Tuscany: Medieval Villages and Cinematic Wines

Introduction

Imagine yourself traveling through golden fields where gently rolling hills stretch to the horizon, dotted with medieval villages that seem to have emerged from a film. Tuscany is a breathtaking dream where history, art and gastronomy converge in perfect harmony. Each village tells a story, each village is a delight, and every glass of Chianti is an ode to the Italian terroir. In this itinerary, you will embark on a sensory journey through the beauty and culture of this magical region.

Prepare to be greeted with warm smiles and aromas that awaken the senses. Tuscany is full of hidden treasures, from the lush vineyards of Chianti to the charming squares of Siena. This carefully curated route is designed for those who seek not just to visit, but to truly live Tuscany.

Must‑experience moments

• Wine tastings at Chianti vineyards
• Explore the medieval towers of San Gimignano
• Stroll through the enchanting city of Siena
• Photograph the breathtaking landscapes of Val d'Orcia
• Visit historic Florence and its world‑class museums

Day 1 — Arrival in Florence and cultural strolls

At 2:00 PM you land in Florence, the jewel of the Renaissance. After checking in to your elegant hotel, pick up a map and allow yourself to be carried along the city's charming cobblestone streets. The fresh scent of baked bread and the perfume of cypresses in the air invite you to explore. Walk to the Piazza della Signoria, where the statue of Michelangelo's David awaits your admiration. Listen to the sounds of daily life, the laughter of locals and the clink of wine glasses.

In the evening, immerse yourself in Tuscan cuisine at Antico Ristorante di’Nerone, where dishes such as pici with ragù and the famed Chianti awaken your palate. Textures and flavors dance across your taste buds as you prepare for the adventures to come.

Day 2 — San Gimignano: the town of towers

After breakfast with a view of the Duomo, at 9:00 AM head to San Gimignano, the town famed for its 14 medieval towers. Upon arrival, breathe in the fresh hilltop air and hear the bells ringing across the town. Wander the historic center, a UNESCO World Heritage site, and admire the medieval architecture. Pause at Gelateria Dondoli, acclaimed as one of the best in the world, and taste the Vernaccia wine gelato — an explosion of flavor.

In the afternoon, visit a local winery to sample Vernaccia wines. Feel the texture of the wines, hear the stories of passionate winemakers, and admire the stunning valley views. The colors of sunset illuminate the landscape, creating a cinematic scene.

Day 3 — Pane e Vino: a day in Chianti

Begin the day at 8:00 AM with a visit to the local market in Greve in Chianti. The scent of artisan cheeses and fresh bread fills the air. After a simple breakfast, embark on a wine tasting experience. At 10:00 AM, visit renowned estates such as Castello di Verrazzano and sample the region's full‑bodied reds and refreshing whites.

In the afternoon, stroll through the vineyards, observe the harvest and immerse yourself in the rich winemaking culture. With each sip you taste the winemakers' passion reflected in soft tannins and aromatic notes, celebrating Chianti's unique terroir.

Day 4 — Siena: the enchanted medieval city

Free yourself from morning stresses with a leisurely coffee, and at 9:00 AM make your way to Siena. The vibrant atmosphere of the Piazza del Campo, home to the famed Palio horse race, awaits. Explore the narrow lanes and discover shops of local craftsmanship.

In the afternoon, visit Siena Cathedral with its intricate details and magnificent façade. Feel history reverberate as you walk through this sacred space, and don’t miss the chance to climb the Torre del Mangia for unforgettable views of the city and beyond.

Day 5 — Val d'Orcia: breathtaking landscapes

After breakfast at 8:00 AM, depart for Val d'Orcia, a postcard‑perfect landscape. Rolling fields of wheat and iconic cypress trees make you feel as though you are in a film. Visit Pienza, renowned for its pecorino cheese, and enjoy an alfresco lunch savoring local specialties while the sun bathes the valley.

In the afternoon, stop at a winery and indulge in a Brunello tasting while listening to the winemakers' stories. Feel the gentle breeze and the tranquility of this magical place, where time seems to stand still.

Day 6 — Cortona: Tuscan charm

On the sixth day, after a refreshing breakfast, at 9:00 AM explore Cortona, the charming town that inspired the film “Under the Tuscan Sun.” Wander its stone streets as you discover boutiques and local cafés. Enjoy the aroma of espresso and ask the locals about Tuscan traditions.

In the afternoon, ascend to the Sanctuary of Santa Margherita and relish spectacular views of the surrounding countryside. Feel the energy of the place and let yourself be carried by the town’s calm, welcoming rhythm.

Day 7 — Farewell in Florence

On your final day, savor breakfast at a traditional café and complete your last purchases. Reserve time to visit the Uffizi Gallery and admire works by Da Vinci and Botticelli. Each brushstroke tells a story that echoes through the centuries.

With your heart full of memories, it’s time to bid farewell to Tuscany. At 4:00 PM board your flight, carrying with you the essence of Tuscany and the promise to return to this enchanting paradise.