Written By: The Planet D
Tuscany is one of Italy’s most beautiful regions. Centered around the capital of Florence, Tuscany is home to rolling hills, Renaissance architecture, and traditional Italian hospitality. It is an iconic place to visit in Italy, and everyone should experience Tuscan living. While Florence is certainly the most famous city in Tuscany, there are beautiful villages and towns in Tuscany that you must set to explore as well.
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When we traveled to Tuscany, we rented a car to explore and found it to be the best way to really explore the less frequented Tuscany villages and attractions. You can compare car rental prices here. Make sure to book a room in an authentic Tuscan villa to really experience the beauty and culture of Tuscany to the fullest. You can read more about our experience here.
Tuscany is also home to some of Italy’s most beautiful towns. You’ll find beautifully located small towns in Tuscany surrounded by rolling hills and vineyards lined with Cypress trees. Many medieval towns still have old Roman walls and buildings dating back to the Middle Ages. Exploring Tuscany is dreamy; Tuscany villages are both romantic and photogenic. You may also like 15 Most Beautiful Cities in Italy for Travelers
So, which Tuscan towns should you visit? This guide will cover all the best towns in Tuscany. From tiny towns with narrow cobbled streets and medieval buildings to scenic spots in the Chianti wine region, these are the best small towns to visit.
Chances are you will make a base in Florence when visiting Tuscany. We have several articles dedicated to Florence that you can read listed below. We are going to focus on the lesser known towns and villages but no trip to Tuscany would be complete without a stop in Florence.
Make sure to plan your visit to the number 1 attraction in Tuscany and book your timed entrance to see David
San Gimignano is on our list because of its dashing good looks. The town is enclosed in medieval walls that date back to the 13th century and is packed with medieval architecture. Nicknamed the ‘Town of Fine Towers” this town is a brilliant choice. The town is so impressive that it is recognized as a UNESCO World Heritage Site.
You can book day trips from Florence to San Gimignano. This highly rated tour includes highlights to some of the best towns including Pisa, Siena, and tasting wine in the Chianti Region.
This medieval town can be visited in half a day, although a longer visit is always better if you have more time. San Gimignano has two main squares, the central piazza, Piazza del Duomo, which is surrounded by the towers that give San Gimignano its namesake.
You can grab a coffee (or a gelato if you have a sweet tooth) and sit al fresco at one of the little cafes around the square. Piazza Della Cisterna is the second main square in San Gimignano and is an unusual triangle shape surrounded by 13th-century buildings.
The other main highlights include sampling Vernaccia di San Gimignano, a white Italian wine produced in and around its surrounding valley. Wine lovers can easily organize a visit to one of the local wineries when visiting San Gimignano. You can also visit the Etruscan Academy Museum, which is dedicated to preserving the history of the Etruscan civilization.
San Gimignano is the perfect destination for those wanting a beautiful, historical destination. And for wine lovers, it is one of the best wine towns in Tuscany, thanks to its Vernaccia di San Gimignano vineyards.
Cortona is one of the best hill towns in Tuscany. Cortona has found a place in this guide because of its medieval architecture and scenic hilltop locale, which provides sweeping views of the Tuscan countryside below and some impressive sunsets. For those wanting a quiet countryside experience, Cortona is a fantastic option.
It’s also worth mentioning that Cortona was the setting for the movie ‘Under the Tuscan Sun’ – so it is pretty enough to catch the attention of movie directors.
If you are staying in Florence, you can book a day tour to Cortona that includes a stop in Assisi as well. Besides exploring Cortona, you’ll see where Under The Tuscan Sun was set, and experience one of Umbria’s most beautiful cities, Assisi. Watch the movie on Prime or rent it here.
The beautiful hilltop town is surrounded by Roman walls. Cortona is small, but it is full of museums. Allow a few hours if you want to explore and admire the town on foot, pausing to appreciate any countryside views. But if you want to visit all the museums, plan to spend a day in Cortona.
Cortona’s main highlights are the Girifalco Fortress, Santa Margherita Sanctuary, and Diocesan Museum. Girifalco Fortress is an ancient Etruscan fortification that you can tour and learn more about Cortona’s ancient history. Santa Margherita Sanctuary is a neo-gothic Roman Catholic church with striking architecture. Finally, Diocesan Museum is an art museum that includes works by Luca Signorelli, a renowned local artist.
Cortona is a pretty hill town in Tuscany and ideal if you want to experience one of the region’s countryside towns. The town is full of museums and beautiful natural views.
Set the mood for your Tuscany visit by reading the book Under the Tuscan Sun
Suvereto might be a bit too small to be considered a town, but it is so beautiful that it just had to have a place on our list. Suvereto is somewhat of a hidden gem, sandwiched between the Etruscan Coast and Tuscan hills.
The village has an idyllic atmosphere, surrounded by olive groves, coastal woodland, and full of medieval houses connected by a network of cobbled streets. The seaside location means that Suvereto is a peaceful spot, never far from an ocean view or the scent of Mediterranean shrubs.
Like most Tuscany towns, the village is protected by medieval walls, and Suvereto is also full of beautiful churches and historical buildings. Suvereto’s size makes it a breeze to explore on foot. It has a more remote, laidback atmosphere than the rest of the towns and villages in this guide – best suited to those wanting to get off the beaten track.
The best things to do in Suvereto include visiting Rocca Aldobrandesca, a stunning viewpoint located on a hilltop outside the city walls. It offers a picturesque view of the village and its old medieval layout. Visiting Suvereto’s churches is also a must.
The Romanesque Church of San Giusto and the Church of the Madonna di Spora la Porta are the most popular. You can also use Suvereto as a base to explore the nearby Montioni Natural Park, where you’ll find wildlife like wild boar and roe deer.
Monteriggioni is one of the most beautiful towns in Tuscany and is located in its Chianti region. The fortified Tuscan small town is set on slightly higher ground overlooking the surrounding valley and vineyards. Monteriggioni is one of the more famous towns in Tuscany. The medieval town even functioned as the setting for the Assassin Creed saga.
Monteriggioni is a great place to enjoy walking ancient medieval streets and visiting small museums and historical attractions like the Church of Santa Maria Assunta. If you visit at the beginning of July, there’s also the Monteriggioni Medieval Festival.
During the festival, the town steps back in time, with locals wearing medieval costumes and wearing traditional games. Out of all the towns, Monteriggioni is the best town to have an immersive experience of medievalism.
Not visiting in July? No problem. There is still plenty to do in Monteriggioni. You can drop by the Armory Museum for a history lesson on Medieval and Renaissance weaponry and armor. Walking the walls is always fun; at just a few euros, it is also a budget-friendly activity. If you are a wine lover, Monteriggioni is also a great base to go wine tasting in the wine-renowned Chianti region.
Monteriggioni is an excellent choice if you want a general taste of a Tuscan town and a tried-and-tested tourist destination.
This highly rated tour from Tuscany includes some of the top stops in the region. You’ll taste wines in favourite region in Tuscany, Chianti.
Montepulciano is another one of Tuscany’s incredible hill towns. The quaint town is gorgeous with elegant palaces and dramatic architecture to admire. Pack your camera; Montepulciano is known for the beauty of its historic town center. That isn’t all, though, as Montepulciano has multiple strings to its belts.
Montepulciano is also one of the best wine towns in Tuscany. Its surrounding countryside is full of wineries – most notably producing Nobile. For vineyards, valley views, and elegant surroundings, Montepulciano is a fantastic place to visit.
The town is centered around Piazza Grande, a monumental square overlooked by the giant clock tower of the town hall. Piazza Grande has a stately atmosphere. Visit in August, though, and you’ll find festivities in full flow. In August, Montepulciano hosts the barrel-racing Bravio Delle Botti competition. Bravio Delle Botti involves teams of two runners attempting to be the first to roll an 80kg wine barrel through the town’s streets. Piazza Grande acts as the all-important finish line.
Apart from its annual barrel race, there are plenty of things to do all year round in Montepulciano. You can take a guided walking tour, visit the Cathedral of Santa Maria Assunta, climb the tower of the City Hall, and stop by the Fortress of Montepulciano.
Make sure to leave time to go on a wine tour as well, as the regional vino nobile red wine is delicious. You can stop by one of the wine bars in the city, such as Contucci Winery or La Dolce Vita – some of which have an underground wine cellar. Alternatively, tour one of the vineyards just outside the city to sample local wine.
Montepulciano is a great town to mix wine and history. You can visit a 13th-century fortress in the morning and sample velvety red wines in the afternoon, all within walking distance. If you want a wine break with plenty of extra things to do, Montepulciano is fantastic.
Collodi is another of Tuscany’s best small towns. The town has a unique layout, with buildings running in a narrow line down a steep hill, almost obscured by woodland. Collodi was built on the remains of an ancient medieval castle. However, it lacks the traditional walled layout of most towns in Tuscany. Collodi is an exciting, unusual spot to visit – ideal for those wanting a more unique experience of a Tuscan town.
At the base of the hill, Collodi has a massive fortress. Collodi also has an ‘old town’, where the buildings date back to the end of the 12th century. If you like ancient architecture and history, it is an exciting spot to explore on foot and learn more about. Collodi’s unique layout is linked to its history. It acted as a tactical position where locals would flock to the top of the hill when attacked, leaving the attackers vulnerable at the bottom.
The highlights of a visit to Collodi are the castle, the view from the Church of San Bartolomeo, colorful wildlife at the Butterfly House, and Villa Garzoni and its Italian Garden. Villa Garzoni is most famously known for its beauty, but it was also the workplace of the creator of Pinocchio’s father. It is said that Carlo Collodi took inspiration from Collodi while creating the novel.
Collodi is a stand-out destination in Tuscany and a brilliant place to embrace a more unusual example of Italian history.
Certaldo is a beautiful medieval village in Tuscany. It is full of character and one of the prettiest Tuscan villages to visit. Certaldo is most famous for being the birthplace of the famous writer Giovanni Boccaccio, considered one of the fathers of literature and the author of the Decameron. Apart from its beauty, Certaldo is full of culture, and it is an excellent destination for any lovers of Italian literature.
Certaldo’s cultural draw booms during July, when the Mercantia Festival is in full flow. The Mercantia Festival is a beautiful street art festival, with live art performances and displays that whir into action at nightfall. As you admire the artwork, performers in costumes wander the street – usually wearing stilts and dressed as clouds.
Must-do activities in Certaldo include visiting the Giovanni Boccaccio Museum, which is situated in his old house and houses rare artifacts that once belonged to the writer. The Palazzo Pretorio is another brilliant attraction, and the former palace dates back to the 12th century. Finally, art enthusiasts will love the Museum of Sacred Art, which displays various art types.
Certaldo is where to visit for culture – whether you want to learn about literary history or attend the Mercantia Festival. The village is a great spot to appreciate traditional medieval architecture and the culture and arts that accompany it.
Anghiari is another beautiful Tuscan town bursting with culture. However, Anghiari is famed for its artisan studios and antique shops instead of literature. The town has been known for its traders and artisans for centuries. You’ll find all sorts of products created from wood, textiles, and even ceramics.
The narrow, cobbled streets are lined by shop after shop – perfect for window shopping and relaxing wandering. Forget about souvenir shopping; Anghiari is somewhere you can source everything to redecorate a house.
When you aren’t shopping, you can visit the different palaces in Anghiari. As a Renaissance town, the architecture is striking, and the gothic details on the palaces are beautiful to admire. Of course, art enthusiasts might also wish to visit the town’s art museum, the Popular Tradition Museum. The museum houses all artwork, from frescos taken from local churches to sculptures and secular monuments.
Anghiari is where to visit if you want to go shopping and love browsing artisan products. It is a shopping haven for retail enthusiasts and a cultural hot spot for art and architecture. Not to mention that it is stunning and easy to explore on foot as well.
Looking for a historic old town with plenty of charm? Pienza is a charming town, and its historic town center is a designated UNESCO World Heritage Site. Pienza is nicknamed by many the ideal city of the Renaissance, and it was also the birthplace of Pope Pius II.
Pope Pius II became a notable humanist and aided with the transformation of Pienza in the Renaissance period. He wanted a Utopian city, and now, visitors flock to see the town centuries later.
Pienza is one of the most beautiful towns in Tuscany for its architecture. Palazzo Piccolomini was even used for scenes in Romeo and Juliet. When it comes to finding things to do, you really won’t be stuck for options. You can visit the Romanesque church Pieve di Corsignano. You can also sample the town’s specialty Pecorino cheese and admire the Cathedral of Assunta.
If you are interested in the Catholic church’s history, Pienza’s links to a past pope are very intriguing. Pienza is atmospheric enough to warrant a visit and a place on our list.
File courtesy Wikimedia
Get ready to add another hilltop town to your list. Casale Marittimo is scenically perched on a small hill overlooking the Cecina River Valley and Etruscan Coast. It is best known for its ancient castle ruins and is another old town overflowing with history.
Casale Marittimo’s original castle still peeps out of the modern city in fragmented sections. The town is enclosed by just half a remaining city wall. Casale Marittimo’s medieval architecture is dilapidated yet preserved enough to make wandering the town feel like visiting an immersive museum.
The best things to do in and around Casale Marittimo are to explore the castle ruins, visit the Church of Sant’Andrea, and take a day trip to the necropolis of Casa Nocera. Of course, you will be situated right in the middle of the Tuscan countryside, too, so you’ll have hiking and photography opportunities galore.
Casale Marittimo is best for those with an interest in archaeology. Walking around the half-modern town, half-ancient ruins feels a bit like a gigantic puzzle – which archaeology and history lovers will adore. Plus, you are never too far from the coastline and stunning beaches.
Volterra is one of the most famous towns in Tuscany and one of the oldest. The medieval town dates back to the Middle Ages, and you’ll find a historic center and ancient, traditional city walls. Like Casale Marittimo, Volterra is like a living, breathing archaeology site.
Volterra is also specifically known for alabaster artisan products. Alabaster is a typically white form of gypsum or calcite, popularly used to create ornaments. You can wander Volterra window shopping for the perfect alabaster souvenir or stop by one of its historical attractions.
As you may have guessed, Volterra has a long list of attractions and highlights for visitors. The town especially has a lot of historical attractions. You can stop by the Roman Theater, the Acropolis, or walk around the old city walls.
Volterra is an excellent destination for anyone interested in history and open to dabbling in a bit of window shopping or actual souvenir shopping. The town has plenty of attractions and local shops to keep you entertained.
Lucca is a Renaissance town with well-preserved Renaissance walls and those cobbled streets that make you swoon. The Italian town sits alongside the Serchio River and at the foot of the dramatic Apuan Alps, which makes for a beautiful backdrop. It is the most famous town near Pisa. Pisa
It is ideally located to enjoy quiet, authentic living and travel into Pisa if you want to. Of course, Pisa has major attractions like the Leaning Tower of Pisa, so being nearby is always a plus. You can find our top tips on visiting the Leaning Tower of Pisa here.
And as for Lucca, its location and good looks have earned it a spot on this list.
The best things to do in Lucca are to walk the town walls, admire Lucca Cathedral, scale Guinigi Tower, and visit the Roman Amphitheater. Lucca’s architecture is stunning, and the city layout is perfect for exploring on foot.
The town is best for those wanting a pretty place to visit in Tuscany, with lots of striking architecture and beautiful scenery. Given its location, Lucca is also well-combined with a visit to Pisa’s historic city center. It is proof that you can (and should) detour to small towns in Tuscany rather than just staying in a major city.
Did you know that Tuscany has been influenced by a longstanding old Jewish community? Monte San Savino is a good choice for those interested in specifically Jewish history or just social history in general. While Jewish history in Tuscany is longstanding, you’ll probably struggle to find Jewish attractions and history overtly displayed. Monte San Savino is the answer to this, and it still features a synagogue and ghetto.
Aside from its Jewish history, Monte San Savino has plenty of other history to uncover. The town has seen clashes between the Guelphs and Ghibellines and has fallen in and out of Florentine rule. Monte San Savino is a beautiful small Tuscan town with many stories.
One of the best things to do in this small town is to visit the Cassero Museum, which pays tribute to the town’s ancient ceramic traditions. You’ll also find the Sanctuary of Santa Maria Delle Vertighe and many beautiful churches. Monte San Savino has a strong creative and religious influence. Because of this, it is best suited to those interested in Judaism, Christianity, or social history.
Photo courtesy of Crima66, CC BY-SA 4.0 via Wikimedia Commons
Hilltop towns tucked away in rolling hills and mountains are dreamy. But what about beachfront towns in Tuscany? Can you combine a historic town center with a beach holiday? The answer is yes, and Forte Dei Marmi is the place to do so. This coastal town is known for its beaches. While you can still see the Apuan Alps on the horizon, Forte Dei Marmi is a town associated with beach living.
When in Forte Dei Marmi, you should (of course) make use of the beaches. But once you’ve had a beach day or two, there are plenty of other things to do. You can walk the Pontile, a long pier that sandwiches you between the sea and the town, with views of the Apuan Alps behind you.
If you enjoy shopping, you can head downtown to some high-end luxury stores like Louis Vuitton and Versace. And to splurge, even more, you can check out one of the town’s five Michelin restaurants.
Forte Dei Marmi is a luxury town to visit in Tuscany. It is the perfect fit for anyone wanting high-end wining, dining, and shopping. Plus, you have the constant bonus of easy beach access.
Did you know that there are 7 UNESCO World Heritage Sites in Tuscany? Besides the sites in Pisa and Florence, another not to miss Tuscan City is Siena. Siena’s historic center on its own is a UNESCO World Heritage Site and is worth visiting. WHile not exactly one of the small towns in Tuscany, its main square is not to be missed.
It is here that we missed a turn and drove right downtown to its historic old town by mistake. When we returned to Canada so the moral of the story is to keep an eye on traffic signs.
Tuscany is not short of beautiful towns, as you now definitely know. We’ve covered the best of the best, from small towns to busy towns and even a few Tuscan villages. These are the most beautiful Tuscany villages and best towns to visit – which one caught your eye the most?
Don’t forget to check out Florence’s capital after exploring Tuscany’s towns. The capital is packed with things to do, and spending a day in Florence is one of the best things to do in Italy. Have a great visit to Tuscany.
Tuscany is quite easy to get to with highways linking the region to major cities in Europe. It has an excellent train system and my airports are nearby. You can fly into Rome, Pisa, Forli, Bologna, and Florence Airports and either rent a car or take the train.
From the airport, make sure to book a transfer in advance to make your travels easier.
We have taken the train to Pisa, Florence, and Siena when visiting Tuscany.
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Dave Bouskill and Debra Corbeil are the owners and founders of The Planet D. After traveling to 115 countries, on all 7 continents over the past 13 years they have become one of the foremost experts in travel. Being recognized as top travel bloggers and influencers by the likes of Forbes Magazine, the Society of American Travel Writers and USA Today has allowed them to become leaders in their field.
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