Tuscan Getaway Guide

Where to sip, sup and stay on your Tuscan getaway.


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Featuring rolling hills blanketed with vineyards and medieval hill towns topped with castles, Tuscany looks as if it’s been lifted straight out of a Renaissance painting. Add to its natural beauty delicious food, fantastic wines and a new wave of luxury hotels, and you have yourself your next must-book vacation. The best time to visit is during Fall season, when crowds have dispersed and the local wineries—many among the most lauded in Italy—are harvesting their grapes. Here’s where to sip, sup and stay—and smell the sweet scent of fermenting juice—while on your Tuscan getaway.

1. Chianti Classico’s hills, spanning between Florence and Siena, produce one of Italy’s most popular and storied wines. Villages not to miss include Panzano, where a visit to the wine bar Enoteca Baldi is a must. They offer an array of local wines by the glass and more by the bottle, which you can buy and bring to the onsite trattoria to pair with the authentic Tuscan dishes. Next, hit Radda and visit the magnificent Castello d’Albola estate for a winery tour and tasting. Nearby, in the town of Castelnuovo Berardenga, the stunning San Felice estate is worth a stop for sips before supping at the onsite upscale restaurant. After over indulging in the various delights, you’ll want to spend the night a their luxurious onsite hotel, Borgo San Felice.

2. Montalcino, crowned by its hilltop fortress, is home to Brunello di Montalcino, one of the country’s most celebrated wines. Wineries here are spread throughout the medieval town, but must-sees include Biondi Santi’s Tenuta Greppo, where Brunello was invented in the latter half of the 1800s, as well as Fuligni, Col d’Orcia, Ciacci Piccolomini d’Aragona and Canalicchio di Sopra, which also offers upscale apartments fitted out in country-chic. In the town of Montalcino, you’ll discover hot spots like Taverna del Grappolo Blu,where you can enjoy authentic local dishes, and Enoteca Osteria Osticcio,the town's best wine bar, where you can also try light, seasonal fare.

3. Montepulciano is home to Italy’s legendary Vino Nobile, a wine lauded as far back as the late 1600s by Francesco Redi in his poem Bacco in Toscana. No visit to this town would be complete without a stop at Contucci winery, located in the town center. The Contucci family has been cultivating grapes here since the 1700s, and their ancient cellars—vaulted tunnels with large casks piled to the ceilings—are a site to see. Other wineries worthy of visiting include Avignonesi, Cantine Dei, Montemecurio and Canneto. Match the great wines with a luxurious spa vacation by lodging at Hotel Adler, a mere half hour away, with its warm thermal springs, onsite restaurant and avant-garde spa treatments for a taste of La Dolce Vita.

4. Bolgheri, Italy’s Gold Coast, lies just south of Livorno and is widely considered the birthplace of the Super Tuscans. It’s also the home of Sassicaia, one of Italy’s most revered wines. This blend of Cabernet Sauvignon and Cabernet Franc put Bolgheri on the map and ushered in the era of must-drink Super Tuscans. Although the Sassicaia estate, Tenuta San Guido, is closed to the public, nearby Ornellaia is open by appointment—or simply stop in to Enoteca Tognoni, just inside the village walls, for lunch.

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