Crossing into the Tuscan countryside is a dizzying experience. Medieval stone castles rise from the hilltops as torrents of lush greenery cascade gracefully into the distance. Vineyards cover entire hills, and towering 12th century fortresses keep watch over historic walled cities. After sunrise, mist rolls in like a soft-focus photograph, hanging in the olive, cypress, and hazelnut trees clinging to the slopes. This provincial snapshot has long attracted painters, poets, writers, and other artists, and has served as the backdrop for several films, including Russel Crowe’s home in the Academy Award-winning Gladiator.

Often called Italy’s heart, the Tuscan region is the fifth largest in the country, stretching 8,900 square miles (about the size of New Jersey) and encompassing 237 municipalities and eight world heritage sites, offering one of the densest concentrations of UNESCO sites in the world. They include the Piazza del Duomo in Pisa, the medieval town of San Gimignano (known as the Manhattan of the Middle Ages), and Val d’Orcia, a rich verdant valley and the first rural area to be granted the UNESCO award. The entire historical center of Tuscany’s capital city of Florence is also a heritage site, housing the world’s largest collection of Renaissance art and architecture. Michelangelo’s David at the Galleria dell’Accademia and Botticelli’s Birth of Venus are must-see works in the Renaissance City.

Viticulture dates back to the 8th century when the ancient Etruscans first settled the area, and today the region produces approximately 360 million bottles of wine each year. Sangiovese is the signature grape and it’s used in several of the region’s most popular wines, including Chianti, Montepulciano, and Brunello. The dessert wine Vin Santo produced here is excellent and pairs beautifully with biscotti. Tuscany is also considered the leading producer of extra virgin olive oil in the world, famous for its rich, peppery flavor. Many vineyards produce their own olive oil and offer tastings alongside the wine.

Autumn is a lovely time to visit, typically marked by warm days and mild evenings. Many towns host harvest festivals sometime between late September and early October to celebrate the  flavors of fall and the upcoming arrival of “novella wines” (new wines of the season). Stalls of olive oil, truffles, and chestnuts line the streets, so be sure to leave room in your suitcase to bring a taste of Tuscany home. Many producers also offer international shipping.

Florence is an excellent starting point, and several airlines offer nonstop  flight from JFK, including Iberia, Virgin Atlantic, Delta, and American. Be sure to pack comfortable walking shoes and leave ample time for exploring the numerous museums, cathedrals, and palaces. 


The city is also the country’s leading producer of fine leather goods and is peppered with shops offering jackets, belts, wallets, et al. From there, the best way to explore the idyllic countryside is by car – rent a Fiat 500 or Alfa Romeo convertible and cruise the cypress tree-lined roads in style, stopping to taste revered Super Tuscans and dine in traditional stone houses.


Though Italy has a history of producing high-quality wines that span millennia, several factors led to diminishing quality in the first half of the 20th century, including a devastating phylloxera infestation and the economic hardship following the two world wars.

A movement emerged in the mid- 1900s, largely led by journalist Luigi Veronelli, to safeguard the integrity of Italian wines, and in 1963 the government employed a rigorous classification system based on France’s Appellation d’Origine Contrôlée laws. The classification system includes four tiers: VDT, IGT, DOC, and DOCG. All DOC and DOCG must meet strict requirements for quality, production standards, geographic area, and grape varieties, with the DOCG label reserved for the highest quality wines. This system led to a modern renaissance of superior Italian wines, with 41 DOC and 11 DOCG titles in the Tuscan region today. But strict guidelines inevitably breed rebels, and Super Tuscans – high-end vino that’s made outside traditional rules – emerged, offering exquisite options such as Sassicaia, a Bordeaux-style red wine from Tenuta San Guido. There are more than 100 operating wineries, spanning castle family estates like Castello Banfi to contemporary farmsteads like Antinorinel Chianti Classico (pictured above). We recommend visiting as many regions as possible, as varying soil composition yields distinct flavor profiles, and wines produced near the Apennine Mountains will taste vastly diferent than coastal varietals.

About two hours south of Siena lies one of the area’s best-kept secrets, a quaint spa town boasting natural thermal hot springs fed by a nearby volcano. Carved into the green countryside, the topaz tinted Saturnia springs stay a constant 98 degrees and flow into travertine stone pools. Use of the springs is free of charge. Be sure to bring water shoes as the rocky ground can be a bit rough.

Truffles are a mainstay of Tuscan agriculture, and while you’ll find their presence in most restaurants and markets, the region’s resident “Truffle Hunter,” Giulio Benuzzi, offers intrepid truffle lovers the opportunity to forage for their own. The truffle walking experience includes a guided hike through the forest, tracking down the notoriously hard-to-find delicacy in the Florentine hills. The excursion includes a picnic of truffle sandwiches and red wine. An expert guide dog also comes along for the journey.



Escape to this timeless hilltop refuge, blending old-world regality with modern opulence against exquisite views of the rolling countryside. Set on one of the largest private landholdings in Italy, the 4,200-acre estate dates back to the Bronze Age, and the hotel proudly displays ancient artifacts discovered on the grounds. The restored castle spans 39 rooms and suites, outfitted with dressings and materials as timeless as they are elegant; wood-beam ceilings, stone walls, and hand-plastered finishes juxtapose against modern fabrics and fixtures. Meditate in the massive private outdoor garden, indulge in a Millefiori honey infused massage, bike through vineyards and olive groves, or get lost in the countless stars lighting up the Tuscan night sky. Rooms start around $1,000 per night.

The only five-star luxury boutique hotel located in the historical center of Siena – and mere steps from famed landmarks like the Duomo cathedral and Piazza del Campo – this restored 17th century hideaway is a stunning tapestry of the Renaissance era, garnished with exquisite frescoes throughout. The property’s history is teeming with royalty and prestige; it was formerly the home of the queen of Italy, Margherita of Savoy, and a favorite among intellectuals involved in the 19th century Grand Tour (a jaunt through Europe undertaken by young upper-class European men).

In the early aughts, the residence was thoughtfully reimagined as a world-class resort, comprising 51 rooms and suites inspired by 16th century nobility. Opt for the Panoramic Suite for a sweeping 360-degree view of the historic medieval city, and sleep among regal luxuries like walls covered in precious silks, full marble bathrooms, and preserved centuries old antiques. Rooms start around $250 per night.



Led by master chef Annie FĂ©olde, aka the Diva Chef, and the  first female cuisiner in Italy to earn three Michelin stars, Entoeca Pinchiorri is a sensorial experience.  The presentation is as delectable as the fare itself, and the candlelit, old-world atmosphere offers a passage back in time. To curate an authentic Tuscan dining experience, the chef pored over rustic Florentine recipes that have been passed down for centuries and reimagined them for the gourmet palate.

Ingredients like chiocciole di vigna, a form of tiny snail found on vines, and young Mora Romagnola, a breed of pig from northern Italy, are staples. Féolde’s husband, sommelier Giorgio Pinchiorri, spearheads the sweeping wine list, offering his expert recommendations for pairing everything from fusilli al ferretto and squids to potato doughnut with fegatini sauce.

Equally enchanting as Tuscany’s undulating hills is its jagged coastline, and set on the edge of Porto Ercole lies one of Italy’s most storied boutique hotels with a hilltop restaurant that boasts some of the best views in the country. Il Pellicano is a Michelin-starred masterpiece, helmed by chef Michelino Gioia, a true maestro of local ingredients.  The fish is caught daily and the bone steaks arrive from nearby Chianina.  The chef grazes the gardens each morning to select Mediterranean herbs. Nab a table on the terrace, offering panoramic views of the cobalt-tinted sea, and dish on scallops with pork crackling, creamed potatoes, apple sauce, and red wine, or indulge in cuttle sh with prawns, almonds, and bottarga with fusilloni pasta.

Italians are as serious about their gelato as they are pasta, and there’s heated debate over who crafts the best sweet cream. Embarking on a quest to  find the perfect scoop can be a daunting – yet delicious – endeavor, and this worldfamous gelateria in San Gimignano is a great place to start. Owner Sergio is lauded for his unique and inventive flavors, including Crema di Santa Fina (saffron with pine nuts), Champelmo (pink grapefruit and sparkling wine), and Dolceamaro (cream with aromatic herbs). The parlour also offers gelato making classes.