DAY 1

Check in Hotel Siena Countryside

DAY 2 - Chianti

Our day offers an exquisite loop ride through the rolling hills of Chianti, with its wooded groves and hilltop vineyards. Our morning drive through the beautiful vineyards of Chianti takes us to Brolio Castle. The estate is still home to the descendants of the Baron Ricasoli, “inventor” of the blend of grape varietals that make up the now-famous Chianti Classico appellation. You will have a chance to sample some of the estate’s famous reds while partaking in a delicious lunch of homemade pasta with cinghiale (wild boar), the regional specialty. After lunch we'll visit the well-known villages of Gaiole and Radda, and after that we're in for treat: we've been specially invited to a private tasting in one of the region's top wineries, complete with a million euro view across the Chianti landscape. We won't give away any more details, however, lest we ruin the surprise!

Towns to explore: Gaiole in Chianti, Radda in Chianti

Vineries: Barone Ricasoli, Capannelle

DAY 3 - Val D'Orcia

From the hotel we drive to tiny San Quirico d'Orcia, arriving in time for lunch at the cozy trattoria Il Vecchio Forno. We will get then to Pienza in time for a gelato or a glass of wine with a local Pecorino cheese before heading to Montepulciano where we will visit one of the oldest vinery in Italy: Redi. Have you tried the famous Florentine T-bone steak? Dinner tonight is at La Grotta restaurant, whose meat is the talk of the town.

Towns to explore: San Quirico, Pienza, Montepulciano

Vineries: Redi

DAY 4 - Cortona, Lucignano

On today's drive we'll see some of the most stunning scenery of the week as we drive up to the Etruscan town of Cortona. We will explore the town and find the best spot for our lunch. After lunch we drive down to one of the largest vinery of Tuscany: Avignonesi. On the way back to hotel we stop in the charming town of Lucignano.

Towns to explore: Cortona, Lucignano

Vinery: Avignonesi

DAY 5 - San Gimignano, Florence

Getting out of Chianti you'll head to San Gimignano. San Gimignano or the “medieval Manhattan” can be spotted from the distance: its bringing tall towers profile (now 17 but once were 72!) make it one of the most amazing skylines in the world. Standing astride the pilgrims route from Canterbury to Rome it prospered in the thirteenth century: San Gimignano has retained all its old streets, its walls, gates, palaces, strongholds and seventeen towers. After lunch we reach the nearby cellars of Antinori where we have been granted access to the normally off-limits cellars of Solaia, Tignatello and Badia a Passignano and we'll enjoy a glimpse of the famous Tuscan light streaming over these exclusive vineyard before heading to the heart of Renaissance: Florence.

Towns to explore: San Gimignano, Florence

Vinery: Antinori