your way to Piazza Pio II, the central square within the historic center, named after Pope Pius II, who was born in Pienza. Check out all of the buildings around the square including the Duomo, Palazzo Piccolomini, Palazzo Borgia, and Palazzo Comunale. Branch off and explore the beautiful buildings along Pienza’s charming little side streets. Don’t worry about getting lost, Pienza is so small it’s nearly impossible.

I would describe Pienza as adorable, lovely, and romantic. Others seem to agree, as the town boasts charmingly named streets like Via del Bacio (Kiss Street) and Via dell’Amore (Love Street), reflecting its romantic atmosphere.

 

MONTEPULCIANO

If you’re a wine lover, you’re going to love Montepulciano, renowned worldwide for its Vino Nobile di Montepulciano. The medium bodied wine is made with Sangiovese grapes, which must make up at least 70% of the blend. There are many wineries in this area, so if you’d like to sample a few, I recommend doing a wine tour. We did our tour with Franco Faddo, a great guide that has a passion for these regional wines. He is a wealth of information and has relationships with nearly all of the boutique wineries in the area.

If a guided tour isn’t your thing, check out Contucci Cantine in the historic center. This Contucci family has over 1,000 years of history of wine production.  In addition to tasting the wines, you can order some nibbles, and take a self-guided tour of the underground cellar.

Montepulciano has many of the Renaissance architecture typical of Tuscany, but this walled hill town has a more regal and grand charm than others. It is located in the beautiful Val d’Orcia region and offers breathtaking views of the surrounding vineyards and landscapes.

If time permits, have lunch in Montepulciano’s Piazza Grande at one of the numerous trattorias. Here you’ll find an energetic and lively atmosphere, great for people watching. After lunch, work off those calories by climbing to the top of the Bell Tower, or if you’ve eaten too much, take the elevator:-) The views from up here are stunning.

The biggest annual event in Montepulciano is the Bravio delle Botti, which takes place in late August. The town’s districts (contrade) hold barrel rolling competitions through the town’s steep, cobbled streets. There are multiple celebrations over the week, including parades, dance performances, and flag processions.

The town boasts numerous specialty shops and galleries. Whether you’re seeking a memento of your Italian journey—a hand-painted Tuscan landscape from one of the town’s art galleries, an Italian-made jacket or handbag, or handcrafted ceramics—you’ll find the perfect piece to cherish.

Whether it’s visiting one of many vineyards, exploring the shops along its cobblestone streets, people watching in Piazza Grande, or taking in the beautiful landscapes, Montepulciano is a Renaissance gem not to be missed when visiting Tuscany.

A few additional things to consider when visiting Tuscany:

Where to stay? If you have less than 4 days, I recommend staying in Florence and taking day trips. If you have more time, consider staying a few days in Florence and few days in another location, such as Cortona or Siena.

How to get around? I recommended getting a rental car if you’re staying outside of Florence. If you’re basing in Florence, keep in mind that parking is difficult and there are many restricted traffic zones (ZTL). So, if you opt for a car, do your homework.

Are advanced reservations needed? Tuscan towns can get busy, especially in peak season, so I highly recommend making dinner and tour reservations well in advance.

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