The Hill Towns of Tuscany

With Florence or Siena as your base camp, explore an Italian nexus of authentic wine and food.



You’ve heard of island hopping, bar hopping and table hopping. Only in Tuscany, however, can you practice the truest form of town hopping.

Located in the heart of Italy, this large (8,800 square miles), somewhat circular region is covered with postcard-perfect hilltop hamlets, most dating back to the Middle Ages. Perfectly preserved or restored, each town is never more than an hour apart by car. All thrive in their gorgeous natural settings, consisting of rolling hillside vineyards, cypress-lined drives, farmhouses and other exhilarating flashes of iconic imagery.

Town hopping, known as pilgrimage in ancient times, is a force in Tuscan history and is responsible for the region’s rise in wealth, power and influence. In the Middle Ages, the Via Francigena, which connected England’s Canterbury to Rome, cut straight through Tuscany. It carved a corridor of commerce and communication, thanks to the thousands of travelers, merchants and clergymen who walked its path. Towns along the route, such as Lucca, San Gimignano, Monteriggioni and Siena, experienced economic booms that fueled the artistic and institutional momentum of the Renaissance. Italian cuisine benefited as well: Spices and exotic ingredients like chocolate were carried here from faraway lands.

Many of today’s travelers who make their own pilgrimages to Tuscany are already familiar with attractions such as Florence and Siena. Both of these cities make an excellent base from which to explore Tuscany’s massive collection of hill towns. Here are our favorite picks, selected for the quality of exciting new restaurants, wine venues, quirky things to see and overall charm.

San Gimignano

La Città delle Torri, or “the city of towers,” is by far the most ostentatious example of Via Francigena abundance. This medieval Manhattan once boasted 72 soaring towers visible for miles around.

Just as New York City’s skyline added the Chrysler Building and Rockefeller Plaza during times of prosperity, the inhabitants of San Gimignano erected stone towers as symbols of their collective aspiration. Petty jealousies and one-upmanship resulted in a tower-building frenzy that even dwarfed the main church steeple. Such exploits put the vulnerable town in the crosshairs of outside enemies and warring neighbors. Today, only 14 towers survive.

The appeal of San Gimignano, however, is much more than architectonic hubris. It’s home to the Gelateria di Piazza, considered by many to make the best artisan ice cream in Italy. It certainly wins top prize for creativity: Rosemary essence, lavender, Gorgonzola, saffron and chili peppers are popular ingredients. There’s even a vin santo-flavored offering that pays homage to Tuscany’s celebrated dessert wine.

If you crave savory foods, the Osteria del Carcere is a popular choice for hearty Tuscan classics such as ribollita (white bean and vegetable soup), pappa al pomodoro (a bread and tomato soup) and l’arista di maiale (roast pork loin). Finer cuisine can be had at La Collegiata. Housed in a former convent, this restaurant and Relais & Château property borrows ingredients from afar such as truffles, prawns and squid ink.

A 45-minute drive southeast from San Gimignano is the tiny town of Monteriggioni, with its circular walls and 14 preserved military towers. Outside of town is the excellent La Leggenda dei Frati restaurant. A great selection of local wines and artisanal beers accompany tortelloni stuffed with pigeon, or lasagna made with chestnut flour and wild boar sauce with leeks and Pecorino.

Volterra

Far off the beaten wine trails, Volterra offers a perspective on Tuscany that’s uniquely Etruscan—reflecting the region’s indigenous population (Etruschi) for whom the Romans named the region. With commanding mountaintop views, alabaster mines and an important collection of Etruscan and Roman artifacts—Volterra was the last Etruscan stronghold to fall to the conquering Romans—the town really has an authentic Tuscan feel.

Equally compelling are the food offerings, starting with Del Duca Ristorante-Enoteca. Traditional dishes are served with modern flair, featuring locally sourced mushrooms, meats and garden greens. Slightly less formal is the awesome Ristorante Ombra della Sera, which offers a surf and turf menu based on the freshest ingredients. Try the beef carpaccio with black truffle or the delicate linguine pasta with calamari and bottarga (dried fish roe). The service is excellent and you’ll love the outdoor seating area. Because Volterra is located on the crest of the mountains that eventually lead to the Mediterranean Sea, fish dishes from baccalà to raw seafood appetizers can be found here.

Panzano

At the bucolic heart of Tuscany and one of the most important vineyard sites for Chianti Classico, Panzano is a natural intersection where great food and wine meet. It also makes a great resting stop for those intent on exploring the main towns of Chianti Classico, such as Greve in Chianti (home to the historic butcher Antica Macelleria Falorni, Castellina in Chianti and Radda in Chianti.

The superstar of Panzano is Dario Cecchini. This eccentric butcher’s celebration of ciccia (the local word for succulent red meat) finds its voice in encyclopedia-sized cuts of T-bone steak that come in three versions: la Bistecca alla Fiorentina, la Costata and la Panzanese. Just a few years ago, Cecchini opened the Officina della Bistecca, a restaurant serving dinner several nights a week, with tables set around an open grill. Wine is included in the price of a meal—you do have the option of bringing your own bottle without a corkage fee, but you absolutely must bring a hearty appetite.

Bolgheri

Birthplace of Sassicaia, Ornellaia and Solaia, Bolgheri’s influence on modern Italian wine is significant. Located on Tuscany’s unspoiled coast between natural reserves of native scrub oak and the shimmering sea, Bolgheri is gaining popularity with wine tourists, foodies and cyclists (thanks to the hundreds of kilometers of scenic roads).

At the base of the cypress-lined road that leads to the town and Castello di Bolgheri is the informal Osteria San Guido, owned by legendary Sassicaia proprietor Niccolò Incisa della Rocchetta. With outside seating in a grassy field, the restaurant serves authentic country foods paired with the iconic wines of the area. Another fun spot in Bolgheri is the Enoteca Tognoni. Besides its offering of excellent food, this wine shop is a great place to fill in gaps in your Italian wine collection (the prices are very reasonable, too).

Coastal Tuscany offers a fish-based cuisine all its own, and Marina di Bibbona (a 20-minute drive from Bolgheri) is home to one of Italy’s best seafood restaurants, La Pineta. Chef Luciano Zazzeri offers the freshest catch of the day and local dishes such as cacciucco alla Livornese (a hearty fish soup from Livorno). Don’t be surprised to see famous vintners such as Angelo Gaja, Piero Antinori or Cinzia Merli of Le Macchiole sitting at the next table.

Ravioli with fava bean purée at the Castello Banfi Taverna in Montalcino.Montalcino

The town of Montalcino is synonymous with Brunello, one of Italy’s most cherished red wines. But Montalcino is also on its way to becoming Tuscany’s most popular smalltown destination.

Up until a few decades ago, Montalcino was the poor and desolate backwater of rural Italy. Today, it pulls in millions of tourism dollars, thanks to its wine shops, restaurants, boutique hotels and tasting rooms. Montalcino offers a 360-degree vista of one of the greatest cru areas in the wide world of wine.

Here, some the best eating opportunities are found on wine estates. The Ristorante di Poggio Antico has been attracting attention with its gorgeous outdoor patio and excellent food. Poggio Antico’s wines are some of the best in town and are excellent when paired with dishes like ravioli stuffed with foie gras, baby shrimp served in an asparagus cream sauce or beef filet marinated with porcini mushrooms.

Castello Banfi’s Taverna serves up wine and food pairing menus featuring fusilli with porcini and sausage and Chianina tagliata (beef cut into strips). Le Potazzine’s Ristorante La Vineria  boasts an amazing selection of Brunello and Rosso di Montalcino, as well as beautiful outdoor seating.

Where do Montalcino’s winemakers eat? Many book dinner at Ristorante Il Leccio in the nearby hamlet of Sant’Angelo in Colle. If you’re lucky, you’ll find a handwritten sign that reads tartufi freschi (“fresh truffles”) on the door. In that case, expect heaping shavings of Tuscany’s best tubers over your pasta, meat and more.

Pienza

The philosophical opposite of San Gimignano, Pienza was built during the Renaissance as an experiment in humanist ideals. It was envisioned as a utopian city in which palaces and public squares were calculated to be the perfect fit for its inhabitants. The socalled città a misura d’uomo (the human-sized city) is not too big to be daunting, nor is it too small to be ignored.

In keeping with those ideals, this beautifully designed and proportioned town offers restaurants that straddle that happy space between rustic, country kitchens and elegant culinary experiences. Latte di Luna, in the city center, is a friendly trattoria that serves zuppa di pane (soup with bread and vegetables), pici con ragù di cinghiale (thick pasta with wild boar) and agnello scottadito (lamb chops served so hot they “burn your fingertips”). The modest wine list offers options from nearby Montepulciano and Montalcino.

A second informal eatery, located slightly outside Pienza in the village of Monticchiello, is Osteria La Porta. Typical Tuscan dishes, ranging from appetizers like salumi di cinta senese (salami made with the local species of pig) to desserts such as panna cotta, can be enjoyed on an outdoor terrace. The same owners also run the more upscale Ristorante La Cantina for evening dining.

Capalbio

On the Tuscany-Lazio border, 93 miles south of Florence, Capalbio is the quintessential Tuscan town. It occupies the crest of a perfect hill the way a crown rests on a prince’s head. This is definitely the most rustic of the towns featured here because of its location in the Maremma, known for rugged horse wranglers (i butteri), lonely prairies and tufa-stone villages. But in summer months, Capalbio attracts an artsyintellectual crowd to its pristine beaches and wild landscapes. The trendiest spot in town is part bookstore, part art gallery and part restaurant. Il Frantoio puts on a fantastic outdoor aperitivo as the sun begins to set, and serves local delicacies late into the evening.

Towns with Character

Scenic Tuscan hill towns have made cameos in—or provided luscious backdrops for—a handful of Hollywood hits, including 1999’s star-studded A Midsummer Night’s Dream (Montepulciano); the 1968 production of Romeo and Juliet (Pienza); The English Patient (Pienza); Twilight: New Moon (Montepulciano); Under the Tuscan Sun (Cortona); and Where Angels Fear to Tread (San Gimignano).

Three Options for Getting Around the Hills of Tuscany

Air Balloons: Volare in Mongolfiera
Tuscany’s Leonardo da Vinci was among the first to design a human flying machine, and his native land is today a hub for hot-air ballooning. Experienced companies such as Balloon Flights Italy, Balloon in Tuscany and Chianti Ballooning average 250 euros ($350) per person. Some serve Champagne breakfasts in the sky.

Classic Cars: Noleggio Auto d’Epoca
Tuscany epitomizes the slow lane philosophy. One of the best ways to take in the surroundings is with a leisurely drive in a classic car. Rent a Fiat 500 or an Alfa Romeo Duetto from Chianti Classic Car or Drive in Style. For more horsepower in the sensual shape of a Ferrari, Maserati or Lamborghini, go to Noleggio Auto Toscana. Racing enthusiasts should not miss the Mille Miglia classic car rally or Tuscan Rewind, both held in May.

Scooters: Vacanza in Vespa
The excellent panorama vs. pavement ratio that Tuscany offers makes it ideal for scooting around on two wheels. Agencies such as Tuscany by Vespa, Scooter Bella and Strada Nova and offer scooter tours (insurance and helmets included).

For pairing tips from Tuscan butchers, click here.

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