Tuscany, Italy

Cycling Tuscany. As you move through Tuscany, you notice cyclists everywhere. There are paved roads that meander through forests and fields, offering vistas that are unparalleled anywhere. Paved lanes give way to gravel as we wend our way through olive groves and forested boundary lands. Olive groves turn to vineyards, with their perfectly spaced rows climbing hillsides and making serpentine patterns that catch the light, then let it go.

Cycling Tuscany is anything but flat or monotonous, but it’s far from a sufferfest dealt out by steep mountain passes to the north and east; cycling in Tuscany is pure bliss, with ear-to-ear smiles to prove it.

Florence, Siena, Montelcino, Montefalco, Val d’Orcia and more. 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 Uffizzi Gallery or Museo Galileo or Brancacci Chapel or any of a hundred 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 hundred hilltop villages that, in and of themselves, are works of art equal to any found in Florence.

From our home base, we’ll venture by ebike and van to hilltop villages in every direction. We’ll explore Siena and learn the importance of its Contradas. We’ll visit Pienza, home to Popes and dignitaries going back centuries, and we’ll explore Montalcino and Montepulciano and Querico and World Heritage Sites including Val d’Orcia. Wineries, monasteries, castles, medieval villages, and so much more beckon us as we cycle and explore from first light to last. And at the end of each day’s adventures, our villa will await, welcoming us to its hearth as it has for so many before us.

A villa of our own. We’ll stay in a fabulous villa in the Tuscan hills between Florence and Siena—in a magnificent mano house surrounded by vineyards and olive groves. Luxuriously furnished bedrooms and private baths provide personal space, while expansive indoor and outdoor common areas invite the group to assemble and share experiences. We’ll enjoy meals prepared in our gourmet kitchen, and we’ll lounge by our private pool or take walks through the gardens. Our home for this week will ground us and nourish us an bring us closer to the Tuscany that those lucky enough to live here treasure. For one lucky week, we’ll call this villa home.