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

This article covers Siena, Pisa, San Gimignano, and a number of other towns in Tuscany that are worth exploring. All of them can be visited as intraday trips from a base in Florence, which, of course, deserves its own entry. Quite a few can easily support overnight stays and more in-depth exploration.



Siena ♥♥♥, overshadowed a bit by its erstwhile rival Florence, is a remarkable place that easily awes its visitors. The medieval center of the town, a UNESCO World Heritage site, is the largest in Tuscany while remaining relatively compact and walkable (although there are some 30° climbs along certain side streets). The concentration of magnificent palaces dating to the 11-13th centuries is probably even greater than in Florence. Automobile traffic is limited in the town core.

The heart of Siena, Piazza del Campo ♥♥♥, is one of those places that makes your jaw drop no matter how many times you see it. Laid out in the shape of a giant shell, it is the setting of Siena’s famous horse race/festival Palio delle Contrade, and its entire expanse is often full of lounging people. Cafés, restaurants, and fine medieval palazzi line the Campo’s fringes, dominated by Palazzo Pubblico ♥, the graceful Gothic town hall. Its former magistrate apartments offer a dozen of grand rooms with frescoes in different states of preservation, and some additional exhibits in a couple of rooms. The palace also allows access to Torre del Mangia ♥, the second-highest medieval tower ever built in Italy. The view from the top is pretty good, albeit through wire mesh, but keep in mind the access to the tower is regulated for a maximum allowed number of people at any given time; there may be a wait before you can climb. The ascent is not very hard, since each flight of steps is reasonably short, but the steps are extremely narrow, and two people going in opposite directions cannot pass without brushing against each other.

Make sure to take a look at Fonte Gaia on the piazza’s northern edge. In addition to exquisite reliefs, the fountain has the distinction of getting its drinkable water from a 500-year-old aqueduct.

When you walk around town, pay attention to the street lamps. They change their shape and colors based on which contrada – the urban ward – you are currently in. There are 17 contrade in Siena; the central area of the town is usually decorated with flags in colors of the one that most recently won the Palio.

Siena’s Duomo ♥♥♥ is one of Italy’s grandest cathedrals, a spectacular mixture of sculpture, painting, and Romanesque-Gothic architecture. Among its treasures are masterpieces by Donatello and Michelangelo and the inlaid marble pavement composed of 56 panels. Do not miss Libreria Piccolomini with its magnificent fresco cycle. Many façade statues are copies, with originals on display in the Museo dell’Opera. The museum holds several floors of iconography and religious statuary, including works by a famous Sienese, Duccio. Access to the roof with panoramic views may require a significant wait here as well since the platform can only hold 25-30 people, with a new group let in every 15 minutes.

Note: Access to the cathedral is not free; you can buy your tickets by the baptistry, which has negligible lines compared to those by the main cathedral entrance; you can then walk straight to the entrance, bypassing the long line.

Opposite the cathedral on Piazza del Duomo is Antico Ospedale di Santa Maria della Scala ♥ whose grand Sala del Pellegrinaio is worth lingering at for a while.

Basilica di San Domenico ♥ is spacious and airy, devoted largely to St Catherine of Siena. On the way between the grand church and the city center, you can find Santuario di Santa Caterina ♥, a beautiful small church and no less beautiful separate chapel, certainly worth a look if you are passing by.

There are several other churches and palaces that may be worth a visit. Some of the palaces open the doors to their courtyards and some hold exhibitions or allow tours. One of our favorites is the serene courtyard of Palazzo Chigi-Saracini, graced by an old well.

Pinacoteca Nazionale is one art museum that should be worth considering.



You may be forgiven for seeing just a single square in Pisa, as that square is among the most magnificent anywhere in the world. Piazza dei Miracoli ♥♥♥ (also known as Campo dei Miracoli or Piazza del Duomo) more than justifies a trip to the city.

The piazza, a UNESCO World Heritage site all in itself, is home to the known-world-over Torre Pendente ♥♥♥. Hordes of tourists photographing themselves in a “propping-up-the-tower” pose notwithstanding, it is an amazing sight, both close up and from the distance when the tower appears to be peeking out from behind the Duomo.

Small groups of people at half-hour intervals are allowed to climb to the top. For those expecting a sideways climbing adventure, you may be disappointed: The steps run largely inside the tower and the tilt is entirely non-discernible. The view from the top is great with respect to the piazza below; the rest of the city is not really inspiring when viewed from above. Advance ticket purchase is necessary during peak season; there is a restriction for children under 8.

The tower stands next to the Duomo ♥♥, with its wonderful four-tiered façade with creamy colonnades and blind arcades. The cathedral is uncharacteristically bright inside due to the large clerestory windows.

The other major building on the green field is the baptistery ♥, which is both imposing and graceful. The look at the interior is worth the entry fee for those who enjoy Gothic and Romanesque lines. The fourth element of Piazza dei Miracoli is the Camposanto (cemetery), which most visitors are likely to bypass.

The city has a couple of museums – such as Museo Nazionale di San Matteo or Museo delle Navi Antiche – and interesting churches – such as, for instance, quayside Santa Maria della Spina – which are worth considering if you budget for more time in Pisa.

San Gimignano

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 and another of the Tuscan UNESCO World Heritage sites. There used to be over 70 towers in this relatively small hilltop town, of which 14 remain today.

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 from their origin centuries ago so one could even say that San Gimignano feels a bit artificial, sort of a small theme park built especially for tourist consumption.

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 Duomo, contains many frescoes of biblical scenes. A few interesting frescoes can also be found at Museo Civico ♥ which occupies several rooms at Palazzo del Popolo, especially in its spacious Sala di Dante. The most important function of the museum, though, is acting as the gateway to Torre Grossa ♥♥♥, the tallest of the remaining 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 and the Tuscan countryside.

Another great perspective is from Rocca di Montestaffoli ♥♥, the castle ruins at the western edge of town. 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, 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 town towers that unmistakably resemble the fallen World Trade Center twins…

Other Notable Places in Tuscany

Volterra ♥♥ is San Gimignano without towers but instead 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 most importantly, access to the bell tower for great vistas over the town and countryside. Museo Etrusco Guarnacci ♥ holds an important collection of Etruscan pieces bequeathed to the town by a local ruler in the 18th century. Nearby Parco Archeologico ♥ is a pleasant space with a few other ancient artifacts, such as stone bathtubs, on open-air display. There is also a pretty good children’s playground to provide a diversion for the youngest. The entry to Acropoli Etrusca is through the park as well.

There is both a Roman Theatre and a Roman Amphitheatre. Both can be toured, and the former can be easily viewed from a high vantage point on Via Lungo le Mura del Mandorlo.

Certaldo ♥ consists of two parts: a fairly unremarkable large village and a noteworthy medieval upper town. 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, of which Palazzo Pretorio merits a visit. The former seat of the Florentine governors is richly decorated with terracotta coats of arms as well as many frescoes in various stages of preservation.

Pienza ♥♥ is a small picture-perfect medieval town. Although it is also a UNESCO World Heritage site, its relative distance from the main cities means that 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.

Val d’Orcia ♥♥ is simply breathtaking and well worth a drive-through on SP146 with frequent stops to admire the perspectives. Although it fully encompasses Pienza, it has a separate World Heritage designation.

Another drive worth taking is along the Chianti Road ♥♥, the stretch of S222 that connects Florence with Siena and goes through the heart of the Chianti Classico region. Dozens of wineries lie on or within a short distance of this prime wineries-touring and wine-tasting thoroughfare. Among our past stops here: a half-day tour-and-lunch experience at Castello di Verrazzano ♥♥, the erstwhile birthplace of the New York Harbour pioneer; a tasting at the shop of Castello Viacchimaggio ♥; and a visit to Castello di Gabbiano ♥♥ (a small detour from the main road toward Mercatale in Val di Pesa).

Greve in Chianti is one of the main towns on the Chianti Road, centered on the pleasant Piazza Matteotti.

Barberino Val d’Elsa is another pretty town a bit off the beaten path on the edge of the Chianti country. Its small fortified hilltop core is full of well-preserved buildings headlined by the notable Palazzo Pretorio.

Monteriggioni is a tiny walled-up hill town close to Siena that is frequently mentioned in guidebooks. The town walls can be ascended in two places, but the surrounding vistas are only marginally impressive. The only square is charming with a tiny Romanesque-Gothic church.

We have spent a total of over a month in Tuscany and still have not been to Lucca, Cortona, Arezzo, Montepulciano, and forty or so other villages that pop up in various “best destinations” lists. One lifetime may not be enough to see all there is to see in Toscana.



In the “memorable stays” category, Villa Antica Sosta (link) sits 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, a large kitchen with modern amenities mixed with period details, three full bathrooms, huge living room. The views are only partial but of the fantastic hillside variety, especially from the upper floor bedrooms. Large territory, great pool, patio, trampoline, and 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. Dinners prepared at the villa by the hosts as well as cooking lessons are enjoyable add-ons to the stay.

On two other locations, we stayed at Agriturismo Le Pianore (link), close to Montespertoli, at its separately situated satellite villas. That was even more memorable, but unfortunately, the villas have been sold to private buyers in the years since. I still consider Le Pianore as a great option for a stay based on my knowledge of the main hotel area and the owners.


As far as eating out is concerned, whether you reserve a table in advance based on online ratings or just pick a restaurant at random, it is hard to have a truly disappointing meal in Tuscany.

Places worthy of specific recommendations in the Montespertoli area are C’era una volta (“Once upon a time” – in a tiny hamlet of Lucardo), a family-run eatery serving the full complement of Tuscan staples that happens to be one of just two restaurants that we had meals at in at least three separate visits to the area (the other one is in Paris);  Trattoria Montalbino (in another tiny hamlet of the same name), which specializes in mushrooms and truffles but serves enough of dishes that do not include either; La Nuova Villamagna (located literally in the middle of nowhere off Via Montelupo north of Montespertoli), a large modern establishment with a not very extensive menu but excellent menu. One other specific recommendation goes to Il Gusto e Il Tatto (at the edge of Castelfiorentino), both for the tasty food and for the great valley views from the terrace.

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