Discover the 5 Best Hilltop Towns in Tuscany
Step back in time in Tuscany’s five most beautiful hilltop towns.
Tuscany’s landscape is dotted with enchanting hilltop towns where history, culture, and spectacular views converge in perfect harmony. If you’re dreaming of wandering through medieval streets, tasting world-class wines, and savoring authentic Tuscan cuisine—all framed by rolling vineyards and golden sunsets—then the hilltop towns of San Gimignano, Montepulciano, Cortona, Pienza, and Volterra should be at the top of your itinerary. Each of these towns offers a unique window into Tuscany’s rich heritage and vibrant present, making them essential stops on any Tuscan journey.
In this comprehensive travel guide, we’ll share with you our favorite hilltop gems with in-depth overviews, top things to do, standout places to eat, and the best accommodations to make your visit unforgettable. Whether you’re a first-time visitor or a seasoned Italy traveler, this guide will inspire you to dive deep into Tuscany’s hilltop magic.
Best Time to Visit
Tuscany’s hilltop towns are enchanting year-round, but the best times are spring (April to June) and fall (September to October) when the weather is mild, the landscapes lush, and plenty of festivals. Winter is our favourite time to travel in Tuscany it’s quiet and peaceful, perfect if you’re seeking no crowds and lower rates.
Tuscany’s hilltop towns offer some of the most breathtaking views in Italy. San Gimignano, Montepulciano, Cortona, Pienza, and Volterra each feature charming cobblestone streets, rolling landscapes, and a vibrant local wine culture. These towns are perfect for wandering leisurely through narrow alleys, sampling traditional Tuscan cuisine, and enjoying sweeping views of vineyards and olive groves. Whether you’re tasting prized reds like Vino Nobile di Montepulciano or exploring artisan markets, these destinations blend authentic charm with unforgettable scenery, making them must-visit spots for any traveler seeking a true taste of Tuscany’s countryside.
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.
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.
- Cantina del Redi: A fantastic place to sample Vino Nobile with light bites and regional specialties.
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.
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.
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 BC. 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.
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.
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.
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. 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.