ALL FOODIES DREAM of a vacation in Tuscany — the challenge is figuring out just where to go. Stretching 8,900 square miles, the region is as vast as its wines and cuisine are irresistible, so you’ll want to narrow it down lest you spend all your time in the car navigating rather than lounging under the Tuscan sun sipping a dry red and nibbling on pecorino.

First things first: If you really want to see the countryside, you’ll need to rent a car, which you can easily do in Florence. If you care to spend an evening or two adjacent to Tuscany’s capital in all her art-soaked and leather market splendor before venturing further out, consider booking a room at Villa la Massa. The 5-star property lies just close enough to make the city’s museums, restaurants and sights like Ponte Vecchio and Michelangelo’s David accessible yet removed enough to give you a taste of the bucolic lifestyle. Lush gardens surround the hotel, which overlooks the Arno River. Begin the day with a breakfast of charcuterie, cheese pastries, a mimosa and espresso on a patio table at its restaurant Verrocchio, while away a few hours in the pool with an Aperol spritz, and savor a nightcap of grappa or a Negroni at the cozy Medicean Bar.

Aperol spritz at
Villa la Massa © KELLY MAGYARICS

Continue on about an hour-and-a-half ’s drive to the town of Montepulciano, a medieval and Renaissance town in the province of Siena. You can’t miss it since the walled city sits higher than anything else in the area — an area renowned for its pork; cheese; lentils; pici (a hand-rolled wide pasta similar to spaghetti); and Vino Nobile, a Sangiovese-based wine that’s dry, grippy and age-worthy. The town itself isn’t navigable by car. (You’ll need to park outside the wall — if you can even find a spot.) But you won’t need to drive there at all if you check into Agriturismo Nobile. Located a stone’s throw from town (with a splendid view), this working farm and winery rents five bedrooms, five one- to three-bedroom apartments and a separate cottage dubbed La Casina. Apartment Stalla, especially inviting, boasts a large working kitchen with a communal hardwood table; all apartments feature local décor including brick archways, terra cotta-tiled floors and exposed stone walls. The pool beckons during hot summer afternoons, and owners offer niceties like a barbecue area, washing machine and drying racks, on-site restaurant and free shuttle service to and from town.

Book a table in town on the terrace at sunset at Osteria del Borgo and settle in for a plate of pici topped with cinghiale (wild boar) or bistecca Fiorentina. It’s oh-so-fun to peruse the wine list and see so many bottles of red produced within just a few miles (don’t worry, it’s all but impossible to select a bad one), but it can be even more satisfying to order a liter carafe of the house red, sure to beat anything you can find back home. You’re in Italy, so save some room for a few scoops of gelato at the coffee bar at Caffe Poliziano in flavors like fiordilatte, nocciola IGP of Piedmont and stracciatella.

Ice cream is nice, but you most likely came to explore the vino. Think of Rosso di Montalcino as the region’s “house red”; a step up in quality is Brunello di Montalcino, and the highest quality is Vino Nobile di Montepulciano. (Just like Chianti, they are all made from the Sangiovese grape; what differentiates them is where the grapes are grown, how long they are aged and other legal qualifications.) And none should be confused with Montepulciano d’Abruzzo, a grape hailing from a region east of Rome.

A 15-minute drive from the agriturismo lies Villa S. Anna, a small, charming winery operation owned by Simona Fabroni and her daughters, Anna and Margherita. They make an amazing Vino Nobile that’s rarely exported, making it even more special. Email or call to let them know you are coming, and they will taste you through their offerings and even show you their cellar, featuring bottles dating back decades. When you find something you like (and you will), buy it, because you probably can’t get it at home. The winery produces a Chianti Colli Senesi, hailing from what most consider the region’s second-best subzone after Classico, thanks to its high-quality soil. Fabroni calls it easy and fresh and perfect chilled as an aperitif. (Can you say “patio wine by the pool”?)

For a much different winery experience, drive an hour west to Castello Banfi. Up on a hill surrounded by vineyards and tall cypress trees sits an impressive structure and grounds practically made for your Instagram story. Banfi Vintners introduced Brunello di Montalcino to consumers in the 1970s; today the company is known for a vast portfolio of stellar Italian reds. Book one of the daily tours held at 11 a.m. or 4 p.m. and taste the still and sparkling wines, grappa, extra virgin olive oil and Salsa Etrusca in L’Enoteca. Afterward, lunch at La Taverna, where you can enjoy a 3-, 4- or 5-course meal with or without wine pairings, or select from à la carte dishes like beef carpaccio, duck ravioli with carrot cream and eggplant cannolo. If you have a few minutes, breeze through the bottle and glass museum, with artifacts dating back to the fifth century B.C.

And for a laid-back ending to the day, dine in the casual dining room at Osteria del Conte back in Montepulciano. Its warm and welcoming staff may recommend tagliatelle with porcini mushrooms, rosemary-seasoned grilled pork chops and caramel panna cotta. Deceptively simple yet complex in flavor, these dishes define the region itself.