This Gorgeous Region of Italy Has Rolling Vineyards, Hilltop Medieval Villages, and Incredible Food

Rolling hills blanketed with vineyards and olive trees, medieval towns that make you feel like you’ve stepped back in time, a beautiful Mediterranean coastline, and delicious cuisine made using fresh ingredients — this is what Tuscany is all about. The central Italian region that’s home to Florence — consistently ranked among the best cities in Europe in Travel + Leisure’s World’s Best Awards — is a favorite destination for travelers, myself included.

I live in Rome, so Tuscany is just a couple of hours away, and I visit every chance I can get. Over the years, I’ve explored cities and towns like Siena, Lucca, Pisa, San Gimignano, and Volterra; soaked in the thermal hot springs in Saturnia; relaxed on the beaches of Forte dei Marmi and Porto Ercole; visited wineries in the countryside; and learned to make pici and other local dishes during cooking classes.

But Tuscany is such a vast region with so many incredible things to do that narrowing down the best of the best is a nearly impossible task. That’s why I enlisted the help of two experts: Giulia Scarpaleggia, a cookbook author who pens the Substack newsletter Letters from Tuscany and teaches cooking classes at her home in Colle di Val d’Elsa, and Christian Scalisi, a lawyer and co-owner of Villa Ardore, who splits his time between California and Tuscany. Read on for our intel about the best hotels and resorts, things to do, where to shop, where to eat and drink, best cities and towns to visit, and how to get around.

Best Hotels & Resorts

Borgo San Felice

This Relais & Châteaux hotel breathed new life into a medieval hamlet in the countryside near Siena. Rooms and suites are spread out in old stone buildings and decorated in a traditional style. Guests can relax by the pool, enjoy treatments at the spa inside an old olive mill, savor gourmet meals at the Michelin-starred restaurant, and sample homemade pastas at the casual osteria.

Il Salviatino

Scalisi and his husband love to stay at this family-owned five-star hotel in Fiesole, a quick drive away from Florence. “​​It is filled with special details, from frescoed ceilings to a panoramic terrace with manicured gardens, and views over the Duomo and beyond,” he says. The 15th-century villa has just emerged from a renovation that refreshed its 39 rooms and suites and added a new spa.

Agriturismo Il Rigo

When in Tuscany, consider staying at an agriturismo, an authentic and budget-friendly type of accommodation consisting of a rustic bed-and-breakfast attached to a farm. “You feel at home at Il Rigo, likely because at this family-run farm, Luisa and her husband Mathias are always nearby, making you feel immediately like one of the family,” says Scarpaleggia.

La Roqqa

This new boutique hotel in the under-the-radar town of Porto Ercole on Monte Argentario boasts a sleek, modern design featuring blue-chip furniture by the likes of Gaetano Pesce, a rooftop restaurant serving contemporary Italian cuisine, and a beach club on a secluded cove with plush sunbeds and a casual restaurant.

Villa Ardore

Scalisi and his husband Stephen Lewis restored this 16th-century farmhouse in the heart of Chianti and transformed it into a luxurious private residence that can accommodate groups of up to 16 guests. With an infinity pool with panoramic views of the surrounding vineyards, a spa, a vegetable garden, bocce court, and fully equipped kitchen, the villa is ideal for families or groups of friends seeking seclusion and tranquility within easy reach of Tuscany’s best attractions.

Best Things to Do

Visit the Siena Cathedral.

Scarpaleggia recommends visiting the Siena Cathedral to admire its marble mosaic inlay floor. “The floors can be admired by walking up and down the church aisles, or from on high, thanks to the special Porta del Cielo (“Heaven’s Gate”) tour,” she says. Inside the cathedral, you can also see Pinturicchio’s incredible frescoes in the Piccolomini Library.

Go for a wine tasting.

Tuscany is famous for its excellent wines, and visiting a winery is a must. Antinori Nel Chianti Classico is a marvel of modern architecture run by one of Italy’s oldest and most distinguished winemaking families, which has been producing wine for 26 generations. Be sure to book a tour in advance, as they’re very likely to sell out.

See contemporary art at Galleria Continua.

“For contemporary art in Tuscany, Galleria Continua in San Gimignano is a must,” says Scalisi. “It was founded in 1990 with the intention, evident in the name, to give continuity to contemporary art in a landscape rich with ancient art. Occupying a former cinema, it has established itself in an entirely unexpected location in San Gimignano – a town that is steeped in history.”

Relax on the beach.

Whether you prefer dramatic, rocky beaches where you can dive into the deep blue sea or beach clubs with sunbeds and umbrellas in neat rows on golden sand, Tuscany has a beach for you. For the former, head to Monte Argentario, an island connected to the mainland via a causeway. For the latter, plan a trip to Forte dei Marmi, the stomping ground of wealthy Florentines, where sidewalks are paved in marble from the nearby caves of Carrara.

Learn to make local specialties in a cooking class.

One of the best ways to get to know Tuscany is through its food. Scarpaleggia offers half-day cooking classes at the kitchen studio attached to her home in Colle di Val d’Elsa. You’ll start at the market or in the studio and learn to make local specialties such as pici pasta with seasonal sauce, chicken cacciatore, and olive oil cake before sitting down to enjoy the four-course lunch you’ve just prepared with Scarpaleggia’s help.

Best Shopping

Arezzo Antiques Fair

“It’s a magical way to spend a weekend, browsing the stalls that pop up in the town of Arezzo and which showcase incredible collectibles and rare design pieces,” says Scalisi. “We recommend this fair to all the design lovers who want to take home something very special and authentic from Tuscany.” It takes place every first weekend of the month.

Berti

“Berti is a family-run company based in Scarperia, crafting artisan knives in Tuscany since 1895,” Scarpaleggia explains. “Visit their shop to see how they continue to make knives using traditional techniques, and receive expert advice while selecting from their beautiful collection.”

Ceramiche Artesia

This is the place to come for one-of-a-kind tabletop pieces. At this little ceramics workshop in Certaldo Alto, artisans make beautiful pieces of pottery by hand. You might find a serving platter painted with pomegranates or little bowls with lovely geometric designs.

Best Restaurants

Osteria di Fonterutoli

Scalisi raves about this elegant restaurant on the estate of the Mazzei winery. “The setting in the gardens overlooking the quintessential Tuscan landscape is a true showstopper,” he says. “You can linger over a long lunch with a glass of Chianti classico from the estate. I recommend ordering the eliconi pasta with wild boar ragù and wild mushrooms. It’s a star dish!”

Trattoria Bel Mi’ Colle

“Fresh, local, seasonal ingredients are the protagonists of the cuisine of Chef Gabriele Borgianni in this trattoria that is probably our favorite in our hometown, Colle di Val d’Elsa. Beef tongue and stuffed chicken neck are my go-to choices when it comes to appetizers,” Scarpaleggia says, adding that the cheese selection is outstanding.

Enoteca I Terzi

This wine bar and restaurant in the historic center of Siena has more than 1,800 labels to choose from, and the bottles are displayed on shelves right inside the restaurant. Start with a meat and cheese board, then choose from classics like the bistecca alla fiorentina or seasonal dishes such as risotto with radicchio, Castelmagno cheese, hazelnuts, and a Barolo reduction.

Gigliola

Scarpaleggia recommends this “modern osteria where you can stop by for lunch, dinner, a quick aperitivo, or a brunch,” in the charming city of Lucca, adding that they serve, “excellent bread and fresh pasta, natural or biodynamic wines, and unusual dishes like falafel or Chinese ravioli.”

Il Pellicano

The Michelin-starred restaurant at Hotel Il Pellicano, a legendary member of the Leading Hotels of the World in Porto Ercole, is no doubt one of the most romantic places for a special dinner in Tuscany. Choose one of the tasting menus or order Chef Michelino Gioia’s sublime dishes à la carte and soak up the atmosphere on the terrace overlooking the sea.

Best Time to Visit

There’s really no bad time to visit Tuscany. When you choose to go just depends on what you want to do. Summer is the high season, so that’s when you can expect the most crowds and the highest rates at hotels. In winter, some hotels in the countryside and the coast shut down, but you can still enjoy cities like Florence and Siena. Spring and fall are ideal for good weather.

Scalisi’s favorite month in Tuscany is May. “The countryside is simply gorgeous, the weather is usually very pleasant (warm but not hot) and it’s the perfect time to explore rural Tuscany,” he says.

There are various festivals and events throughout the year, including the Palio di Siena horse race in July and August, the Lucca Summer Festival in June, and the Incontri in Terra di Siena, a renowned music festival in July that unfolds in various locations, including La Foce, a spectacular estate in Val d’Orcia. The last Sunday of August, the Bravìo delle Botti in Montepulciano sees locals race while pushing wine barrels uphill. Fall brings harvest festivals, including the White Truffle Festival in San Miniato.

How to Get There

Amerigo Vespucci Airport (FLR) in Florence and Galileo Galilei Airport (PSA) in Pisa serve the wider region of Tuscany. You could also fly into Rome or Milan and take a train or drive to Tuscany, depending on where you’re going.

Cities to Visit

Siena

Historically, there’s always been a fierce rivalry between Florence and Siena, Tuscany’s two most important cities. Nowadays, Siena is considered one of Italy’s best-preserved medieval cities, and walking through the historic center feels like stepping back in time. The fan-shaped Piazza del Campo, presided over by the Palazzo Pubblico with its tall bell tower, is especially enchanting.

Pietrasanta

“The fascinating medieval city of Pietrasanta is considered the historic capital of Versilia and the capital of marble processing,” explains Scalisi. “Attracting artists from all over the world, the city has turned into an open-air museum where you can admire a constant and continuously renewed display of top-tier contemporary artworks and sculpture in the many galleries and squares.”

Lucca

Originally a Roman settlement, Lucca developed over the centuries into a prosperous and influential city. Go to admire curiosities like the Guinigi Tower, which has a tree growing on top, admire the oval Piazza del Anfiteatro (built atop a Roman amphitheater), walk or bike on the old ramparts, and shop for antiques and artisan-made goods in the charming boutiques.

Val d’Elsa

“Val d’Elsa, the valley of the river Elsa, is nestled right in the heart of Tuscany, halfway between the provinces of Florence and Siena, traversed by the ancient pilgrim route Via Francigena that once wound through the hills,” says Scarpaleggia. “Unknown to many and certainly less popular with tourists than San Gimignano and the Chianti area, Val d’Elsa is dearer to me, with its lovely farmed countryside between Casole, Colle Val d’Elsa, and Sovicille, the woods close to my home and the vine- and olive tree-covered hills around Certaldo.”

Pienza

Designed as the ideal Renaissance city, Pienza is nestled in the Val d’Orcia, one of the most scenic valleys in the region. The historic center is a UNESCO World Heritage Site, where you can admire churches and visit the hanging gardens at Palazzo Piccolomini. Many shops around town sell pecorino di Pienza, the sheep’s milk cheese produced in the hills just outside the town.

How to Get Around

Tuscany is a vast region, so the best way to get around really depends on where you’re going. Most cities and many small towns are served by trains, but if you plan to explore the countryside, it’s best to rent a car.

Trenitalia: Italy’s state-run railway operator has a large network of high-speed, inter-city, and regional trains that connect many of Tuscany’s cities and towns. You can find routes and buy tickets at trenitalia.com or italiarail.com.

Car rental: Your best bet for renting a car is to pick one up at the airport when you arrive. It’s always advisable to book in advance, especially if you’re traveling in high season or need an automatic car.