The Ultimate Guide to San Gimignano: Uncovering Hidden Gems in Tuscany

Embarking on this journey has been our long-standing dream. From gorgeous landscapes adorned with vineyards and olive groves cascading over the hills to enchanting medieval towns and delectable cuisine, we chose sunny Tuscany for these reasons and more! Our carefully selected base is in the vicinity of San Gimignano, one of the most picturesque towns in the Siena province, for exploring this captivating region. In the section below, explore our ultimate guide to San Gimignano, discovering what to see and where to eat in this beautiful city.

The Ultimate Guide to San Gimignano: Introduction

San Gimignano, situated along the former trade route connecting the region’s main cities, Siena and Florence, gained prominence for its well-preserved medieval towers, primarily dating back to the 12th century.

Serving as defenses during the rivalry between the Guelphs and Ghibellines, these towers are also linked to a theory suggesting rich fabric producers constructed them during the city’s textile production peak.

Guarding the secret of a yellow dye obtained from a special saffron variety, the towers reflected the city’s historical significance.

At one point, boasting 70 towers, the town now showcases only 14, symbolizing its evolving heritage.

The Ultimate Guide to San Gimignano: What to See?

Piazza della Cisterna

When in San Gimignano, a visit to the vibrant Piazza della Cisterna is inevitable. This square, one of the city’s two main squares, stands out with its interesting triangular shape.

Named after the 13th-century well at its center (cisterna), which was once the primary water source for residents, the square features medieval buildings like the 13th-century Salvestrini house and Palazzo Tortoli.

The towering structures of Torre del Diavollo and Ardinghelli add to the square’s charm. Piazza della Cisterna also offers a variety of restaurants, bars, and is home to some of the world’s best ice cream (more information can be found below).

Piazza del Duomo

Heading northwest of Piazza della Cisterna, you can reach another charming square named Piazza del Duomo.

On the eastern side of the square stands the 13th-century former town hall, Palazzo Podesta, distinguished by a huge loggia and the Rognosa tower rising for over 50 meters.

In addition to medieval towers and historic palaces, in Piazza del Duomo, you can also admire the majestic facade of the collegiate church – Collegiata di Santi Maria Assunta. This cathedral, built in the 12th century and later extended by Giuliano da Maiano, is a perfect example of Romanesque style.

The interior is adorned with beautiful frescoes depicting stories from the New and Old Testament, painted by outstanding artists of the fourteenth-century Sienese school.

Particularly noteworthy are the paintings depicting the life of Christ by Barna da Siena, located in the southern aisle.

Wide stone stairs leading to the collegiate church cannot be overlooked. Similar to the entire historic center of the city, the church is inscribed on the UNESCO World Heritage List.

Practical information: Visiting the cathedral is possible only at specific times, and an admission fee of 5 euros must be paid (details available on the collegiate church’s website).

Palazzo del Popolo and Torre Grossa

Undoubtedly, one of the most significant monuments in the city is the 12th-century Palazzo Del Popolo, situated near the collegiate church in Piazza del Duomo.

Also known as the Palazzo Comunale, or Municipal Palace, this building serves as the primary seat of the municipal authorities and is crowned with a 54-meter high tower named Torre Grossa, offering unforgettable views of the city rooftops and the surrounding area.

Completed in 1311, this tower is the tallest among the remaining towers in San Gimignano (requiring the ascent of over 200 stairs to reach!).

While the ground floor of Palazzo Del Popolo is occupied by officials, the upper floors house the Museo Civico, showcasing remarkable paintings by Florentine and Sienese artists.

On the first floor, in the Grand City Chamber, also known as Dante’s Hall (in honor of the poet’s visit in 1300), visitors can admire Maesta, a masterpiece created by Lippo Memmi, and beautiful paintings depicting hunting scenes.

Practical information: During the peak season (from April to October), the Museo Civico is open every day from 10:00 am to 7:30 pm. An entrance ticket, valid for two days and including access to the tower, costs 9 euros.

The Ultimate Guide to San Gimignano: Where to Stay?

Podere Sant’Elena

If, like us, you seek the intimate and authentic atmosphere of the Tuscan countryside, consider staying at Villa Podere Sant’Elena, located southwest of the city, just fifteen minutes away.

Nestled in the heart of the Chianti region, surrounded by picturesque vineyards and olive groves, this farmhouse offers comfortable accommodations with a swimming pool that provides breathtaking views of San Gimignano.

A notable advantage of this place is its owners, Barbara and Marisa, who take care of each guest to ensure a vacation-like experience. Every morning, enjoy a delicious breakfast featuring local specialties such as cheese, sausages, frittata, panini, homemade preserves, and excellent extra virgin olive oil.

Additionally, unlimited quantities of coffee and fresh pastries from Gianni Bakery, located in the city center and owned by Barbara’s husband, enhance the experience. What more could you want? 🙂

The Ultimate Guide to San Gimignano: Where to Eat?

Osteria Quattro Gatti

The first restaurant we highly recommend in San Gimignano is Osteria Quattro Gatti, nestled in a quaint side street off Via Quercecchio. Besides its exquisite Tuscan cuisine, one of the standout features of this establishment is its serene terrace, where diners can relish their meals in the shade of trees.

The restaurant offers a delectable array of regional dishes, including beef tagliata with truffles, rabbit in white wine with olives, and the famed Florentine steak (bistecca alla Fiorentina). Main course prices typically range between 15 and 40 euros. During our visit, we savored classic pasta with fresh truffles and exceptionally aromatic ravioli with spinach in saffron sauce.

Pairing these delights with a generous serving of pecorino cheese (and, naturally, wine) created the perfect recipe for an authentic Italian feast! We wholeheartedly recommend this charming establishment.

Gelateria Dondoli

You simply cannot afford to miss this gem. When in San Gimignano, treat yourself to the unparalleled delight of the world’s finest ice cream at Gelateria Dondoli, nestled on Piazza della Cisterna. Trust us, one visit won’t be enough 😉

These frozen delights are practically legendary, evidenced by the snaking queues that form outside the ice cream parlor, all thanks to the award-winning mastermind, Sergio.

With his wealth of experience and penchant for experimentation, Sergio has concocted an array of unconventional yet surprisingly delectable flavors. Picture Crema di Santa Fina (ice cream infused with saffron and pine nuts), Champelmo (sorbet crafted from pink grapefruits and sparkling wine), Dolceamaro (vanilla ice cream with aromatic herbs), and our personal favorite – Vernaccia Sorbet (sorbet made from Vernaccia di San Gimignano, the oldest Italian white wine).

Each scoop is crafted with the utmost care, utilizing premium-quality ingredients, predominantly sourced locally. Think organic milk, fruit straight from the orchards, and a special variety of saffron cultivated in the region for centuries. It’s no wonder everything tastes so divine at Gelateria Dondoli 🙂

As for prices, expect to shell out 3.5 euros for one scoop, two for 4 euros, four for 6 euros, and six for 7 euros. We couldn’t resist and found ourselves leaving the ice cream shop with four scoops each time.

After all, how often do you get the chance to savor the world’s finest ice cream?

Il Ceppo Toscano

For those craving the epitome of regional cuisine, the renowned Florentine steak, a visit to the somewhat off-the-beaten-path restaurant – Il Ceppo Toscano – is a must.

This traditional Tuscan delicacy, known as bistecca alla Fiorentina, features a thick cut of tender beef, typically sourced from native cattle breeds like Chianina or Maremmana.

Weighing around one and a half kilograms, it’s usually grilled over a wood-burning grate. The result is a succulent, juicy steak that practically melts in your mouth!

However, indulging in this culinary delight comes with a significant price tag. We paid approximately 75 euros for a half-kilo portion of beef, bone included.

To top off the meal, we couldn’t resist the temptation of the classic tiramisu—an exquisite finale to the evening!

Osteria San Giovanni

While strolling through the historic center of San Gimignano, make sure to visit the Osteria located on Via San Giovanni.

Some tables are arranged outside, directly on the historic street, offering a unique ambiance, especially after dark. Unlike other restaurants in the area, this Osteria distinguishes itself with its excellent service.

You can indulge in traditional Tuscan cuisine here, such as fettuccini with truffles, the renowned ribollita (bean and cabbage soup), or grilled lamb in pea sauce.

For starters, we enjoyed beef carpaccio and a platter of meats and cheeses, followed by saffron risotto for our main course. Every dish was delicious, and the total cost came to 66 euros. We highly recommend it!

Ricca Pizza

If, like us, you find the opening hours of restaurants quite unpredictable in Italy (which we’ve experienced more than once), you can always opt for a crispy pizza at Ricca Pizza.

The place is open every day from 11:00 am to 9:00 pm, making it extremely popular. A large slice of any pizza, whether for takeaway or to enjoy at one of the bar tables, costs 3 euros.

For lovers of delicious Italian pizza, it’s a must-visit place!

Palagetto Winery

No visit to Tuscany would be complete without indulging in the experience of a local wine tavern. If you find yourself near San Gimignano, a visit to Palagetto Winery is a must for wine enthusiasts.

Operated by a native Tuscan family for generations, the winery offers a diverse range of regional wines including Chianti, Brunello Montalcino, and the renowned Vernaccia di San Gimignano.

There are various options available for wine tasting, and you can also savor a traditional Tuscan dinner featuring homemade pasta. Additionally, you have the opportunity to explore the wine cellar through an organized tour guided by an expert. The tour encompasses a visit to the vineyard, cellars with barrels, and areas dedicated to bottling and aging wine.

During our visit to Palagetto, due to time constraints, we opted for a tasting of select wines. Departing from the winery, our spirits were lifted, and we carried away a few bottles of wine with us. It was unquestionably a worthwhile experience!

The Ultimate Guide to San Gimignano: Summary

San Gimignano in Tuscany is an ideal destination for an unforgettable Italian vacation. With its stunning landmarks, mouthwatering cuisine, and awe-inspiring vistas, it is a must-visit place. We sincerely hope that our guide to San Gimignano above has sparked your interest in exploring this remarkable gem. Immerse yourself in its captivating history, wander through its charming streets, savor the flavors of local delicacies, and soak in the breathtaking scenery of Tuscany. San Gimignano promises unforgettable experiences for culture, history, and beauty enthusiasts alike. May this exceptional journey bring your Italian dreams to life and create memories that will last a lifetime!

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What places in San Gimignano do you recommend? Let us know in the comments!