Chianti Wine and Medieval Towns: A 4-Day Adventure in Tuscany Itinerary

Take a day trip to Florence, the birthplace of the Renaissance. Start your day with a visit to the iconic Uffizi Gallery, home to masterpieces by Michelangelo, Leonardo da Vinci, and Botticelli. After immersing yourself in art, enjoy a light lunch at Ristorante Oltre il Giardino, a charming restaurant with a garden setting.

Explore the historic center of Florence, visiting the Duomo, Ponte Vecchio, and the Palazzo Pitti. Take a break with a coffee at Trattoria La Sosta di Pio VII, a local favorite. In the late afternoon, head to the Florence Food Market Tour to discover the city's culinary delights.

Indulge in a gourmet dinner at Ristorante Pizzeria Da Delfina, known for its creative pizzas and seasonal dishes. After dinner, take a stroll along the Arno River, enjoying the romantic atmosphere of Florence at night.

Travel to Siena, a UNESCO World Heritage Site known for its medieval architecture. Begin your day with a visit to the Siena Cathedral, a masterpiece of Italian Romanesque-Gothic architecture. After exploring the cathedral, enjoy a light breakfast at Trattoria da Verrazzano.

Take a guided walking tour of Siena, visiting the Piazza del Campo, the Palazzo Pubblico, and the Torre del Mangia. For lunch, savor the flavors of Tuscany at Osteria Cacio e Pepe, a cozy restaurant offering traditional dishes.

In the evening, experience the vibrant local life at Siena Evening Walking Tour with Dinner. Explore the narrow streets and hidden corners of Siena before enjoying a delicious dinner at a local trattoria.

Embark on a day trip to San Gimignano, a medieval hill town famous for its towers. Start your day with a visit to the San Gimignano 1300, a museum that offers a glimpse into the town's medieval past. Enjoy a light breakfast at La Locanda di Pietracupa, known for its homemade pastries.

Explore the town's narrow streets and squares, visiting the Piazza della Cisterna and the Duomo di San Gimignano. For lunch, try the local specialty, Vernaccia Wine Tasting, paired with a delicious meal at Ristorante Malborghetto.

Before leaving San Gimignano, treat yourself to a scoop of gelato at Gelato Making Class. Then, head back to Chianti for a farewell dinner at Osteria di Passignano, where you can enjoy a variety of Tuscan dishes and wines.

Travel to Lucca, a charming town surrounded by Renaissance walls. Start your day with a Bike Tour of Lucca, cycling along the town's ancient walls and through its historic center. After the bike tour, enjoy a light breakfast at Ristorante Badia a Coltibuono.

Visit the Lucca Cathedral and the Giardino Botanico Garzoni, a beautiful garden with a historic villa. For lunch, try the local olive oil at Olive Oil Tasting in Lucca, paired with a meal at Ristorante Albergaccio di Castellina.

In the evening, attend a Lucca Summer Festival, a music event that attracts international artists. Enjoy the lively atmosphere and the performances before returning to Chianti for a relaxing night.

Take a break from sightseeing and indulge in a Spa Day in Chianti. Enjoy a relaxing massage and the thermal waters of a local spa. After the spa, have a light breakfast at Ristorante La Cantinetta di Rignana.

Learn the secrets of Tuscan cuisine with a Cooking Class in Chianti. Prepare traditional dishes with fresh ingredients and enjoy the fruits of your labor for lunch. After the cooking class, visit a nearby vineyard for a wine tasting and a tour of the estate.

As the day winds down, head to a scenic spot to watch the sunset over the Chianti hills. Enjoy a picnic dinner with local products and wines, savoring the flavors of Tuscany as you bid farewell to this beautiful region.

Spend your last morning in Chianti exploring the Market of Greve in Chianti, a vibrant market where you can find local products, crafts, and souvenirs. Enjoy a light breakfast at Antica Trattoria La Torre.

Visit the Chianti Sculpture Park, an open-air museum that combines contemporary art with the natural beauty of the Chianti landscape. For lunch, savor the flavors of the region at Ristorante Enoteca Borgo Antico.

Before leaving Chianti, take a Cooking Class in Chianti to learn how to make traditional Tuscan dishes. Enjoy the dishes you prepared for dinner, paired with local wines. Raise a glass to the memories you've made in Chianti before heading to your next destination.