14 Most Beautiful Towns in Tuscany That You MUST Visit

Searching for the most beautiful towns in Tuscany to add to your Tuscany travel itinerary? Keep reading!

Tuscany is one of Italy’s most beautiful and romantic regions known for its rolling hills, rows of Cypress trees and charming towns. No trip to Tuscany is complete without visiting some of the magical towns scattered around, and lucky they are pretty close together so visiting 4 or more is more than achievable in just a few days in the region!

Discover the awe-inducing beauty that is in Tuscany by visiting one or more of the most beautiful towns in Tuscany.

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14 Most Beautiful Towns in Tuscany

Florence

Florence – the capital of the Tuscany region – is easily one of the most beautiful towns in Tuscany and possibly even the world! Its charm and magic radiate through the streets that are home to some of the world’s most magnificent pieces of architecture. Find here the famous Florence Cathedral – The Duomo, Basilica of San Lorenzo, Basilica of Santa Maria Novella, and much more!

A visit to Florence is a must when touring Tuscany to see and experience one of the most popular and iconic cities in Italy. Be sure to budget around 2 days so you can see all of the beauty this city has to offer. Plus, if you only have time to do a quick Tuscany tour staying in Florence and doing day trips is a great option.

Siena

Siena is undoubtedly one of the most beautiful towns in Tuscany, known for its rich history, stunning architecture, and charming atmosphere. Here’s why Siena stands out among the many picturesque towns in the region:

Siena’s centerpiece is Piazza del Campo, one of the most magnificent squares in Italy. With its unique shell shape and beautiful medieval buildings, it provides a stunning backdrop for social gatherings and events. The Siena Cathedral, or Duomo di Siena, is a breathtaking example of Italian Gothic architecture. Its intricate façade, adorned with statues and decorative details, is a testament to the city’s artistic and architectural prowess.

The medieval streets of Siena are a delight to explore, with their narrow lanes, hidden corners, and well-preserved historic buildings. Take a stroll through neighborhoods like the Contrada dell’Onda or the Contrada della Torre, and immerse yourself in the medieval ambiance.

Siena’s Palio horse race, held twice a year in Piazza del Campo, is a spectacle that shouldn’t be missed. Experience the intense rivalry between the city’s contrade (districts) as horses race around the square, accompanied by cheering crowds.

With its stunning architecture, rich cultural heritage, and vibrant atmosphere, Siena is undeniably one of the most beautiful towns in Tuscany. Its timeless beauty and enchanting charm continue to captivate visitors from around the world.

Pienza

Pienza, located in the heart of the Val d’Orcia region, is one of the most beautiful towns in Tuscany. Known as the “Ideal City of the Renaissance,” Pienza was designed by Pope Pius II as a utopian city. Here’s why Pienza is a must-visit destination:

The town’s architecture showcases harmonious Renaissance design, with its well-preserved buildings, elegant palaces, and charming narrow streets. The main square, Piazza Pio II, is the focal point of Pienza and features the stunning Cathedral of Santa Maria Assunta and the Palazzo Piccolomini.

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Pienza is also famous for its delectable pecorino cheese. Don’t miss the chance to visit the local cheese shops and taste the flavorsome pecorino, which has been produced in the area for centuries.

Surrounded by picturesque rolling hills and vineyards, Pienza offers breathtaking views of the Tuscan countryside. Take a leisurely stroll along the town’s walls to enjoy panoramic vistas of the Val d’Orcia, a UNESCO World Heritage site.

Immerse yourself in the relaxed and authentic atmosphere of Pienza, exploring its charming streets, visiting artisan workshops, and savoring the local cuisine. Whether you’re captivated by its architectural beauty or enchanted by its tranquil surroundings, Pienza is a true gem among the most beautiful towns in Tuscany.

San Gimignano

San Gimignano, often referred to as the “Medieval Manhattan,” is undeniably one of the most beautiful towns in Tuscany. Known for its iconic skyline dotted with medieval towers, San Gimignano offers a captivating glimpse into the region’s rich history. Here’s why San Gimignano is a must-visit destination:

The town’s distinctive feature is its fourteen medieval towers that soar into the sky, creating a unique and enchanting skyline. These towers, originally built by noble families as a symbol of their wealth and power, create a remarkable architectural spectacle.

Wandering through the narrow streets of San Gimignano, you’ll encounter well-preserved medieval buildings, charming squares, and hidden corners. The town’s historic center, a UNESCO World Heritage site, offers a delightful atmosphere with its artisan shops, traditional eateries, and inviting gelaterias.

Don’t miss the chance to visit the Piazza del Duomo, where you’ll find the magnificent Collegiate Church of Santa Maria Assunta. Step inside to admire its stunning frescoes and soak in the sacred ambiance. As you explore San Gimignano, take in the panoramic views of the rolling Tuscan countryside that surrounds the town. The picturesque landscapes provide a picturesque backdrop for your visit.

With its medieval charm, remarkable towers, and scenic beauty, San Gimignano exemplifies the allure of Tuscany’s most beautiful towns. It’s a place where history comes alive and the magic of the past is preserved.

Lucca

Lucca, a hidden gem in Tuscany, is undeniably one of the most beautiful towns in the region. Encircled by well-preserved Renaissance walls, Lucca offers a unique blend of history, culture, and charm. Here’s why Lucca stands out among the picturesque towns of Tuscany:

The town’s medieval and Renaissance architecture is remarkably well-preserved, with narrow streets, charming squares, and elegant palaces. The Piazza dell’Anfiteatro, built on the ruins of an ancient Roman amphitheater, is a highlight, with its circular layout and colorful buildings.

Lucca’s crowning glory is its intact city walls, which provide a scenic promenade and offer panoramic views of the town and its surroundings. Walk or cycle along the tree-lined walls to experience the town from a unique perspective.

Lucca is also known for its exceptional culinary delights. Indulge in local specialties, such as buccellato (a sweet bread) and tortelli lucchesi (stuffed pasta), as you explore the town’s charming streets. Take a moment to visit Lucca’s stunning churches, including the Cathedral of San Martino and the Basilica of San Frediano, which showcase impressive art and architectural details.

With its well-preserved architecture, peaceful ambiance, and culinary delights, Lucca offers a delightful retreat from the bustling cities. It’s a town that exudes timeless beauty and invites visitors to immerse themselves in its enchanting atmosphere.

Montepulciano

Montepulciano, perched atop a hill in southern Tuscany, is undoubtedly one of the most beautiful towns in the region. Known for its medieval charm, Renaissance architecture, and world-renowned wine, Montepulciano offers a captivating experience for visitors. Here’s why Montepulciano should be on your list of must-visit towns in Tuscany:

The town’s historic center is a treasure trove of architectural wonders, featuring magnificent palaces, churches, and narrow cobblestone streets. The Palazzo Comunale and the Cathedral of Santa Maria Assunta are notable landmarks that showcase the town’s rich cultural heritage.

Montepulciano is renowned for its exceptional wines, particularly the Vino Nobile di Montepulciano. Wine enthusiasts can explore the town’s ancient cellars, visit local wineries, and indulge in wine tastings to savor the unique flavors of the region.

Take in the panoramic views of the rolling hills and vineyards that surround Montepulciano. The town’s elevated position offers breathtaking vistas and picturesque landscapes that are a feast for the eyes.

Stroll through the town’s main street, Via di Gracciano nel Corso, lined with elegant shops, artisan boutiques, and charming cafes. Sample local delicacies, browse for souvenirs, and soak in the vibrant atmosphere.

With its medieval beauty, exceptional wines, and captivating vistas, Montepulciano captures the essence of Tuscany’s most beautiful towns. It’s a destination that promises a perfect blend of history, culture, and gastronomy for an unforgettable experience.

Cortona

Cortona, nestled on a hilltop in eastern Tuscany, is undeniably one of the most beautiful towns in the region. With its ancient Etruscan origins, stunning architecture, and panoramic views, Cortona is a captivating destination for visitors. Here’s why Cortona deserves a spot on the list of the most beautiful towns in Tuscany:

The town’s historic center boasts a charming maze of winding streets, medieval buildings, and picturesque squares. Explore the Piazza della Repubblica, the heart of Cortona, and admire its architectural gems, including the Palazzo Comunale and the Palazzo del Capitano del Popolo.

Cortona offers breathtaking panoramic views of the surrounding countryside, with vistas extending across the Val di Chiana and Lake Trasimeno. Take a moment to soak in the beauty of the landscape from viewpoints such as the Piazza Garibaldi or the Santa Margherita Belvedere.

Immerse yourself in the town’s rich history by visiting the Museo dell’Accademia Etrusca, which houses a remarkable collection of Etruscan and Roman artifacts. Explore the beautiful churches, such as the Cathedral of Santa Maria Assunta and the Basilica of Santa Margherita, which are adorned with intricate artworks.

Cortona is also known for its vibrant cultural scene, with art exhibitions, music festivals, and theatrical performances held throughout the year. Embrace the artistic spirit of the town by visiting its galleries and attending cultural events.

With its timeless beauty, historical significance, and breathtaking vistas, Cortona captures the essence of Tuscany’s most beautiful towns. It’s a place where history, art, and natural splendor converge, offering a memorable experience for all who visit.

Pitigliano

Pitigliano, perched on a tuff cliff in southern Tuscany, is undeniably one of the most beautiful towns in the region. Known as the “Little Jerusalem” for its historic Jewish community, Pitigliano offers a unique blend of natural beauty, ancient history, and architectural wonders. Here’s why Pitigliano is a must-visit destination in Tuscany:

The town’s most distinctive feature is its medieval architecture, with houses and buildings seemingly carved into the rock. The narrow streets, archways, and ancient staircases create a maze-like charm that invites exploration.

Pitigliano’s Jewish Quarter is a testament to the town’s rich cultural heritage. Visit the synagogue, which dates back to the 16th century, and explore the Jewish Museum to learn about the history and contributions of the Jewish community.

The town offers stunning panoramic views of the surrounding countryside, with picturesque landscapes stretching as far as the eye can see. Be sure to visit the Vie Cave, ancient Etruscan roads carved into the tuff cliffs, and marvel at their archaeological significance.

Indulge in the local cuisine and taste the region’s renowned white wine, Bianco di Pitigliano. The town’s restaurants and wine bars offer a delightful culinary experience.

Pitigliano’s timeless beauty, rich history, and unique setting make it a captivating destination in Tuscany. Whether you’re wandering through its ancient streets, exploring its historical sites, or simply admiring the breathtaking views, Pitigliano offers an unforgettable experience for visitors.

Volterra

Volterra, situated atop a scenic hill in central Tuscany, is undoubtedly one of the most beautiful towns in the region. With its rich Etruscan heritage, medieval charm, and breathtaking landscapes, Volterra offers a captivating experience for visitors. Here’s why Volterra should be on your list of must-visit towns in Tuscany:

The town’s historic center is a treasure trove of architectural wonders, featuring well-preserved medieval buildings, charming squares, and ancient gates. The Piazza dei Priori, with its impressive Palazzo dei Priori, showcases the town’s historical and artistic significance.

Volterra’s Etruscan origins can be explored at the Guarnacci Etruscan Museum, which houses an extraordinary collection of Etruscan artifacts and funerary urns. The city’s ancient Etruscan walls, gates, and tombs add a fascinating layer of history to your visit.

Wander through the atmospheric streets of Volterra, filled with artisan shops, traditional trattorias, and local boutiques. Take in the town’s tranquil ambiance and soak up the authentic Tuscan atmosphere.

The surrounding countryside offers breathtaking vistas of rolling hills, vineyards, and cypress-lined roads. From viewpoints like the Balze and the Medicean Fortress, you can enjoy panoramic views that extend for miles.

With its rich history, artistic heritage, and stunning landscapes, Volterra captures the essence of Tuscany’s most beautiful towns. It’s a place where time seems to stand still, inviting you to immerse yourself in its timeless beauty and heritage.

Monteriggioni

Monteriggioni, a small walled town in the heart of Tuscany, is undeniably one of the most beautiful towns in the region. Known for its well-preserved medieval walls and charming atmosphere, Monteriggioni offers a glimpse into the past and a true sense of enchantment. Here’s why Monteriggioni should not be missed on your visit to Tuscany:

The town’s iconic walls, featuring 14 towers, encircle the entire town, creating a remarkable sight that transports you back in time. Walking along the walls, you can admire panoramic views of the surrounding countryside, vineyards, and olive groves.

Stroll through the town’s narrow streets, lined with medieval buildings and traditional shops. Explore the Piazza Roma, the heart of Monteriggioni, where you can relax at a café and soak in the charming ambiance.

Visit the Monteriggioni Castle, the town’s central attraction. The castle houses a small museum that provides insights into the history of the area and offers a glimpse into medieval life.

Immerse yourself in the authentic Tuscan experience by sampling local wines, olive oil, and traditional cuisine at the town’s restaurants and enotecas.

With its perfectly preserved walls, timeless beauty, and romantic atmosphere, Monteriggioni captures the essence of Tuscany’s most beautiful towns. It’s a place where history comes alive and the magic of the Middle Ages can be felt at every turn.

Arezzo

Arezzo, located in eastern Tuscany, is undoubtedly one of the most beautiful towns in the region. With its rich history, artistic heritage, and charming streets, Arezzo offers a captivating experience for visitors. Here’s why Arezzo stands out among the picturesque towns of Tuscany:

The town’s historic center boasts stunning medieval architecture, elegant palaces, and picturesque squares. The Piazza Grande, a UNESCO World Heritage site, is the heart of Arezzo and features magnificent buildings, including the Vasari Loggia and the Church of Santa Maria della Pieve.

Arezzo is renowned for its art treasures, including the works of renowned artists such as Piero della Francesca and Giorgio Vasari. Explore the Museo di Arte Medievale e Moderna, which houses an impressive collection of paintings and sculptures.

Wander through the town’s charming streets, filled with artisan workshops, antique shops, and traditional eateries. Don’t miss the chance to sample local delicacies, such as the famous biscotti di Prato.

Climb to the top of the Medici Fortress for panoramic views of the town and the surrounding countryside. From this vantage point, you can appreciate the beauty of Arezzo’s landscape.

With its rich cultural heritage, artistic legacy, and charming ambiance, Arezzo is a true gem among the most beautiful towns in Tuscany. It’s a place where history and art intertwine, inviting visitors to discover its treasures and immerse themselves in its timeless beauty.

Montalcino

Montalcino, nestled in the heart of the Val d’Orcia region, is undeniably one of the most beautiful towns in Tuscany. Known for its enchanting landscapes, ancient fortress, and world-renowned wine, Montalcino offers a truly unforgettable experience. Here’s why Montalcino should be on your list of must-visit towns in Tuscany:

The town’s historic center is a picturesque blend of narrow streets, charming squares, and well-preserved medieval buildings. Explore the Piazza del Popolo, the main square, and soak in the vibrant atmosphere.

Montalcino is famous for its production of Brunello di Montalcino, one of Italy’s most prestigious wines. Discover the local wineries, take part in wine tastings, and indulge in the rich flavors of this exceptional wine.

Climb to the top of the imposing Montalcino Fortress, which offers panoramic views of the town and the surrounding countryside. The breathtaking vistas extend as far as the eye can see, showcasing the beauty of Tuscany’s rolling hills.

Wander through the vineyards and olive groves that surround Montalcino, enjoying the tranquility of the countryside and the fragrant aromas that fill the air.

With its timeless beauty, exquisite wines, and stunning vistas, Montalcino captures the essence of Tuscany’s most beautiful towns. It’s a place where history, culture, and natural splendor intertwine, offering a memorable and immersive experience for all who visit.

San Quirico d’Orcia

San Quirico d’Orcia, located in the scenic Val d’Orcia region, is undeniably one of the most beautiful towns in Tuscany. Surrounded by rolling hills, cypress trees, and vineyards, San Quirico d’Orcia offers a serene and picturesque setting. Here’s why San Quirico d’Orcia deserves a spot among the most beautiful towns in Tuscany:

The town’s historic center is a delightful blend of medieval and Renaissance architecture, with charming streets, ancient walls, and elegant palaces. Explore the Collegiate Church of San Quirico, a stunning Romanesque church that dates back to the 8th century.

San Quirico d’Orcia is known for its beautiful gardens, including the Horti Leonini, a Renaissance garden that showcases geometric patterns, fountains, and sculptures. Take a leisurely stroll through these serene green spaces and enjoy the tranquility they offer.

The town is an ideal base for exploring the breathtaking Val d’Orcia region, with its UNESCO World Heritage landscapes. Visit nearby picturesque villages, such as Bagno Vignoni and Pienza, which offer their own unique charms and attractions.

San Quirico d’Orcia also hosts various cultural events throughout the year, including music festivals and art exhibitions. Immerse yourself in the town’s cultural scene and experience the vibrant atmosphere.

With its enchanting beauty, serene ambiance, and proximity to the stunning Val d’Orcia landscapes, San Quirico d’Orcia captures the essence of Tuscany’s most beautiful towns. It’s a destination that invites visitors to slow down, embrace the beauty of the surroundings, and immerse themselves in the authentic Tuscan experience.

Pisa

Pisa, located in central Tuscany, is undeniably one of the most beautiful towns in the region. Renowned for its iconic Leaning Tower, Pisa offers much more than just its famous landmark. Here’s why Pisa stands out among the most beautiful towns in Tuscany:

The Piazza dei Miracoli, or Square of Miracles, is a UNESCO World Heritage site and the main attraction in Pisa. It is home to the magnificent Leaning Tower, the Cathedral, the Baptistery, and the Camposanto Monumentale. The combination of these architectural wonders creates a truly mesmerizing sight.

Exploring the narrow streets of Pisa’s historic center, you’ll discover charming squares, elegant palaces, and lively markets. The Borgo Stretto and Corso Italia are popular shopping streets lined with boutiques, cafes, and local shops.

Don’t miss the chance to stroll along the Arno River, with its picturesque views and lovely bridges. The Lungarni, the tree-lined promenades that run alongside the river, offer a perfect spot for a leisurely walk.

Pisa’s vibrant university atmosphere adds a youthful energy to the town. The University of Pisa, founded in 1343, is one of the oldest in Europe and contributes to the lively atmosphere of the city.

With its striking architecture, historical significance, and lively atmosphere, Pisa is a captivating destination in Tuscany. Beyond the Leaning Tower, the town offers a rich cultural heritage and an inviting ambiance that is sure to enchant visitors.

Where to Stay in Tuscany

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With so many beautiful towns in Tuscany, it can be hard to pick which ones to visit and which to skip!

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