Tuscany (Toscana)

Tuscany is one place on Earth where everything comes together for me: the food, the vistas, the people, the wine, the history, the architecture…

Several destinations in Tuscany stand above others. First and foremost is certainly Florence (Firenze), reviewed in a separate article, as are Siena and Pisa. In addition, there are literally dozens of interesting places in this divine region of Italy.

San Gimignano

In 6 words: Manhattan of Tuscany; well-preserved, too.
For your visit half-day should be enough to explore the town.
Distances are walkable in all cases.
Worthy attractions: Duomo; Palazzo del Popolo with its Museo Civico and Torre Grossa.
Last visit: August 2013.

San Gimignano

San Gimignano, famous for its medieval towers, can be touristy to the point of being overrun, but it is still a gem of a town.

There are two interconnected central squares, Piazza della Cisterna ♥♥ and Piazza del Duomo ♥, and two major streets running away from them that attract most of the visitors. The buildings that line the streets are extremely well preserved (and/or restored) from their origin of centuries ago, so that one could even say that San Gimignano feels a bit artificial, sort of a small theme park built especially for tourists.

There are tons of shops on the main streets that emphasize that notion somewhat, selling souvenirs of all kinds. However, here and there are sprinkled very inviting gastronomical emporiums, and among souvenir shops there are many that sell attractive and inventive crafts.

Side streets are much quieter, projecting quite surprising tranquility. The buildings around them maintain fine quality.

Collegiata ♥, the local duomo, contains many frescoes (which somehow manage to present various biblical scenes as invariably killings or fights). A few interesting frescoes can also be found at Museo Civico ♥ which occupies several rooms at the Palazzo del Popolo, especially in its spacious Sala di Dante. The most important function of the museum is the gateway to Torre Grossa ♥♥♥, the tallest of the remaining 13 towers. It is comparatively easy to climb – modern stairs are fitted inside the hollow tower for most of the way – and it provides unparalleled views over the town, its towers, and the Tuscan countryside.

Another great perspective is from Rocca ♥♥, the ruins of the castle. Climb up to a tower lookout for a stunning view of San Gimignano’s skyline.

Take in the view, linger on the steps of the duomo for a while, walk around the town and look into the shops. At some point, go down Via San Matteo away from Piazza del Duomo, and after a couple of hundred meters turn around and look back. Your heart may skip a bit if you are a New Yorker at the sight of the two of the town towers that unmistakably resemble the fallen World Trade Center twins…

There are a couple of other minor attractions, including three separate museums of torture, which can be safely skipped.

Car parking

There are a couple of lots outside city walls, each of which will require about 10 minutes walk to the town center. I prefer Park #1, located near Porta San Giovanni, but it is the first one to fill up on a busy day.

Places to Eat

Our stops in San Gimignano normally include only light meals at pizzerias and cafés on Piazza della Cisterna; all adequate, no more. In 2003, we stayed in town through the evening and had dinner at Le Terrazze, in Albergo la Cisterna. I have a faint memory of a nice view over the valley below and a pretty good rabbit dish, but no specific records were taken at the time to confirm my recollections.

On the very last visit, however, we had a full lunch at Beppone, on a narrow side street not far from Duomo. It was a random choice that somewhat backfired. Food is ok, from bruschetta to pasta to pizza. In this family establishment kids of the owners serve as waiters, which makes service not just spotty, but uncomfortable. The biggest problem was the price. We were charged twice as much as what we habitually paid elsewhere for pasta bianca for children and the bill included 15% service charge beyond the food total, a rare occurrence in Italy, which brought the total damage to €213 for eight people (one small child, one person had only a coffee), including a carafe of wine. Too costly for a middling meal – not recommended at all.


Volterra is San Gimignano without towers, but with rich Roman and Etruscan history. Its medieval core is preserved quite well, and there are several attractions that may be worth checking out, most of them within a stone’s throw of the central Piazza dei Priori.

Palazzo dei Priori ♥ has a small exhibition, consisting of a couple of council rooms, a floor given to artifacts related to the history of the town (including a couple of nice models), and access to the bell tower, with not sweeping but still pretty good vistas over the town and countryside.

We also stopped by Museo Etrusco Guarnacci ♥, which is slightly off from center on Via Don Minzoni. It holds an interesting collection of Etruscan pieces bequeathed to town by a local ruler in 18th century. Nearby Parco Archeologico ♥ is a pleasant space with a few other ancient artifacts, such as stone bathtubs, on open-air display. The entry to the Acropolis, which we did not tour, is through the park as well. There is also a pretty good children playground to provide diversion for the youngest.

The magnificent Roman Amphitheatre can be viewed from a high vantage point from within the city walls or toured (we chose the former).

Places to Eat

One of our best meals in Italy was at Trattoria Bada Ganzo ♥♥♥, less than 100 yards away from the main piazza. Small place, 4 or 5 tables outside, less than a dozen inside. Fantastic menu, appetizers, soups, salads, pastas, main dishes. Of our choices, crostini toscani, served as separate bread and pâté, and panna cotta con ciocolatto, served inventively in vial-like cups, were the highlights, but all other selections were perfect. Friendly service, pleasant atmosphere. Our damage: €113 for five people (one small child) with a bottle of wine. Last visit: Summer 2013.

We had a pretty good lunch at Ombra della Sera ♥ on Via Gramsci. Nothing spectacular, but a very well-prepared Tuscan cuisine. Fairly extensive menu and friendly service. Our damage: €65 for four people, including wine. Last visit: Summer 2008.


Certaldo is an otherwise unremarkable large village in the heart of Tuscany, a bit off the beaten path. Its medieval upper town, though, is well worth a visit.

Located on a towering hill, the old village is most easily reached via Il Funiculore. The area to explore is very small, with the main street not longer than a few hundred yards and the side streets not extending for more than a hundred yards in any direction. The buildings lining the streets are very well preserved, and with reasonably few tourists around, you may feel truly transported into Middle Ages.

There are a couple of old churches and museums. We only visited Palazzo Pretorio, the seat of the Vicars, Florentine governors. It is an interesting building, richly decorated with terracotta coats of arms and containing many frescoes in various stages of decay. There is no furniture or decorations otherwise, but instead a somewhat incongruous modern painting exhibition that nevertheless provides a curious contrast to ancient wall art.

Weekly Wednesday market in Certaldo did not impress us, compared with other places.

Places to Eat

Osteria di Casa Chianti ♥♥, is not really in Certaldo, but rather on SP79 between Fiano and Certaldo. Very pleasant service, very nice setting on the outdoor terrace (although overlooking car park). One person in our party counted this as her best meal on the entire two-week trip to Italy. Excellent vegetable soup, coniglio, pollo, mezzaluna con pecorino e tartufo, very good other choices and desserts. Our damage: €175 for 8 people (one small child), with a bottle of wine. Last visit: Summer 2013.

Pienza and Val d’Orcia

Pienza is a very little and authentic picture-perfect medieval town. It is located some distance to the main cities and as a result is not too overrun with tourists and not too commercialized. Narrow streets, no cars, well-maintained buildings, great views over the valley. A couple of churches and civic buildings are worth stepping into for a look, but wandering the narrow streets is a highlight all of its own.

The valley is simply breathtaking, and well worth a drive-through on SP146.

Chianti Road

The road, also known as S222, connects Florence with Siena and goes through the heart of the Chianti Classico region. Dozens of wineries lie on or within short distance of the road, making this a natural prime wine-tasting thoroughfare.

In 2003, we had an excellent experience on a wine-tasting tour at Castello di Verrazzano ♥♥, the erstwhile birthplace of the New York Harbour pioneer. Presented with an option of staying for lunch in addition to the tour, we took it. The lunch featured local meats, lively conversation with the owners and the staff, and vin santo and grappa in addition to half a dozen vintages of wine to taste. Great experience!

In 2013, we stopped at Cantinella San Jacopo ♥, which is the property of Castello Viacchimaggio. Pleasant tavern environment, 3 wines as part of the standard tasting, not bad.

Another stop in 2013 was at Castello di Gabbiano ♥♥, which is not exactly on Chianti Road, located close to San Casciano in Val d’Pesa. It is not just a winery, but a luxury hotel, with outstanding vistas all around. Excellent tasting experience – we were offered 6 different wines (although the price tag said 4), great variety of Chianti, but certainly not cheap to buy.

Although we drove the length of the Chianti Road in 2003, and large portions again in 2013, we did not make other stops. If you are driving, two tasting sessions is probably a limit for a given day. Sometimes, one is more than enough.


Greve is one of the main towns on the Chianti Road, but we only made an effort to explore it separately on a Tuscan holiday on which we otherwise did not venture into the Chianti Classico country.

Even then, we only looked around the central Piazza Matteotti, whose overall attractiveness is somewhat negated by the car park taking up most of its space.

Places to Eat

There are a dozen restaurants located around Piazza Matteotti, around its irregularly-shaped porticos and above on flower-decked terraces. We chose Il Portico ♥. Excellent crostini and cold cuts for the first course; good Tuscan beef stew, vitello con funghi and spaghetti alla ragu del coniglio for the main dishes. Our damage: €89 for four people, including house wine. Last visit: Summer 2008.

Barberino Val d’Elsa

A pretty town off the beaten path on the edge of the Chianti country, Barberino offers its own small fortified hilltop core with well-preserved buildings and a notable Palazzo Pretorio. We came to Barberino on a late-afternoon undemanding visit and were pleasantly surprised with what we saw.

Places to Eat

A forced selection, Il Campanellino ♥ on Via Veneto. Less extensive menu than at the next restaurant, which was full, but still a pretty good meal. Meat lasagna was especially well-received and sampled by all in attendance, in addition to crostini, bruschetta, minestrone toscana, ravioli del formaggio e spinaci and spaghetti al ragu del coniglio. Damage: €88 for five people (three children). Last visit: Summer 2008.


Montespertoli does not have anything to attract a tourist. What it does have is quite possibly an unbeatable location for reaching Tuscan destinations. Florence is a half-hour away, and none of the other major sights in Tuscany is more than an hour away from Montespertoli in different directions; only Arezzo and Cortona are a bit too far for an easy day-trip – but they would be farthest away from anywhere.


In 2011, the villas that we had stayed at in Montespertoli a couple of times were sold to new owners and taken out of rental market.

Places to Eat

These restaurants were all recommended to us by the owners of Le Pianore, the agriturismo villas where we used to stay. All turned out to be superb, as each of these places does an excellent job in serving typical Tuscan cuisine.

C’era una volta ♥♥♥ (which translates as Once upon a time) is positioned on a main – and practically only – street of the tiny village of Lucardo to the south of Montespertoli (local highway 79). The setting is that of a rustic family-run eatery, with sweeping views over the valley below. The menu includes every Tuscan staple and the house wine goes down easy. Very prompt and pleasant service. We have been to the place 5 times overall and always come away satisfied. Our favorites are crostini misti, tagliatelli a funghi porcini, coniglio and osso bucco. Freshly prepared tiramisu is exceptional. The damage: between €90-110 for a meal for four, often decided by the quantity of wine ordered. Last visit: Summer 2013.

Trattoria Montalbino ♥♥ specializes in mushrooms and truffles, but serves enough of dishes that do not include either. It is part of an inn that is located in a hamlet of Montalbino, the only road through which is a tributary to highway 79. The dining room is quite plain, but the food and the service are extremely good. The wine is local, but slightly more expensive. Our damage: €90 for a meal of four, including one bottle of wine. Last visit: Spring 2007.

La Nuova Villamagna ♥♥ is located literally in the middle of nowhere, off the road towards San Donato north of Montespertoli. The road is challenging in itself, and then the turnoff is marked by an arrow sign that is easy to miss in the darkness. The setting is considerably more modern: A large dining room with wall-length windows. The menu is less extensive than at the other places; wine choice is minimal – rosso della casa or bianco della casa. But the quality of the food is very good, and it is literally half as expensive as the others (everyone in the party can have primo, secondo, dolce, plus a half of a bottle of wine, and the cost will be under €20 per person). Service a bit spotty. Cash only. Last visit: Spring 2007.

Il Battibecco ♥♥, unlike the other restaurants mentioned above, is located within Montespertoli village itself, on Via Enrico Berlinguer. We went there for a mid-day meal, which consisted more of primi than secondi. Very extensive menu, with lots of regional choices. The most exceptional was coniglio, but other selections went quite well. One person in our party spoke fairly respectable Italian, and the restaurant owner spent several minutes patiently explaining specifics of Tuscan cuisine to us. Of all panna cotta that we tried for dessert, the one at Il Battibecco was arguably the best. Our damage: €117 for a party of seven (four adults, three children), including house wine. Last visit: Summer 2008.


A fairly sizeable town, with not very much to look at. The central square in front of the Teatro Popolo looked lively on a couple of occasions that we chanced by.


Villa Antica Sosta ♥♥♥ (website) is high in the hills above Castelfiorentino. It is a beautifully appointed and tastefully decorated house, with tons of atmospheric and authentic details. Five good-sized bedrooms, large kitchen with modern amenities mixed with period details, three full bathrooms, huge living room. The view is only partial, but of the fantastic hillside variety, especially from the upper floor bedrooms. Large territory, great pool, patio, trampoline, parking, all fenced and gated. It is part of a hamlet which is not that easy to find even with a GPS, but once you find it, getting to and from the villa presents no problem.

The owners offer a dinner prepared at the villa for extra cost (which will be higher than a comparable restaurant meal, but is worth the experience). The main downside is that the same menu have to be picked for everyone present, which could be an issue with differing food tastes. There are several menus to choose from, which you would do on the day of arrival. The food is very tasty and prepared and served with flair by Maria and her daughters. Our menu consisted of crostini toscani, pasta with meat sauce, and lamb, plus tiramisu.

You can also order cooking lessons with Maria, right in the villa’s kitchen. You will prepare pasta from scratch, sauce and all, as well as meat and cookies. The lesson is nice, not too long, not overwhelming, very interactive. Followed by family consumption of everything prepared. Last stay: 2013.

Places to Eat

Il Gusto e Il Tatto ♥♥, at the edge of town. Nice hillside views from the veranda, friendly service, very good menu and tasty food. Menu degustazione, consisting of antipasto misto, crespelle, and tagliato, was very good. So were crostini misti, mixed grill, papardelle with wild boar ragu. Our damage: €152 for eight people (one small child) with a bottle of wine. Last visit: Summer 2013.

Other notes for Italy