“Step Back in Time: Discover Tuscany’s 5 Best Medieval Towns
There’s something about Tuscany that makes you want to slow down.
Maybe it’s the way the afternoon light hits the terracotta rooftops, or the sound of church bells echoing through quiet stone lanes. But it’s in Tuscany’s medieval towns—those timeworn places perched on hillsides or tucked behind fortress walls—where the magic really settles in.
On our travels through the region, we found ourselves drawn again and again to these ancient towns. Some like Siena, with its proud palazzos and famous piazza. Others, like Monteriggioni or Volterra, feel almost untouched, their cobbled streets winding through centuries of history and local life. What they all share is that unmistakable sense of the past—alive, tangible, and beautifully worn.
In this guide, we’re sharing our five favorite medieval towns in Tuscany. Whether you’re planning a slow road trip through the countryside or just want to escape the crowds for a day, these towns offer something special: incredible views, rich local food, warm hospitality, and stories written in stone. We’ll show you what to see, where to stay, how to get there, and the best time to visit—so you can experience them just as we did.
Table of Contents
1. San Gimignano – The Medieval Manhattan
Why Go
San Gimignano is one of the most iconic medieval towns in Italy, famous for its skyline of 14 medieval towers. Once there were 72—each built by rival families eager to flaunt their wealth. Today, the town is a UNESCO World Heritage Site and feels like a real-life film set.
Best Things to Do
Climb Torre Grossa: The tallest remaining tower offers panoramic views of the surrounding hills.
Visit the Collegiate Church (Duomo): Its interior is covered in 14th-century frescoes depicting scenes from the Old and New Testaments.
Walk the Walls: Stroll along the town walls for a unique view of the countryside.
Gelato World Champion: Try the award-winning gelato at Gelateria Dondoli in Piazza della Cisterna.
Where to Stay
Hotel L’Antico Pozzo: A charming stay in a restored 15th-century building on Via San Matteo.
La Cisterna Hotel: Overlooking the main square, offering views and classic Tuscan decor.
Where to Eat
Ristorante San Martino 26: A creative take on Tuscan cuisine with local wines.
Le Vecchie Mura: Great for sunset dining with views over the valley.
How to Get There
San Gimignano doesn’t have a train station. The easiest and best way is by “Rental car“, or via a bus from Poggibonsi train station. From Florence, the trip takes about 1.5 hours.
2. Siena – A Living Medieval Masterpiece
Why Go
Siena is the beating medieval heart of Tuscany. Enclosed within ancient walls, the city feels like a step back into the 13th century—when it rivaled Florence in wealth, power, and artistic expression. Today, it’s one of Tuscany’s most beautifully preserved towns and a UNESCO World Heritage Site. Its winding lanes, soaring towers, and ochre-colored buildings are a dream for history lovers and culture seekers alike.
Best Things to Do
Piazza del Campo: One of Europe’s greatest medieval squares, shaped like a shell and home to the thrilling Palio horse race held every July and August.
Climb Torre del Mangia: For panoramic views of the red rooftops and rolling hills beyond.
Visit Siena Cathedral (Duomo di Siena): A Gothic masterpiece with black-and-white striped marble, intricate mosaics, and a jaw-dropping inlaid marble floor.
Wander the Contrade: Each district has its own animal symbol, flag, and deep history—especially around Palio time.
Museo dell’Opera del Duomo: Offers a close-up look at medieval art and an incredible terrace view of the cathedral.
Where to Stay
Hotel Athena: Inside the old city walls, with parking and a rooftop terrace—great value and views.
Palazzo Ravizza: A charming historic hotel with a garden overlooking the Tuscan countryside.
Relais degli Angeli: Elegant, centrally located boutique hotel with frescoed ceilings and luxurious touches.
Where to Eat
Osteria Le Logge: Upscale Tuscan dining in a refined setting just off Piazza del Campo.
La Taverna di San Giuseppe: Set in a historic 1100s cellar, known for its handmade pasta and rich local flavors.
Pasticceria Nannini: Try traditional Sienese treats like panforte or ricciarelli almond cookies.
How to Get There
Siena is easy to reach from Florence or Rome.
By car: About 1.5 hours from Florence. Parking is available outside the walls, with escalators into town. Compare these “Car Rental” prices.
By bus: More convenient than the train. Direct buses run frequently from Florence and stop near the historic center.
By train: Siena’s train station is outside the old town—expect a short bus or uphill walk.
3. Volterra – The Alabaster City
Why Go
Perched high on a rocky plateau, Volterra is less crowded than its neighbors but rich in history. Originally Etruscan, it became a thriving medieval city. Its stark beauty and misty atmosphere often give it a mysterious edge.
Best Things to Do
Palazzo dei Priori: The oldest town hall in Tuscany, with a tower you can climb.
Roman Theatre and Baths: Dating back to the 1st century BC—one of the best-preserved in Italy.
Alabaster Workshops: Watch artisans carve the delicate translucent stone for which the town is famous.
Museo Etrusco Guarnacci: An impressive collection of Etruscan artifacts.
Where to Stay
Palazzo Carletti: Luxurious suites in a noble residence.
La Locanda di San Francesco: Offers panoramic rooms and a cozy wine bar.
Where to Eat
Osteria Acquacheta: Famous for its Fiorentina steak—rustic, loud, and loved by locals.
La Porta di Bacco: Ideal for traditional Tuscan dishes and wine pairings.
How to Get There
Driving is the easiest and most convenient. By public transport, take a train to Chiusi-Chianciano Terme and then a bus or taxi (25 minutes)
Book your “Car Rental” here.
4. Monteriggioni – The Fortress on a Hill
Why Go
A true medieval gem, Monteriggioni is one of our favorites, a perfectly preserved hilltop village encircled by a complete set of 13th-century walls and 14 towers. It’s so iconic that even Dante referenced it in the Divine Comedy.
Best Things to Do
Walk the Walls: You can walk portions of the walls for commanding views of the Chianti hills.
Visit the Arms Museum: Try on medieval helmets and armor.
Attend the Medieval Festival (July): The entire town transforms into a medieval fair with jousts, music, and costumed locals.
Where to Stay
Hotel Monteriggioni: Inside the fortress walls with elegant rooms and a pool.
Castel Pietraio: A short drive away, this castle-turned-hotel offers a romantic countryside escape and beautiful wineries.
Where to Eat
Il Feudo: Known for handmade pasta and wild boar dishes.
Antico Travaglio: Cozy ambiance and excellent local wine.
How to Get There
Easiest by car from Siena (15 minutes). Buses run from Siena a few times a day.
Compare “Car Rental ” rates
5. Cortona – A Timeless Tuscan Town Steeped in History
Why Go
Famous from Under the Tuscan Sun, Cortona’s charm goes beyond the big screen. This ancient town has Etruscan roots, medieval alleyways, and one of the most magical atmospheres in Tuscany.
Best Things to Do
Museo dell’Accademia Etrusca: A treasure trove of Etruscan and Roman finds.
Piazza della Repubblica: The heart of town, lined with cafes and the 13th-century Palazzo Comunale.
Basilica of Santa Margherita: A peaceful walk uphill leads to this ornate church and stunning views.
Hike to the Fortezza Medicea: For panoramic views across the Val di Chiana.
Where to Stay
Monastero di Cortona Hotel & Spa: A luxurious hotel in a former monastery with spa facilities.
Hotel San Luca: Mid-range comfort with stunning balcony views.
Where to Eat
Trattoria Dardano: Local favorite with generous portions.
La Bucaccia: One of the best in town for gourmet Tuscan fare in a stone-walled setting.
How to Get There
Take a train to Camucia-Cortona station, then a short bus or taxi up to the old town. Best and most convient is by car, you could also add in a short drive to the beautiful medieval town of “Arezzo“, well worth the visit.
Compare “Car Rental” rates here.
Best Time to Visit Tuscany’s Medieval Towns
Tuscany is magical year-round, but the seasons offer different charms depending on your travel style:
Spring (April to June)
Arguably the best time—mild temperatures, blooming countryside, and fewer crowds. Ideal for walking tours and photography.
Summer (July to August)
Great for festivals like Monteriggioni’s Medieval Festival, but expect heat and tourist crowds. Book well in advance, especially in San Gimignano and Siena.
Autumn (September to October)
Harvest season! Enjoy wine tastings, truffle fairs, and golden landscapes. Fewer tourists, cooler days—perfect for exploring hilltop towns.
Winter (November to March)
Quiet and atmospheric, our favorite time to visit, but some small-town accommodations and restaurants may close. Great if you want to avoid crowds and enjoy a cozy, slower pace.
Final Thoughts
The medieval towns of Tuscany are more than just postcard-perfect—they are living museums where history, food, art, and nature blend effortlessly. Each one offers something unique: San Gimignano’s towers, Siena the heart of Tuscany , Volterra’s alabaster, Monteriggioni’s intact walls, and Cortona’s soulful beauty.
Whether you’re sipping wine in a Renaissance piazza or watching the sunset over terracotta rooftops, these towns promise unforgettable moments. “Rent” a car for flexibility, stay at least one night in a few of them, and embrace the slower life that Tuscany is so famous for.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – SKYSCANNER – we always start here and usually always finish here. They price check over 1,200 travel sites to help you find the best prices. You can also try GOING to search prices across a variety of sites.
TRAVEL OPTIONS
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – TRAINLINE – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.