On the Wine Road — A Tuscan Road Trip Following the Scent of Wine

If you want to experience Tuscany at its most Tuscan, rent a car in Florence and set out on a road trip through the beautiful small towns nearby. Across rolling hills, vineyards and cypress trees spread out like a painting, a romantic journey awaits: discovering charming towns tucked into every corner and savoring the wines of Tuscany.

Words & Photos Parc Jinmyoung
In collaboration with * Booking.com
* For this trip, we traveled with Booking.com’s Connected Trip, which offers an integrated travel experience covering flights, accommodation, transportation and activities. The heart of the service is the seamless link between bookings, itineraries and payments in the Booking.com app. Like a personal travel guide, it also impressively suggests tailored travel products based on your past trips, current location and interests. If you need to change a reservation or have a question, you can handle it right inside the app.

How to Travel Through Tuscany, a Land of Abundance, by Car

Tuscany is a destination that offers not only beautiful natural scenery but also small towns, each with its own character. Florence and Pisa, centers of Renaissance culture; Siena, which preserves the prototype of the medieval city; Chianti, Tuscany’s leading wine-producing region; and Arezzo, one of the filming locations of “Life Is Beautiful” all belong to this region. A road trip between Tuscan cities, driving through endless vineyards and olive groves, is one of the best ways to take in the region. You can drive from Rome to Florence and stop in several cities along the way, or choose a route that explores the countryside around Florence.
Tuscan roads are generally wide and not heavily trafficked, so they are manageable for travelers behind the wheel, but don’t forget that Italy has some of the strictest speed enforcement in Europe. It is also notorious for issuing speeding fines that target travelers in rental cars. With many hidden enforcement cameras, it is wise to strictly follow speed limits and other traffic rules even on country roads. The most important thing to watch out for is the ZTL (Zona a Traffico Limitato). These are restricted traffic zones set up in the centers of Italian cities, where only authorized vehicles may enter during designated hours. Entering a ZTL carries a fine of about 100,000 won. To avoid Italy’s rigorous enforcement, we recommend the navigation app “Waze,” which alerts you in real time to speed cameras and ZTLs. With ZTLs, however, the app only shows their locations and does not provide detour guidance, so extra caution is needed. If your hotel is inside a ZTL, the safest approach is to ask the hotel in advance how to get your car in.

Tuscan Town 1. Gaiole in Chianti

Travel through Chianti, between Florence and Siena, and you will come across images of a black rooster everywhere. The symbol comes from a legend tied to the long territorial dispute between Florence and Siena, which were city-states in the Middle Ages. Today it serves as the certification mark for authentic Chianti Classico wine, produced under strict regulations. Chianti Classico must contain at least 80 percent Tuscan Sangiovese, be aged for a minimum of 12 months, and strictly prohibits blending with white varieties. Gaiole in Chianti, a small village in the heart of the Chianti region, offers ideal conditions for growing Sangiovese, which is sensitive to moisture and cold. Its vineyards, laid out along the slopes, drain well, get long hours of sunlight, and sit on a varied mix of soil layers. If you want to properly taste a Chianti Classico, with its red fruit and violet aromas enveloping the palate, head to one of the area’s historic wineries. Well-known options include Ricasoli 1141, where you can enjoy a traditional winery with a castle as its backdrop; Marchesi Antinori, with its modern yet elegant winery facilities; and Castello di Volpaia, known for its impressive organic philosophy.

Where to Stay
Borgo Casa al Vento
After about 20 minutes of driving along the foothills from the center of Chianti, vineyards suddenly appear, stretching vastly across the hills. You have arrived at Borgo Casa al Vento, an agriturismo (farm stay). From its 26 rooms you can enjoy beautiful views of the Tuscan hills, and the on-site restaurant serves traditional Tuscan dishes made with fresh local ingredients. There is an outdoor pool overlooking the vineyards, along with a range of activities such as winery tours, wine and olive oil tastings, and cooking classes, so there is never a dull moment all day long.

Price: About €200 per night

Address: Loc. Casa Al Vento, 53013 Gaiole in Chianti SI

Website: www.borgocasaalvento.com

Tuscan Town 2. Montepulciano

On the road across the Tuscan plain toward Montepulciano, a walled town atop a hill soon comes into view. Red terracotta roofs and weathered limestone buildings still show off their medieval grandeur, standing proud and majestic. Built on a hill about 600 meters above sea level, Montepulciano has a distinctive charm, where medieval alleys blend with Renaissance architecture. Start your visit at Montepulciano Cathedral, at the highest point of the town, and Piazza Grande, its heart. Tasting Vino Nobile di Montepulciano, known as the “noble wine,” is another pleasure not to be missed. Made from Tuscany’s Sangiovese grape, this wine has earned a reputation as a premium wine: nobles and popes have long enjoyed it, and it was the first wine in Italy to receive DOCG status (the highest classification for protected designation of origin). Visit wineries full of character, from Avignonesi, with a history stretching back to the 16th century, to Boscarelli, small in scale yet world-renowned, and Cantine Dei, which offers a unique wine tour combining music and art, and taste Montepulciano wines with their distinctive balance of acidity and structure.

Where to Stay
Agriturismo Merigge Wellness & Spa Montepulciano
This small agriturismo has just four rooms and sits about a 10-minute drive from the center of town. A broad field of lavender and a small vegetable garden line the path between the rooms and the garden, while vineyards stretching along gentle hills on the other side complete the scenery. The rooms are housed in a traditional Tuscan building with thick stone walls and a terracotta roof, and wooden furniture and vintage accents combine to create a simple yet elegant atmosphere. Lunch features traditional Tuscan dishes made with ingredients harvested from the garden, and an Italian-style spa program using lavender is also available. Reservations are required.

Price: About €300 per night

Address: Via di Montenero 36, Cervognano, Montepulciano

Website: www.agriturismomerigge.com

Tuscan Town 3. Montalcino

Arrive at the center of Montalcino, a village about 564 meters above sea level, and the view before you will captivate anyone, especially at sunset. Look down over vineyards rolling like waves across the hills, with cypress trees drifting through them, and time itself seems to slow into a calm, peaceful ease. Montalcino sits on a hilltop between the Val d’Orcia and Monte Amiata. Its high elevation made it a vital defensive stronghold in the Middle Ages. Besides the antique atmosphere typical of a medieval walled town, Montalcino is known as the home of the world-famous Brunello di Montalcino wine. The large difference between day and night temperatures gives the grapes high sugar levels and produces wines of deep flavor. The wine shops and wineries scattered around town also draw wine lovers to linger.

Where to Stay
Borgo Canalicchio Sopra Relais
This agriturismo is run by Brunello di Montalcino Canalicchio di Sopra, a historic Montalcino winery. The space builds on the winery’s tradition, handed down through generations since 1962. Five two-story rooms cluster around an outdoor swimming pool surrounded by vineyards and olive groves. Each room is named after a wine made here, and the interiors blend the coziness of the Tuscan countryside with modern elegance. The suite’s floor was reclaimed from the large oak barrels once used for winemaking in the 1960s and 1970s. Every room is stocked with Canalicchio di Sopra wine, so settle in and enjoy a leisurely glass that carries the terroir.

Price: About €200 per night

Address: Località Canalicchio Di Sopra, Montalcino

Website: www.canalicchiodisoprawinerelais.com/