The Chianti region, nestled in the heart of Tuscany, is a land of rolling hills, lush vineyards, and charming villages. Known for its world-class wines, particularly the Chianti Classico, this region offers a perfect blend of natural beauty, history, and culture. The area is dotted with medieval towns, each with its own unique character and attractions. From the bustling markets of Greve in Chianti to the serene landscapes of Radda in Chianti, this itinerary will guide you through the best of what Chianti has to offer.

Chianti's history is as rich as its wines, with roots dating back to the Etruscans and Romans. The region's strategic location made it a battleground during the Middle Ages, leaving behind a legacy of castles and fortifications. Today, Chianti is a haven for food and wine lovers, offering a taste of authentic Italian cuisine and hospitality. Whether you're exploring ancient vineyards, savoring local delicacies, or simply soaking in the stunning views, Chianti promises an unforgettable experience.

Before embarking on your journey, consider flying into Florence, the nearest major city, and renting a car for the most convenient way to explore the region. The scenic drives between villages are an attraction in themselves, offering panoramic views of the Tuscan countryside.

Day 1: Arrival in Greve in Chianti

Afternoon

Arrive in Florence and pick up your rental car. Drive to Greve in Chianti, the gateway to the Chianti region. Check into your accommodation and take a leisurely stroll through the town's main square, Piazza Matteotti, lined with charming cafes and shops. Visit the Wine Museum to learn about the region's winemaking history.

Evening

Enjoy dinner at Ristorante La Cantina, known for its traditional Tuscan dishes and extensive wine list. Try the pappardelle al cinghiale (wild boar pasta) paired with a local Chianti wine.

Day 2: Exploring Greve in Chianti

Morning

Start your day with a visit to the Saturday market in Piazza Matteotti, where you can sample local cheeses, meats, and produce. Then, head to the nearby village of Montefioralle, a beautifully preserved medieval hamlet with stunning views of the surrounding vineyards.

Afternoon

Visit the renowned Castello di Verrazzano for a guided tour and wine tasting. Learn about the estate's history and enjoy a selection of their finest wines. Consider booking a lunch at the estate's restaurant for a farm-to-table experience.

Evening

Return to Greve for dinner at Osteria Mangiando Mangiando, a local favorite offering hearty Tuscan fare. End your evening with a gelato from Gelateria di Piazza.

Day 3: Radda in Chianti

Morning

Drive to Radda in Chianti, a picturesque village surrounded by vineyards and olive groves. Explore the town's narrow streets and visit the Palazzo del Podestà, a historic building with a fascinating history.

Afternoon

Enjoy a leisurely lunch at La Botte di Bacco, known for its creative take on traditional Tuscan dishes. Afterward, visit the nearby Castello di Volpaia for a wine tasting and tour of the medieval village.

Evening

For dinner, head to Ristorante Le Vigne, offering stunning views of the Chianti hills and a menu featuring local ingredients. Try the bistecca alla fiorentina, a classic Tuscan steak.

Day 4: Castellina in Chianti

Morning

Travel to Castellina in Chianti, a charming town with Etruscan roots. Visit the Rocca di Castellina, a fortress offering panoramic views of the countryside. Explore the town's shops and boutiques for local crafts and products.

Afternoon

Have lunch at Osteria del Gallo Nero, known for its rustic Tuscan cuisine. Afterward, visit the nearby Fonterutoli estate for a wine tasting and tour of their modern winery.

Evening

Enjoy dinner at Ristorante Albergaccio di Castellina, a Michelin-starred restaurant offering a refined take on Tuscan cuisine. End your day with a stroll through the town's charming streets.

Day 5: Panzano in Chianti

Morning

Head to Panzano in Chianti, a small village known for its vibrant food scene. Visit the famous butcher shop Antica Macelleria Cecchini, where you can sample local meats and delicacies.

Afternoon

Enjoy lunch at Dario Doc, a casual eatery run by the renowned butcher Dario Cecchini. Try the "Mac Dario" burger, a local favorite. After lunch, explore the village and visit the nearby Pieve di San Leolino, a beautiful Romanesque church.

Evening

For dinner, head to Ristorante Oltre il Giardino, offering a cozy atmosphere and a menu featuring seasonal ingredients. Pair your meal with a glass of Chianti Classico for the perfect end to your day.

Day 6: Wine Tasting and Countryside Exploration

Morning

Spend the day exploring the Chianti countryside, visiting local wineries and vineyards. Consider booking a wine tour with Viator for a guided experience. Small-Group Wine Tasting Experience in the Tuscan Countryside

Afternoon

Visit the charming village of Gaiole in Chianti, known for its beautiful landscapes and historic sites. Have lunch at Osteria Il Papavero, offering traditional Tuscan dishes with a modern twist.

Evening

Return to your accommodation and enjoy a relaxing evening. Consider a light dinner at a local trattoria, savoring the flavors of the region one last time.

Day 7: Departure

Morning

Spend your final morning in Chianti with a leisurely breakfast and a last stroll through the village. Take in the serene beauty of the Tuscan countryside before heading back to Florence.

Afternoon

Return your rental car and prepare for your departure from Florence. Reflect on the unforgettable experiences and memories made during your week in the Chianti region.

Chianti's small villages offer a perfect blend of history, culture, and natural beauty. From wine tastings to exploring medieval towns, this itinerary provides a comprehensive guide to experiencing the best of Tuscany. Whether you're a wine enthusiast, a history buff, or simply seeking a relaxing getaway, Chianti promises a journey filled with unforgettable moments.