HOW TO BEST EXPLORE TUSCANY’S MEDIEVAL TOWNS FROM FLORENCE

Last Updated on 2nd March 2026 by Bejal

Tuscany is one of Italy’s most popular regions and it’s easy to see why. When you think of the area, what comes to mind immediately is rolling hills, rustic farmhouses, olive groves, vineyards, Tuscany’s medieval towns, cypress trees and not to forget the renaissance architecture. Florence, is the capital city of the region of Tuscany and is very well known as the renaissance city which led to the rediscovery of classical art and culture. Florence also serves as a great base to explore the region and take day trips out to the neighbouring towns and villages that make up the more rural landscapes that we resonate with Tuscany.

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Where Are Tuscany’s Medieval Towns located?

Tuscany or Toscana, as its called in Italian, lies in the central to west of Italy and lies along the Tyrrhenian and Ligurian seas. It is known as the birth place of Renaissance (the late 13th to the early 14th century).

This map shows some of Tuscany’s medieval towns. This list is by no means exhaustive and there are quite a few towns that haven’t been mentioned.

How to use the map: Click on top left hand corner square to reveal legend.

The Best Time To Visit Tuscany’s Medieval Towns

Tuscany is a popular holiday destination and can get very busy during the peak summer months of June, July and August. Additionally this is also the hottest time when temperatures can get uncomfortably warm as well as accommodation and travel prices being elevated due to the school holidays. Shoulder seasons such as April, May and early June is a lovely, calm time to visit as are the autumnal yet warm months of September and early October. 

How Long To Explore Tuscany’s Medieval Towns?

To spend some time in the city of Florence and Pisa at least and then head to some of the villages, five to seven days is an ideal length of time. If you can spare more like ten, that would be perfect and the trip can be taken a little more leisurely. If you’re short of time we’d advise on organised day trips from the city into rural Tuscany to maximise time and to get a flavour of some of the other destinations, with a view to returning one day.

How To Get To Tuscany’s Medieval Towns

Most people travelling to Tuscany’s Medieval Towns will use either Pisa or Florence as a base. 

Flights

Both Pisa and Florence have airports which serve a number of airlines, so travelling to Tuscany is super easy with direct flights to each from most destinations in the world. Galileo Galilei Airport in Pisa is actually the main airport in Tuscany with Florence Peretola Airport, being the second busiest.

Car

One of the most flexible ways to travel around Tuscany is to drive. Once you’re out of the hustle and bustle of the city of Florence, driving is pretty laid back and the roads are sign posted well. You can also hire a Sat Nav with your car if it helps or download google maps when you’re in a WIFI zone. There are plenty of places you can park outside most of the walled medieval towns for a reasonable price. 

Be-lavie Tip: Unlike the UK, driving in Europe, is on the right.

When it comes to hiring a car, the smaller the better, so you can get down the country lanes and cute roads that lead to and connect Tuscany’s medieval towns.

Train 

Many of Tuscany’s medieval towns are accessible by train too, for example, Lucca, Arezzo, Siena. You can get direct trains from either Pisa Centrale train station or Santa Maria Novella in Florence.

How To Get Around Tuscany’s Medieval Villages

The easiest way to get around is by car

Hiring a car and driving is the best way to get between the towns. Most of the towns have car parks just outside of the walled entrance which are marked so parking isn’t too troublesome. 

Organised tours and day trips

If you aren’t a fan of independent travel and much prefer to go in a group or a privately organised tour then you’ll be spoilt for choice of the number of tours that can take you out into the Tuscan countryside. From visiting villages and hilltop towns to vineyards and even cookery classes.

Exploring Tuscany’s Medieval Towns From Florence

Florence

Florence, the capital city of Tuscany and the birth place of the Renaissance is literally an out door museum. The city has so much to see and do from incredible architecture, such as the Duomo, incredible views from it’s many viewpoints including Piazza Michelangelo, a wonderful dining scene including a host of Michelin star restaurants, awe-inspiring museums, like the Uffizi and Accademia as well as beautiful gardens like Bobboli and Bardini.

// Related Article: Things to see and do in Florence

Florence Tours (For First-Time Visitors)

Florence is all about the: History, Food, Romance, Artisans, Art

Pisa

• Driving Distance from Florence: 88km
• Driving Approximate time: 1hr 16 mins.
• Google Map Details

Pisa is easily accessible by train from Florence and is a must-visit when in Tuscany if you are not using it as a base already. Apart from the obvious reason for visiting the leaning tower of Pisa, getting a glimpse of the Baptistry, Piazza del Duomo, Catterdrale di Pisa and the Baptistry, Pisa is worth a day visit if you can spare the time.

There is so much more to the city than just the main complex. Think beautiful walks along the Arno, world- renowned gelato, a historic town centre and much more.

// Related Article: How to best spend one day in Pisa, Tuscany

Pisa Tours

Pisa is all about the: Shopping, History, Photography

Monteriggioni

• Driving Distance from Florence: 62km
• Driving Approximate time: 56 mins.
• Google Map Details

Located in the wine producing area of Chianti in Tuscany, Monteriggioni is beautiful due to it’s views out to vineyards and a lush green landscape. The town is a great example of a fortified Tuscan walls and is set a little higher to benefit from the valley and vineyard vistas.

 The town can get pretty busy as it is well known to many visitors. 

Things to do in Monteriggioni

• Stroll the ancient medieval streets.
• Visit the Church of Santa Assunta.
• Discover Renaissance weapons and armour at the Armoury Museum.
• Use the town as a base to head into the Chianti region for s spot of wine tasting.
• July sees the Monteriggioni medieval festival where locals dress up in traditional medieval costumes and take part in medieval games.
• If its your first time in Tuscan, Monteriggioni is a must and a very typical Tuscan town.

Be-lavie Tip: Did you know Assassin Creed saga is set in Monteriggioni

Monteriggioni Tours

Monteriggioni is all about the: Family Travel, Photography, History, Wine

Siena

• Driving Distance from Florence: 78km
• Driving Approximate time: 1hr 5mins.
• Google Map Details

Located in the southern portion of Tuscany, the whole town on Siena is a UNESCO World Heritage Site. It’s well known for its terracotta rooftops, pretty narrow cobbled-stoned streets and is story-book material. 

Things to do in Siena

• The Cathedral of Siena, Palazzo Pubblico.
• Palazzo Salimbeni.
• Walk around the main square of Piazza del Campo.
• The huge Basilica of San Domenico.
• Stroll through picturesque courtyards.
• Renaissance period filled museums.

Be-lavie Tip: In July and August (twice a year) the Piazza del Campo acts as race track for the Palio di Siena, which is a historical horse-racing event dating back to the medieval times.

Tours from Siena

Siena is all about the: History and Piazza vibes.

San Gimignano

• Driving Distance from Florence: 59 km.
• Driving Approximate time: 1hr 2mins.
• Google Map Details

San Gimignano is a fine example of a medieval walled town dating back to the 13th century. The town is also known as the ‘Town of Fine Towers’ and has been declared as a UNESCO World Heritage site just like Siena. A half day visit is great but if you’re combining with wine tasting, a full day is ideal.

Things to do in San Gimignano:

• Hang out in the town’s two main squares, Piazza del Duomo (surrounded by the towers which give San Gimignano its name) or the Piazza dell Cisterna (named after its cistern), with its unusual triangular shape circled by 13th century buildings.
• Enjoy a coffee in the squares and watch the locals go about their daily business.
• Try an award winning gelato at Gelateria Dondoli, in the main square. Former gelato world champion Sergio Dondoli is a member of Italy’s ice cream world championship team and among his most famous creations are Crema di Santa Fina (saffron cream) gelato and Vernaccia sorbet. His creations are so delicious that some devotees even sign up for a two-hour gelato-making workshop (€400). 
• You can easily book day trips from Florence to San Gimignano or combine it with the medieval towns of Pisa, Siena and Chianti for some wine tasting at the famous Vernaccia di San Gimignano vineyards.
• Pay the Etruscan Academy Museum a visit where you can learn about the Etruscan civilisation (in Cortona).

San Gimignano Tours

San Gimgnano is all about the: History, Vineyards and Photography locations.

Cortona

• Driving Distance from Florence: 116 km.
• Driving Approximate time: 1hr 30mins.
• Google Map Details

Cortona is a small hilltop town with spectacular views of the surrounding valley and Lake Trasimeno. This is also where Etruscan academy museum is located. Exhibits include, an extensive collection of bronze and ceramic items reflecting the town’s Etruscan past. 

Things to do in Cortona

• Walk around the Girifalco fortress, an ancient Etruscan fortification which preserves the history of Cortona.
• Head to the Santa Margherita sanctuary, a neo-gothical Roman Catholic church with incredible architecture.
• Wander the Diocesan museum, full of arts by local artists such as Luca Signorelli.

Be-lavie Tip: Cortono is where the movie ‘Under the Tuscan Sun’ was filmed so make sure you watch it before you head here to be able to spot all the scenes.

Cortona Tours

Cortona is all about the: Foodies, History and photography.

Arezzo

• Driving Distance from Florence: 76 km.
• Driving Approximate time: 1hr 5 mins.
• Google Map Details

Arezzo is a small city located in the province of the same name situated to the South East of Florence. Arezzo is a great place for a day trip and can be accessed really easily by train and only takes around 40 minutes travel time from Florence. The town is full of stunning medieval architecture, churches, parks, a jewish cemetery and loggias with outdoor cafes and restaurants. Arezzo is most commonly known for its antique shops and worth visiting if you are a collector, there are some beautiful pieces

Things to do in Arezzo:

• Climb the hill to see the  Duomo of Arezzo.
• Walk through the Medicea Park.
• Explore the Medicea Fortress.
• Hang out in Piazza Grande.
• Climb up the Palazzo della Fraternity del Lalci.
• Arezzo’s oldest church, Pierre di Arezzo.
• Find out the history of Arezzo at the Roman Amphitheatre and National Archaeological Museum.
• Check out Basilica is San Francesco.
• Don’t miss antique shopping.
• Walk the medieval streets.
• Marvel the 14th and 15th century frescos at San Domenico church.
• Have a coffee and pastry at Arezzo’s oldest cafe, il Caffe deli Constant.
• Have lunch at an Arezzo institution, Logge Vasari Antica Trattoria.

// Related Article: How to spend one day in Arezzo

Arezzo Tours

Arezzo is all about the: History, Photography, Foodies and Antiques.

Lucca

• Driving Distance from Florence: 94 km.
• Driving Approximate time: 1hr 10 mins.
• Google Map Details

Lucca is a very popular town these days and no longer remains a hidden gem but that is no reason why you shouldn’t go because it is still quieter than the more busier places like Siena and San Gimignano.

Lucca has an incredibly well-preserved wall right around the town with cobbled streets and having prime position right beside the Serchio river. Lucca also sits at the foot of the Apual Alps  and a wonderful backdrop to the existing terracotta cypress tree landscape.

Be-lavie Tip: You could tie visiting Lucca in with Pisa to save time as they’re very closely situated.

Things to do in Lucca

• Walk the walls.
• Visit Lucca Cathedral.
• Have a coffee and sweet pastry in the many cute squares.
• Climb the Guini Tower for incredible views of the city. 
• Visit the Roman Amphitheatre.
• The city can be very easily explored by foot. 
• Head to Lucca’s botanical museum (a combined ticket with the towers is a good option).
• Pop into one of the many delis and buy a picnic lunch to eat along the walls. 

// Related Post: How to Spend One Day in Lucca

Lucca Tours

Lucca is all about the: History, Views and Photography locations.

Pienza

• Driving Distance from Florence: 116 km.
• Driving Approximate time: 1hr 45 mins.
• Google Map Details

Pienza is your historically charming old town, the town you’ve been searching for. The town centre is a designated UNESCO world heritage site. Pienza is the birthplace of Pope Pius II and is often refereed to as the ideal city of the Renaissance. Pope Ious II helped with the transformation of Pienza during the Renaissance and had the dream to create an almost utopian town, he certainly achieved that as so many come to see Pienza to this very day!

Things to do in Pienza

• Visit the Piece di Corsignano, the Romanesque Church.
• Try the famous Pecorino cheese.
• Admire Palazzo Piccolomini.
• Marvel the Cathedral of Assunta.

Be-lavie Tip: Palazzo Piccolomini was used to film scenes in Rome & Juliet.

Pienza Tours

Pienza is all about the: History, Photography and Foodies.

Volterra

• Driving Distance from Florence: 81 km.
• Driving Approximate time: 1hr 19 mins.
• Google Map Details

Volterra is one of the more older towns in Tuscany and date back to the middle ages with a traditional town look with a centre, ancient walls and feels very much like an archaeological excavation site. 

One of the most fascinating things about Volterra is that it’s known for alabaster artefacts. If you’re looking to purchase a souvenir, Volterra is the place to scope out the little boutique store.

Things to do in Volterra

• Head to the Roman Theatre.
• Check out the Acropolis.
• Stroll along the old city walls.

Volterra Tours

Volterra is all about the: History.

San Miniato

• Driving Distance from Florence: 49 km.
• Driving Approximate time: 51 mins.
• Google Map Details

A very small hilltop town located halfway between Pisa and Florence and easily accessible by train (although you’ll need to take the bus up the hill) is a great day trip or half day trip option. San Miniato is famous for its truffles and even have a truffle festival three weekends in November known as the Mostra Mercato di Tartufi Aquilone.

Things to do in San Miniato:

• Pursue the main square-Piazza della Repubblica. 
• Take time to appreciate the Cathedral of San Miniato.
• Culture vultures can head to the Museo diocesano di Arte Sacra.
• Don’t miss the Rocca di federico II -the reconstructed tower.

San Miniato Tours

San Miniato is all about the: History and Truffles.

Poppi

• Driving Distance from Florence: 57 km.
• Driving Approximate time: 1hr 12 mins.
• Google Map Details

A small utterly charming town that’s located around 35 Km from Arezzo in the eastern part of Tuscany. The town has a very well preserved 13th century castle and still has its own medieval porticos, two churches and a breathtaking view of the Casentino Valley.

Things to do in Poppi

• Visit the Castello di Poppi (The Poppi Castle).
• Abazzia di San Fedele (Boutique version of a grand cathedral).
• Walk around the medieval centre of the town which is encased by a wall.
• Explore the surroundings by hiking in the Casentino forest.

Tours to Poppi

Poppi is very small and can be explored independently quite easily therefore there are no tours.

Poppi is all about the: History and Panoramic views.

Montepulciano

• Driving Distance from Florence: 109 km.
• Driving Approximate time: 1hr 28 mins.
• Google Map Details

Another fine example of a hilltop town, Montepulciano is incredibly beautiful especially it’s town centre and is also one of the best wine towns in the whole of Tuscany. The vineyards and wineries surrounding the town are most well known for vino Nobile.

As with a lot of the Tuscan towns, the heart of the town is its main square, Piazza Grande, which is overlooked by a big clock tower of the town hall.

If you are visiting Montepulciano in August, you’ll be in for a treat as the town hosts the barrel-racing Bravio Delle Botti competition. The competition involves two team runners who compete to be the first to roll a 80 kg wine barrel through the town. The Piazza Grande is the finish point. 

Things to do in Montepulciano

• Visit the Cathedral of Santa Maria Assunta on. Guided tour.
• Climb the City Hall tower.
• Check out the 13 the century Montepulciano Fortress.
• Don’t forget to go on a Vino nobile wine tour or head to the wine bars such as Contucci winery or La Dolce Vita, some of these will also have an underground wine cellar.
• Alternatively head to one of the vineyards that surround the town for a rustic wine tasting experience accompanied with lunch or a charcuterie board.

Be-lavie Tip: The Volterra scenes in the Twilight: New Moon trilogy were actually filmed in Montepulciano and not Volterra.

Tours to Montepulciano

Montepulciano is all about the: Food, History and  Wine Lovers.

Pitigliano

• Driving Distance from Florence: 197 km.
• Driving Approximate time: 2hr 46 mins.
• Google Map Details

Situated on a stone cliff, this medieval town consists of buildings that were mostly built from the same stone that the cliff is on. Pitigliano is quite unusual as it has a longstanding Jewish community that resides here.

Things to do in Pitigliano:

• Look out for the ancient caves, carved into the cliffside, one though to have been synagogues during the Roman persecution.
• Head to the former Cathedral of Santi Pietro Paolo.
• Scope out the medieval Orsini fortress.

Pitigliano Tours

Pitigliano is all about the: History and Photography-lovers.

Vicopisano

• Driving Distance from Florence: 71 km.
• Driving Approximate time: 1hr 16 mins.
• Google Map Details

Vicopisano is located about 25 minutes from Pisa and sits on hilltops known as Monte Pisano. The town has not yet been discovered by the masses and therefore has a very local and authentic vibe about it. It’s surrounding landscape is full of pine-covered hills, olive groves and gorgeous lush green vistas.

Things to do in Vicopisano

• Wander through the central piazza with a fountain, winebars an artisan ice-cream shop and grocery shop.
• Head to the farmers market on Wednesday or general Market on Saturday.
• Vicposiano is known for it’s ceramics so do pop into the artisan shops to check these out.
• Olive groves means that you can see the production of this from October – January.
• Do not miss Filippo Brunelleschi impressive medieval fortress. Vicopisano once had 100 towers but today only 13 are visible.

Vicopisano Tours

https://www.getyourguide.co.uk/tremezzina-italy-l144420/vicopisano-torre-e-camminamento-del-soccorso-guided-tour-t480329/?partner=true

Vicopisano is all about the: History, Local Food Producers roducers and Towers.

Saturnia

• Driving Distance from Florence: 186 km.
• Driving Approximate time: 3hrs 3 mins.
• Google Map Details

Saturnia is a spa town in the province of Grosseto in Tuscany and has been inhabited since the ancient times. The town is known for its natural spas with both locals and visitors frequent the spas.

Things to do in Saturnia

• Take a guided tour of the Terme di Saturnia (Spa).
• Go on a vineyard tour or olive oil tasting session.
• Take a local picnic.

Saturnia Tours

Saturnia is all about the: History lovers and Spa Worshippers.

Where to stay in Tuscany

Tuscany has a wonderful range of accommodation options from the luxury hotels of Florence and the chianti vineyards to rustic villas and farmhouses as well as apartments. Lots of options mean you can make the trip as budget friendly or splurge on special occasion too.

Search & Book your Florence accommodation with Booking.com

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FAQ’s Medieval Towns in Tuscany

Are Tuscany’s Medieval Towns Worth Visiting?

Tuscany most definitely deserves a place on your list if you love beautiful medieval towns and rustic surroundings, vineyards, history as well as being in rural authentic surroundings. 

Are Tuscany’s Medieval Towns Expensive?

Tuscany is a popular destination and so prices in recent years have risen, however it is possible to keep costs down as always. Opt to do tours independently by hiring a car and heading to the spots of your choice. Stay in Air BnBs as opposed to hotels will also help. Fresh food is great value in Italy for the cost so self-catering or having a picnic lunch will be more economical. Also if eating out opt to have your main meal at lunch and more of an aperitif with a cheese and bread board in the evening. Pizza by the slice is also a great options available from some outlets too, especially in Florence.

Where Is The Best Place To Stay in Tuscany?

We would recommend Florence, as a great city location due to great transport links with the rest of Tuscany. Accommodation is slightly more costlier but there are plenty of well priced Airbnbs. Additionally, Siena, San Gimignano and even Montepulciano are great options.

What Is The Quietest Town in Tuscany?

From personal experience we would say Pienza. Stay over and once the tourists have disappeared late afternoon in the peak season, it is a dream. Also autumn is a great time to visit Pienza as it is pretty much quiet all day.

Which Towns Are Best For Fodo & Wine Tasting?

The answer here is those that are home to established vineyards and wineries. Here are some of teh small towns and wines associated with them:

• Montepulciano – the Vino Nobile wine regions
• San Gimignan – where the best Tuscan wine, Vernaccia di San Gimignano is produced
• Pitigliano – try the white wine, Bianco di Pitigliano

//Related Article: Tuscany wine tours: Chianti country

Be-lavie Top Tips for Visiting Tuscany’s Medieval Towns

• If you’re travelling by car, carry some cash and change in Euros to pay for car parking at the small Tuscan town car parks.
• Try and see the more popular places like San Gimignano and Siena as early as possible in the day as later in the day sees the arrival of tours buses and cruisers.
• Try and find a medley of of towns closest to your base if you’re short of time.
• A day tour incorporating a few villages such as Montepulciano, San Gimignano and Siena is great if you don’t have many days to play with.
• If you’re booking wine tours, do this responsibly and book transport back to your base,
• Support the local towns by purchasing food, wine and local artisanal products as well as paying entrance to museums and other points of interest.

Exploring Tuscany’s Medieval Towns Round-Up

Tuscany’s medieval towns are an absolute joy to visit, especially if you love all things rustic Italian. This includes renaissance and medieval history, great architecture, beautiful views, olive groves, vineyards and not to mention all things foodie. The list above is not exhaustive and there are so many more hilltop as well as Tuscan village that deserve to be explored and given a place on the list. The hardest decision to make is which towns you’ll be adding to your itinerary based on where you intend to stay in Tuscany. This guide shows that there is a beautiful town in the region for everyone, based on your interest.

Related articles to Tuscany’s Medieval Towns Hotels

• Luxury I Belmond Villa San Michele: A retreat in the Fieosle Hills
• Chic Bed & Breakfast I Soprarno Suites
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Resources For Planning Your Travels

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