I have taken many shorter day and more extended week long trips to the Toscana region over the last decades. With the expansion of the high-speed train network in Italy, it is quite convenient to reach many cities in Tuscany for a day trip from a base city in another region, from Rome, for example. Another option, of course, is to choose a base in Tuscany, rent a car, and be able to drive through the rolling hills visiting tiny hilltop town and cantine (wineries) throughout the region. This section is only a preview of what innumerable Tuscan towns have to offer.

Montalcino

Montalcino was one of my first loves in terms of Tuscan towns. It is best to drive there as the closest well-connected train stations are Chiusi (which is very small) and Siena, but they are both still 40-50 km away. If you look on a map (at right), the hilltop town is surrounded by green space without major roadways or train lines.

This may seem obvious, but these medieval (and in many cases ancient) hilltop towns were placed ‘on top of hills’ for the purpose of protection. Thus, today, we benefit from the strategic position for the pure aesthetic pleasure they offer; albeit, they are more difficult to reach. The views from the town are gorgeous and sweeping. What’s more, the tiny town has a large connection to wine from the region. The Brunello di Montalcino is a highly regarded DOCG wine which is produced exclusively in the vineyards around the town. In fact, the “Brunello was the first wine to be awarded Denominazione di Origine Controllata e Garantita (DOCG) status”. Montalcino is quite small, but I preferred it to the neighboring (and oft confused) town of Montepulciano. Don’t get me wrong, we are comparing two utopias. Also, as a quick clarification (I was confused by this for a long while!) Montepulciano, the Tuscan town, is also associated with a wine, but this wine is called the Vino Nobile di Montepulciano and it is made, primarily, from the Sangiovese grape. There is also a Montepulciano grape, but it is primarily grown in the region of Abruzzo, not Tuscany. Alas, there is no deeper connection between the town and the grape that go by the same name.

Back to Montalcino. The town has a population of just over 5,000 people, and I was just smitten with it upon visiting. One day is enough to appreciate the charm but stay for longer and fully embrace the magic if you can!

Visit La Fortezza di Montalcino (the Fortress of Montalcino). Constructed in 1361, thus making it a perfectly medieval structure, this fortress is a place to take in views of the Val d'Orcia, that is the official name for the valley area below Montalcino. Rather appropriately, if not ironically, the grand Fortress today has become part Enoteca, where you can shop and enjoy wine tastings. The view from the Fortress was granted UNESCO status in 2004. The natural landscape was recognized as an “exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures.” Thus, when you get the feeling that you are gazing upon the landscape in a Renaissance painting, you can feel validated!

The interior of the Fortezza di Montalcino with the extensive wine shop inside.

Eat at the Taverna del Grappolo Blu. The restaurant is commended and recommended by the Michelin guide as featuring “traditional Tuscan dishes made from carefully chosen ingredients served in a pleasantly convivial atmosphere.” There is no lack of beautiful views on the descent to the restaurant either.

Taste local wines, either at one or many of the Enoteche (wine shops/restaurants) throughout the town or take a tour to some of the local producers in the area. If you have a car, you will have more freedom to visit some of the wine producers around the area, but you could also book with a guide creating a custom tour or a larger group tour, depending on your budget and priorities. Here are some options for package tours leaving from Rome, Florence or Siena, and here is a Sommelier who seems to offer a more custom experience.

Lucca

I very recently visited the town of Lucca, and I found it absolutely delightful. You can take the train from Rome, but you will need to change to a slower regional train in Florence. Still, there is a convenient train station that lies just outside of the city walls of Lucca. The city walls are particularly special in Lucca, which I will explain below. Once you are inside the walls you will feel enveloped by a magical Tuscan atmosphere. I stayed in a perfectly characteristic Airbnb called Suite Magnolia, a five-minute walk from the train station, just inside the city walls. Even the views from the window of the Airbnb are charming.

One of the main activities on a visit to Lucca is walking. Start with the walls.

Walk around the fully intact Renaissance city walls. The walls we see today were completed in 1650, after a century of work. They continued to be expanded upon well into the 1800s. These Renaissance walls were built upon medieval city walls, and evidence suggests that there was a first defensive wall built in Roman times. The beauty of traversing the 4.2 km (or 2.6 miles) around the perimeter of the city involves the tangible appreciation of the second longest circuit of city walls in Europe (only the walls in Nicosia, the capital city of Cyprus, are longer) but also an elevated view of the entire city of Lucca. Thus, I recommend walking the walls in the morning upon arrival before starting your exploration in the city center.

The interior of the restaurant Buca di Sant'Antonio in Lucca

Eat at Buca di Sant'Antonio, an elegant restaurant very near the Duomo di Lucca (also known as the Cattedrale di San Martino). The restaurant has been in this spot since 1782. The interior is tastefully decorated with old utensils, pots and pans hanging on the walls creating a warm domestic feel.

*Toretelli al Sugo (The specialty pasta at the Buca di Sant’Antonio*

This restaurant has also been praised by the Michelin guide. Waiters are attentive but quite formal, and certainly take pride in their establishment and the work they do. The food was exquisite. I dined alone and was pleasantly surprised by the option to order half portions of the primi and secondi. Thus, I got to try the house specialty of I Nostri Tortelli al Sugo (stuffed tortelli, which are similar to ravioli, with homemade meat sauce), and I followed with the cinghiale in umido (tender wild boar). You will notice that many dishes are identified as ‘Lucchese’ on the menu; thus, they are typical not only from the region of Tuscany, but even more specific to Lucca. The restaurant also has an easy online system for booking a table on their website, and you should book at least a week in advance.

The Guinigi Tower at the end of a picturesque Tuscan street in Lucca

Experience the unique sites of Lucca. In the regions of Tuscany and Emilia-Romagna, in particular, there are many ‘towers’, mostly Medieval and Renaissance in origin, to experience. The Tuscan city of San Gimignano is famous for medieval towers that “noble families and upper middle-class merchants who controlled the free town built…[there are] many fortified tower houses (probably 72) as symbols of their wealth and power,” as noted on the UNESCO website. In Bologna, you can admire the sister towers of the Torre Degli Asinelli (taller) and Torre Garisenda (shorter). However, here in Lucca, there is the most peculiar tower, in my opinion. It is a Romanesque-Gothic tower, The Guinigi Tower, from the 1300s, but on top of the 232 steps, there are trees growing.

A selfie at the top of the Guinigi Tower with the trees peeking into the gorgeous panoramic view

You can admire the strange sight from your walk on the walls, but then climb the steps of the tower (after paying a nominal entrance fee) and sit under the umbrage of trees, 45 meters above the streets of Lucca, with panoramic views of the city and countryside all around. According to the Visit Tuscany website, the patrons, that is the Guinigi family intended the trees to represent rebirth and renewal. Their wish was granted, I must say, because upon gazing at this rather uncanny sight, one questions assumptions and the laws of nature.

Another interesting perspective in the city of Lucca is the Piazza dell'Anfiteatro, a massive piazza in the center of the city constructed on top of the remains of an old roman amphitheater, where gladiators would have performed. Wander through the expansive square and then explore the shops and streets in the vicinity.

Florence

I must provide a disclaimer here: I am not the most fervent mistress of Florence. You might have noticed that I abuse the term ‘favorite’ throughout this website; I have many ‘favorites’ throughout the 20 regions of Italy, but I must admit, Florence is not one of my personal favorites. For a ‘taste’ of Tuscany, I prefer the quainter (slightly more obscure) cities I have highlighted, Cortona, Montalcino and Lucca. It is the feeling, the magic, that for me, does not always manifest in Florence with the number of tourists packed into a smaller city than Rome, for example. That said, Florence is home to some of the most precious artistic masterpieces on earth, and you should see them. I guess I am trying to be honest by saying, consult other sources as well, other true Florence enthusiasts, when planning a trip. They will share their passion, perspective, and knowledge of hidden treasures. Below, I offer a starting place.

I personally recommend at least one full day to visit the Uffizi and the Accademia; then, compliment this trip with at least one other town in Tuscany for the atmosphere. Since the further development of the high speed train service (the Freccia Rossa with Treinitalia and now the competitor Italo) you can travel from Rome to Florence in less than 1 hour and 30 minutes; thus, a day trip to Florence is more than feasible from Rome or many other major cities in Italy. Again, this is my opinion, and others will argue that a day trip certainly will not due justice to the ‘culla del Rinascimento’ (cradle of the Renaissance). Therefore, I leave you with some of the requisite Florence experiences, and one restaurant that was divine, as only an introduction.

Michelangelo’s David; photo credit to my friend Shelley

Visit the world class museums and Boboli gardens. The Gallerie degli Uffizi (Uffizi gallery) holds, arguably, the most important collection of Italian Renaissance artworks. The museum itself was designed by Giorgio Vasari, a famous biographer of Renaissance artists who first coined the term Renaissance. In addition to being a biographer, Vasari was an artist and architect himself and he designed the Uffizi for Cosimo I de’ Medici; it was built between 1560-1580. The website for the museum is quite educational and functional; you can find out how to purchase tickets online and plan an itinerary ahead of time After the Uffizi, head to the Galleria dell'Accademia, which is where Michelangelo’s grand sculpture of the David lives. Created between 1501-1504, Michelangelo used only one block of Carrara marble to sculpt his masterpiece. What I enjoyed most about the museum upon my last visit was further understanding Michelangelo’s process through the works in process lining the hall leading up to the great David. You can see a block of marble with an unfinished figure coming to life.

You can buy tickets for the Galleria dell'Accademia ahead of time online, and you absolutely should. The Boboli gardens are a part of the Gallerie degli Uffizi network, so you can find out information and purchase tickets through the same website. In addition to being a gorgeous green space to walk around, the gardens, conceived in 1549, have become the prototype for an Italian Renaissance garden and have been emulated in green spaces around the world.

Eat at Olio e Convivium (which now seems to be going only by the name ‘Olio’). This restaurant, and gourmet shop is located across the Arno river, not too far from the Pitti Palace and Boboli gardens. This quieter side of the city is very pleasant. The restaurant itself is housed in the Palazzo Capponi, a historical building acquired in 1500 by the wealthy Capponi family. The space is gorgeous, the menu is both traditional with some seasonal creativity, and service is attentive. You can explore the menu further and book a table online through their website.

Explore the Churches of Santa Maria Novella and the Duomo. You will come upon Santa Maria Novella as soon as you exit the main train station in Florence; in fact, the church is the namesake of the station. Santa Maria Novella is an art history nerd’s dream. Inside you will find Masaccio’s Trinità, a fresco that was created between 1424-1425. This fresco is important to the history of art as it is hailed as one of the first known works to demonstrate the art of perspective.

The Duomo of Florence (also known as Cattedrale di Santa Maria del Fiore) dominates the cityscape. In fact, you should take in the view from Piazzale Michelangelo, an elevated 19th century square with a replica of Michelangelo’s David on the south side of the Arno River. The cathedral has the largest masonry dome in the world which was engineered by Filippo Brunelleschi. Although construction on the building started in in the late 13th century, it took almost 140 years to complete. The Duomo is a part of the Historic Center of Florence which became an UNESCO World Heritage site in 1982. In addition to the Dome of the cathedral, the Campanile (bell tower) created by Giotto and the baptistery are considered architectural wonders. I would recommend a tour to truly appreciate the significance of the place.

After a visit to the Duomo, do wander through the Sant'Ambrogio food market. Here is a video my former partner filmed highlighting one of the well established butchers. The Piazza della Repubblica is also a large historical square worth a stop by, and on your way to the Boboli Gardens, be sure to pass over the Ponte Vecchio (pictured above); it is the most famous bridge in the city, and “the only bridge across the Arno in Florence until 1218.” Find out more here.

Regional Features

Food and Wine

Spots in Cortona