Tuscany in Spring

Tour 1: May 9 – 15, 2023
Tour 2: May 17 – 23, 2023

    7 days, 6 nights / Breakfast, lunch, two group dinners included
    $4,850 per person, double occupancy

    • Florence, Italy
    • Gaiole in Chianti, Italy
    • Siena, Italy
    • Montepulciano, Italy
    • Cortona, Italy
    Fully booked

    Small Group Sizes

    Full-Time Van Support

    Fabulous Lodging

    eBikes for All

    Photo Workshops

    Small Group Sizes

    Full-Time Van Support

    Fabulous Lodging

    eBikes for All

    Photo Workshops

    We begin our 2023 Grand Tour in Tuscany because springtime in Tuscany is pure magic. In fact, we love it so much we’ll do it twice; same trip, two back-to-back weeks.

    Our trip starts in Florence, home of the Uffizi Gallery and Michelangelo’s David and Brunelleschi’s Duomo and a million other museums and galleries and enticing places that could take a lifetime to explore. We’ll stay a bit, but soon move southward, climbing quickly into the hills and wending our way towards Siena.

    Florence’s medieval archrival, Siena, is another place worthy of immersion. A special place frozen in time by isolation, it retains the same character that made it a center of Renaissance culture. Its neighborhood Contradas are the foundation of civic pride that bursts forth twice each summer in the running of the Palio, a free-for-all horse race around the Piazza del Campo that has infinitely more to do with rivalry and intrigue than horses and riders. Siena, in all its past and present glory, stands as the beating heart of Tuscany, a crown amongst a field of gems.


    We’ll linger in Siena for a couple of days, then traverse the Crete Senesi, a hilltop ridge that divides the northern Chianti wine region from the southern Tuscan hills. Montepulciano, a hilltop village straight out of the 12th century, will be our home for the next two days, as we loop out and around the region, hopping from one hilltop village to another. The one thing we quickly learn about Tuscany is that there are hundreds of beautifully preserved villages and towns, all of which sit at the top of a hill. The reason that towns were located on high was for fortification and defense, but now they welcome all willing to tackle a climb to the top.

    We wind up our week by rolling into the hill town of Cortona, on the eastern edge of Tuscany. You may leave Tuscany after this Nomads adventure, but we can assure you that Tuscany will stay within you forever.

    Day Zero
    Gather in Florence

    Nomads staff will gather in Florence on the afternoon of May 8 (Tour 1) or May 16 (Tour 2) at the Horto Convento Hotel located just across the Arno River from the historic heart of Florence. Though this evening is not an official part of the trip, guests are welcome to connect with us at the hotel; we’ve made arrangements just in case and, space permitting, a room may be available for you. Take in a museum, visit the Duomo, or just relax and prepare to explore Tuscany, the first stage of our amazing journey.

    Day One

    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.

    Day Two
    Florence to Gaiole in Chianti

    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.

    Day Three
    Gaiole in Chianti to Siena

    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.

    Day Four

    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.

    Day Five
    Siena to Montepulciano

    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.

    Day Six

    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.

    Day Seven
    Montepulciano to Cortona

    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.

    2023 eBike Nomads Tours

    Tuscany in Spring

    Florence to Cortona
    May 9 – 15 and May 17 – 23, 2023

    Bohemian Rhapsody

    Passau to Prague
    June 14 – 21, 2023

    Dolomites, Dolomites

    Valbruna to Treviso
    September 2 – 8, 2023

    Shakespeare to Alps

    Verona to Lienz
    May 23 – June 3, 2023

    Danube and Alps

    Vienna to Klagenfurt
    August 16 – 23, 2023

    Tuscany in Fall

    Florence to Cortona
    September 13 – 19, 2023

    Alps to Amadeus

    Lienz to Passau
    June 5 – 12, 2023

    Finding Slovenia

    Klagenfurt to Kranjska Gora
    August 25 – 31, 2023

    Umbria in Fall

    Perugia to Orvieto
    September 21 – 26, 2023
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