You’ve heard of island-hopping, bar-hopping and table-hopping. Only in Tuscany, however, can you practice the truest form of town-hopping—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.
In the Middle Ages, pilgrimages to and between these towns were responsible for the region’s rise in wealth, power and influence. 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.
Here are our favorite picks of towns, selected for the quality of exciting new restaurants, wine venues, quirky things to see and overall charm and distinctiveness.
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. But such exploits put the vulnerable town in the crosshairs of outside enemies and warring neighbors. Today, only 14 towers survive.
San Gimignano is home to the Gelateria di Piazza, considered by many to make the best artisan ice cream in Italy, and creativity is not lacking either: Rosemary essence, lavender, Gorgonzola cheese, saffron and chili peppers are popular ingredients. There’s even a vin-santo-flavored offering.
For savory foods, the Osteria del Carcere serves up 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 & Chateau property borrows ingredients from afar such as truffles, prawns and squid ink.
At the bucolic heart of Tuscany and set amid some of the most important vineyard sites for Chianti Classico, Panzano is a natural intersection where outstanding wine and food meet. It’s also an ideal resting stop for tourists intent on exploring the main towns of Chianti Classico, such as Greve in Chianti, 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. Cecchini’s restaurant, Officina della Bistecca, serves dinner several nights a week, with tables set around an open grill. Wine is included in the price of a meal, though you have the option of bringing your own bottle without a corkage fee.
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—città a misura d’uomo (the human-sized city). Today, this beautifully designed town straddles that happy space between rustic, country kitchen and elegance.
Latte di Luna, in the city center, is a friendly trattoria that serves hearty traditional fare. 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.
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.
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. The Enoteca Tognoni has excellent foods and a great collection of Italian wines for sale, at reasonable prices.
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).
On the Tuscany-Lazio border, 93 miles south of Florence, Capalbio is 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 artsy-intellectual 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.
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 welcoming and intimate Trattoria Da Badò in the San Lazzaro area. Because Volterra is located on the crest of mountains that eventually lead to the Mediterranean Sea, dried fish dishes such as baccalà and stoccafisso (both codfish) can be found here.
Getting around Tuscany
Air balloons: Volare in Mongolfiera
Experienced companies such as balloonflightsitaly.com, balloonintuscany.com and chiantiballooning.com average 250 euros ($325) per person. Some serve Champagne breakfasts in the sky.
Classic Cars: Noleggio Auto d’Epoca
Rent a Fiat 500 or an Alfa Romeo Duetto from chianticlassiccar.com or driveinstyle.it. For more horsepower in the sensual shape of a Ferrari, Maserati or Lamborghini, go to noleggioautotoscana.it.
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 tuscanybyvespa.com, scooterbella.com and stradanova.com offer scooter tours (insurance and helmets included).
5 Best Hotels in Tuscany
One of the most celebrated and luxurious hotels in rural Tuscany, the Relais di Fizzano near Castellina-in-Chianti offers apartments with unique touches such as ancient feeding troughs, tiled floors, wood-beamed ceilings and huge fireplaces.
In addition, guests of the property will receive a 10% discount on all purchases made at the Rocca delle Macìe tasting room.
If you are looking to travel further off the typical tourist track, Poggio al Casone offers an excellent package of activities and amenities in western Tuscany located near the Pisa Airport as well as proximity to some of the best beaches in Tuscany. The beautiful estate is surrounded by cypress-lined drives and vineyards and resort and spa services are included. There is a beautiful swimming pool, golf, horseback riding, wine and food pairings, and winemaking lessons are offered to novice enologists.
Badia a Coltibuono
Acres of vineyards and forests surround this beautiful 11th-century abbey at the heart of Chianti Classico. Run by the energetic Emanuela Stucchi Prinetti, Badia a Coltibuono has an excellent restaurant using many ingredients from the property’s organic farms, as well as Renaissance gardens, a pool and a long list of outdoor activities. What sets this venue apart is its cooking school, which covers everything from shopping at a local market to chopping, kneading and of course eating.
Nestled within the vineyards and rolling hills of Radda-in-Chianti, the family-run Castello di Volpaia offers gorgeous accommodations, an excellent cooking school and ample outdoor activities such as hiking and horseback riding. The Borgo di Volpaia is actually its own medieval town and the venue is perfect for weddings and bigger groups.
For a quarter century, German art dealer Peter Femfert and his Venetian wife Stefania Canali have collected beautiful works of modern art, sculpture and precious antiques, and much of it is on display throughout this property.
Guests can choose between the Casa Padronale and its medieval stone tower or the Casanuova (a few kilometers away). Two apartments can accommodate up to six people each and there are additional apartments for couples or small families. Guests are asked to stay a minimum of four nights.