All of our Tuscan trips begin and/or end in Florence and most include stops (although so far, not stays) in Florence’s large, millennia-old rival, Siena. Although it is a lovely city and we still intend to get back, especially for the Palio di Siena horserace, we skipped it on this trip to focus more time on the small towns, the countryside and the more rural experiences that really make Tuscany unique.

In fact, we were so intent on exploring these areas that we dedicated only one day (and two nights) to Florence. (While we would never, ever recommend that anybody so shortchange this incredible city, this was our fourth visit to Florence and we had spent much more time in the city on our previous trip, including those two and four years ago.) We also skipped other fascinating towns, such as Corona in the Eastern corner of the province and Lucca in the West, as well as some of the classic stops in Pisa, like the Cathedral and the iconic Leaning Tower (each of which we have done in recent trips.

This trip was dedicated almost exclusively to central Tuscany, and especially many of the small towns and experiences—including wine tastings, cooking classes, exploring farmers markets, and foraging for truffles—that make this area unique. But, as discussed in our previous blog, Planning an Exploration of Tuscany, even central Tuscany is a large area. Driving distances can be long, most roads require slow speeds and signage is inconsistent—you will get lost and you will get frustrated. (I swore more during one week of Tuscan navigating than I had in the past year!). So, while we spend our entire trip in a lovely, remote villa, I now, as discussed in our previous blog, strongly recommend dividing Tuscan trip into segments. So, after leaving Florence, you can, for example, stay in:

• Greve, to explore for northern Chianti;
• Siena, to experience that city, to explore wonderful neighboring towns as Monteriggioni, Volterra, San Gimignano, Certaldo and surrounding areas;
• Montepulciano for the town itself, its Vino Nobile de Montepulciano wineries, and for neighboring towns including Montalcino (and its Barolo wineries), Cortona, San Giovanni d’Asso (for truffle foraging) and for brief explorations of Western Umbria (Lago Trasimeno and Perugia;
• Lucca for that town, for the primary sights of Pisa and the rest of northwestern Tuscany, and as a launching pad for a side trip into southwestern Liguria and the lovely towns of Cinque Terra (see our following blog).

Favorite Central Tuscan Towns

But which of the many towns are most interesting and most fun? Following are some of our favorite towns:

San Gimignano

This is one of our, and most other visitors’ favorite towns, as well as being a UNESCO World Heritage Site. Most of the streets, buildings and iconic towers date to the 13th and 14th centuries. While there are certainly churches (especially the Collegiata) to see, museums (such as the Civic and Etruscan museums) to visit and towers and city walls to climb, the greatest treat is just wandering the streets. While no visit would be complete without walking the primary commercial streets (Via San Giovani and Via San Mateo) and Plazas (Duomo and Cisterno), be sure to get off the beaten path to explore the many side streets. This being said, however, there are a few must-do stops on the shopping streets. First are some of the many cheese, salumi and specialty food shops. Then a couple of leather goods stores, if for nothing else but to smell and feel the satiny smooth hides. There is also one must-visit art gallery–Galleria Arte Contemoranea on Via San Giovani. It has some of the most interesting pieces we have seen in years.

Our San Gimagnano restaurant experiences, including this one, have been nothing to write home, or even blog about. Lunch was at La Magngiatoia. While the restaurant is very pretty and comfortable, my lamb chops were overcooked, Joyce’s wild boar ragu too oily and the service (albeit on the outside) was somewhat inconsistent. Although we will certainly return to the town, we hope to have better luck with restaurants.

Greve in Chianti. Chianti has a number of very nice towns, such as Gaiole, Radda and Castelena. We, however, particularly like Greve. It has a pretty historic area and a great town square. And it didn’t hurt that one of our visit’s coincided with a celebration.

Just as importantly, the square houses our absolute favorite Tuscan store–Antica Macelleria Falorni, which, as discussed in our Tuscan Winery and Culinary Experiences blog, makes, ages and sells a huge selection of Tuscan sausages, cheeses and wines. It has nice shops–including some very well stocked entecas and is surrounded by some of the best Chianti Classico wineries. It is also relatively centrally located, allowing you to get to more segments of the Tuscan wine region with somewhat less driving. This can become an important consideration if you are long to at least modestly reduce the 60-90 minute drives that it seems to take to get from anywhere, to anywhere in this sprawling region.

Montepulciano. One of our absolute favorite Tuscan towns. While this is one of the larger and most beautiful–both itself and for its setting and it’s views–of the medieval walled cites. Montepulciano also has something going for it that few others have. It was and still is he home of Italy’s Vino Nobile, a wine that was traditionally available only to nobility. Some of Tuscany’s oldest and finest vineyards and wineries are located in the areas and a few of these wineries are located right in the town. These ancient cellars, which are open for exploring and tastings, are buried meters below the main square (Plaza Grande), which is surrounded by medieval palaces and churches. There are dozens of Entecas at which you can taste and buy wine, specialty shops that offer all types of Tuscan foods leather goods and many restaurants—including one of the best restaurants of our trip. We enjoy Montepulciano so much, and there is so much to do, that we devoted a blog specifically to the town and one of its nearby Vino Nobile wineries.

Pienza. This town, another UNESCO World Heritage Site, which is absolutely lovely, is also famous for its Pecorino cheese. Not really on much of a hill, but lovely nonetheless. Unfortunately, we arrived after dusk, could stay for only a few minutes and most of its shops were closed. We did, however, have time to get at least a feel for the town and were able to visit one cheese shop at which we browsed the offerings and, after discussing our likes and dislikes with the owner, left with a pecorino aged in grape must. Sitting at home with this, a bottle of Montipulciano Vino Nobile and charcuterie from Greve’s Antica Macelleria Falorni (see our Tuscan Winery and Culinary Experiences blog)—heaven.

Montalcino. While the walled town has a nice fortress and cathedral, its primary attraction is its wine tasting/retail stores that explain and allow you to taste different type of currently drinkable Rosso di Montalcinos and much more complex and age-able Brunello di Montilcinos.

Montergiorno. A small town with nice walls and ramparts, stores and wine tasting/retail rooms.

Volterra. We we’re also told of another town that "could not be missed." unfortunately, we had to miss it. Oh well, we have to save something for our next trip.

A number of moderate sized Tuscan towns were founded in and increasingly built around medieval walled hilltop centers that housed the castle, the town hall, the church and many local merchants and restaurants. We had two such towns on either side of the remote hilltop town in which our villa for this stay was located:

• Certaldo Alta This is the old, walled, hilltop section of the town of Certaldo that’s accessable from the town square by road, stone-paved trail and funicular. The highlight is the Palazzo Pretorio, which is can be toured, and the Artesia pottery, where you can buy, and take classes to learn to make, majolica ceramics. While Certaldo Alta makes for a pleasant walk if you are in town, we don’t see it as being worth a special trip, especially in light of so many other Tuscan villages.
• Barberina Alta. a similar, albeit somewhat smaller medieval walled town a top a much smaller hill.