Tuscany is the kind of place that begs to be explored at a slower pace. Beyond the well-known cities of Florence and Siena, its winding roads lead to mediaeval villages, rolling vineyards, and sun-drenched fields that stretch to the horizon. A road trip is the perfect way to experience the charm of Tuscany, where every turn reveals a hidden trattoria, a quiet hilltop town, or a breathtaking valley untouched by time.
For those planning holidays to Tuscany, the journey itself becomes part of the adventure. Whether it’s stopping at a small village market in Greve in Chianti, tasting fresh pecorino cheese in Pienza, or admiring the golden landscapes of Val d’Orcia, the region’s beauty lies in its details. Exploring by car during Tuscany holidays allows travellers to embrace the rhythm of local life and uncover places that guidebooks often overlook.
Planning the perfect Tuscan getaway is all about balance—between famous sights and hidden gems, scenic routes and leisurely detours. With carefully crafted itineraries and an all-inclusive holiday deal, you can enjoy Tuscany. The packages by online travel agencies like Travelodeal help the explorer to find the best trip.
Start in Florence—A Taste of Renaissance & Local Markets
Begin your journey in Florence, the artistic soul of Italy. But before heading to the countryside, stop by Mercato di Sant’Ambrogio, a local market where Florentines shop for fresh produce, cheese, and handmade pasta. Grab some porchetta (roast pork sandwich) for the road and get ready to explore.
Chianti Wine Region – Vineyards, Castles & Slow Travel
A short drive south takes you to Chianti, Tuscany’s world-famous wine region. But don’t just stop at any winery—venture to Castello di Brolio, a historic castle where Chianti Classico was born. Enjoy a wine tasting with a view, surrounded by mediaeval walls and rolling vineyards.
For a scenic detour, take the Chiantigiana Road (SR222), one of the most beautiful drives in Italy, winding through olive groves, cypress trees, and charming villages like Greve and Panzano.
San Gimignano – The Medieval Manhattan
Nicknamed the “Mediaeval Manhattan” for its towering skyline, San Gimignano is a must-visit stop. Stroll through the cobbled streets, discover hidden courtyards, and climb the Torre Grossa for panoramic views of the Tuscan hills on your holidays to Tuscany. Don’t leave without visiting Gelateria Dondoli, home to the world’s best gelato—their saffron and pine nut flavour is a unique treat.
Val d’Orcia – Tuscany’s Most Photogenic Countryside
As you drive into Val d’Orcia, you’ll feel like you’ve entered a postcard. The landscape here is pure magic—winding roads lined with cypress trees, golden wheat fields, and mediaeval towns perched on hilltops.
Stop at Pienza, a Renaissance town famous for Pecorino cheese. Visit a local cheese shop, pick up a wheel of aged Pecorino Toscano, and enjoy a picnic overlooking the Tuscan countryside. Another gem is Bagno Vignoni, a tiny village with a hot spring-fed mediaeval bath in the main square. It’s the perfect place to soak in the ancient Roman thermal waters.
Montalcino – Brunello Wines & Sunset Views
For wine lovers, Montalcino is an essential stop. This hilltop town is the birthplace of Brunello di Montalcino, one of Italy’s most prestigious wines. Visit a family-run winery, sip on a glass of Brunello, and watch the sunset over the rolling vineyards.
For an off-the-beaten-path experience, hike up to the Rocca di Montalcino, a 14th-century fortress offering stunning views of the surrounding valleys.
The Hidden Roads of Southern Tuscany
Before heading back to Florence, take the long way through Tuscany’s lesser-known countryside. Drive through Monticchiello, a tiny village with stone houses and breathtaking panoramas. Stop at a local olive farm to taste some of the region’s finest cold-pressed olive oil.
End your road trip in Cortona, a charming town perched high above the valley. Wander through its art galleries, cosy cafés, and quiet alleyways, soaking in the authentic Tuscan atmosphere.
Experience Tuscany on Your Terms – The Ultimate Road Trip Awaits!
A road trip through Tuscany is more than just a vacation—it’s a journey into the heart of Italy’s most beautiful landscapes, rich traditions, and unforgettable flavours. From the hidden villages to the vibrant local markets, this adventure is about experiencing Tuscany like a true local.
