The Experience

Ancient Footpaths in Medieval Italy

Tuscany must be experienced up close. Taste the Brunello. See the bread toasted in a stone fireplace, glistening with freshly pressed olive oil. Look out over the Arno River winding through the patchwork landscape. Walk on the gently sloping hills of the Val d’Orcia to ancient hilltop towns. Smell the wild cypress and rosemary. Stroll through the vineyards and olive groves of Chianti. Let your eyes linger on timeless villas and imagine the possibilities. There is no better – or closer – way to experience Tuscany.

Unforgettable rambles though the Chianti Classico wine region, blanketed with vineyards and olive orchards

Enjoy a warm welcome at Agriturismo Il Rigo for an authentic pasta making demonstration

Discover the World Heritage site of Siena, where medieval architecture meets contemporary culture

Explore classic hill towns including Pienza, Radda, Gaiole, Panzano and Greve

Join a wine expert to sample a variety of the San Felice estate wines and other regional vintages


Days 1-2 From the hamlet of Monticchiello, discover the picture-perfect landscape of the Val d’Orcia Have a look around Renaissance-style Pienza, Pope Pius II’s utopian village, perhaps stopping to try the superb local pecorino cheese In springtime, the surrounding hills provide a backdrop of emerald green, while in the fall, hay bales turn the landscape a brilliant shade of gold Sample a variety of regional vintages at our hotel’s exclusive tasting room Follow a quiet route up to the majestic Castello di Brolio, where Baron Bettino Ricasoli formulated the modern method of producing Chianti Classico in the 19th century.

Days 3-4 Explore the heart of the Zona del Chianti From Radda, amble through pristine vineyards and pine forests en route to Gaiole in Chianti, the center of Chianti Classico wine country Learn the secrets of Tuscan cuisine at an exclusive cooking demonstration Head into the Chianti countryside and walk from one castle to the next Take a break in Vertine’s cozy piazzetta to enjoy a cappuccino and observe the friendly pace of local life In Panzano, learn of ancient recipes and the region’s finest meats at Dario Cecchini’s renowned macelleria.

Days 5-6 In the Elsa River valley, get a feel for the Colli Fiorentini (Florentine hills), where expansive vineyards and wildflower fields greet you at every turn Stride along the crest to Montefioralle, birthplace of Amerigo Vespucci Hike hilly roads through oak forests and along ridges offering sweeping views that once inspired Renaissance artists.


The Route

Start with our vacation planner so we can match you with our most suitable travel advisor. We do it all for you, air, car, accommodations, tours, you name, it in a seamless luxury vacation experience you will treasure for a lifetime.