Tuscany is a region where the past merges seamlessly with the present, offering landscapes of rolling hills, sprawling vineyards, and timeless towns. Whether it's your first visit or one of many, Tuscany never loses its magic. This 3-day Italy itinerary takes you through the heart of this enchanting region, blending scenic drives, historical explorations, wine tasting, delicious good, and immersive cultural experiences. From the art-filled streets of Florence to the medieval wonders of San Gimignano, let's dive into this unforgettable road trip through Tuscany.
Table of Contents
My 3 Day Road Trip Itinerary through Tuscany, Italy
Day One: Florence to Chianti
Dinner in Chianti
Our adventure began with a picturesque drive from Florence to Greve in Chianti, a quaint town surrounded by endless vineyards and olive groves. As you leave the city behind, the landscape quickly transforms into a painter's dream: winding roads lined with cypress trees and hilltop villages that seem untouched by time.
Arriving in Greve by late afternoon, we settled in for dinner at Trattoria Sotto L'Arco, a small family-run restaurant. The traditional Tuscan menu didn't disappoint—starting with the osso buco, a dish made with braised veal shanks, rich in flavor and tenderness. Accompanied by a glass of Chianti Classico, Tuscany's signature wine, the meal was the perfect introduction to the region's culinary excellence. As the sun set, we enjoyed the peaceful atmosphere, a far cry from Florence's bustling streets.
Where to Stay in Chianti: Apartment with Pool on Chianti Hills
Tucked into the scenic Chianti Hills, Agriturismo II Cole was our home for the night. This family-run agriturismo blends rustic Tuscan aesthetics with modern comforts, offering apartments with sweeping countryside views. We were welcomed with a plate of local tagliere misto, including prosciutto, salami, and fresh cheeses, paired with a bottle of their own wine.
The property's peaceful isolation, surrounded by olive groves and vineyards, made it feel like a sanctuary. Framed by panoramic vistas, the pool area became our favorite spot for morning coffee and sunset aperitifs. If you're looking for an authentic Tuscan stay, Agriturismo II Cole's charm will win you over.
Day Two: Chianti to San Quirico
Wine Tasting in Chianti
No visit to Chianti would be complete without delving into its world-renowned wines. We began the day with a tour of Antinori nel Chianti Classico. This cutting-edge winery, resembling a modern fortress amid the ancient vines, was a sight to behold. The Antinori family's six-century-old wine-making tradition was evident in every corner of their estate. The winery tour offered a fascinating insight into how ancient techniques blend with modern technology to produce one of Italy's finest wines, a truly unique and exciting experience.
We then visited Castello di Ama, where wine meets art. This vineyard produces exceptional Chianti Classico and features contemporary art installations scattered across the estate. The contrast between the historic stone buildings and modern art pieces made it feel like walking through Tuscany's past and future simultaneously. Each sip of wine here came with a story, making it a true cultural and sensory experience.
Stop for lunch in Castellina in Chianti
Midday brought us to Castellina in Chianti, a historic town perched high in the hills. Castellina boasts a rich history dating back to Etruscan times. Its medieval fortress and underground tunnel, Via delle Volte, still stand, offering glimpses into its past. After a brief exploration, we stopped for lunch at Panificio Porciatti, a local bakery and deli famed for its fresh ingredients and hearty dishes. Their pappardelle al cinghiale (wild boar pasta) was absolutely divine, and full of earthy flavors that are quintessentially Tuscan.
Castellina is also home to several artisan shops selling handmade ceramics and leather goods, perfect for picking up souvenirs that embody Tuscany's craftsmanship. These shops offer a wide range of products, from intricately designed ceramics to high-quality leather goods. On weekends, don't miss the outdoor market, where you can taste local products like honey, olive oil, and cheeses straight from the producers.
Explore San Quirico d’Orcia
Leaving Chianti, we drove south towards San Quirico d'Orcia, a medieval village in the heart of the Val d'Orcia. This UNESCO World Heritage site is famous for its dramatic landscapes, with rolling hills punctuated by cypress trees and farmhouses. San Quirico itself is a charming walled town with narrow, cobbled streets and historic churches.
We spent the afternoon wandering through Horti Leonini, a 16th-century garden offering beautiful views of the surrounding countryside. Before dinner, we visited La Bottega Di Portanuova, a small shop where local artisans sell their handcrafted goods—perfect for picking up unique souvenirs.
For dinner, we chose Ristorante Fonte Alla Vena. While it came recommended, the food felt a bit underwhelming compared to our earlier experiences. In hindsight, I'd suggest exploring one of the smaller, family-run restaurants in the town center.
Where to Stay in San Quirico: Dimora Del Poggio
We spent the night at Dimora Del Poggio, a quaint apartment in the heart of San Quirico. The apartment was spacious, with a rustic feel that matched the medieval charm of the village. It's an ideal place for those looking to unwind after a day of exploring, with comfortable beds, a well-equipped kitchen, and a cozy living area.
Day Three: San Quirico to San Gimignano
Bagni San Filippo & White Whale Hot Springs
The next morning, we drove to the Bagni San Filippo hot springs, a hidden gem in southern Tuscany. These natural thermal pools, carved into limestone formations, are known for their milky-white waters, giving rise to their nickname, the White Whale. The springs have been used for centuries, dating back to Roman times, and are believed to have healing properties due to their high sulfur content. Soaking in these warm waters, surrounded by the tranquility of the forest, felt like a true retreat.
Exploring Val d’Orcia and Beyond
Our journey continued through the picturesque Val d'Orcia, a region known for its postcard-perfect views of golden fields and cypress-lined roads. The beauty of this region, with its rolling hills and charming towns, was truly awe-inspiring. Along the way, we made a stop in Pienza, a Renaissance town designed by Pope Pius II. Pienza is famous for its pecorino cheese, and we couldn't resist sampling some at a local shop. The views from Pienza's terraces are stunning, stretching out over the valley towards Monte Amiata in the distance.
We also visited Montalcino, home to the renowned Brunello di Montalcino wine. The town's fortress offers panoramic views over the vineyards, and the wine itself is a must-try for any wine lover. A quick stop in Montepulciano, with its ancient streets and charming piazzas, rounded out our exploration of the Val d'Orcia.
San Gimignano
Our final destination was San Gimignano, a medieval town famous for its towering skyline. The 14 stone towers still standing today give the town its nickname, "The Manhattan of Tuscany." As we wandered through its narrow streets, we felt transported back in time. Each corner revealed something new—a bustling piazza, a historic well, or a shop selling local vernaccia wine.
Dinner at Ristorante Bel Soggiorno provided delicious food and an unforgettable view of the rolling Tuscan hills bathed in soft evening light. The restaurant's traditional menu, featuring dishes like bistecca alla Fiorentina, was the perfect way to end our day.
Where to Stay Near San Gimignano: II Defizio
Our last night was spent at Il Defizio, a serene bed and breakfast nestled in the countryside near Gambassi Terme. Its charming garden and peaceful atmosphere made it the ideal place to reflect on our Tuscany adventure. The hosts were incredibly welcoming, making sure every detail of our stay was perfect. If you're looking for a quiet escape after exploring San Gimignano, Il Defizio offers a tranquil retreat.
Day Four: San Gimignano to Florence
Journey Back to Florence
The final leg of our trip took us back to Florence, but not without a few last glimpses of Tuscany's breathtaking landscapes. As we drove through the winding roads, passing vineyards and sunflower fields, we couldn't help but reflect on the incredible experiences of the past three days. With its rich history, world-class wines, and picturesque towns, Tuscany had left an indelible mark on us.
To further inform the rest of your trip to this incredible region, check out our other Tuscany posts!
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