A route through Tuscany: 23 unmissable places to visit

Cast away your watch, your worries and the incoming messages on your Smartphone. Brush everything aside because today you and I are going on a tour around Tuscany. No rush, no schedule. Time to drift along the hills, the Renaissance architecture, the works of its painters, the culinary heritage… with 23 unmissable places to visit.

Just like multimillionaires are not likely to know how much money they have, I am not exactly aware of all the places you should know in Tuscany. Basically because its wealth is boundless. Even so, I have selected 23 towns that are well worth a visit. You will enjoy a circular route around Tuscany with no set agenda. You decide about the time (it’s advisable to err on the long side to fully enjoy the route).


The beginning and the end. The cradle of the Renaissance, of our values and mastery. The heart of Tuscany. There is so much to see, to feel and to savor that it is worthy of an article on its own. You can cross the Ponte Vecchio, admire Titian’s Venus of Urbino, overlook the city from the dome of the Cattedrale di Santa Maria del Fiore designed by Brunelleschi or indulge in the taste of a bistecca alla fiorentina at the Piazza Santo Spirito.

With a small bunch of words I’ve almost set the agenda for a day in Florence and this is just a portion of all there is to see and do in this wonderful city. I would need quite a few paragraphs to portray it more completely.

The Duomo and Cathedral (right) with the Palazzo Vecchio (centre) on the Florence skyline, view at dusk, Italy. The Ponte Vecchio can be seen to the far left crossing th River Arno. (The Duomo and Cathedral (right) with the Palazzo Vecchio (centre) on


On this trip the best vehicle is a car because of the convenience and the possibility of enjoying all the landscapes between one destination and the next. It’s time to leave the city and visit the hometown of a towering master: Leonardo da Vinci. The name of the town is none other than Vinci, 20 miles from Florence and with plenty of olive groves along the road.

There you can see the house where Leonardo was born or visit the Leonardino Museum at the castle of the Guidi Counts, where you can enjoy a spectacular view of Vinci and its surroundings.


Italy’s Capital of Culture in 2017. Quite a cover letter, isn’t it? The Piazza del Duomo is the center around which all the important religious and political buildings are arranged. For instance, the Ospedale del Ceppo, with works by the sculptors Benedetto Buglioni and Giovanni della Robbia. In July they recreate Mediaeval times in the Giostra del Orso. You’re sure to find something unexpected.

Baptistery of San Giovanni in corte or Ritondo (1303-1361) in Cathedral square (Piazza Duomo). Pistoia, Tuscany, Italy


If anyone mentions Pinocchio you are automatically taken to Collodi. Set up on a hill, in the midst of untamed nature, the town stands out majestically. It is impressive from the distance and when you visit it you’ll find it equally striking. The streets of this town were the stomping grounds of Carlo Lorenzini, the author of the famous tale.

Here you can discover the majestic Villa Garzoni, and climb up the hill surrounded by art, water and flowers, sculptures and even labyrinths. Enjoy a Chianti wine and some Carapelli olives, because this is a place where you can relax and enjoy the calm atmosphere.

view of Collodi, a typical and traditional village in tuscany


Barga is a most beautiful town–not only of Tuscany, but one of the finest in the whole of Italy. But there is more to it–there is mastery all over. In the 13th century it was a key location for the silk trade. Its rise was the source of many conflicts. Its historic and artistic heritage is such that it’s best for you to discover it on your own.

il quartiere della Fornacetta architettura organica all’ambiente


What can we say of Lucca, “the city of a hundred churches and a hundred towers”? Its Mediaeval walls, which are intact, contain Renaissance beauty at its highest. The historic quarter is not very big but the possibilities are infinite.

Here’s a tip: there are signs indicating a route through the city. You can stroll calmly through the streets and stop in any of the many restaurants to enjoy the typical tordelli lucchesi, prepared with the best extra virgin olive oil.

Duomo di San Martino at the Piazza di San Martino in Lucca.


There is a lot more to Pisa than its leaning tower (yes, you shouldn’t miss it; the surroundings are also worth a visit). There are many churches meriting a visit in Pisa. Take a stroll along Borgo Stretto, one of the most charming and picturesque streets, the ideal place to capture the spirit of this university town.

Pisa is every one of its piazzas. It is Via San Martino with its ancient Etruscan tombstone that many are not aware of. Pisa is also the legacy of its master Galileo Galilei, the Renaissance scientist, among many others.

Leaning Tower of Pisa – Aerial – December 2017 – Sunset


On the road from Pisa to Volterra (next stop), I recommend paying a visit to Casale Marittimo, a small town of Tuscan stone on a hill surrounded by meadows, olive groves and vineyards. It won’t take up much time, although it might prey on the memory in your camera. The beautiful streets lead you to the hilltop, from where you can enjoy the surroundings–the countryside and the sea. Stop for a second, take a deep breath of the sea breeze and then enjoy a bruschetta with some fine extra virgin olive oil.

Houses and Clocktower in the old city of Casale Marittimo, Tuscany, Italy. The late evening sun casts a warm light. This image is a tonemapped HDR image of three exposures.


Arriving at the Mediaeval city of Volterra will surely speed up your heartbeat, because there is a steep climb before entering its walls and accessing the citadel. The Palazzo dei Priori was the inspiration for the Palazzo Vecchio in Florence, such is its historical value.

Volterra is one of the culinary and artistic points of reference in Tuscany. It’s best that you go there with your eyes wide open and on an empty stomach.


I’m most likely right in asserting that this is one of those towns that is little known by tourists. Certaldo Alto is the historical quarter of Certaldo, which you can access by funicular (an attraction in itself). Certaldo is the birthplace of Giovanni Boccaccio, the author of the Decameron.

You can walk through the streets flanked by Mediaeval buildings that are conserved intact, contemplate the frescos of the church of San Tommaso and Prospero, admire the handicrafts (especially the pottery), try the filetto di maiale arrosto al lardo di Colonnata con cipolle di Certaldo, and, especially, sit at a terrace and look on to the next stage in the route: San Gimignano.

Scenic panorama of medieval old town of Certaldo, Tuscany, Italy, with San Gimignano towers in the background, typical Italian and Tuscany countryside landscape


This town is one of my most coveted jewels along the route. Its 14 towers rise up surrounded by cypresses, sunflowers, olive groves and vineyards. It’s a remarkable number for such a small town, but just think that they built up to 72 towers back in the day.

I do not have the time to tell you about everything this town has to offer. Your first task in San Gimignano is to get a map. The second one is to buy a combined ticket so that you can have access to the many monuments at a reasonable price. The third recommendation is to drink a glass of Vernaccia, a typical white wine from this area. And the fourth thing is to walk to wherever the cobblestone streets may lead you.

San Gimignano medieval town towers skyline and countryside landscape panorama at sunrise. Tuscany, Italy, Europe.


The mediaeval town of Monteriggioni rises up surrounded by a wall and olive groves. As you get closer you will be able to make out this small 13th century fortress that tops one of the many hills shaping my beloved Tuscany. A couple of streets and a large square are more than enough to take in the Mediaeval spirit and imagine the many battles in the feud between Siena and Florence to secure control over this little fortress town.

An aerial view of Monteriggioni, Siena.


Another one of my soft spots. There was a time when it was my greatest discovery in Tuscany and it could happen to you too. Indulge in the unique sensation of walking through the steep cobblestone streets flanked by sumptuous palaces, majestic fountains and magnificent churches.

Siena has something special in the air, heightened by the beauty of the Duomo, the Piazza del Campo with the Torre dei Mangia and the Mirador of the Basilica of San Domenico. This city is well worth a whole day with no hurries. You can finish the evening by dining at Via Bianchi di Sopra and having a ‘panforte’ as your dessert.

Parade with people wearing traditional and historical clothes before the race at Siena city, Italy, during the August 16th, 2018 The “Palio di Siena”, known locally as “Il Palio”, is a famous horse race held twice a year in July and August since 1656. Ten horses representing ten of the seventeen districts (“Contradas”) with jockeys riding bareback compete during a three-lap race around the city’s central square (Piazza di Campo).


In the midst of a forest landscape we find Murlo, south of Siena. This town, deeply rooted in its Etruscan heritage, hasn’t changed much over the last seven centuries. If you happen to visit this town in May you can enjoy the ‘Fiesta in Collina,’ where you can try out artisan foods and admire the local handicrafts. It won’t be a very long stop but it is surely worth your while.


Montalcino is the home of one of the most famed red wines in Italy. I’ve always thought it’ a good idea to sit down to a nice glass of wine inside the Fortezza. But there is much more to this town than enjoying its wine or the local cuisine in s Mediaeval castle (Il Castello Banfi). You can visit San Salvatore, the Madonna del Soccorso, climb to the top of the walls and contemplate the landscape, visit the Piazza del Popolo or the Palazzo dei Priori.

Montalcino town in Tuscany over sunset


A place included on the World Heritage List is a mandatory visit. No arguing against that. Here you will find the legacy of Pope Pius II, who made his hometown a Mediaeval burgh with Renaissance architecture. A charming place that could have grown further if the pope hadn’t died, because that brought the project to its end. Aside from all the other charms, make it a point to try out the exquisite Pecorino de Pienza, one of Italy’s many wonderful cheeses.

Radicofani street view. Radicofani is a comune in the Province of Siena in the Italian region Tuscany, located in the natural park of Val D’ Orcia.


Hollywood chose this town as the setting for a movie thanks to the wonderful mixture of well-conserved Mediaeval and Renaissance architecture. The Piazza Grande, the highest point of the city, seems to set the layout for all the monuments when looking at a map. Its monuments consist of the cathedral, the various palaces (for instance the Palazzo Comunale and its imposing tower) and the churches.


The silence of the streets winding up to the hilltop always inspired me and drew me into a relaxing mood. It may be the peaceful and picturesque of all the towns along this route. It is not surprising that this town is known as ‘the city of love’. The rooftop terrace facing the Collegiata de San Michele Arcangelo is an invitation to disconnect while you look at the turrets along the wall. Strikingly, you may not disconnect after all if you use the free WI-FI at the Piazza de San Francesco. Life never ceases to surprise you.

Street in the historical center of Lucignano in Tuscany – Italy


‘Under the Tuscan Sun’ rises the town of Cortona. The setting for the famous movie, it is one of the most beautiful stops along the entire route. Not only for its streets but also the views of the Tuscan countryside. There are many legends to be told about this town. I cannot pick out what you have to visit here because the list would go on and on. There are certain pleasures that you need to discover on your own.

Main square with city hall in Cortona, Tuscany Italy


Sadly for me, we are reaching the final destinations of this voyage. But there’s still a lot to see. The origin of Castiglion Fiorentino goes back to the 4th century A.D. Plenty of history in just a few square miles that will take you to different periods within Italy’s boundless history.


Arezzo is pure gold. Don’t get me wrong–the main industry is the crafting of jewels made of this precious metal. World War II was harsh on this town and many of the narrow alleys became large avenues following the reconstruction. Even so, the historical quarter retains plenty of its charm.

Going on with movie connections, in Arezzo ‘Life Is Beautiful’. Not only because of the motion picture, but also thanks to the antiques fair at the Piazza Grande, the basilica of St. Francis, the church of San Domenico, the view of the city from the Medicea Fortress and the Castle of the Medici.

The Antique Fair in Arezzo is the outdoor event dedicated to antiquarian, modern and vintage antiques and bigger in Italy. It was born in June 1968 from an idea of the historic antiquarian Ivan Bruschi and, uninterruptedly since that date, is held every first Sunday of the month and the previous Saturday in the streets of the historic center of Arezzo


The second-to-last stop, assuming that Florence is a place with plenty to see not only at the beginning but at the end. I adore Montefioralle not only because of its beauty and history, but also because local families often welcome visitors and cook meals to share with them in their homes. Not a bad way to try out Tuscan cuisine with olive oil in the center, is it?

You can also walk through its streets. Some of them were part of a castle, because this town was a fortress in the times of continuous battles between Florence and Siena. It is s good place for enjoying nature thanks to the various hiking paths around the town.

Small town Montefioralle in Tuscany, Italy


Yes, Florence again. Florentia was the name in the times of the Roman Empire. As I stated above, it’s complicated to cover Florence in just one visit. The good think about this circular route is that it gives you a second chance. Time to check the list and see anything you missed or even go back to places that captivated you the first time around.

The list could have been longer and I’ve got to admit it was hard to leave out a few towns. Surely we have managed to discover many delightful places that are worth visiting. Altogether, a drive of around 400 miles. The distance can comfortably be covered in a few days of travel. Now if you do complete this trip, I’ll be looking forward to your remarks once you get back.