We assemble on this first official day of our trip at 11:00 AM to gather our Nomads clan, get a proper bike fit, share a first lunch, then head out for a short 24-mile ride into the hills north of Florence. On our way out, we’ll navigate to the sculpture plaza with the replica statue of Michelangelo’s David (and much, more), cross over to Brunelleschi’s Duomo, an architectural marvel of its time, then exit the busy tourist district. We’ll find quieter lanes in the countryside, then loop back to our start along the Arno River. With a mid-afternoon return to our hotel, you’ll have time to explore Florence before we gather to share a dinner. Tonight, we begin to form bonds with our fellow Nomads; tomorrow, we start our journey through Tuscany.

Today, we head south into the Chianti region of Tuscany. We’ll have breakfast, load our gear on the van, hop onto our bikes, and head straight into the formidable hills that rise to the south of Florence. As is our custom, we’ll travel on smaller lanes and paths and go cross-country on unpaved roads wherever possible. As Nomads, we seek out authentic places, off-the-beaten-path places, places where locals wonder where we came from… and where we’re going.

Our 43-mile ride will take us through the village of Gaiole in Chianti, to a nearby hilltop castle now converted to a beautiful country inn. Castello di Tornano, dating back to the 11th century, defines what is unique about Tuscany. Both are a living dichotomy: ancient and modern, fortified and welcoming. They speak clearly of our past, inviting us to feel history, which is what we’ll find all through Tuscany, so long as we take our time and accept the gifts offered.

There should be time following arrival to rest, take a swim, or explore the castle grounds. Dinner is on your own, or you can join the “Nomads Table,” a place where the Nomads team will welcome any who wish to join.

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 is 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. The only exceptions are the intermittent patches of deep green forest that stand as emcees to introduce the next celebrity. In all, our 40-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.

Our lodging for this night and the next will be either Il Chiostro del Carmine (week one) or Pensione Palazzo Ravizza (week two), both within a short walk to the historic center of Siena. Siena is a feast, and you will want to start consuming its delights as soon as possible. Dinner will be on your own or you can join us at the Nomads table.

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, 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 decline; its 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 much the same as it was centuries ago. Architecturally, it 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.

We also continue our explorations of the Tuscan countryside today, as we set out for a 30-mile ride into the hills and fields northeast of Siena. Our route mostly holds to off-road paths but finishes on one of Tuscany’s most famous stretches of pavement, the Crete Senesi. With endless fields falling away north and south, this roller-coaster ridge demarcates the geographic boundary between the Chianti wine region to the north and the Tuscan hill country to the south. Of course, all we’ll care about is the sheer joy we experience as we roll along.

We’ll return to our hotel with plenty of time to allow you to resume your exploration of Siena. Dinner is 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 hills region. Home to Popes and other dignitaries going back centuries, Montepulciano is the quintessential Tuscany hill town, winding lanes leading to its church and piazza anchoring the upper-most place. Our 46-mile ride takes us across broad, open fields, through vineyards renowned for the wines they produce, and down narrow, forested lanes. We’ll have a choice of riding steadfastly the entire route, or taking part of the day to visit a fabulous monastery just off our route. Either way, this day will etch itself into our memories as a hallmark event. The best of Tuscany… and on a bike, no less.

Our lodging for this evening and the next is the Il Rondo Boutique Hotel (week one) or La Terrazza di Montepulciano (week two). Both provide ready access to explore the town at your leisure. Dinner is on your own or you can join us at the Nomads table.

Using Montepulciano as our base, we’ll set off today on a large loop to the west. The terrain will change constantly as we ascend steep hills, drop into valleys, and cross the famed Val d’Orcia region. Val d’Orcia, designated as a UNESCO World Heritage site, is an agricultural landscape that retains much of its Renaissance layout, character, and aesthetic. It is quintessential rural Tuscany.

Our planned 54-mile route also takes us to other important Tuscan hilltop villages, including Pienza and Montalcino, where we can pause, linger, or pass by with a glance. How many miles we ride, or how many cities we explore will be decided by the group’s interest of the day, with no bad choices. Our van is always nearby and ready to shuttle us forward if we choose the latter.

We’ll likely arrive back at our hotel late in the day, so a short rest may be all that we can accomplish before dinner. On this, our last night together as a Nomad clan, we’ll share a meal and stories and talk of our return. Oh, yes… you will return.

We’ll share one last breakfast, toss our gear in the van one last time, and head out on our bikes for a final 23-mile ride. 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 other side of the valley, we find the train station in Camucia or the hillside town of Cortona, setting for the movie “Under the Tuscan Sun.” We end our trip here, allowing you to catch a train north or south, or shuttle back with us to Florence. However you leave us, we’ll be glad for having had you as part of our Nomad clan for this short week in one of the most beautiful places on Earth.