One of the most-Googled questions about Tuscany, and a question that many thinking of planning their first vacation in Tuscany may have, is, “What is the prettiest town in Tuscany?” This, of course, is quite a contentious query with many potential answers depending on of whom you ask it (lots of patriotic locals will be quick to boast about their own hometowns and nostalgic visitors who fondly remember their own trips will choose places that mean something to them, in particular), when you're planning on travelling, what things you like to see and do, what kinds of scenery you prefer, and more. To single out just one town is not only selling Tuscany short – as it truly does boast seemingly endless stunning towns just waiting to be explored and to endear themselves to you – but it will also lead to the traveller asking it to potentially miss out on many other perfectly charming and utterly picturesque spots.
However, if you want a list of some especially lovely examples to get you started on your quest to uncover and discover some of the prettiest towns in Tuscany, then read on to our picks of just some of the best of the best among them...just don't complain if you're one of the aforementioned locals or Tuscany aficionados who don't happen to find their choice on the list!
However, if you want a list of some especially lovely examples to get you started on your quest to uncover and discover some of the prettiest towns in Tuscany, then read on to our picks of just some of the best of the best among them...just don't complain if you're one of the aforementioned locals or Tuscany aficionados who don't happen to find their choice on the list!
1. Pienza
Pienza was literally designed under the instruction of Pope Pius II to be a town that adhered to Renaissance ideals of perfect proportions and harmony. It is no surprise, therefore, that its streets, squares, and buildings are strikingly lovely and that the town, as a whole, is incredibly picturesque. Added to this is the fact that the town is perched on a hilltop in the Val D'Orcia, affording astounding panoramas over one of the most spectacular landscapes in all of Tuscany from various vantage points throughout Pienza. Simply wandering around Pienza will lead to discovering pretty little cafes where you can sit outside and sip on a delicious coffee, ivy-draped buildings and cobbled streets that look too picture-perfect to be real and acted as the backdrop to Zeffirelli's stunning 1968 film adaptation of Romeo and Juliet, truly incredible architectural gems, and gaps between buildings or terraces that afford the most wonderful framed views of the rolling hills, wheat fields, vineyards, and olive groves of the Val D'Orcia. While this magic town was at the centre of an important moment in history, it is a name that is unfamiliar to many travellers who decide to vacation in Tuscany. However, if you're a discerning film buff and art-lover who enjoys lovely views, then Pienza will likely get your vote as one of the prettiest towns in Tuscany and a luxury villa in Pienza will certainly be the perfect choice for a magical and exceptionally charming holiday destination.
Pienza was literally designed under the instruction of Pope Pius II to be a town that adhered to Renaissance ideals of perfect proportions and harmony. It is no surprise, therefore, that its streets, squares, and buildings are strikingly lovely and that the town, as a whole, is incredibly picturesque. Added to this is the fact that the town is perched on a hilltop in the Val D'Orcia, affording astounding panoramas over one of the most spectacular landscapes in all of Tuscany from various vantage points throughout Pienza. Simply wandering around Pienza will lead to discovering pretty little cafes where you can sit outside and sip on a delicious coffee, ivy-draped buildings and cobbled streets that look too picture-perfect to be real and acted as the backdrop to Zeffirelli's stunning 1968 film adaptation of Romeo and Juliet, truly incredible architectural gems, and gaps between buildings or terraces that afford the most wonderful framed views of the rolling hills, wheat fields, vineyards, and olive groves of the Val D'Orcia. While this magic town was at the centre of an important moment in history, it is a name that is unfamiliar to many travellers who decide to vacation in Tuscany. However, if you're a discerning film buff and art-lover who enjoys lovely views, then Pienza will likely get your vote as one of the prettiest towns in Tuscany and a luxury villa in Pienza will certainly be the perfect choice for a magical and exceptionally charming holiday destination.
2. Montecatini Terme
Montecatini Terme is famously one of Tuscany's best and most well-known spa towns but it is also famously beautiful. Boasting natural hot springs that first made it an attraction, the town was enhanced by the addition of the incredible spa buildings that were built in the Art Nouveau style in the 19th and 20th centuries. In addition to these wonderful architectural gems that made the town an important centre of this, “new style,” Montecatini Terme is full of lush, leafy parks and an array of charming little shops, bars, restaurants, and more. Impossibly elegant, with nine different thermal centres and endless places to avail of various therapeutic, relaxing, and aesthetic treatments, services, and experiences, this remarkably beautiful gem of a town is the perfect place to come and get away from it all, forget your worries, and soak in some relaxing thermal waters, while also soaking up some of the most undeniably pretty surroundings in all of Tuscany. Be sure to check out our luxury villas in Montecatini Terme and get planning your trip today if you're looking for a pretty town in Tuscany that is also a perfect spa destination!
Montecatini Terme is famously one of Tuscany's best and most well-known spa towns but it is also famously beautiful. Boasting natural hot springs that first made it an attraction, the town was enhanced by the addition of the incredible spa buildings that were built in the Art Nouveau style in the 19th and 20th centuries. In addition to these wonderful architectural gems that made the town an important centre of this, “new style,” Montecatini Terme is full of lush, leafy parks and an array of charming little shops, bars, restaurants, and more. Impossibly elegant, with nine different thermal centres and endless places to avail of various therapeutic, relaxing, and aesthetic treatments, services, and experiences, this remarkably beautiful gem of a town is the perfect place to come and get away from it all, forget your worries, and soak in some relaxing thermal waters, while also soaking up some of the most undeniably pretty surroundings in all of Tuscany. Be sure to check out our luxury villas in Montecatini Terme and get planning your trip today if you're looking for a pretty town in Tuscany that is also a perfect spa destination!
3. Suvereto
If you like your pretty towns to also have some coastal views then the charming medieval village of Suvereto will be right up your alley. Nestled among the foothills where the Cornia Valley unfolds beneath the Colline Metallifere, the village is located about half an hour from the Tuscan Coast and is about 60km from Livorno. Still circled by defensive stone walls that date back to the Middle Ages, Suvereto is perched high enough up on the aforementioned hills to offer stunning, sweeping views across iconic rolling Tuscan hills, cork oak trees (for which the village is named), olive groves, and vineyards and also right over the Tyrrhenian Sea, the Gulf of Follonica, and right to Elba Island in the distance on clear days. The town itself is also a looker. Dating back more than a millennium, one would be forgiven for thinking that time has stopped here and the tangle of little streets, alleys, and staircases that march up to the ancient fortress crowning the town like a jewel have gone untouched and undisturbed. In fact, much of the historic centre has been lovingly and carefully restored in recent years. Utterly picturesque and quaint, this is just the sort of sleepy, impossibly pretty town that one might picture when thinking of Tuscany. If you have found a vacation rental on the Tuscan Coast and you're looking for the prettiest towns around to visit and explore, Suvereto should certainly appear high on the list of must-see gems.
If you like your pretty towns to also have some coastal views then the charming medieval village of Suvereto will be right up your alley. Nestled among the foothills where the Cornia Valley unfolds beneath the Colline Metallifere, the village is located about half an hour from the Tuscan Coast and is about 60km from Livorno. Still circled by defensive stone walls that date back to the Middle Ages, Suvereto is perched high enough up on the aforementioned hills to offer stunning, sweeping views across iconic rolling Tuscan hills, cork oak trees (for which the village is named), olive groves, and vineyards and also right over the Tyrrhenian Sea, the Gulf of Follonica, and right to Elba Island in the distance on clear days. The town itself is also a looker. Dating back more than a millennium, one would be forgiven for thinking that time has stopped here and the tangle of little streets, alleys, and staircases that march up to the ancient fortress crowning the town like a jewel have gone untouched and undisturbed. In fact, much of the historic centre has been lovingly and carefully restored in recent years. Utterly picturesque and quaint, this is just the sort of sleepy, impossibly pretty town that one might picture when thinking of Tuscany. If you have found a vacation rental on the Tuscan Coast and you're looking for the prettiest towns around to visit and explore, Suvereto should certainly appear high on the list of must-see gems.
4. San Miniato
The foodies among our readers who also happen to like pretty towns will probably think San Miniato among the loveliest they've ever laid eyes on before. Another gem that is full of well-preserved architectural marvels, charming little streets, and astounding views over pastoral Tuscan landscapes from its position perched high on a hillside in the province of Pisa, it is most famous today as one of the best places to find truffles in the world but was once a key destination along the via Francigena pilgrimage route. With a rich history, the town is full of things to see and do and is impossibly picturesque, boasting a wonderful, well-preserved historic core that is stuffed full of incredible buildings like the distinctive red brick Duomo and institutions such as the Duomo's museum that houses works by the likes of Filippo Lippi, Fra Bartolomeo, and Verrocchio, to name but two of many attractions. For those who came for the food though, the town squares will be at their most appealing when filled with food stalls selling local delicacies and truffle-based dishes during the last three weekends of November for the annual Mostra Mercato di Tartufi fair. The lovely woods that surround the town where you can join in on the traditional truffle-seeking expeditions in search of the highly-coveted ingredient will also be a major draw. If you're a food-lover in search of a pretty Tuscan town for your next getaway, then a villa in Pisa and a visit to San Miniato is just the thing!
The foodies among our readers who also happen to like pretty towns will probably think San Miniato among the loveliest they've ever laid eyes on before. Another gem that is full of well-preserved architectural marvels, charming little streets, and astounding views over pastoral Tuscan landscapes from its position perched high on a hillside in the province of Pisa, it is most famous today as one of the best places to find truffles in the world but was once a key destination along the via Francigena pilgrimage route. With a rich history, the town is full of things to see and do and is impossibly picturesque, boasting a wonderful, well-preserved historic core that is stuffed full of incredible buildings like the distinctive red brick Duomo and institutions such as the Duomo's museum that houses works by the likes of Filippo Lippi, Fra Bartolomeo, and Verrocchio, to name but two of many attractions. For those who came for the food though, the town squares will be at their most appealing when filled with food stalls selling local delicacies and truffle-based dishes during the last three weekends of November for the annual Mostra Mercato di Tartufi fair. The lovely woods that surround the town where you can join in on the traditional truffle-seeking expeditions in search of the highly-coveted ingredient will also be a major draw. If you're a food-lover in search of a pretty Tuscan town for your next getaway, then a villa in Pisa and a visit to San Miniato is just the thing!
5. Asciano
Screensavers and stock images that appear first when searching for Tuscany tend to featuring romantically winding roads lined with cypresses set amongst rolling green hills and these images are often of a part of the region called the Crete Senesi. Among all of the towns and villages in this area, the area in and around the town of Asciano is the most picturesque of all and it is considered its centre. Small, with a pretty little historic centre that is partially encircled by Medieval stone walls, Asciano boasts beautiful architectural gems, wonderful little museums with impressive collections, excellent restaurants with terraces where you can enjoy incredible meals while watching the world go by, and some of the best hiking in Tuscany in the area that surrounds the town. So, find a holiday rental in Asciano to enjoy the perfect pace of life in this sleepy town and the utterly picture-perfect views that abound both in the historic centre and the entire area that surrounds it.
And if you're still in search of the perfect, pretty destination in Tuscany? Well, contact us and our team of villa experts will be glad to help you find your dream holiday location in this beloved part of Italy...
Screensavers and stock images that appear first when searching for Tuscany tend to featuring romantically winding roads lined with cypresses set amongst rolling green hills and these images are often of a part of the region called the Crete Senesi. Among all of the towns and villages in this area, the area in and around the town of Asciano is the most picturesque of all and it is considered its centre. Small, with a pretty little historic centre that is partially encircled by Medieval stone walls, Asciano boasts beautiful architectural gems, wonderful little museums with impressive collections, excellent restaurants with terraces where you can enjoy incredible meals while watching the world go by, and some of the best hiking in Tuscany in the area that surrounds the town. So, find a holiday rental in Asciano to enjoy the perfect pace of life in this sleepy town and the utterly picture-perfect views that abound both in the historic centre and the entire area that surrounds it.
And if you're still in search of the perfect, pretty destination in Tuscany? Well, contact us and our team of villa experts will be glad to help you find your dream holiday location in this beloved part of Italy...
Photo credits
Picture 3: Alexmar983 / CC BY-SA 4.0;
Picture 4: Sailko / CC BY-SA 3.0;
Picture 6: Deensel / CC BY 2.0
Picture 3: Alexmar983 / CC BY-SA 4.0;
Picture 4: Sailko / CC BY-SA 3.0;
Picture 6: Deensel / CC BY 2.0
