Tuscany, Italy

Birthplace of the Renaissance. We’ll gather for the start in Florence, but we’ll quickly relocate south to the Tuscan hills. Florence is filled with word-class museums and galleries that showcase its place as birthplace of the Renaissance. We urge you to spend a few days before or after our trip in Florence, to visit the Uffizi Gallery or Museo Galileo or Brancacci Chapel or the many other significant places that house great works of art and architecture because time is short and we won’t be spending much time there. Our journey will instead take us to the Tuscan countryside and a hundred hilltop villages that, in and of themselves, are works of art equal to any found in Florence.

Two nights in Gaiole in Chianti. At the end of our first ride through the Tuscan hills south of Florence, we’ll glide into Gaiole in Chianti and our home for the first two nights. Gaiole in Chianti is pure charm, offering all the amenities we want, without the crowds of Florence. Technically, we’ll be staying just outside of town—in a converted castle! We’ll explore other amazing towns and villages, and eventually head farther south to Siena. The area between Florence and Siena is the Chianti region (yes, this is home to Chianti wine), the most lushly vegetated and, probably, the hilliest part of Tuscany. What we’ll quickly learn about it is the simple fact that the hillsides, planted with vineyards and olive groves over most of it, are beautiful beyond description. To be here is, likewise, good fortune beyond belief.

Two nights in Siena. Siena stands as a special city among many special places in Tuscany. Formerly a powerful city-state, Siena’s history dates to 900 B.C. as an Etruscan settlement. Siena’s wealth and importance during Medieval and Renaissance periods resulted in the construction of fantastic abbeys, monasteries, churches, and municipal buildings, many of which remain in use to this day. By the dual effects of Black Plague and defeat at the hands of the Spanish in the 16th century, Siena entered an extended period when growth came to a halt and its society turned inward.

But this is a case where hardship came with a golden lining. Siena’s stasis held development in check, resulting in a present city center that is a magnificent living museum. Its revival as one of Italy’s premier cities owes much to its twist of fate. Step into Siena and you step back in time. It’s architecture and citizens hold the past as one holds a precious relic. We are so very fortunate that they have taken such care… and that they share it with us.

Two nights in Pienza. On leaving Siena, we point our bikes towards Pienza, another gem Tuscan hill towns. Our ride takes us along the famed Cresta Sinese, a winding ridge that separates the Chianti region to the north from the Tuscan hills to the south, leading us to our home for the next two nights. Within moments of arrival, we’ll understand why Pienza and the broad Val d’Orcia have earned designations as World Heritage Sites.

We’ll make time to visit a living monastery in a fairytale forest setting, plus Montelcino, San Querico d’Orcia, and dozens of other small towns and villages that surround our Pienza base. On our second morning, we’ll continue our exploration of this incredible area, making our way east to Montepulciano for our last night of this trip.

Final night in Montepulciano. Home to Popes and other dignitaries going back centuries, Montepulciano is the quintessential Tuscan hill town, with narrow, winding lanes leading ever higher to its church and plaza. We’ll reserve time to explore the town, then will gather for a farewell dinner. Tomorrow we leave Tuscany, ever more understanding of what has earned this place one of the most coveted of all European vacation destinations.