ALL FOODIES DREAM of a vacation in Tuscany — the challenge is figuring out where to go. Stretching across roughly 8,900 square miles, the region is vast and its wines and cuisine are irresistible, so narrow your itinerary to avoid spending every hour driving rather than lounging under the Tuscan sun with a dry red and pecorino.
First things first: to truly explore the countryside you’ll want to rent a car, which is easy to do in Florence. If you’d like an evening or two near Tuscany’s art-soaked capital before heading into the hills, consider a stay at Villa la Massa. This 5-star property is close enough for easy access to Florence’s museums, leather market and landmarks like the Ponte Vecchio and Michelangelo’s David, yet removed enough to offer a taste of rural life. Lush gardens surround the hotel, which overlooks the Arno River. Start the day with charcuterie, pastries and espresso on the restaurant patio, relax by the pool with an Aperol spritz, and finish the night with grappa or a Negroni at the cozy Medicean Bar.
Aperol spritz at
Villa la Massa © KELLY MAGYARICS
About an hour-and-a-half drive from Florence lies Montepulciano, a medieval and Renaissance hilltop town in the province of Siena. The walled city sits prominently above the surrounding countryside, a region celebrated for pork, pecorino, lentils, pici (a wide, hand-rolled pasta) and Vino Nobile, a Sangiovese-based wine that’s dry, structured and age-worthy. The historic center is best explored on foot—parking is outside the walls—so consider staying nearby at Agriturismo Nobile. This working farm and winery, a short walk from town with splendid views, offers five bedrooms, several one- to three-bedroom apartments and a separate cottage called La Casina. Apartment Stalla is especially inviting, with a large kitchen and communal hardwood table; all accommodations feature local details like brick arches, terracotta floors and exposed stone. The pool is perfect for hot afternoons, and the owners provide conveniences such as a barbecue area, laundry facilities, an on-site restaurant and shuttle service to town.
In town, reserve a sunset table on the terrace at Osteria del Borgo and enjoy pici with cinghiale (wild boar) or bistecca alla Fiorentina. Montepulciano’s wine lists are filled with high-quality local reds—choosing any should serve you well—but ordering a liter carafe of the house red is a reliably satisfying option. After dinner, stop by Caffè Poliziano for gelato in classic flavors like fiordilatte, nocciola IGP and stracciatella.
Of course, wine is a major draw. Consider Rosso di Montalcino the region’s everyday “house red,” Brunello di Montalcino a step up, and Vino Nobile di Montepulciano among the top-tier local wines. All these wines are made primarily from Sangiovese; what distinguishes them are the vineyards, aging requirements and appellation rules. Do not confuse Vino Nobile di Montepulciano with Montepulciano d’Abruzzo, which refers to a different grape and region east of Rome.
About 15 minutes from Agriturismo Nobile is Villa S. Anna, a small family-run winery where Simona Fabroni and her daughters produce a noteworthy Vino Nobile that is seldom exported. Contact them ahead to arrange a tasting and cellar visit—many vintages are stored there for decades. Their Chianti Colli Senesi is praised for freshness and ease, and they suggest enjoying it slightly chilled as a delightful aperitivo or poolside patio wine.
For a contrasting experience, drive an hour west to Castello Banfi. Perched on a hill amid vineyards and cypress trees, the estate is an impressive setting for tastings and tours. Banfi helped popularize Brunello di Montalcino in the 1970s, and today it produces a wide range of acclaimed Italian wines. Daily tours typically include tastings of still and sparkling wines, grappa, extra virgin olive oil and the local salsa in the enoteca. Lunch at La Taverna offers multi-course menus with optional pairings or à la carte choices like beef carpaccio, duck ravioli or eggplant cannoli. If time allows, visit the bottle and glass museum to see artifacts dating back centuries.
End a day in Montepulciano with a relaxed dinner at Osteria del Conte. The welcoming staff often recommend regional classics—tagliatelle with porcini, rosemary-grilled pork chops and caramel panna cotta—that appear simple but deliver layered, satisfying flavors. These dishes capture the essence of the region: straightforward ingredients treated with care and respect.