Perched atop the rolling hills of Tuscany, San Gimignano’s picture consists of a striking skyline of ancient towers that stand as proud sentinels over the verdant landscape of vineyards and olive groves. Each of the 14 remaining towers, a testament to the town’s medieval wealth, offers a glimpse into a past where power was measured by height and grandeur.

The town’s historic center, a UNESCO World Heritage Site, is a treasure trove of art and architecture, where every piazza, every church, and every palazzo tells a story of the town’s illustrious past. From the richly frescoed Collegiata di Santa Maria Assunta to the panoramic views from Torre Grossa, San Gimignano invites you to savor its rich cultural heritage at every turn.

San Gimignano, Tuscany, photographer Laura Chouette on unsplash.com

An amazing stay in Tuscany

The town’s boutique hotels and luxury guesthouses offer intimate, yet opulent accommodations that perfectly blend old-world charm with contemporary comforts. Imagine staying in a beautifully restored medieval tower, where original stone walls meet plush, modern interiors, all while offering stunning views of the Tuscan countryside.

The town’s historic center, a UNESCO World Heritage Site, is a treasure trove of art and architecture, where every piazza, every church, and every palazzo tells a story of the town’s illustrious past.

San Gimignano’s culinary scene is equally enticing, with greatrestaurants and gourmet trattorias serving up exquisite Tuscan cuisine. Here, you can indulge in dishes crafted from the finest local ingredients, perfectly paired with a glass of Vernaccia di San Gimignano, the town’s signature white wine that has been celebrated for centuries.

Tuscany wine tour — San Gimignano winery, photographer: Flo P on unsplsah.com

History and architecture

San Gimignano’s origins date back to the Etruscan era, but the town flourished during the Middle Ages. By the 12th century, it became a significant trading center due to its location on the Via Francigena, a key pilgrimage route connecting France to Rome. Wealthy families in the town competed to build the tallest towers as symbols of their power and influence. At its peak, there were 72 towers in San Gimignano; today, 14 of these historic towers remain, giving the town its unique and recognizable skyline.

The town’s historic center, a UNESCO World Heritage Site, is a stunning example of medieval urban planning. The Piazza della Cisterna, a triangular square lined with cafés and shops, and the Piazza del Duomo, where the Collegiata di Santa Maria Assunta (the main church) is located, are the town’s focal points. The Collegiata is famous for its frescoes depicting scenes from the Old and New Testaments, created by renowned artists of the time.

Why choose to stay in San Gimignano during your vacation in Tuscany?

Choosing to stay in San Gimignano during your vacation in Tuscany offers a unique and enchanting experience that combines the best of medieval charm, stunning landscapes, and convenient access to the broader region. Here are several compelling reasons to make San Gimignano your base in Tuscany:

Central Location for Exploring Tuscany

San Gimignano is strategically located in the heart of Tuscany, making it an excellent base for exploring the region. It’s within easy driving distance of other popular destinations such as Florence, Siena, Pisa, and the Chianti wine region. Staying here allows you to enjoy day trips to these nearby cities and attractions while returning to the tranquility of San Gimignano at the end of the day.

Authentic local experience

San Gimignano provides a glimpse into traditional Tuscan life. By staying in a local guesthouse or boutique hotel, you can connect with the town’s residents, shop at local markets, and experience the slower pace of life that is characteristic of this region. This authenticity adds depth to your Tuscan vacation, making it more personal and memorable.

Local wine and cuisine

San Gimignano is renowned for its Vernaccia di San Gimignano wine, one of Italy’s finest white wines. Staying in the town gives you the opportunity to visit local vineyards, enjoy wine tastings, and savor the authentic flavors of Tuscany. The town’s restaurants offer delicious traditional dishes made with local ingredients, providing a true taste of the region.

Medieval atmosphere

San Gimignano is often referred to as a living museum, thanks to its well-preserved medieval architecture and iconic towers. Staying in this town allows you to immerse yourself in its rich history and unique atmosphere. Waking up in a place where cobblestone streets, ancient walls, and historic towers are part of your daily surroundings creates an unforgettable experience.

Stunning panoramic views

Perched on a hilltop, San Gimignano offers breathtaking panoramic views of the surrounding Tuscan countryside. Whether you’re sipping your morning coffee, enjoying a glass of local wine in the evening, or simply strolling through the town, you’ll be treated to vistas of rolling hills, vineyards, and olive groves that are quintessentially Tuscan.

vacation in Tuscany — San Gimignano, Tuscany, photographer: Bjorn Agerbeek on unslpash.com

Top attractions in San Gimignano and around

San Gimignano and its surrounding area in Tuscany offer a wealth of attractions that cater to history buffs, art lovers, wine enthusiasts, and those seeking natural beauty. Here’s a list of top attractions in San Gimignano and the nearby regions.

Torre Grossa

The tallest of San Gimignano’s towers, Torre Grossa stands at 54 meters and dates back to 1311. Climbing to the top rewards you with stunning panoramic views of the town and the surrounding countryside.

Piazza della Cisterna

This triangular square is the heart of San Gimignano and is surrounded by medieval buildings, shops, and cafés. The ancient well in the center adds to its charm, making it a perfect spot for soaking in the town’s atmosphere.

Collegiata di Santa Maria Assunta (Duomo)

San Gimignano’s main church, also known as the Duomo, is famous for its stunning frescoes by artists such as Lippo Memmi and Bartolo di Fredi. These frescoes depict scenes from the Old and New Testaments and are a must-see for art lovers.

Museo Civico

Located in the Palazzo del Popolo, the Museo Civico houses an impressive collection of medieval and Renaissance art. Don’t miss the Sala di Dante, named after the famous poet who once visited San Gimignano.

Sant’Agostino Church

This lesser-known church is a hidden gem with beautiful frescoes by Benozzo Gozzoli, depicting the life of Saint Augustine. The church is a peaceful retreat, offering insight into the religious art of the period.

Piazza del Duomo

Another central square in San Gimignano, Piazza del Duomo is home to the Duomo and several of the town’s most important medieval buildings, including the Palazzo Comunale and the Loggia del Comune.

Top things to do in Tuscany

Looking for countryside accommodation in Tuscany? Take a look at our villas in Tuscany for an amazing vacation

cover photo credits: Mattia Bericchia on unsplash.com

If you dream of traveling to a place full of history, culture and nature, then Tuscany is the perfect destination for you. This region in central Italy will delight you with its picturesque landscapes, its artistic cities and its delicious gastronomy. Remember that in order to explore all the facets of this wonderful region, a dream tour in Tuscany must include both the city of Florence and the countryside.

A circuit in Tuscany is the ideal choice to discover the beauty and richness of a splendid region!

Of course, in Tuscany, you will find many properties and villas for rent, ideally for an amazing vacation. See our villas in Tuscany here.

Florence: the starting point of a memorable trip to Tuscany

The circuit starts in Florence, the capital of Tuscany and one of the most beautiful cities in the world. Here you will be able to admire the Renaissance works of art by great masters such as Michelangelo, Leonardo da Vinci, or Botticelli, in famous museums such as the Uffizi Gallery or the Academy Gallery. You will also be able to visit impressive monuments such as the Santa Maria del Fiore Cathedral, with its famous dome made by Brunelleschi, or the Vecchio Bridge, which crosses the Arno River and is full of jewelry shops.

villas for rent in Florence, Tuscany — Florence, Italy

Siena: The untouched Medieval charm of a historical region

Siena is a city with impressive architecture and a lively atmosphere. This town retains its medieval charm intact and is known for the Palio horse race, which takes place twice a year in Piazza del Campo. Here you will be able to admire the Gothic Cathedral, with its black and white facade and its richly decorated interior, or the Public Palace, the seat of the town hall and the civic museum. Siena is also an ideal place to enjoy famous Tuscan wines such as Chianti or Brunello di Montalcino.

Siena, Tuscany — Siena, Italy: Piazza del Campo e Torre del Mangia – photographer: Antonio Ristallo on Unsplash

San Gimignano: “the Medieval Manhattan”

San Gimignano is a fortified village with 14 tall and elegant towers that dominate the landscape, a fact that made it earn the nickname of “the Medieval Manhattan”. Here you can visit the Museum of Torture, where you will see macabre instruments used to punish criminals in the Middle Ages, or, in contrast, you can enjoy a delicious ice cream at Gelateria Dondoli, which has won the title of the best gelateria in the world several times. Reserve some time to admire the well-preserved medieval architecture and visit the Palazzo Comunale or the Church of Sant’Agostino.

Montepulciano: the iconic landscape of Tuscany

The beautiful Renaissance hilltown town of Montepulciano stands haughty, contemplating its natural surroundings and the weight of its remarkable history. Here, in Montepulciano, in any direction you will look, you will be “struck” by the iconic image of the Tuscan countryside, where boundless and painted hills and fields, surrounded by tall cypresses create an unforgettable landscape.

Montepulciano is famous for its large area of prestigious vineyards, a fact that attracts many lovers of high-quality wines.

In Montepulciano, you must visit the historic center, together withe the Piazza Grande and the Renaissance Palace. Close to those are also the Palazzo Comunale and the Cathedral that has been watching over the town since the XVI-th century.

villas for rent in San Gimignano, Tuscany — San Gimignano, Tuscany

Pienza: when small things impress without effort

A small town with just a few narrow cobbled streets, but with a hidden architectural richness, Pienza welcomes his curious guests with many pots of colorful flowers. Even for just a few hours overlooking, Pienza will enchant you with its charming stone walls and romantic atmosphere, world-famous cheese and local cuisine, and craved panoramas of stunning landscapes.

villas for rent in Tuscany, Pienza — Pienza, Tuscany

Looking for villas in Tuscany? See our villas available for vacation rental in Tuscany here.

Perugia: the city in the Umbria region, close to the River Tiber

Perugia is a city with a rich history which is definitely worth a visit. Walking around the city, you will find many beautiful points of interest, including huge Etruscan city gates, Roman arches, Medieval Government buildings, and Renaissance palaces. And last but not least, many great places to eat, but this is already obvious…

Lucca: a walled city from the 16th century, which will offer you a relaxing walk through history

In Lucca, you will be able to visit Piazza dell’Anfiteatro, a square built on the ruins of a Roman amphitheater, the birthplace of Puccini, the famous opera composer, or Torre Guinigi, a tower with trees on top.

But Lucca also has a lesser-known side. To discover it, visit the Museum of Torture, where you will see macabre tools used to punish criminals in the past. Or attend the Comic and Games Festival, where you’ll meet fantastic characters and buy all kinds of souvenirs.

villas in Tuscany for rent — Lucca, Italy – photographer: Cristina Gottardi on Unsplash

Val d’Orcia: the Paradise of Tuscany

Between Montepulciano and Montalcino, is located the fascinating Val d’Orcia, the place that contains the emblematic image of Tuscany. Here you will discover beautiful medieval towns, thermal baths, green valleys, sun-burnt hills, rustic houses, and of course, the amazing cypresses on the side of the roads.

Val d’Orcia is a region protected by UNESCO, but also by an extinct volcano, Monte Amiata, which watches over it. You can start exploring from Radicofani, where you’ll feel like you’re in a movie with knights and castles. Then you can go to Pienza, Zeffirelli’s ideal city, where Romeo and Juliet swore eternal love.

If you are a fan of Brunello wine, don’t miss a visit to Montalcino. And if you want to relax after so much walking, you can take a bath in the thermal waters of Bagno Vignoni or Bagni di San Filippo.

Val d’Orcia is a place full of charm and authentic tastes, such as pecorino cheese from Pienza, extra virgin olive oil, saffron, mushrooms, chestnuts, and truffles.

A stay in San Gimignano: tune in to the heartbeat of Tuscany