We assemble on this first morning at the Florence train station, then ferry by van to our bikes at our start point in the hills to the south. Following a proper bike fit and a shared lunch, we’ll head out for a short ride through the countryside to our first night’s lodging, Hotel Le Pozze Di Lecchi, in Gaiole in Chianti.

Dinner this first night will be a time to get to know each other better and to share what each person hopes to take home from their time in this magical place. As the sun sets over fields and vineyards, the golden glow will give us a hint of the treasure that is Tuscany.

Our destination for today is Siena, but we won’t be taking the direct route. Rather, we’ll meander and wander in all directions, visiting fabulous hilltop towns such as Radda in Chianti and Castellini in Chianti along the way. What we will have learned by the end of this day are two important things: Every town is at the top of a hill, and between those hills are endless vineyards and olive groves that paint a landscape unlike any other. In all, our 25-mile ride will lull us into a serenity, a sort of hypnotic state of calm that is Tuscany’s magic trick played upon us. But this magic is good, as all magic should be.

Siena stands as a special place 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, most of which are 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 of stasis and its society turned inward.

But this is a case where hardship came with a golden lining. Siena’s challenges held development in check, resulting in 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.

Our second day’s ride continues the charms of the first, this time winding into the hills to the west. We’ll spend more time in forests and open vineyards and less in hilltop villages, but the beauty and wonder will be no less.

Our lodging for our two nights in Siena will be Il Chiostro del Carmine, located a short walk to the historic Piazza del Campo. Dinners will be on your own or you can join us at the Nomads table.

We leave Siena today and point or bikes towards Montepulciano, on the eastern end of the Tuscan hill region. Home to Popes and other dignitaries going back centuries, Montepulciano is the quintessential Tuscan hill town, with winding lanes leading to its church and piazza anchoring the upper-most place. Our route takes us across broad, open fields, through vineyards renowned for the wines they produce, and down narrow, forested lanes. Our ride endpoint on this day is Abbazia di Monte Oliveto Maggiore, a century-old monastery that is still active, but graciously welcoming travelers. We’ll load bikes there, spend some time exploring, then drive the remainder of the way to Montepulciano.

On our second day, we’ll travel a loop through the heart of Tuscan landscape, crossing the famed Val d’Orcia, designated as a UNESCO World Heritage site, then proceeding on to Pienza and as many other medieval hilltop villages as we can muster. One thing about Tuscany is for certain: each village is unique and there’s never a reason not to explore at least one more.

Our lodging for the these two evenings is Il Dobile di Montepulciano, in the heart of the medieval city. Dinner each night is on your own or you can join us at the Nomads table.

Today, we’ll drop out of the hills into the broad Val di Chiana abutting the Umbria region to the east. Landscapes, agriculture, colors, and temperatures change as we move forward. On the south end of the valley, low forested hills rise, the landscape changing again. Partway up lies the hilltop village of Panicale, our destination for this evening.

On this, our final day of the trip, we’ll join for a shared dinner, recount favorite memories, and give thanks for the opportunity to have spent the previous week in such a beautiful place and amongst new friends. Tomorrow, we’ll finish up with either a short ride or drive to Chiusi, where we’ll find a quaint but busy train station ready to whisk you off for your next adventure.