Falling In Love with Tuscany: The Best Villages to Visit in Tuscany

If you’ve been following our travels for a while then you will know that we absolutely loooooove everything about Italy! I’ve been lucky enough to visit four times and Dan twice! We spent three weeks there last year during our European summer and it was during this time that I fell head over heels in love with Tuscany! I first fell in love with Tuscany when I saw the film Under the Tuscan Sun many years ago! On previous trips to Italy I had only visited Florence in this region and so this time we took a few extra days to explore as much of beautiful Tuscany as possible and it is certainly a place we plan on returning to and spending a few weeks whenever we get the opportunity! A lot of people also visit Tuscany on cruise ships when they dock in Livorno. From our past cruising experience we recommend pre-booking your Tuscany excursion with local suppliers and not the cruise ship as this enables you to disembark the ship and travel on your Livorno tour with local guides which also saves you a lot of money! We’re sharing some of our favourite Tuscan villages to inspire you to live out your own Under the Tuscan Sun dreams by visiting this incredible part of the world.

Girl in Tuscany with San Gimignano in BackgroundTuscany is without a doubt one of the most beautiful parts of Italy and has an incredible history, beautiful countrysides, a wealth of art, the most charming villages, delicious food and superb wines! There really is nothing like strolling through and admiring gorgeous, medieval Tuscan villages and stopping for wine, food or gelato whenever we felt the need! Here are some of our favourite and some of the most gorgeous villages in Tuscany…

Girl walking through streets of San Gimignano

Whilst Siena is probably considered more of a city than a village, it is without a doubt one of Italy’s loveliest and most charming towns. The historic centre of Siena has been declared by UNESCO as a World Heritage Site. The heart of this charming medieval city is it’s central piazza which is known as Il Campo and is known worldwide for the famous Palio race which sees horses and riders from each district of Siena race around the Piazza two times every summer! In addition, Siena its famous for its cuisine, art, musesums, Universities, medieval cityscape and its gorgeous Tuscan surroundings.

Siena Tuscany Italy

San Gimignano is a small, walled medieval hill town in Tuscany and was by far my favourite village in all of Tuscany! San Gimignano is known as the Town of Fine Towers, or as our guide said, the “Manhattan of Italy” due to its medieval towers. The town is famous for its medieval architecture and unique, unrivalled preservation of a dozen of its tower houses! The towers, city walls and hilltop location create an unforgettable skyline and will ensure you never forget your visit to charming San Gimignano! The town also has a gelateria which has won the title of “world’s best gelato” in an international competition, and we can tell you from our own experience that it was that good (oh, and so was the wine here too)!

San Gimignano Tuscany Italy

Beautiful Lucca is a Tuscan city located on the Serchio River, at the foot of the Apuan Alps. Lucca is known for its well preserved Renaissance walls encircling the historic city centre which are now a pedestrian promenade around the town. Most of Lucca’s attractions today show its ancient history including the traces of a Roman amphitheatre and the various towers and villas dotted around. Unlike many Tuscan villages, it isn’t a hilltop village and so for anyone with mobility issues it can be a good choice to visit!

Lucca Tuscany Italy

Pitigliano is a a quaint old town that rises dramatically from the tufa ridge it sits on and is surrounded on all sides by a deep ravine. Pitligliano is known as little Jerusalem, due to the historical presence of a large Jewish community who call Pitigliano home and have since the 16th century. The area is full with interesting and unique Etruscan remains that have been carved out of the soft tufa, along with interesting tombs and carved churches!

Pitigliano Tuscany Italy

Monteriggioni is one of the most important medieval, walled castles in the region and dominates the surrounding landscape. It is incredibly preserved as an intact structure as if time had never passed. During the conflicts between Siena and Florence in the Middle Ages, the castle was built for defensive purposes as a lookout for any armies approaching Siena. It withstood many attacks from both the Florentines and the forces of Volterra but in 1554 in an act of reconcilliation, the town’s garrison handed the keys over to the Medici’s, which was considered the greatest betrayal by the town’s people. Today you can walk the intact fortified wall and stroll between the 14 towers and the two gates, one which faces Rome and the other which faces Florence.

Monteriggioni Tuscany Italy

Volterra is a charming, walled mountaintop village which dates back to before the 7th Century BC and has structures from the Etruscan, Roman and Medieval periods. Volterra also attracts a lot less tourists than some of the other villages and cities such as San Gimignano and Siena. One of the best views of San Gimignano and it’s iconic towers is actually from Volterra! Volterra offers a rich selection of ruins, art and architecture from different historical periods, beautiful and quiet streets and squares and of course wonderful Tuscan cuisine! Stroll the ancient city walls and historical centre before exploring the shops and maybe purchasing an alabaster hand-made souvenir, something that Volterra is famous for worldwide!

Volterra Tuscany Italy

Not too far from Siena you will find Montepulciano, a beautiful medieval town standing atop a hill. The city boasts elegant Renaissance palaces, ancient churches, charming squares and has the most stunning panoramic views of the whole region! Montepulciano has a lovely position which makes it a perfect village to base yourself in to explore beautiful Tuscany! The Twilight sequel, New Moon was filmed in Montepulciano so just be prepared to share it with a lot of others but it is worth it as it is without a doubt one of the most beautiful villages in all of Tuscany.

Montepulciano Tuscany Italy

Collodi is a small village in Tuscany that is the home of Pinocchio Pistola. Collodi is famous throughout the world for having given its name to Carlo Collodi the pen name of Carlo Lorenzini, the Italian author and journalist who is best-known as the creator of Pinocchio! The village of Collodi has since been developed into a tourist destination that has the charming, old-fashioned Pinocchio Park which contains statues and fountains of all the Pinocchio characters. You can also watch a delightful puppet show with all the famous characters which will allow your imagination to escape into fairytale whilst also relaxing in the beautiful Tuscan landscape that surrounds you.

Collodi Tuscany Italy

Tuscany  was every bit as beautiful and romantic as I imagined and I am so excited to come back one day and explore further, relax in the magical countryside and indulge in more incredible Chianti wine! We had a truly magical four days exploring Florence and Tuscany and we’ve now added to our incredibly long list the need for an extended stay in a Tuscan villa in the gorgeous countryside!

Have you too fallen in love with Tuscany or is it a place that you have always wanted to visit?

Tuscan wineries Italy
Girl overlooking towers of San Gimignano Tuscany Italy
Couple drinking Chianti Wine in Tuscany