Your trekking adventure begins with an overnight stay in Florence, the home town of Michelangelo. After you arrive and check in at your hotel, take some time to wander through Florence's historic city center. Depending on your arrival time, options include: - Visit the Duomo, the cathedral dedicated to Santa Maria del Fiore, and the adjacent Baptistery with its famous bronze doors; - View world-famous art at the Uffizi Gallery (advance tickets recommended); - Stroll along the Arno River and explore shops in the Ponte Vecchio, a bridge dating back more than 650 years; - Admire the sculptures in the Loggia dei Lanzi, a real open-air museum. If you are arriving by car, you may wish to detour to Pisa and Lucca before heading to Florence. Your total driving time will be approximately 1.5 hours.

This morning, you'll travel by bus or drive yourself to Radda in Chianti, where you will stay for two nights. The trip will take you about 1.5 hours. Then, it's time to hit the trail. From the village, the route crosses vineyards and olive groves on an old mule track through the Tuscan countryside. In the evening, enjoy a relaxing dinner in Radda in Chianti.

Today you'll travel by bus to Panzano, a 20-minute trip, and trek from there back to Radda in Chianti. You'll pass through the village of Volpaia, built in the 11th century as a fortified village on the border between Florence and Siena. Walking Time: 5 to 6 hours Elevation Gain: 1,642 feet (500 m) ascending, 1,476 feet (450 m) descending

If you are driving, consider making a detour to the medieval town of San Gimignano before heading to Siena and San Quirico. The bus trip will take about an hour, and a detour to San Gimignano will take approximately three hours. You'll spend the day visiting Siena on your own. Options include: - People-watch in the seashell-shaped Piazza Del Campo, site of the annual Palio horse race; - Visit the 13th-century Palazzo Pubblico (Town Hall) to see its famous frescoes and climb its clock tower; - Explore Siena's Cathedral and view the art treasures in the Museo dell’Opera - Metropolitana del Duomo, the Cathedral's museum. After your day in Siena, you'll travel by bus or rental car to San Quirico d ́Orcia. The trip will take about an hour.

From your hotel, you'll trek to the Val d'Orcia (Orcia Valley) a UNESCO World Heritage Site. After a short climb, you'll have a great view of the valley of oaks and vineyards with the citadel of Ripa d'Orcia and Monte Amiata, the highest point in southern Tuscany, in the background. You'll descend through the vineyards and, if you wish, cool off at Bagno Vignoni, a spa town with a Roman pool in its main square. As you head back to San Quirico, you'll go through the forest, sheltered from the heat. Walking Time: 4 to 5 hours Elevation Gain: 1,642 feet (500m) ascending and descending

Today you'll hike from your accommodation to Pienza, rebuilt in the 15th century in the humanist spirit of the Renaissance and listed as a UNESCO World Heritage Site. Spend some time in Piazza Pio II (Square of Pope Pius II), Pienza's central square, which is surrounded by four important buildings: the Cathedral of Santa Maria Assunta, the Municipal Palace, the Borgia Palace, and the Palazzo Piccolomini. After exploring Pienza, you'll head back to San Quirico by bus. Walking Time: 3 to 4 hours Elevation Gain: 1, 148 feet (350 m) ascending / (492 feet (150 m) descending

Today you'll take a 10-minute bus ride to Pienza and hike through one of the most famous areas in Tuscany to discover the fortified village of Monticchiello. Spend some time exploring this tiny medieval walled town. Next, you'll visit the village of Montepulciano, known for its wines and built on a peak of Monte Poliziano. After your hike, you'll return by bus to San Quirico d'Orcia, the endpoint of your trip. Walking Time: 4 to 5 hours Elevation Gain: 656 feet (200 m) ascending, 328 feet (100 m) descending