Tuscany has earned a glowing reputation among European travelers, with its verdant landscape, Chianti vintages, and Renaissance splendour. It’s a wide-reaching region – both geographically and culturally – and so it’s not enough to pop into one renowned city and check it off your list. For an authentic Tuscan experience, you need to explore the nooks and crannies, both the hilltop towns and towering cities, to understand just what this land is all about. From pre-Roman roots to a medieval legacy that has hardly paled over six centuries, there is an abundance of history, tradition and ritual that shines through these ten must-see Tuscan sites.

 

Florence

shutterstock_173846513

A city famous for its culinary prowess, Renaissance overtones, and Medici majesty, Florence is a must-see for every Tuscan traveler, but there’s more to see here than the Uffizi and the Duomo. Florence is a pretty big city, with a few interesting pockets outside of the central Piazza della Signoria: take the bridge across the Arno River to the Boboli gardens and onto the hip Oltrarno neighbourhood, a stretch of sophisticated cocktail bars, artist hangouts, modest but delicious restaurants, and the tree-lined San Spirito square. Check out the various markets of San Lorenzo, the towering medieval remnants, and the wealth of ornate churches. When the sun dips down, sidle up to a street-side enoteca to sip on a glass of Chianti with the locals.

 

Siena

2

Siena’s medieval elegance and gothic flourish make it a shining highlight in any Tuscan tour. While other cities boast a similar array of crumbling castles and cobbled piazzas, the winding lanes of old Siena are drawn together with the sprawling central Piazza del Campo: here you’ll find theatrical performances, horses races, and the casual daily gathering of people within the semi-circle of Gothic facades. With an impressive array of museums and restaurants to round out the old city, Siena attracts a good deal of attention from Italian travelers and foreign travelers alike.

 

Lucca

shutterstock_104296931

A soft-spoken city with a tremendous Roman heritage, Lucca has a welcoming historical flavor that stands out among the surrounding villages and rolling hills. Lucca is contained by one of the most well-preserved walls in Italy, with a wide footpath that runs along the top, lined with gardens and promising some pretty outstanding views. Take the path right around Lucca’s ancient city center, then walk down to explore its medieval towers, exquisite churches, and sunny squares dotted with restaurants and adorned with flowers. It may not have the jaw-dropping art galleries of Florence, but Lucca is a museum unto itself.

 

Garfagnana

4

Just north of Lucca you’ll find the green expanse of the Garfagnana Valley, crossed with forested paths set against mountain peaks. This is Tuscany’s highlands, and it’s filled with idyllic villages, Renaissance manors, and surprisingly, some Scottish influence. The spa center of Bagni di Lucca brings in travelers seeking a bit of R&R, and the wooded trails attract walkers and hikers after a big breath of fresh air. The main town in the region is Castelnuovo di Garfagnana, housing an impressive Duomo, a fortress, and the Rocco Ariostesca, a castle-turned-museum showcasing some excellent artifacts from the region.

 

San Gimignano

5

Just off the road between Florence and Siena, perched atop a little hill on the horizon, San Gimignano offers a remarkable silhouette. Much of the medieval wall is still intact, and there are 14 tall towers that are testaments to the city’s noble ancestry; the wealthy families of the city originally built 72 towers to showcase their power and affluence, but most have crumbled through the centuries. The stony city is still an impressive site, with a handful of excellent museums and countless little cobbled roads and pretty boutiques peddling saffron and the region’s white wine – Vernaccia di San Gimignano.

 

Cortona

6

A storybook town with an unmatched view, Cortona is tucked into the southern reaches of Tuscany. Since it’s off the main tourist trail, you’ll find a charmingly serene atmosphere amid the fortress walls and Roman ruins of this hilltop town – the village enjoyed a highly strategic positon for centuries. Today, it boasts some of the best Etruscan archeological finds in the whole province, exhibited in the MAEC museum and the Archaeological Park. Pop outside the city walls for a visit to the Franciscan Hermitage le Celle, built in 1211 by Saint Francis of Assisi.

 

Pistoia

7

Pistoia may be small, but it offers a bit of the best art, architecture, food and landscape in the region. It has picked up the endearing moniker “Little Florence” with a formidable concentrations of world-class renaissance and gothic treasures. The main square, Piazza del Duomo, is outfitted with gothic grandeur – ornate stone facades stretch around the space, including the 14th century Baptistery of San Giovanni in Corte. You’ll also find seven museums within a hundred meters, and the medieval marketplace will take you several centuries back in time. There’s definitely enough going on to warrant an overnight stay, but Pistoia can also make a nice day trip from Lucca or Florence.

 

Montepulciano

8

Another medieval town strategically placed atop a hill in Tuscany’s south, Montepulciano has a good helping of fortress remnants and romantic towers, but the city stands out from its neighbours in a few appealing ways. For one, the main road leads uphill to a splendid mix of Renaissance palaces, pristine squares and wine-tasting shops (this is, after all, the heart of the Vino Nobile wine growing region). And unlike many other villages in the area, Montepulciano is relatively lively town, with summer festivals and traditional events that bring locals and visitors to the astounding central piazza. It’s also a wonderful spot for further exploration, so consider hanging around for a day or two.

 

Arezzo

9

An exceptionally old town with a storied history, Arezzo dates back to the 9th century B.C, when it was known as “Arretium” and stood at one of the most important cities in the region. Today, Arezzo is one of the wealthiest cities in Tuscany, and it wears its wealth well: incredible Renaissance frescoes, a Roman fortress and amphitheatre, clean and ornamented streets, and an array of pleasant boutiques and trattorias. Summer is the season of fairs and festivals, and there are a number of quaint villages just a short drive away. One great virtue of Arezzo is the relative calm: it’s far enough off the tourist track that most people just ignore it altogether.

 

Val d’Orcia

10

This beautiful valley south of Siena is home to some of the prettiest landscape in the country: rolling hills of vineyards, olive groves and little villages suspended in time decorate the green fields. In fact, the area is a designated UNESCO Heritage Site, and continues to inspire visitors as it had inspired Renaissance painters centuries ago. The valley is also home to a few celebrated wine brands, given this is home to the prestigious Brunello di Montalcino and Nobile di Montepulciano varietals. You’ll find countless charming buildings along your way, from castles and abbeys to unique towns and hamlets. Pienza is perhaps the most intriguing of all, known as the “Ideal City” in Renaissance terms (and times) – enjoy the winding streets and gorgeous Palazzo Piccolomini.

Trains and planes can get you into major hubs, but a car is almost always a good idea when you’re traveling around Tuscany. Remember, most sites aren’t very far from another significant spot; an itinerary can be strung together with one or two-hour drives, and you can actually fit quite a bit in a week or two. Of course, you may also be tempted to rent a countryside villa and settle in for a delicious and enlightening summer!