The Best Small Towns in Tuscany for a Dreamy Italian Escape

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There’s no way around it – Tuscany is home to some of the most charming small towns in the world. From awe-inspiring hilltop perches offering panoramic views of rolling vineyards to hidden gems nestled within lush valleys, each exudes a distinct character and beckons with a rich tapestry of history and culture.

Imagine wandering through ancient alleyways, where centuries-old facades whisper secrets of the past and local artisans beckon with their traditional craftsmanship. This is a land where life moves at a leisurely pace, allowing you to savor every moment of discovery, where warmth and hospitality come naturally, making you feel like a welcomed member of the community. Indulge in the symphony of flavors as you sample the renowned Tuscan cuisine, each bite a celebration of the region’s culinary prowess. And as the sun sets over the charming squares, you’ll find yourself immersed in a captivating ambiance, where laughter and stories fill the air.

Brimming with romance, history, and fabulous food & wine, we’re sure you’ll find the Italy you’ve been dreaming about among Tuscany’s best small towns.



Perched atop a sun-kissed hill in the heart of Tuscany, Volterra exudes an undeniable allure that captivates travelers seeking an authentic Tuscan experience. With medieval walls and timeless charm, this pretty Italian town effortlessly transports visitors to a bygone era, and there’s a wealth of history and architectural wonders waiting to be discovered along its cobbled streets.

Must-try experience: Visit a Tuscan farm set in the rolling hills of Volterra for a private picnic lunch or dinner.

Top things to do: Explore the Etruscan heritage, stroll through the historic center, marvel at the Medicean fortress, discover Alabaster artistry, uncover Roman ruins.

Where to eat: Trattoria da Bado, for its traditional Tuscan cuisine and warm, welcoming atmosphere; Osteria dei Poeti, for a taste of the Mediterranean in the heart of Tuscany; La Carabaccia, for those seeking plant-based delights in Volterra.

Where to stay: Albergo Etruria, a delightful boutique hotel nestled within the historic center. Experience warm Tuscan hospitality, comfortable accommodations, and a perfect location to explore the town’s treasures right at your doorstep.

San Gimignano

San Gimignano

Impeccably preserved architectural wonders, romantic winding alleys, and sweeping panoramas make San Gimignano one of the best small towns in Tuscany. Snuggled amidst the rolling hills of Tuscany, its majestic medieval towers punctuate the sky, luring travelers into a timeless world of storied charm and elegance. Home to the best gelato in the world, memorable wine tastings, and world-class art, this superb Italian hilltop town serves up a perfect scoop of Tuscan magic.

Must-try experience: This romantic vineyard dinner is the stuff of Tuscan fantasies.

Top things to do: Explore the charming Piazza della Cisterna, encircled by medieval structures steeped in history. Ascend Torre Grossa to witness breathtaking Tuscan panoramas. Discover the town’s artistic heritage at the Civic Museum, and wander picturesque alleys, uncovering artisanal shops selling unique handicrafts and revered Vernaccia wine, a true emblem of San Gimignano’s rich cultural legacy.

Where to eat: Tempting palates with artisanal pasta and Tuscan flavors, La Grotta di Fulignano offers a rustic dining experience infused with authentic regional charm; Adored for panoramic vistas and exquisite Tuscan cuisine, Le Vecchie Mura crafts a memorable culinary affair with bistecca alla fiorentina and hearty soups; Cum Quibus, where creative reinterpretations of classic Tuscan dishes harmonize with an exceptional wine selection.

Where to stay: With its prime location, Hotel Bel Soggiorno provides the perfect starting point to explore medieval treasures and immerse yourself in the rich cultural heritage that surrounds this enchanting small town in Tuscany.


Medieval village in Tuscany

Ready to step into a fairytale? Nestled amidst the rolling hills of Tuscany, Monteriggioni is filled with pretty cobblestone streets, charming squares, and breathtaking views of the surrounding countryside. Encircled by imposing walls and crowned with watchtowers, this impeccably preserved medieval village offers an enchanting glimpse into the past. Here, time seems to stand still, allowing visitors to immerse themselves in the magic of a bygone era while savoring the delights of Tuscan cuisine and reveling in the beauty of this medieval jewel.

Must-try experience: Experience the essence of Tuscany with a scenic country trek, delightful farm lunch, and a memorable olive oil tasting.

Top things to do: Stroll along the ancient walls, basking in panoramic views of the Tuscan countryside, explore the narrow, stoned streets lined with medieval buildings, and delve into the village’s rich history and heritage at the Museum of Medieval Armory.

Where to eat: Il Pozzo, known for its exquisite Tuscan cuisine; Ristorante Il Feudo, a family-owned restaurant that serves traditional Tuscan cuisine; Antico Travaglio, for a taste of traditional Tuscan flavors, with specialties like ribollita, wild boar stew, and homemade gelato.

Where to stay: Experience the ultimate medieval escape at the only hotel nestled within the historic walls of Monteriggioni’s enchanting Medieval Fortress, offering a truly unique and immersive stay.



Nestled in the heart of the UNESCO World Heritage site of Val d’Orcia, the idyllic hilltop town of Pienza is a jewel of Renaissance beauty and harmony. Adorned with graceful palaces, charming squares, and romantic vistas, it’s not hard to see why it’s called the “ideal Renaissance town”. Artisan boutiques and food stores selling local (pecorino) cheese and honey line its storybook alleyways, and a walk along its walls rewards visitors with spellbinding views of the Tuscan countryside.

Must-try experience: For an authentic Tuscan experience in Pienza, embark on this market tour, followed by a delicious home-cooked meal.

Top things to do: Explore Piazza Pio II, a perfectly geometrical square surrounded by architectural wonders, including the Palazzo Piccolomini and the stunning Duomo. Sample the local pecorino cheese, a specialty of the region, and visit artisanal cheese shops for a true taste of Pienza’s culinary heritage. Take in the sweeping views of the Val d’Orcia from the panoramic terrace and immerse yourself in the serene beauty of this Renaissance gem.

Where to eat: The Townhouse Caffe, renowned for its farm-to-table philosophy; Il Rossellino, known for its refined Tuscan cuisine, featuring traditional dishes elevated with innovative twists; Trattoria La Buca delle Fate, beloved for its hearty Tuscan fare, including pecorino cheese, hand-rolled pici pasta, and succulent roasted meats.

Where to stay: With comfortable accommodations, warm hospitality, and a convenient location near the heart of Pienza, Piccolo Hotel La Valle provides a delightful base for exploring the town’s Renaissance beauty and savoring the flavors of the region.



Cortona paints a picture of timeless beauty, where steep cobblestone streets wind through ancient churches and historic buildings, creating an idyllic escape. As you stroll along, breathtaking panoramas of undulating hills and vineyards unfold before your eyes, immersing you in the true essence of Tuscany.

Cortona casts a spell with its harmonious blend of history, culture, and natural splendor, leaving travelers enamored. And just in case it looks familiar, it’s because the film Under The Tuscan Sun was largely shot here.

Must-try experience: Warm Italian hospitality, delicious local wine, and authentic Nonna’s cooking blend seamlessly into this dining experience at a local’s home in Cortona.

Top things to do: Explore the historic Piazza della Repubblica, adorned with charming buildings and the grand Palazzo Comunale. Stroll along the ancient city walls, granting soul-stirring views of the surrounding countryside. Don’t miss the Etruscan Academy Museum, housing an impressive collection of artifacts and art. For a touch of tranquility, venture to nearby Lake Trasimeno for scenic boat rides and lakeside picnics.

Where to eat: Celebrated for its authentic Tuscan recipes, Trattoria Dardano delights palates with dishes crafted from the freshest local ingredients; Known for its delectable truffle-based cuisine, La Bucaccia unveils the region’s gastronomic treasures with every mouthwatering creation; A culinary gem, Osteria del Teatro presents elegant Tuscan fare in an intimate setting, complemented by an extensive wine selection.

Where to stay: Immerse yourself in the charm of the past while savoring the tranquility of the present at Monastero di Cortona – Hotel & Spa, an idyllic choice for a memorable stay in Cortona. Nestled amidst the serene Tuscan countryside, it offers a peaceful retreat with modern comforts, breathtaking views of Lake Trasimeno, and a pampering spa for a truly rejuvenating experience.



Montepulciano’s cultural treasures and unparalleled culinary delights promise a memorable Tuscan escape like no other. Nestled amidst the sun-kissed landscapes of Siena, only a few km from Pienza, the town is a masterpiece of Renaissance charm and world-renowned viticulture. Famous for its Vino Nobile wine sourced from the vineyards that sprawl gracefully around its ancient walls, it is as much a treat for the eye as it is for the palate. Its picturesque lanes and passages adorned with crumbling palazzi, artisanal shops, and inviting cafés are a joy to explore.

Must-try experience: Nothing beats an exclusive wine-tasting experience, complete with a typical Tuscan lunch in an ancient wine cellar in the heart of Montepulciano.

Top things to do: Savor wine tastings at historic cellars, explore the Palazzo Comunale and the Duomo, and take in panoramic views from the majestic Torre di Pulcinella.

Where to eat: Celebrated for its traditional Tuscan cuisine, La Grotta delights with locally-sourced flavors and seasonal dishes; Rustic ambiance complements the exceptional Tuscan specialties and the fine wine selection at Osteria del Conte; Osmosi, a Michelin guide restaurant in Montepulciano that serves creative, contemporary Italian cuisine.

Where to stay: With its stylish and cozy accommodations, Meublé Evoè offers a tranquil escape.


Barga, Tuscany

One of the most unique small towns in Tuscany, Barga is surrounded by painting-worthy landscapes that stretch as far as the Apuan Alps. Famous for its rich musical heritage, it resonates with the sounds of jazz and opera, enticing enthusiasts from far and wide. And, aside from its winding cobbled streets and ochre-hued villas, Barga is known as “the most Scottish town in Italy”, and every summer, it hosts a festival dedicated to fish and chips (Sagra del Pesce e Patate).

Must-try experience: Time your visit to align with the city’s acclaimed Jazz festival.

Top things to do: Immerse yourself in cultural treasures at the Duomo di San Cristoforo and the Teatro dei Differenti; wander the picturesque streets, capturing the essence of this artistic haven; take a day trip to Lucca.

Where to eat: Indulge in Barga’s culinary delights at Ristorante L’Altana with breathtaking views; Al Ro Manzo, a casual restaurant that specializes in grilled meats and seafood; Ristorante Scacciaguai, a family-run restaurant that serves traditional Tuscan cuisine in a rustic setting.

Where to stay: Acchiappasogni Art Boutique Hotel offers discerning travelers a dreamlike escape with its unique artistic decor, intimate ambiance, and captivating blend of creativity and luxury, where every detail is a masterpiece.


Prettiest small town in Tuscany

Famous for its ancient architecture and historical significance, Pitigliano boasts a striking appearance with its winding streets and unique stone structures sculpted into the cliff. The town’s rich Etruscan heritage and the historical significance of its Jewish Quarter add to its cultural allure, earning it the nickname “Little Jerusalem”.

Must-try experience: For first-time visitors, this private tour of Pitigliano and Etruscan cave routes is a must.

Top things to do: Visit the striking Etruscan caves and tombs carved into the cliffs; discover the town’s rich history at the Jewish Quarter and indulge in delicious local cuisine at charming trattorias; don’t miss the breathtaking vistas from the panoramic viewpoints.

Where to eat: Immerse yourself in Pitigliano’s culinary delights at Il Tufo Allegro‘s cheerful ambiance, La Pappalpomodoro Di Foschetti Annalisa‘s home-style Tuscan cuisine, and Hostaria del Ceccottino‘s exceptional local flavors and wine pairings.

Where to stay: With its distinctive arches and rustic charm, La Casa Degli Archi offers a cozy and inviting stay in the heart of this beautiful Tuscan town.



Certaldo is a charming small town in Tuscany that is well worth a visit. It is located about 30 kilometers from Florence, and it is divided into two parts: Certaldo Alto and Certaldo Basso.

Certaldo Alto, the old town, is perched on a hilltop with stunning views of the surrounding countryside. The area is full of well-preserved narrow streets, old buildings, and shops selling traditional Tuscan souvenirs. There are also a number of museums in Certaldo Alto, including the Casa del Boccaccio, which is dedicated to the life and work of the famous Italian writer.

In the valley below Certaldo Alto lies Certaldo Basso, the newer part of town, where you’ll find the train station, as well as a number of shops, restaurants, and bars. There is also a funicular railway that connects Certaldo Basso with Certaldo Alto.

Must-try experience: The Certaldo Museum System offers a convenient way to visit two or three of the town’s famous museums on one ticket.

Top things to do: Visit the Casa del Boccaccio, a museum dedicated to the life and work of the famous Italian writer; take a walk or bike ride through the surrounding countryside; visit the Palazzo Pretorio, a medieval castle that is now a museum; enjoy a glass of wine at one of the many bars or restaurants in Certaldo Basso.

Where to eat: Osteria La Saletta, Ristorante L’Antica Fonte, and Ristorante A Casa Tua are three highly recommended restaurants in Certaldo that serve traditional Tuscan cuisine, offer stunning views, and have reasonable prices.

Where to stay: Cosetta Guest House is a charming 15th-century palazzo in the heart of Certaldo Alto. It offers spacious rooms, friendly staff, and stunning views of the surrounding countryside.

Castiglione della Pescaia

Castiglione della Pescaia
Photo by Rebecca Mosca / Unsplash

Castiglione della Pescaia is a scenic little town situated on a promontory overlooking the Tyrrhenian Sea. The beaches here are some of the most beautiful in Tuscany. They are long, sandy, and backed by pine trees. The town is also home to a number of historical and cultural attractions, including the Rocca di Castiglione, a medieval castle that offers stunning views of the surrounding area.

Must-try experience: Discover Castiglione della Pescaia and uncover its hidden gems with a guided tour.

Top things to do: Explore the Riserva Naturale Diaccia Botrona; relax on one of the town’s beautiful beaches; visit the local markets and shops.

Where to eat: For traditional Tuscan cuisine, try La Fortezza; for seafood with a view, go to Il Corsaro; for fresh pasta and pizza, visit Ristorante L’Arpione.

Where to stay: Hotel C’Era Una Volta is a charming property located in the heart of the town, just steps from the beach. The hotel offers spacious rooms, a rooftop terrace with stunning views, and a spa.

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