Begin your stay at Hotel Le Renaie, a warm, family-run hotel located 4 miles (6.5 km) from San Gimignano. In the evening, your guide will host a welcome meeting to discuss the upcoming week, provide insights about the local area, and address any questions.

Prepare for a day rich in history and nature as you explore a popular Via Francigena section connecting Gambassi Terme to San Gimignano. This ancient pilgrimage route stretches from Canterbury to Rome, though your section is a gentle walk through olive groves and vineyards. In the afternoon, visit an eco-friendly wine estate near Certaldo for a sensory wine experience paired with traditional appetizers.

Dinner is back at the hotel, where you can unwind, play billiards, or enjoy another glass of local wine on the terrace overlooking the garden.

Distance Covered: 9 km / 6 miles

This morning, immerse yourself in the rich history of the Chianti region as you take a scenic circular walk through woodlands, offering stunning views of emerald-green vineyard valleys. In the afternoon, take the opportunity to explore more of the area and join an optional tasting of the famous chianti classico at a local winery, where the region's flavors come alive.

Distance Covered: 8 km / 5 miles

After breakfast, you head to the heart of Siena for a day of exploration. You can have ample time to visit the city's numerous museums, marvel at the stunning duomo (cathedral), and relax at an outdoor café in Piazza del Campo, famous for the Palio horse race. Please note that shoulders should be covered when entering the cathedral. You can also explore boutiques offering local products and Italian fashion. In the afternoon, deepen your wine knowledge with a one-hour Tuscan lecture at the Tuscan Wine School. Led by a local expert, this educational experience provides insights into Tuscany's essential wines, offering a detailed look into their history, techniques, and legends rather than just focusing on tasting.

Distance Covered: 8 km / 5 miles

Today, you can relax by the pool, or if you prefer, your guide can recommend local activities like Chianti wine-tasting tours, cooking classes, or renting an e-bike or Vespa. They can also help with unguided walks or planning day trips.

Today's destination is Florence, the birthplace of the Italian Renaissance, where many greats like Leonardo da Vinci, Michelangelo, and Botticelli lived or passed through. You can explore the city's highlights by joining a free local tour. If you join a morning tour, you can have time to visit the Uffizi Gallery, home to masterpieces like Botticelli's The Birth of Venus and Caravaggio's Medusa. It's advisable to book tickets online in advance to avoid long lines—around 2 pm is ideal if you take the morning walking tour. Tickets can be purchased at www.uffizi.it/en/tickets.

Distance Covered: 4 km / 2 miles

After transferring to the charming hamlet of San Donato, walk through farmland toward Montauto, eventually reaching the medieval town of San Gimignano. This short walk takes about three hours. The afternoon is free for exploring the town, including visits to the 13th-century Palazzo Comunale, home to the Pinacoteca, and the 177ft (54m) Torre Grossa. You can have time to wander and absorb the town's atmosphere. Before the farewell dinner, visit the family-run Cesani estate, enjoying an expertly led tasting, sampling your way through three glasses accompanied by bruschetta, extra-virgin olive oil, and a selection of Tuscan cheeses and charcuterie.

Distance Covered: 10 km / 6 miles

The trip concludes after breakfast. Say goodbye to Hotel Le Renaie and start your journey home.