Discover the 5 Best Hilltop Towns in Tuscany: You Must Visit (2026 Travel Guide)
Timeless Wanderers: Updated May 11, 2026
Step Back in Time Through Tuscany’s Beautiful Hilltop Towns
One of the things we love most about Tuscany is discovering its beautiful hilltop towns.
Every town has its own personality.
Some are famous for their medieval towers, others for Renaissance architecture, local wine, or sweeping views across the countryside.
What they all have in common is a slower pace of life and the feeling that little has changed over the centuries.
From the iconic towers of San Gimignano to the vineyards surrounding Montepulciano, the Renaissance beauty of Pienza, the peaceful streets of Cortona, and the ancient Etruscan history of Volterra, each town offers something completely different.
We’ve visited all of these towns many times over the years, and every visit reminds us why we keep coming back to Tuscany.
In this guide, we’re sharing the five hilltop towns we love most, along with the best things to see and do, where to eat and stay, and our practical tips for making the most of your visit.
Table of Contents
Why We Love Tuscany’s Hilltop Towns
Visiting Tuscany’s hilltop towns is less about ticking off sights and more about slowing down and enjoying the experience.
These towns work beautifully as part of a wider Tuscany itinerary, especially if you’re travelling by car.
The distances between them are manageable, but the drives themselves are part of the fun, taking you through rolling countryside, vineyards, olive groves, and some of the most beautiful landscapes in the region.
Mornings are often our favourite time to explore, when the streets are quieter and you can wander without the crowds.
Later in the day, the piazzas come alive as locals and visitors stop for coffee, aperitivo, or a long Tuscan lunch.
Rather than trying to see everything, give yourself time to wander.
Stop at a small café, browse a local shop, climb a tower, or simply pause at a viewpoint and enjoy the countryside stretching out below.
Taken together, these five towns give you a wonderful introduction to a different side of Tuscany, combining history, food, wine, scenery, and the slower pace of life we love about the region.
We can help you plan your dream trip to Tuscany, with a personalised itinerary designed just for you.
After more than 20 years of travelling to Tuscany—and loving it so much we decided to make it our home—we now live here and explore the region at a relaxed, local pace.
Planning a trip to Tuscany is exciting, but choosing where to go, how long to stay, and how to get around can quickly become overwhelming.
That’s where we come in.
We offer a personalised planning service that helps you decide exactly how to explore Tuscany, based on your travel style, budget, and pace.
Plus, we can help you plan scenic drives, time in hilltop towns, food and wine experiences, and those small local moments that make a trip truly special—making your Tuscany holiday easier, smoother, and full of memories you’ll treasure long after you return home.
“Let us plan your perfect trip with a custom itinerary designed just for you.
Fill out the form and let’s begin your dream.”
Best Time to Visit Tuscany’s Hilltop Towns
Tuscany’s hilltop towns are worth visiting throughout the year, but each season gives you a very different experience.
Spring — April to June
Spring is one of the best times to explore Tuscany.
The countryside is green, wildflowers appear along the roads, and temperatures are usually comfortable for walking around towns and enjoying outdoor cafés.
April and May are particularly good if you want to explore before the busiest summer months arrive.
Summer — July and August
Summer brings long, warm days and plenty of activity, but it is also the busiest time of year.
The most popular towns can become crowded, particularly from late morning through the afternoon.
If you visit in summer, start early and consider staying overnight in one of the towns so you can enjoy it after the day-trippers leave.
Autumn — September and October
Autumn is another favourite time of ours.
The temperatures are generally comfortable, the summer crowds begin to thin, and the countryside starts changing colour.
September is also grape harvest season, or vendemmia, making it an especially good time to combine hilltop towns with a visit to the vineyards.
Winter — November to March
Winter is often overlooked, but it is actually our favourite time to travel around Tuscany.
The towns are much quieter, parking is easier, accommodation can be less expensive, and you get to see a more everyday side of Tuscany without the summer crowds.
The days are shorter and some restaurants or seasonal attractions may close, so it’s worth checking ahead.
But if you don’t mind cooler weather, winter can be a wonderful time to wander through these historic towns at your own pace.
Our Recommendation
For the best combination of comfortable weather and fewer crowds, we’d choose April to June or September to October.
But if you prefer quiet streets, easier parking, and a more local experience, don’t overlook winter.
We’ve spent many winters exploring Tuscany, and some of our favourite days have been when we had these beautiful hilltop towns almost to ourselves.
San Gimignano
The Medieval Manhattan of Tuscany
Known affectionately as the “Medieval Manhattan,” San Gimignano is famous for its skyline of preserved stone towers rising dramatically above the Tuscan countryside.
This UNESCO World Heritage Site dates back to the Middle Ages and retains much of its original charm with narrow cobbled streets, quaint piazzas, and Renaissance-era churches.
San Gimignano sits atop a hill, offering panoramic views over vineyards and olive groves.
The town’s rich history is noticable in every corner, from ancient frescoes to artisan shops selling locally made saffron and Vernaccia wine.
Best Things to Do
Start your day at Piazza della Cisterna, a picturesque square framed by medieval buildings and bustling with lively cafes.
Visit the Collegiate Church of Santa Maria Assunta to admire frescoes by notable Renaissance painters.
Don’t miss climbing the Torre Grossa, the tallest tower in the town, for breathtaking views across the Tuscan landscape.
For wine lovers, a tour and tasting at local wineries specializing in Vernaccia di San Gimignano, Tuscany’s famed white wine, is a must.
Art enthusiasts will enjoy the San Gimignano 1300 Museum, a detailed miniature reconstruction of the town as it appeared in the 14th century.
Wander the artisan shops offering hand-painted ceramics and delicate honey products unique to the area.
Where to Eat
San Gimignano boasts some incredible culinary spots that showcase Tuscan traditions:
- Cum Quibus: An intimate Michelin-starred restaurant offering innovative takes on classic Tuscan dishes, made with seasonal local ingredients.
- La Mandragola: A charming trattoria near the main square with delicious homemade pastas and excellent local wines.
- Gelateria Dondoli: For a sweet treat, try the award-winning gelato here, famous for creative flavors like saffron and Vernaccia.
Best Places to Stay
Stay inside the town walls for a full medieval experience
Hotel L’Antico Pozzo: A romantic boutique hotel with elegant rooms and a historic atmosphere.
- Relais San Gimignano: Offers refined comfort, a swimming pool with hill views, and easy access to the main attractions.
- Agriturismo La Poggiolina: A countryside farmhouse just outside town, perfect for a peaceful stay among vineyards.
Montepulciano
Renaissance Elegance and Vino Nobile
Montepulciano is a magnificent Renaissance hill town perched on a limestone ridge overlooking the Val d’Orcia and Val di Chiana.
It’s renowned for its rich architectural heritage, from grand palazzi to beautifully decorated churches, and most notably for producing Vino Nobile di Montepulciano, one of Tuscany’s most famous red wines.
The town combines the art with rustic Tuscan charm, making it an alluring destination for history buffs and wine lovers alike.
Best Things to Do
Begin your visit at Piazza Grande, the town’s main square, surrounded by stunning buildings like the Palazzo Comunale, which offers panoramic views from its tower.
Explore the Cathedral of Santa Maria Assunta, featuring Renaissance art and beautiful frescoes.
Take a guided tour of Montepulciano’s ancient underground wine cellars carved into the rock—these cool tunnels have stored wine for centuries.
Wine tastings are central here, with numerous cantinas offering Vino Nobile and Rosso di Montepulciano paired with local cheeses and salumi.
Art and history enthusiasts should visit the Palazzo Contucci for its frescoes and the Church of San Biagio, a Renaissance masterpiece just outside the town walls.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable in March.
Where to Eat
- Osteria Acquacheta: Famous for its grilled bistecca alla Fiorentina and traditional Tuscan dishes.
- La Grotta: Set in a former cave, this cozy spot serves hearty, authentic Tuscan fare with locally sourced ingredients.
Best Places to Stay
- Etruria Resort & Natural Spa: A luxurious hotel with spa facilities and panoramic views of the Val d’Orcia.
- Albergo Il Marzocco: Central, charming, and perfect for exploring the town’s historic core.
- Agriturismo Podere Il Casale: A peaceful farm stay offering rustic rooms and local cooking classes.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable in March.
Cortona
A Hidden Gem
Cortona, famously featured in Under the Tuscan Sun, is a beautifully preserved hill town with Etruscan origins.
It sits dramatically on a ridge overlooking Lake Trasimeno and offers a blend of ancient history, vibrant culture, and stunning views.
Cortona’s, artistic heritage shines in its museums and galleries, while its lively piazzas are dotted with cafes and artisan shops.
Best Things to Do
Explore the Piazza della Repubblica, the town’s lively heart, where you can sip espresso while watching daily life unfold.
Visit the Museo dell’Accademia Etrusca to dive into Cortona’s,ancient past, and the Basilica of Santa Margherita, dedicated to the town’s patron saint.
For breathtaking vistas, hike up to the Fortezza Medicea, a fortress offering sweeping views of the surrounding countryside and lake.
Cortona’s,winding streets are perfect for wandering, with hidden churches and artisan workshops around every corner.
Foodies will enjoy local markets selling truffles, pecorino, and homemade pasta.
Where to Eat
- La Bucaccia da Romano: Celebrated for its traditional Tuscan cuisine and cozy atmosphere.
- Osteria del Teatro: Offers refined dishes in a historic building near the main square.
- Trattoria Dardano: Known for authentic local recipes and a warm, welcoming vibe.
Best Places to Stay
- Hotel San Michele: Classic Tuscan elegance with panoramic terrace views.
- Villa Marsili: A countryside retreat with a pool and easy access to Cortona.
- Il Falconiere: A luxurious resort with a Michelin-starred restaurant nearby.
More Accommodation In Cortona
Where to Stay in Cortona, Italy: Best Hotels & Apartments for Every Budget
Pienza
The Perfect Renaissance Town
Pienza, often called the “ideal Renaissance town,” redesigned in the 15th century by Pope Pius II with harmonious proportions and urban planning that set the standard for Renaissance ideals.
Nestled in the heart of Val d’Orcia, Pienza is not only famous for its architecture but also for its pecorino cheese, which you can sample in local shops and markets.
Its charming streets overlook a stunning patchwork of rolling hills, vineyards, and cypress-lined roads.
Best Things to Do
Start at Piazza Pio II, the elegant central square surrounded by the Palazzo Piccolomini and the Cathedral of Pienza, both excellent examples of Renaissance art and design.
Walk the town’s quaint streets to find artisan cheese shops—don’t miss tasting the famous pecorino di Pienza.
For incredible views, stroll along the town walls, which look out over the Val d’Orcia countryside.
Nearby, explore the picturesque villages and nature trails of the Val d’Orcia, a UNESCO World Heritage site.
Food and wine lovers can join local tours focused on cheese, olive oil, and Tuscan wines.
Where to Eat
- La Porta: A cozy spot offering traditional Tuscan dishes with spectacular valley views.
- Il Rossellino: Famous for locally sourced ingredients and a warm atmosphere.
Pecorino Cheese Shops: Various shops offer tastings and sales of award-winning cheeses.
Best Places to Stay
- Hotel Corsignano: A charming hotel within walking distance of the main sights.
- Agriturismo Il Macchione: Enjoy authentic farm life with cozy rooms and homemade meals.
- Relais Il Chiostro di Pienza: A luxurious stay in a former monastery with beautiful gardens.
Volterra
Etruscan Roots and Medieval Mystique
Volterra is a captivating hill town with deep Etruscan roots and a distinct medieval atmosphere.
Known for its alabaster craftsmanship and dramatic fortress walls, Volterra offers a quieter, less touristy alternative to other Tuscan towns but with equally rich cultural treasures.
The town’s historic center is a labyrinth of ancient buildings, Roman ruins, and artisan workshops, surrounded by panoramic Tuscan hills.
Best Things to Do
Visit the Roman Theatre, an impressive archaeological site dating back to the 1st century B.C.
Wander through the Palazzo dei Priori, the oldest town hall in Tuscany, and explore the Ecomuseo dell’Alabastro to learn about the town’s famous alabaster artistry.
Don’t miss the Volterra Cathedral with its striking facade and intricate interior.
Artisans in Volterra create exquisite alabaster sculptures and jewelry—browse local shops to take home a unique souvenir.
The town also hosts vibrant markets and festivals throughout the year.
Where to Eat
- Osteria La Carabaccia: Known for traditional Tuscan dishes and excellent wine selection.
- Ristorante Enoteca Del Duca: A fine dining experience with a focus on local ingredients.
- Trattoria Da Sante: A local favorite for hearty meals in a cozy setting.
Best Places to Stay
- Hotel Etruria: Central location with charming rooms and a rooftop terrace.
- Albergo San Lino: Historic hotel with elegant decor and warm hospitality.
- Agriturismo La Poggiolina: Peaceful countryside lodging close to town.
Other Places To Stay
Where to Stay in Volterra, Italy: Best Areas & Hotels
Our Suggested Itinerary for Visiting the Five Hilltop Towns
For a week-long Tuscan adventure, consider this route:
- Day 1-2: San Gimignano — Explore towers, sample Vernaccia, and enjoy medieval charm.
- Day 3: Montepulciano — Dive into Renaissance art and wine cellar tours.
- Day 4: Pienza — Savor pecorino cheese and scenic valley views.
- Day 5: Cortona — Discover Etruscan history and lakeside vistas.
- Day 6: Volterra — Wander Roman ruins and alabaster workshops.
- Day 7: Relax in the countryside or revisit your favorite town.
FAQs: Discovering Tuscany’s Hilltop Towns
1. What are the best hilltop towns to visit in Tuscany?
The most beautiful hilltop towns in Tuscany include Montepulciano, Pienza, San Gimignano, Volterra, and Cortona.
Each offers incredible views, medieval charm, and authentic Tuscan culture.
2. How do I get to Tuscany’s hilltop towns from Florence?
The easiest way is by car, which gives you flexibility to explore at your own pace.
However, many towns can also be reached by train or bus, with connections from Florence to Siena, Montepulciano, and Cortona.
3. When is the best time to visit Tuscany’s hilltop towns?
The best times are spring (April–June) and autumn (September–October), when the weather is mild, crowds are fewer, and the landscapes are bursting with color.
4. How many days do I need to explore the hilltop towns in Tuscany?
Plan for at least 3–5 days to explore multiple towns at a relaxed pace.
You can visit two towns per day if driving, or focus on one per day for a slower, more immersive experience.
5. Are Tuscany’s hilltop towns accessible by public transport?
Some are, such as Cortona and San Gimignano, which can be reached via bus or train from major cities.
However, smaller villages like Pienza and Volterra are best accessed by car.
6. What should I wear when visiting hilltop towns in Tuscany?
Wear comfortable walking shoes — the cobblestone streets are steep and uneven.
Light clothing in summer, layers in spring/autumn, and a jacket for cooler evenings are recommended.
7. Are there good places to stay overnight in these towns?
Absolutely! Each town offers a range of accommodation, from boutique hotels and agriturismos (farm stays) to historic villas with sweeping views of the Tuscan countryside.
8. What local foods and wines should I try in Tuscany’s hilltop towns?
Don’t miss pici pasta, wild boar ragu, and pecorino cheese from Pienza.
Pair your meal with a local Vino Nobile di Montepulciano or Brunello di Montalcino for the full Tuscan experience.
How to Spend 7 Magical Days in Tuscany by Car
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable in March.
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Do You Need Travel Insurance for Tuscany?
(Short Answer: Yes — It’s Still a Smart Idea)
Travel insurance isn’t legally required to visit Tuscany, but it’s one of the smartest things you can have when travelling in Italy.
Even in a relaxed destination like Tuscany, things can go wrong — from delayed flights and lost luggage to medical issues, rental car damage, or unexpected trip cancellations.
And while Italy has excellent healthcare, medical treatment for visitors can still be costly without proper coverage.
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Final Thoughts
The hilltop towns of San Gimignano, Montepulciano, Cortona, Pienza, and Volterra represent the heart and soul of Tuscany.
Their blend of history, art, cuisine, and breath taking scenery provides a true Tuscan experience.
Whether you’re wandering medieval streets, tasting world famous wines, or simply soaking in the sunset from a hillside terrace, these towns promise memories to last a lifetime.
Other Tours
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 – Going is a great search engine if you are flexible about your travel destination and dates. Sign up for their newsletter and get the latest deals on destinations around the world. GOING is our new go to.
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 – OMIO – 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. FLIXBUS is another terrific website with routes between 20 European countries.
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.