SLOW TRAVEL THROUGH 16 OF TUSCANY’S MEDIEVAL TOWNS FROM FLORENCE

Dreaming of wandering through Tuscany’s medieval hill towns, sipping wine beneath ancient stone towers, and driving along those iconic cypress-lined roads? You’re in the right place.

While Florence is famous for its Renaissance art and architecture, it also makes the perfect base for exploring some of Tuscany’s most beautiful medieval towns from the soaring towers of San Gimignano to the wine-filled streets of Montepulciano and the perfectly preserved walls of Monteriggioni.

After exploring Tuscany’s countryside and charming hill towns over multiple trips, we quickly realised that choosing where to go can feel overwhelming. There are countless beautiful villages scattered across the region, and many guides barely explain which ones are actually worth prioritising or how to visit them efficiently from Florence.

That’s exactly what this guide will help you with.

Whether you’re planning a Tuscany road trip, looking for easy day trips from Florence, or deciding which medieval towns deserve a spot on your Italy itinerary, this guide covers the best places to visit, how to get there, transport options, tours, and practical tips to help you plan an unforgettable Tuscany adventure.

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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 map below which is linked to a Google Map featuring all the destinations included in this guide.

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. We’d suggest doing a few price comparisons on Skyscanner to find some great deals.

Car

One of the most flexible ways to travel around Tuscany is to drive and hiring a car is easy with Discover Cars. 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. We book ours through Omio or Trentitalia which also have a number of fast services.

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. Look for small group or private tours with Get Your Guide or Viator, we have booked some very unique and memorable expereicnes through them.

Exploring Tuscany’s Medieval Towns From Florence

1. 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. If it’s your first time in Florence, our guide has everything you need to know.

Florence Tours (For First-Time Visitors)

• Timed Entry to Michelangelo’s David including Audio App – You’ll get priority entrance to the Accademia Gallery and admire Michelangelo’s David and be able to explore unfinished works like ‘The Prisoners’ and ‘St. Matthew.’ Other interesting exhibiyts include the Cherubini Conservatory masterpieces by Bartolini and other Renaissance artists. We were glad to have booked this tour in advance as there was a huge queue forming outside whilst we could fulyy appreciate the David minus the crowds.
• Brunelleschi’s Dome Climb Entry Ticket & Duomo – You cannot miss this when you’re in Florence. Be in absolute awe of the intricate frescoes created by Zuccari and Vasari. Head up to Brunelleschi’s Dome and soak up the breathtaking views of Florence. the Duomo or Santa Maria del Fiore Cathedral is 150ft wide and 180ft tall. this is one of the best places to visit in Firenze.
• Uffizi Gallery Timed Entry Ticket with App Audioguide – I (Bejal) firts visited the Uffizi as a teen when I was studying Renaissance Art and in my opinion, if you’re an art lover, you will truly appreciate this museum! If you’re short of time, you’ll reap the advantages of this timed entry, and you can stay as long as you like. Do not miss Botticelli’s “Birth of Venus,” a classic work of Renaissance Neoplatonism and discover masterpieces by Michelangelo and other masters of Italian Renaissance like Raphael and Donatello.

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

2. 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. If you’re short of time then spending one day in Pisa will give you a great taste of the city and showcase that it’s not just all about the tower, even though it is quite teh marvel!

Our Top Picks of Pisa Tours

• Square of Miracles Monuments Ticket with Leaning Tower – The perfect tour for first-time visitors and covers the whole main square that most tourists want a glimpse of. It includes climbing the tower for surrounding views with a reserved entrance time, seeing all the religious sites of Piazza dei Miracoli, in Pisa. Head to the Baptistery, Cathedral, Cemetery, Opera del Duomo and Sinopie Museum and the exquisite architecture of the beautiful Pisa Cathedral
• Pisa Sightseeing walking Tour – This 2 hour tour we think is the perfect introduction to Pisa. Marvel at the world-famous Leaning Tower of Pisa, experience the magic Piazza dei Miracoli and Piazza dei Cavalieri, explore narrow streets, markets, the University, and Botanical Gardens and see the unique Palazzo Blu on the River.
• Wine Tasting with Local Bites in Pisa near the Tower – This is the perfect one-hour tasting session following a mooch around the city to get your bearings, providing. you like a glass or two of vino! Savor the flavors of Tuscany with a tasting of four carefully selected wines in this charming locally owned wine shop in Pisa. Wines are paired with cold meets and cheese, oilve oils and bread and is a great way to unwind and partake in the local aperitivo hour that Italy is so well known for!

Pisa is all about the: Shopping, History, Photography

3. 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

The Best Monteriggioni Tour Picks

• Monteriggioni & Siena, San Gimignano with Tasting – This taster of three Tuscan villages in one day is a great way to get into the countryside and sample some Chianti wines at a local estate with homemade snacks. You’ll have teh opportunity to explore Siena’s Piazza del Campo, home of the Palio horse race, have some free time in UNESCO-listed San Gimignano and walk along Monteriggioni’s perfectly preserved medieval walls. We did this tour a few years back and it was a greatw ay to spend a day, although long at around 11 hours, the pace was pretty laid back.
• Monteriggioni & Val d’Orcia Optional Wine Tasting – Another full day tour including the historic walls of Monteriggioni which date back to 1200 AD, head to theTemplar Museum of Monteriggioni and marvel at artefacts, then taste a variety of typical Tuscan wines and local produce and enjoy a enjoy a picturesque stroll through the historic streets of Montalcino. A slow adn relaxed day to be had away from the hustle and bustle of Florence city.

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

4. 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 We Love In Siena

•  Walking Tour and Skip-the-Line Duomo Tickets – A tour perfect for those visiting Siena for the first-time. Explore Siena’s historic center and visit its main attractions such as the Basilica of San Domenico and other historical buildings. You’ll have skip the lineentry to enjoy fast track entry to the Duomo or Cathedral. Be wowed by the impressive masterpieces by Donatello, Bernini, and Michelangelo with an English-speaking local guide. The tour is perfect if you”re short of tiem as it lasst 2 hours and covers the main points of interest.
• Pasta and Tiramisu Cooking Class with Wine – This one is definitley for the foodies. If you’re in Siena book onto this cookery class to learn how to make pasta and tiramisu in a popular Siena restaurant. Discover the secrets of Italian cuisine from a professional chef, whilst enjoying a glass of Prosecco upon arrival to the restaurant. Sip on a glass of wine as you enjoy your homemade pasta and tiramisu.

Siena is all about the: History and Piazza vibes.

5. 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).

Our Recommended San Gimignano Tours

• San Gimignano: The Medieval City – This 2 hour guided tour take syou around well preserved medieval towers of the city centre. Drop by Piazza del Duomo and Piazza della Cisterna, which are the heart of the city as well as the countryside around San Gimignano from the panoramic balcony at Rocca di Montestaffoli. Also see marvelous pieces of art in the church of Saint Augustine.
• San Gimignano: Lunch or Dinner at a Winery with Wine Tasting – A lovely way to spend 2 hours, sipping on Tuscan wines and tasting extra virgin olive oil in the scenic Chianti groves and vineyards. Sit down to a local Immerse yourself in the scenic beauty of the Chianti region. Enjoy a delicious lunch or dinner of local products and traditional dishes and learn more about Italian wines with an expert sommelier. You’ll even be bale to purhcase the wines.

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

6. 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 That We Love

• Cortona Guided historical walking tour – This 2 hour walking tour focussed on the Old Town with a local guide showing some spectacular views of the Valdichiana valley, churches rich in art and history in the heart of the town. Meander downarrow streets, piazzas, and authentic artisan shops, this small group tour is perfect to get your bearings in Cortona.
• Pasta & Pizza cooking class in Cortona –  learn how to cook traditional Tuscan food in this fun pasta, pizza and focaccia cooking class with Chef Samantha. Prepare your own meal complete with Mediterranean sauces, then feast on your creation on an outside terrace with chianti local wine of course. A really laid back small group class.
• Organic wines tasting at Colle Acacia’s vineyards – In this half day tour, savor the flavours of Tuscany with a wine tasting in a scenic vineyard where you’ll try 4 wines, including a Super Tuscan blend, Syrah and a Rosé.Pair your wines with local delicacies like pecorino cheese and ham and then take a leisurely walk through the vineyard to learn about the vines. Theer’s even some relaxation time to just sit and admire the surrounding views.

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

7. 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 and is perfect for a day trip from there, or to stay in for a couple of nights. . 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.

Arezzo Tours That We Love

• 2 hours Arezzo group walking tour – A tour that gives you your bearings in the town so you cna go back and revisit at your pace! Discover Arezzo a real hidden pearl of Tuscany full of architectural beauty coupled with masterpieces, including a trip to the town’s cathedral with its paintings and coloured stained glass windows.
• Pasta and Tiramisu Cooking Class with Unlimited Wine – This 3 hours class features creating handmade pasta and tiramisu with unlimited servings of regional wines as you cook and learn. You’ll learn from expert Italian chefs in a small group with plenty of hands on experience adn step-by=step instructions.

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

8. Lucca

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

Lucca is the perfect place to spend a day, in our opinion. It no longer remains a less visited spot, 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. 

Lucca Tours

• 2-Hour City Center Walking Tour – A great tour to get your orientation in the city, it takes you through the city centre of Lucca with a professional guide where you’ll get to admire the Church of San Michele, which is over 1000 years old and walk along the ancient walls of the city to mention a few.
• Guided Food Walking Tour with Tastings – If you are staying more than a day in Lucca, we’d recommned this half-day tour including savouring cheeses and cured meats, bucellato, local pasta and gelato. It includes a complete meal with drinks included across 4+ stops. You’ll have teh chance to explore Lucca in a relaxed, intimate setting with a guided small group. You’ll be led through Lucca’s center, picturesque streets, and charming neighbourhoods.
• Puccini Festival Opera Recitals and Concerts – Classical music lover’s and in teh home of Puccini, this cultural tour is perfect for you! Enjoy an opera fin a 2,200-year-old church with great acoustics and the great oratorio featuring Puccini’s music in the city where he was born and lived

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

9. 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 Is All About The Foodie Tours

• Dairy Farm Tour with Pecorino Cheese Tasting – A popular tour in Pienza with a visit to a local dairy farm and tasting of cheese at different levels of maturity. Perfect for cheese lovers and those who want to leanr about the cheese-making process of this local-cheese.
• Vineyard Walk & Cellar Tour with Wine & Oil Tasting – This guided vineyard and olive grove walk will allow you to explore a unique cellar carved into ancient Pliocene rock, taste four signature Lignanello wines, including Orange Wine and Orcia DOC. Try extra virgin olive oil with bruschetta and a platter of local delicacies and enjoy picture perfect views of Pienza and the Val d’Orcia landscape
• Olive Oil Mill Tour and Tasting at Fattoria Fregoli – Olive oil fans will love this perosnal tour! See what really goes into olive oil production at Fattoria Fregoli in Pienza including the history and tradition in this mill founded in 1840. Find out how olives are harvested, washed and pressed then go onto to taste the different varities of olive oil paired with local bread and take in how a quality olive oil is recognised when used for cooking.

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

10. 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 We’d Suggest

• Private Walking Tour of Historic Landmarks – explore the historic town of Volterra and the Arch Gate, admire the majestic Palazzo dei Priori, Tuscany’s oldest town hall and see the grandeur of Palazzo Pretorio and its battlemented tower. Go to Cathedral of Saint Maria Assunta and the Battistero di San Giovanni. Some free time allows for meandering the narrow streets and admire the spectacular fortress on the hill
• Fresh Pasta Cooking Class at a Tuscan Farmhouse– Be told the secrets of the traditional recipes of grandmothers and learn from skilled chefs who will help you create fresh pasta and serve it with traditional Tuscan sauces then site down to lunch or dinner accompanied by excellent Diacceroni Family wine.

Volterra is all about the: History.

11. 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 Guided Walking Tour – A must as an introduction to the town. Explore the oldest part of the city with old medieval buildings and take in panoramic views of the city from Prato della Rocca. With your guide you’ll also visit Church of Holy Crucifix, Republic Square, Palace of the Episcopal Seminary
•  Organic Wine Tour & Tasting at a Family-Winery – As local as experiences get here, have an exclusive visit at a family-run Tuscan winery where you’ll explore vineyards and cellar guided by the winery team. Then taste selected wines paired with olive oil and local cuisine. You’ll have an introduction to native Tuscan grape varieties and sustainable organic viticulture.

San Miniato is all about the: History and Truffles.

12. 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 from 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.

13. 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 Choose from In Montepulciano

• Private Renaissance Walking Tour – Marvel at the Renaissance architecture of the Palazzo Comunale and admire the elegant façade and classical portico of the Duomo. See the charming medieval streets and artisan shops then visit the Church of San Biagio, a Renaissance masterpiece and finally take in the panoramic views of the Tuscan hills from Piazzale della Fortezza.
• Dining Experience at a Local’s Home – This 3 hour dinner experience cannot get any local! Taste authentic recipes
• with a demo cooking class in a local Italian families home, Share a real connection and feel thr true warmth of Italian hospitality. Truly a very personal and memorable dinner.
• City Bus Tour with Audio Guide – Valid for one day, this city bus tour takes you around the charming streets and alleys of this Tuscan village. You’ll see Piazza Grande as well as many other points of interest and learn all about the town and sights iwth the audio guide on board.

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

14. 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 To Experience

If you’replanning to visit Pitigliano, we’d suggest spending the time justtaking in the quite town vibes, sit in the square, have lunch or dinner, grab copious cups of coffee, slow down and watch the world go by. Walk the surrounding countryside as most of this area is populated with vineyards so take a tours to pay one a visit!

Ciliegiolo Grape Wine Tasting – This wine tasting experience in Pitigliano includes a visit to their cellar and a chance to learn aboout the grape variety as well as 5 wine tastings made with Ciliegiolo and paired with a selection of local pastries. This is a more intimate exerience than oters we’ve been on.

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

15. 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.

Recommended Vicopisano Tours

We’d recommend if you plan to stay here for a couple of days then look into tours that are advertised from the town that you could well organise by talking to locals. Vicopisano is close to Pisa and perfct to spend a slow day in walking the village, main square, checking out the local small independent cafes adn eateries as well as heading to the famous central 12th-century clock tower and a 15th-century fortress, the Rocca di Brunelleschi, designed by Filippo Brunelleschi. You coudl also head to the Vespa Factory & Museum in Pontedera, Italy (near Pisa)

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

16. 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.

Which Saturnia Tours To Take

When it comes to Saturnia, we recommend an experience that inlcudes the Terme di Saturnia Hot Springs, which really are the feature of this town. Here’s our pick, especially if you’re planning to spend teh day here…

Terme di Saturnia Hot Spring Pools Park Day Ticket – This gull day ticket allows you to immerse yourself in the natural beauty of the Tuscan countryside and enjoy the greenery of Maremma while floating in warm and healing waters. Regenerate your mind and body with a day of rwellbeing and relaxation at the hot springs. Guests have access to 4 outdoor thermal pools, whirlpools, vascular paths, and a sauna plus there’s Wi-Fi, locker rooms, showers, and free parking is available if you’ve hired a car.

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. If you’re looking for a special luxury hotel then the Belmond Villa San Michele: A retreat in the Fieosle Hills mor ethan delivers, a chic bed and breakfast in Oltrarno, head to Soprarno Suites (locally owned) an affordable luxury retreat with beautiful gardens, Ad Astra: A historic Boutique Hotel in Oltrarno, Florence (locally owned) and if it’s sheer opulence you like, how about, Bernini Palace Hotel : An Opulent Stay. Alternatively, choose a fine selection of hotels or apartments that suit your location and budget.

FAQ’s Medieval Towns in Tuscany

Be-lavie Top Tips for Visiting Tuscany

• 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 & Next Steps

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.

If this guide has helped you decide which of the featured medieval towns you’d like to visit in Tuscany, then your next steps are to read some of the related articles below. These will aid with locating hotels and day guides to places like Lucca, Arezzo, Chianti wine region and experiences that will help you craft your own Tuscany itinerary.

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• 9 of the most Amazing Postcard-friendly Views of Florence
• Oltrarno: An Artisanal Neighbourhood in Florence
• A Luxury Stay At The Belmond Villa San Michele, Fiesole
• SoprArno Suites: A beautiful Boutique Hotel in Florence
• Ad Astra Florence: A Beautiful Hotel Located In Private Gardens
• A Luxury Stay At The Beautiful Bernini Palace Hotel
• The Best Fine Dining Restaurants in Florence
• Where To Find Vegetarian-Friendly Food in Florence
• La Bottega del Buon Caffe – Michelin Star Review
• Il Locale Firenze: Contemporary Fine Dining in Palatial Surroundings
• Visiting the Chianti Hills by Vespa from Florence
• Driving through the Tuscan countryside from Florence by Fiat 500
• An Artisan Tour of Oltrarno
• A food tour of Florence with a local
• A cookery lesson in Florence with The Cooking Lab

Resources For Planning Your Travels

À bientôt

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