Last Updated on 25th February 2021 by Sophie Nadeau
From tiny little medieval settlements tucked high on hilltops to busy modern metropolises where the hint of history is never too far away, there’s no shortage of stunning settlements to visit next time you’re in the Tuscan area of Italy. Here’s your ultimate guide to the most beautiful cities, villages, and towns in Tuscany you simply must visit on your next Italian adventure!
Known in Italian as ‘Toscano,’ Tuscany is to be found in the cental-western part of the boot-shaped country and covers an area of about 23,000 square kilometres. Owing to its extensive wine production, not to mention that the Tuscany capital is Florence, one of the most vibrant and beautiful cities in Europe, Tuscany offers many adventures to be had for every kind of visitor.
Siena is Tuscany’s second largest and, as a result, has plenty to see and do for even the most discerning of travellers. Best seen in the shoulder season (i.e. spring or autumn) in order to combat the sheer temperatures of the summer months but be able to enjoy the medieval city with good light and favourable weather conditions, the historic city centre of Siena is listed as a UNESCO world heritage site.
Once in the city, there are plenty of activities you’ll love, and as well as a fantastic Italian food scene, Siena offers plenty for culture and history lovers. While the Piazza del Campo is the city’s main square, around which everything else in the town is situated, the Duomo di Siena (Siena’ Cathedral) is one of the most beautiful in the entirety of Italy.
Located alongside the Serchio river in the heart of Tuscany, Lucca is a must-see for architecture lovers, particularly those of the medieval kind. After all, the Tuscan town boasts well-preserved Renaissance walls which encircle the town, as well as a plethora of churches. So numerous are the ecclesiastical buildings in Lucca, that the settlement is sometimes called ‘the city of a hundred churches’.
Much of the town is constructed around the Piazza dell’Antifeatro, which in turn is constructed on what would have been the central point for Roman life some two millennia or so ago. Other highlights and things to do in Lucca include the Delle Ore Tower and the Guinigi tower.
Of course, the most famous town in Tuscany is actually its capital city. Known as Firenze in Italian, Florence is a beautiful settlement characterised by its beautiful Renaissance architecture and fascinating medieval history.
Best-seen over the course of a long weekend, and even longer if you have the time to spare, highlights include the fantastic Duomo (officially known as the Basilica di Santa Maria del Flore – purchase skip the line tickets here in advance), enjoying the art of the Uffizi Gallery, and admiring the Ponte Vecchio at sunset.
A hilltop Tuscany town with a history dating back all the way to the time of the Eturscans, and perhaps even beyond, Cortona can be found in the province of Arezzo and is well worth visiting over the course of a day or two, provided that you have the time.
Once in Cortona, asides from wandering around the medieval town, one of the best things to do is to visit the Etruscan Academy Museum (Accademia Etrusca), which showcases collections of ceramic, bronze, and funerary artefacts from Cortona’s Etruscan past. The museum also comprises of an archaeological park, which features the ruins of Roman roads and former city fortifications.
Greve in Chianti
If there’s one area in particular in the Tuscan countryside you simply must frequent during your time in the boot-shaped country, it’s the wine-country area of Chianti. Known for its rich reds, the little villages that surround the swathes of vineyards are a must-see and that of Greve in Chianti is simply no exception.
Located around 30 kilometres to the South of Florence, Chianti offers little by way of tourist attractions, with the exception of its many wine-related activities. Instead, the charm of Chianti lies in its laid back nature, not to mention the many beautiful castles which are just a short drive away and can be found set against the backdrop of the beautiful Tuscan countryside.
Enthusiasts of medieval architecture will be delighted to discover Volterra, a hidden gem located a little off the beaten tourist track, but well worth a visit nonetheless. A tiny town located just a few hours away from the town of San Gimignano, the best of Volterra can be seen over the course of a long afternoon.
Once in Volterra, some of the best things to do include admiring the town walls, which include half a dozen gates allowing entry and exit from the city. In the very heart of the Tuscan town, you’ll soon discover the Palazzo dei Priori, which features a belfry offering fantastic views over the town and beyond, as well as medieval frescoes dating back many centuries.
Other highlights of Volterra include visiting the Duomo (Cathedral) and baptistry, as well as delving even deeper into the past and looking at some Roman history. After all, Volterra is home to the ruins of an impressive Roman theatre and the settlement is thought to have been continuously inhabited since at least the 8th-century BCE.
If you’ve ever heard of famous Italian monuments, then no doubt you’ll have heard of the leaning tower of Pisa. Though it must be admitted that, of all the beautiful towns in Tuscany, Pisa is one of the most touristed, you simply must visit at least once… If only to say you’ve been!
Other highlights of the Italian town of Pisa include its cathedral (known as ‘Duomo’ in Italian), botanical garden, and more Medieval buildings than you could possibly count. Easy to visit as a day trip from Florence, I recommend no more than an overnight stay in Pisa if you wish to make the most of your time in Italy.
Though a little smaller and off the beaten path than some of the other Tuscany towns listed here, San Gimignano has the kind of charm which is hard to come by in today’s world, making it one of the most beautiful places to visit in the region.
Best-known for its fourteen well-preserved medieval turrets which rise high above the town’s landscape, and all dating back to the Middle Ages. While the entirety of San Gimigano is encircled by 13th-century, other things to do include admiring the centrally located Piazza della Cisterna and frequenting the local market, which is open every Thursday.
For those wishing to glean a bird’s eye view from above, which offers a glimpse of the rooftops of this Tuscan town, as well as the possibility to gaze onto the rolling hills beyond San Gimignano’s city limits, a trip up the Torre Grossa is an absolute must. The only tower which is open to the public, the structure dates all the way back to the 12th-century. Of all the towns in Tuscany, San Gimigano is most certainly one of the most beautiful!