Tuscany Villas & Vineyards

We meet this afternoon at our base hotel in Florence. If time allows, we'll walk across the Roman city center to the 13th-century cathedral, where we'll climb Giotto's tower for an introductory view of this delightful city. We'll gather in the hotel before walking to dinner together this evening.

We shuttle to Fiesole this morning for a walk to the town’s Franciscan monastery, public gardens and Etruscan ruins. Then we’ll gather picnic supplies and strike out on a 2-hour walk around the amphitheater of hills that ring Florence. It was from Mount Ceceri in these hills that Leondardo da Vinci conducted his experiments in human flight. After a picnic lunch in an olive grove, we’ll continue on to the village of Settignano, where Michelangelo spent his childhood. Dinner on your own this evening, but we’ll recommend some of our favorite trattorie. Today’s walk: 8 km (5 miles).

After breakfast this morning we shuttle south to Passignano, in the heart of the Chianti hills. From there, we’ll walk through some of Chianti’s famous vineyards for lunch together in Montefioralle and then continue on to the main square in Greve, the “unofficial” capital of the region. You’ll have time to enjoy Greve, Giovanni da Verazzano’s birthplace, over a glass of wine. Later in the afternoon we’ll shuttle to San Gimignano for the evening. Dinner on your own tonight. Today’s walk: 14 km (9 miles).

You are free to explore San Gimignano on your own this morning. You will love the fairy-tale feel of this unique village, with its medieval towers and cobblestone streets! After lunch on your own, we’ll lead a walk from town into the nearby hills this afternoon, so you can get some photos back on the famous San Gimignano towers. Dinner together this evening. Today’s walk: 8 km (5 miles).

We walk out of San Gimignano to south and east today toward Colle Val d’Elsa. Those who want can walk the entire way, while we’ll offer a shuttle for those who prefer a shorter walk. After a picnic lunch on your own in Colle Val d’Elsa, we visit the workshop of a crystal engraver. We’ll shuttle on to our hotel in Pienza. Dinner together this evening. Today’s walk: up to 8-16 km (5-10 miles).

This morning you’ll have time to walk around the planned Renaissance town, built by Pope Pius II in the middle of the 15th Century. Have a taste of the famous local pecorino cheese aged under the ashes !! Great supplies for a picnic!! After lunch on your own, we shuttle to San Quirico D’Orcia. Our walk leads us to the Roman baths of Bagno Vignoni. Along the way we’ll enjoy great views of the Orcia valley before heading back to our hotel. Dinner on your own this evening. Today’s walk: 8 km (5 miles).

We head north this morning toward the Abbey of Monte Oliveto Maggiore. Perhaps you’ll recognize the church from the movie, The English Patient. After a visit to the church and its grounds, we shuttle to just outside Siena. Enjoy your final Tuscan picnic before we walk through the countryside near Siena. The red bricks of Siena are so distinctive that medieval travelers named the color we call “sienna” after them. Like Florence, Siena’s wealth grew from commerce. In fact, the city’s shepherds started the first insurance fund, a cooperative venture designed to protect herders against the loss of sheep by natural predators in the nearby hills! Still wealthy, Siena is a wonderful pedestrian city. We’ll enjoy a great farewell dinner together this evening. Today’s walk: 10 km (6 miles).

You are on your own today after breakfast together. What a perfect town to spend an extra few days seeing the sights, or catch a train south to Rome or north to Florence. Whatever you choose, have a great trip!