DAY ONE

Located a one-hour drive south of Florence, Siena is Tuscany’s loveliest medieval city. Resting upon three red clay hills, the city has retained its original medieval atmosphere, with steep narrow streets and predominantly Gothic architecture.

Begin your day in the heart of the city, the shell-shaped Piazza del Campo, where the famous Palio horse race between the different districts of the city is run twice a year. Considered one of the most beautiful places in the world, it is paved in red brick, with lines of travertine forming a fishbone pattern. Nearby visit the impressive Duomo, Siena’s magnificent cathedral, with its striped marble façade and detailed marble floor, which is home to an array of beautiful paintings and sculptures.

You will have several options for spending the day in Siena, accompanied by your local guide:

Visit the City Museum, entered from the Gothic courtyard of the Palazzo Pubblico. The museum houses works by the major artists of Siena’s Golden Age, Ambrogio Lorenzetti and Simone Martini.

You might choose the Museo dell’Opera Metropolitana (Cathedral Museum), home to works from the Duomo that include Duccio’s incredible Maestà, the largest painting of the Medieval period, and Giovanni Pisano’s extraordinary life-size sculptures from the cathedral façade.

Explore The Pinacoteca, the city’s museum of paintings, with its complete collection of works by Sienese artists that range from the 13th century through the 17th century.

After lunch at a local restaurant, you’ll continue on to San Gimignano, which is famous for its perfectly preserved medieval structures and 13 of its original tower houses, which are visible along the horizon as you ascend towards the town. Enjoy a leisurely stroll through the main streets, where you’ll browse in the shops and perhaps stop to sample gelato at the renowned gelateria in the main square.

You may also visit the town’s Duomo with its original 14th-century fresco decorations. These frescoes, covering the entire stretch of the nave walls, depict the stories of the Old and New Testaments, and were painted by two artists from Siena.

Before leaving this charming town, view the life of a local saint as depicted by Domenico Ghirlandaio at the quaint chapel of Santa Fina, a jewel of Renaissance art designed and decorated by Florentines Benedetto and Giuliano da Maiano. Continue to the other side of town and take a moment to go into the church of Sant’Agostino, which houses the famous cycle of frescoes by Benozzo Gozzoli telling the story of the life of Saint Augustine.

DAY TWO

When you imagine quintessential Tuscany, no doubt the image is of a rolling landscape with a tracery of cypress trees running along the spine of a hill. A two-hour drive from Florence, the Val D’Orcia is the epitome of this landscape. The golden hills are fields of grain, and the cypress trees often border country roads that lead to charming villages, ancient abbeys, and towns perched atop hills. This is iconic Tuscany. Protected by UNESCO as a World Heritage Site, the Val D’Orcia is recognized as one of the most beautiful landscapes in the world and is an ideal representation of man coexisting in harmony with nature.

Apart from its famous landscape, the area includes five of Tuscany’s most beautiful towns: Pienza, Montalcino, San Quirico D’Orcia, Castiglione D’Orcia and Radicofani. Your guide will meet you at your hotel this morning for a full day of wandering in this lovely corner of Tuscany. Your first stop will be Pienza, a rare example of an ideal Renaissance town designed by Bernardo Rossellino for Pope Pius II. Apart from its magnificent Renaissance architecture, Pienza is famous for its delicious sheep’s milk cheese, Pecorino, the smell of which pervades the town. You will have a chance to sample the incredibly versatile Pecorino Toscano that ranges from a delicate, young soft cheese to a strong-tasting, hard cheese often used in local recipes for pasta dishes but also a perfect accompaniment to the full-bodied wines produced in nearby Montepulciano and Montalcino.

Enjoy lunch in Pienza at a delicious yet simple family-run restaurant that serves dishes made with local produce. Enjoy handmade pastas with olive oil from the region, salamis from the Siena area, Italian cheeses, and specialties including Florentine steak and wild boar.

Continue your day with a drive through the glorious landscape of Montalcino, taking in the views over the Asso, Ombrone and Arbia valleys. Stop at a local enoteca, for a tasting of the region’s world-famous Brunello wine accompanied by delicious local goods. After, if you feel up to it, climb to the medieval fortress, built in 1361 and perched at the top of the town, to enjoy the 360° views that the ramparts command. It is said that this stunning vantage point inspired Leonardo’s bird’s-eye view of the world.

Meander back to Florence, arriving as the sun sets over the Arno, reflecting its many bridges and quayside palaces.

DAY THREE

Set out with your private car and driver early this morning. You will follow the old road that leads out of Florence into Tuscany’s Chianti region, famed for its glorious countryside, excellent, full-bodied wine and rustic cuisine. Learn about the history of the area, which was fought over for centuries by Siena and Florence and is still dotted with castles perched on hilltops, while you enjoy the lovely scenery of woodlands and meticulously tended vineyards.

You will stop in Greve for a coffee in one of the cafés on the main square and have time to browse in the little shops that surround the square. Next continue to your appointment for a cooking class where you will learn to create some of Tuscany’s most famous dishes while preparing a four course meal. This will be your lunch today, accompanied by some of the delicious wine produced on the property.

After lunch if there is still enough energy, stop briefly at one of the other little Chianti villages for a short stroll before returning to Florence.

Dine on your own in Florence this evening.

DAY FOUR

This morning, following breakfast at your hotel, you will have time to explore the city on your own. Transfer to the airport by private car for your return flight, or to continue on to the next leg of your Willing Foot journey in Italy.