** Disclosure: some of the links on this site are affiliate links and should you make a purchase through these, I may receive a small commission at no extra cost to you. Thank you for your support!**
I’ve been there before – overwhelmed by the sheer amount of beautiful Tuscan towns there are and trying to figure out what the best towns to visit in Tuscany really are….and how are you ever going to fit them into your itinerary? There are many beautiful towns in Tuscany, ranging from hill top hamlets to coastal delights. This guide walks you through the best towns in Tuscany Italy, helping you to make your itinerary planning that little bit easier.
As regions go, Tuscany is quite a perfect one. Famous as the home of Florence, birthplace of the Renaissance and its iconic Duomo, the impact that the glory days of Florence had on the wider region of Tuscany can be felt everywhere you go.
The Tuscan landscape inspired many a great masterpiece by Florentine artists and in turn, the city of Florence and to a lesser extent, Siena, provided alliances and wealth to many of the towns that are dotted around the region.
RELATED READING | How To Spend 2 Days In Florence – A Comprehensive Guide
Many of these former strong-holdings are now well-known as the hill towns of Tuscany, having been placed more often than not on elevated, rocky outcrops that guard the countryside below. Many, to this day, retain a distinct medieval aesthetic and thus carry with them a very unique character and charm.
The history of some towns in Tuscany stretch back even further than that – to the Romans and the Etruscans – and some, even, to the Bronze Age. For lovers of history, the region of Tuscany and its small towns is a fascinating one.
History aside, what else is there to this abundant region that makes it so perfect? Well, there’s the fact that mountain lovers can both ski and in winter and hike in summer in Tuscany’s mountain ranges. And let us not forget either the god-given tapestry that are the softly undulating hills and cyprus trees of the Val d’Orcia that Tuscany has become so synonymous with.
Should you wish to dip your toes in the ocean, then you can have that too – via the Tyrrhenian sea along the Maremma coast. And, quite possibly the cherry on top, is the rich, bountiful food and wine culture of the region.
Tuscan dishes are hearty and filling and local dishes vary from area to area. Tuscany also produces world-renowned wine, amongst its most famous being Chianti and the high-end Brunello di Montalcino. If you’re a lover of wine, then it makes total sense to come to the source!
It can thus be said that discovering these small towns in Tuscany presents an intoxicating proposition. But what are the best towns in Tuscany to visit? The term ‘best’ is a very subjective one, meaning different things to different people, so I’ve asked some fellow travel bloggers, each lovers of the Tuscan region too, to contribute some of their must see towns in Tuscany to give you a more holistic view.
These best towns in Tuscany to see I have split out as follows:
- The most beautiful small town in Tuscany to visit
- The best wine towns in Tuscany
- The best medieval towns in Tuscany, Italy
- The best hilltop towns in Tuscany
- Best coastal town in Tuscany
You’ll find that even the above categorisation is a bit imperfect, as it’s very difficult to corral towns into one distinct category – for example, the town of Montepulcianio is all of the above, except for a coastal town (hint: make sure to include it on your itinerary), but I’ve provided enough information below for you to decide if a town is for you or not! Happy planning!
In this article Hide
- How to get to Tuscany
- Ways to visit to the best towns in Tuscany Italy
- Best towns in Tuscany to stay in
- The best towns in Tuscany to visit
- Best towns in Tuscany map
- Travelling to Tuscany? You might like the following:
- Like this post? Please share or pin for later!
How to get to Tuscany
Getting to Tuscany by plane
Tuscany is home to two airports; one in Florence and another larger airport in Pisa. You may find more extensive flight schedules to Pisa so as a result, prepare to be flexible on which you fly in and/or out of.
Both airports are well connected to other cities and larger towns in Tuscany via the train network. It’s also completely possible and not too taxing to fly to Rome and either drive or get a train to Tuscany.
Getting to Tuscany by train
Having used the train network in Italy throughout various regions of the country, I can confirm that it’s an extremely reliable and efficient way to travel. Major cities are well connected, with smaller towns in turn being well connected to a larger hub.
Trains from Rome to Florence, for example are frequent (running at over 50 a day) and take only around 1 and a half hours.
Getting to Tuscany by bus
If you’d prefer to take a bus (I’d recommend a train, however, if budget is not a concern) then there are also numerous companies that operate bus routes within Italy.
| TICKETS: Plan your route and purchase tickets here.
Ways to visit to the best towns in Tuscany Italy
While you can get around to the larger towns in Tuscany relatively easily via the train network, if you are to reply on public transport to get around Tuscany, you will find it difficult to reach the most small towns in Tuscany as you will be reliant on regional buses that often have sparse and infrequent timetables.
For that reason, I would highly recommend that you rent a car in Tuscany.
I always use rentalcars.com when hiring a car abroad and our road trip to Tuscany was no different. I like them for the following reasons:
- You can compare all car rental companies in a given destination. They also have superior filtering options too, so you really can drill down to what you’re looking for – even to the deposit amount and payment type.
- All the info you need for your relevant booking can subsequently be found in their convenient app – no print outs necessary.
- You can often amend/cancel your booking with no additional charges.
If you don’t fancy driving, then I would instead recommend that you base yourself in some of the larger towns in Tuscany and see more of the best little towns in Tuscany via guided tours and day trips. You can learn more in the section directly below.
Best towns in Tuscany to stay in
This is a tough question to answer, and the answer to what the best towns to stay in Tuscany Italy are is dependent firstly on how much time you have to spend in Tuscany, and secondly, which must-see towns in Tuscany pique your interest the most, and where they are located.
If you are visiting Tuscany for a shorter period of time, then staying in Florence and doing day trips from there might make more sense. You can see and book day trips from Florence here.
However if you do have 5 or more days in Tuscany then great! Make sure that you allocate plenty of time within your Tuscany itinerary to discover a smattering of the more famous towns in Tuscany, together with some of the more under the radar, beautiful small towns in Tuscany.
I’d highly recommend booking accommodation at a Tuscan villa when in the countryside, whether that be one operating as a hotel or as a vacation rental. It’s truly the best way to get that rustic, Tuscan experience. If you are concerned about being close to a town, then I’d recommend positioning yourself close to any of the following:
- Chianti: some of the best small towns in Tuscany to stay near in order to access the Chianti region include Greve-in-Chianti, San Gimignano and Volterra.
- North Tuscany: one of the best small towns to stay in Tuscany’s north is the famous walled town of Lucca.
- Val d’Orcia: I’d highly recommend positioning yourself close to Montepulciano if you’re visiting the glorious Val d’Orcia – it’s one of my favourites and also one of the best small towns to stay in Tuscany due to how fabulous the town is itself, together with how well positioned it is for exploring the area.
Booking a luxury villa in Tuscany
Two websites that I would highly recommend for booking a luxury villa in Tuscany are the following, which have some fantastic properties (with quality guaranteed) on their books:
Booking a hotel in Tuscany
If you’d prefer to be waited on hand and foot, you can discover some great villas operating as hotels in Tuscany to stay in by using the below interactive map. I’ve also included VRBOs in Tuscany too in case you want to search for a villa that way. Just enter your dates and away you go!
The best towns in Tuscany to visit
Best wine towns in Tuscany
By Isabelle, from Issy’s Escapades
Situated high on a rocky outcrop, hewn into the bedrock sits the ancient town of Montepulciano, which presides regally above the expansive plains and hills of the Val d’Orcia below. This medieval hill town is a very special one, carrying a distinct air of uniqueness, spectacular views from its town walls and an ancient and interesting history.
Montepulciano is perfect both as a base from which to explore the other Tuscan villages and historic towns of this beautiful region, or indeed to just pop into for a day trip to take a wander around its ancient streets, admire its beautiful buildings and bask in the panoramic views of the rolling hills. Follow the cobbled streets upward to the historic town center and the marvelously medieval Piazza Grande, where you can still see the Medici insignia emblazoned in the square.
This imposing walled town is also home to a number of excellent restaurants – two that I can highly recommend. First, is Osteria del Borgo, a traditional restaurant located just inside one of the main gates of the old city walls and offers hearty Tuscan dishes and stunning views of the beautiful countryside from its outdoor terrace. Second, is La Bottega del Nobile, a special winebar-restaurant with tables deep down in the wine cellar, glorious food and an extensive wine list.
Situated in the heart of a wine region, Montepulciano is famed for its very special wine, Vino Nobile di Montepulciano. There are lots of great local wineries nearby, so this is the perfect place to undertake some wine tasting if you wish to include it on your Tuscan itinerary.
By Chris from Amateur Traveler
Montalcino is one of those beautiful hill towns that Tuscany is known for. The history in the area goes back to the Etruscans, but the town today is protected by its five sided Fortezza which dates back to the 1300s. These days the town is known for the Brunello wine produced from the vineyards that cover the slopes of the hill. Brunello is one of the most popular of the Italian red wines and there is no better place to sample Brunello than in the Tuscan town which it hails from.
You can walk all the streets of the town in 15 minutes and still have time left over to find a glass of wine. There are a number of small enotecas in town where you can stop for a glass or a bottle of wine, including one in the Fortezza. Take your time as you walk through town and peek into the small private courtyards of this charming town.
Start at the Fortezza where you can climb up to the walls to get the best view in the town. The Main Street runs from the Fortezza across the hill to the humble Sant’Agostino gothic-style church. Across the street from the church is the small Riuniti Museum which has a collection of art from the 14th to the 20th century. The museum is run by the city and the Catholic diocese and its best pieces are religious art.
After the hustle of Florence or Siena, Montalcino is a quiet interlude. The best way to experience Montalcino is to rent one of the villas near town and make it a base for operations in Tuscany. You can easily do day trips from Montalcino.
Most beautiful small town to visit in Tuscany
By Isabelle, from Issy’s Escapades
Without shadow of a doubt, one of the most beautiful towns in Tuscany is the renaissance town of Pienza.
Pienza is located close to Montepulciano, meaning that it is extremely easy to combine a visit to both of these towns in one day, or to visit one while based in the other. On the route between Montepulciano and Siena also, it’s extremely easy to stop off in Pienza if you are transiting between the two.
Upon entering the old historical center of Pienza, it feels like you have stepped into a time warp, as much of the town’s major features date from the Renaissance. In the 15th century, Pienza (then known as Corsignano), struck gold when a citizen from this formerly humble village was elected Pope Pius II.
He set about making Pienza the ideal Renaissance town, enlisting the help of famous architect Leon Battista Alberti to remodel the town based on humanist urban planning principles. Upon Pius’ death, the redevelopment halted and what remains today has been virtually untouched since that time. Its beautiful architecture from this period makes it one of the most prettiest towns in Tuscany.
A UNESCO World Heritage town, Pienza is also home to Pecorino Di Pienza, a sheep’s milk cheese that is added to many of Tuscany’s most delicious dishes and cheese shops are smattered amongst the historic buildings of Pienza’s winding streets.
With its incredibly well preserved Renaissance buildings, its position as the capital of pecorino cheese, and its astounding views of the surrounding fields and cypress trees of the Val d’Orcia, Pienza is an extremely compelling day trip proposition on a Tuscan road trip and is by far and away one of the top small towns in Tuscany Italy to visit.
Best Tuscany Medieval Towns
By Or from My Path in the World
Also known as the Town of Fine Towers or Medieval Manhattan, San Gimignano is a walled hilltop town you don’t want to miss in Tuscany. Just by driving towards it, its unique skyline makes it easy to understand why it is one of the most picturesque towns in the region. Thanks to its iconic well-preserved tower houses and stunning medieval architecture, its historic center was declared a UNESCO World Heritage Site, and indeed, strolling through San Gimignano feels like stepping back time.
Some of the main points of interest of this enchanting town include the Palazzo Comunale (the highest of the towers and an art museum), Porta San Giovanni, and Duomo di San Gimignano (Collegiate Church of the Assumption of Mary), but you’ll find plenty of beauty in each and every corner. Plus, there’s no shortage of panoramic lookout points.
Although it’s a small place, this town is also known for its fantastic food, saffron production, and white wine (Vernaccia di San Gimignano), so you’ll also find many amazing restaurants, wine bars, and wine shops here. A few to check out are Le Vecchie Mura, Il Ceppo Toscano, and La Vecchia Nicchia.
Last but not least – located in the central Piazza della Cisterna, don’t miss Gelateria Dondoli, which was the Gelato World Champion more than once. It is especially known for a few unique flavors you have to try, like Crema di Santa Fina (cream with saffron and pine nuts), Dolceamaro (cream with aromatic herbs), and Champelmo (pink grapefruit and sparkling wine).
By Karen from Bewitched By Italy
Lucca is one of the most popular medieval towns in Tuscany, with Etruscan and Roman origins. In the Middle Ages it was an important city-state, and the architecture and historic centre that are the main attraction for tourists date from this period.
The number one must-do activity here is to walk along the top of the Lucca city walls. These form a complete circuit of around 4 km, built in the 16th century but incorporating earlier sections. The walls are not just of historic interest: they are wide and form an extensive area of parkland, with trees, cafés and children’s play areas.
Elsewhere in the city, look out for the remarkable Piazza Anfiteatro, built on the site of the old Roman amphitheatre. Unlike most piazze this one is round, and shops and restaurants have been built into the spaces where the arches once were. At the centre of Lucca is the Cattedrale di San Martino, notable for its 13th century black wooden figure of Christ and a painting of the Last Supper by Tintoretto.
You can also visit the Palazzo Pfanner (a palace and garden that is now an art museum) and the Puccini Museum, in the house where the composer was born. Or climb to the top of the Torre Guinigi, a 14th century bell tower, for views across the city.
There are several places to eat around the Cathedral area. I enjoyed a meal at the Aria Cafè Restaurant.
Martina – PlacesofJuma
A really amazing tip for a stop on a road trip is the wonderful medieval village of Monteriggioni in Tuscany. The historic fortress, which is located on the hill Monte Ala, is especially beautiful and due to its location, it offers a fantastic view over the Tuscan countryside. In the center of the complex enchants a picturesque old town, which can be explored via a short easy walk. Among the most important attractions are the well-preserved defense towers and the city wall, which you can even climb up.
The medieval flair of Monteriggioni is unique in Tuscany, and that is why a large medieval festival is held here once a year in the summer. Absolutely worth seeing is also the Piazza Romana directly in the center. This picturesque square is the main square of Monteriggioni and with a coffee or a glass of wine in one of the good local restaurants there you can watch the hustle and bustle. If you love wine, don`t miss to try the regional red wine “Chianti Colli Senesi Monteriggioni”, whose vines grow in the vineyards around the castle.
Another interesting place to visit is the church of Santa Maria Assunta, which dates back to the 13th century and is one of the oldest buildings in the old town. If you want to learn more about history, it is best to check out the museum “Monteriggioni in Arms”, where you can learn more about the rich past of Monteriggioni.
All in all, Monteriggioni is a real highlight in Italy and should not be missed on any perfect Tuscany Road Trip!
READ NEXT | 30+ Of The Best Gifts For History Buffs In 2021
By Chrysoula, from Travel Passionate
One of the top towns to visit in Tuscany, the Tuscan hilltop town of Volterra lies conveniently close to Florence. The town has a rich history dating from Etruscan times (5th century BC) when it was one of 12 powerful centers. Remnants of its ancient defensive walls, gateways, and its strange layout are all credited to the Etruscans!
Enjoy a break from driving and slip on comfortable shoes as there is much to see in this pretty town. The center of the town has medieval streets and squares. The Palazzo dei Priori is the oldest town hall in Tuscany. The 12th century Duomo – Cathedral of Santa Maria Assunta- is beautiful. Much of it was renovated in the Renaissance style and it has a richly decorated ceiling and numerous paintings including a famous fresco by Benozzo Gozzoli (1479).
If you enjoy history there is the Guamacci Etruscan Museum and numerous Roman monuments to see including Roman baths, a forum, and an amphitheater. The magnificent Medici Fortress sadly cannot be explored inside as it is used as a top security prison.
Volterra is world-famous for its alabaster carving, so is perfect for souvenir shopping. During mid-March, late October, and early November there are celebrations showcasing local products that include white truffles, cheeses, olive oil, and chocolate.
Best hill top towns in Tuscany
By Kathryn from Wandering Byrd
Cortona is built on the top of a hill, with breathtaking views across the surrounding countryside. The town is quintessentially Italian- think beautiful plazas, cute streets and lots of history. In fact, the villa used in the movie ‘Under the Tuscan Sun’ is located just outside Cortona (you can even rent it for a week’s holiday!)
Cortona is over 2000 years old and its history is full of Greek and Roman stories. One of the biggest attractions in the town is the Accademia Etrusca- a museum full of artefacts and things found in the area. It’s spread over 5 floors in a 13th century building and is well worth a visit. There are several other museums and historic places in the town to visit, including the Cathedral and the main square.
If you’re more interested in Italian food and drink than history, head to La Bucaccia- set in a medieval stables and famous for its beef and pasta dishes. For wine, you can’t beat Taverna Pane e Vino, where you can enjoy Tuscan and Italian wines along with bruschetta and cheese.
If you’re campervanning in Italy, there are some wonderful campsites to stay at within walking distance of the town, but if you’re road tripping by car, there are plenty of hotels and BnBs to choose from
Cortona is also famous for its jazz festival, which usually happens over several days around the end of April and is definitely worth arranging your travel to be there for the festival atmosphere which spreads through the town.
By Isabelle from Issy’s Escapades
Pitigliano is one of Tuscany’s famous ‘Tufa’ towns, which are towns that have been carved from volcanic (or ‘tufaceous’) rock. Pitigliano is the most recognisable Tufa town in Tuscany, in part due to the dramatic setting it occupies atop a particularly elevated and prominent rocky outcrop.
South of Montepulciano and close too to the thermal mineral waters of Bagno San Filippo, its relative proximity to other popular Tuscan towns, together with its fascinating historical and cultural heritage, make Pitigliano one of the best small towns in Tuscany to visit.
Pitigliano’s earliest signs of inhabitance are rather ancient, dating back to Neolithic times. There are also signs to suggest that there was an Etruscan community here in the 6th century, followed by the Romans, before the Medicis left their mark on this historic town in the 16th century, with the construction of an aqueduct that can still be seen to this day in the town center.
Extremely interesting too, is the fact that Pitigliano is also known as “Little Jerusalem”, due to the role it played as an important refuge to the Jewish community who fled persecution from other areas of Italy from the 14th century onwards. They played an important role of shaping the culture of this interesting Tuscan town and it is possible today to visit the former Ghetto area of the town.
As one of the best hill towns in Tuscany, there is a lot to fit in during a visit to Pitigliano. Make your way to the north-western part of the town to discover ancient Etruscan walls and the Porta Sovana, an entrance to the town hewn from the tuff that leads to the vie cave and the necropolis of Sovana.
The vie cave (meaning, simply “excavated roads”) are a bewildering set of tunnels – as no one knows for certain why they exist – which you can explore with or without a tour guide. Look out too for the “Tempietto“, which is a small temple that may lead back to Etruscan times.
As such a historic town in Tuscany, it is a given that Pitigliano is home to some museums, should you wish to learn more about its heritage. These include the Alberto Manzi Outdoor Archaeological Museum, which brings Pitigliano’s history to life, the Civic Archaeological Museum of Pitigliano, which includes a range of artefacts from the Bronze Age to the Etruscans, and the Palazzo Orsini and Museum of Sacred Art.
The lovely town of Barga is one of the most important hilltop towns in Tuscany, known also as the Gem of the Garfagnana. The Garfagnana is an area within the province of Lucca, in Tuscany’s north-west, that is famous for its sprawling and varied landscape. Barga is one of the top towns in Tuscany to visit or base yourself if you love the great outdoors and all the activities that go with it!
The town itself is contained within a marvelous mountain setting and is around an hour from the town of Lucca. It is a wonderful location in which to wander narrow streets and discover the pastel-hued Renaissance buildings housed within Barga’s centre.
Historically, the town of Barga was linked to the powerful Renaissance city of Florence for centuries and reaped the rewards that this strategic alliance offered. In this regards, it is therefore thoroughly unsurprising that you will the Medici coat of arms of the columns of the Florentine Marzocco (the lion symbol of Florence’s political strength) beside the Loggia dei Mercanti. This was the town’s medieval marketplace located in the town’s main square, Piazza Salvi.
Barga is also home to one of the most important Romanesque churches in Tuscany, the Cathedral of San Cristofano. The church sits high above the town, on a vantage point called the “Arringo”, where citizens used to meet to discuss important matters and also, for executions. Rather interestingly, the Arringo has earned itself the nickname of “Prataccio“, or “nasty lawn” as a result of the latter!
Best coastal town in Tuscany Italy
By Emma from Emma’s Roadmap
One of the cutest towns in Tuscany is definitely the small harbour city Portoferraio on the island of Elba. If you’d like to get away from mainland Italy and explore more of its coast, this is definitely the place to be!
The name Portoferraio actually means iron harbour in English and refers to the history of this city as the place to trade iron. However, this is not the main reason why Portoferraio is mostly known. In 1814, the one and only Napoleon Bonaparte was banned to the island of Elba and lived in Portoferraio for almost a year. Because of this, Portoferraio also attracts many tourists. One of the top attractions in this harbour town is one of Napoleon’s houses, Villa dei Mulini. Here, you can experience how the emperor used to live in exile and learn more about his history!
Another great activity in this city is Martello Tower. This tower used to be a prison and is located right at the harbour with an amazing view of the bay of Portoferraio. Originally, it was built as part of a defense infrastructure for the island, but right now you can visit it together with its museum.
Of course, you can’t visit the island Elba or Portoferraio without trying the local cuisine! Very popular dishes you should try on the island are Rio-style rockfish, stuffed sardines and boiled octopus. Also, don’t forget to try one of the local wines while visiting Portoferraio, one of the best coastal towns in Tuscany!
Best towns in Tuscany map
To aid you in your trip planning, I’ve included the above best Tuscany towns to visit on a map. Unless you have at least 10 days, it is highly unlikely that you will be able to visit all of these towns in Tuscany Italy in one visit, so choose a handful that pique your interest and combine them other visits to the best cities in Tuscany like Florence and Siena.
Travelling to Tuscany? You might like the following:
TUSCANY ITINERARY | Tuscany Guide – How To Have A Very Memorable Tuscan Road Trip
FLORENCE GUIDE | How To Spend 2 Days In Florence – A Comprehensive Guide
SIENA GUIDE | The Perfect Way To Spend A Day In Siena, Italy
FLORENCE VACATION RENTALS | Ultimate List Of The Best 17 Airbnbs In Florence Italy For Luxury Lovers
SIENA VACATION RENTALS | The Best Airbnb Siena Italy – A Luxury List Of Siena’s Loveliest Listings