Walking in Tuscany

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Period: Any time
Location: Tuscany
What is included: personalized tour with a local natural guide

Walking in Tuscany nature will give you memorable experiences, above all if you travel off the beaten tracks. We rely on local and naturalistic guides who know the territory better than anyone else and will give you a unique and personal look on this amazing region. The number of itineraries are endless, so we will plan a walking tour personalizing it to your needs. Our guide will help you choosing the area and the paths according to your level of training, the duration of the tour, the landscapes you wan to see and the specialty of the territory you want to focus your experience on.

Following are our main areas of interest, but we can organize walking experiences all over Tuscany.


  • AREZZO COUNTRYSIDE. If you pass the most touristic areas of Tuscany, you can discover an amazing countryside made of hills and different landscapes. These areas are not affected by mass tourism, and you can see what Tuscany really is, the genuine soul of this magnificent region. This is the Arezzo countryside. Arezzo is located in the Eastern part of Tuscany, near Siena and the border with Umbria region. Although nowadays Arezzo is not listed among the most famous destinations in Tuscany, it is a real wonder and a hidden spot really worth visiting. Historically speaking it has been very important since Roman times, and it has been the homeland of Giorgio Vasari, Petrarca, Masaccio and has inspired many Italian artists and personalities, like Michelangelo, Leonardo da Vinci and Saint Francis, the patron of Italy. Also contemporary artists and directors have shot many scenes for famous films, such as “Life is Beautiful”, by Roberto Benigni.
    The valleys of Casentino, Valdarno and Valtiberina are the beautiful frames for endless walking tours. Colorful hills, Arno and Tiber rivers, vineyards and olive tree groves, as well as ancient castles, ruins, hermitages and picturesque medieval villages or Renaissance country houses contribute all to create harmonious landscapes.
    HIGHLIGHTS: taste the local products like Pecorino cheese, mushrooms, truffles and chestnuts; taste local wine; Apennines and Pratomagno mountains; visit hamlets and castles; walk on the ancient pilgrimage routes; follow the trails of the Etruscans; Casentino Forests National Park; La Verna and its Franciscan Sanctuary, and much more… Ask us for all the possibilities in the area.
  • VAL D’ORCIA. This valley stretches outside Siena and it is the best example of the perfection of the landscapes, where gentles hills follow one another alternating shiny colors to tenuous shades according to the season. In 2004 it became UNESCO heritage because of the perfection of the redesigning of the landscapes happened during the Renaissance, reflecting the ideals of good governance. This splendid area was celebrated also by the painters of the Sienese School, depicting how people were living in harmony with the nature. Val d’Orcia is known for its famous “Strade bianche“, white gravel roads that twist through the hills and vineyards of the region. Via Francigena crosses this valley too: it is the ancient route that connected Canterbury to Rome during the Middle Age and now it can be walked following the tracks of the pilgrims through hills, country roads and vineyards.
    HIGHLIGHTS: taste the local Pecorino cheese; taste Montalcino and Brunello wine; walk along Via Francigena; walk along “Strade Bianche”; visit Crete Senesi; visit San Quirico d’Orcia, Pienza, Montalcino, and Buonconvento and medieval hamlets, and much more… Ask us for all the possibilities.
  • CHIANTI HILLS. Famous all over the world, the Chianti area is the perfect destination for those who love the typical postcard pictures of the stunning landscapes of Tuscany. Countless hills covered with vineyards and olive groves as wells as enchanting stone little villages and medieval hamlets will give you unforgettable images and experiences to take home. This is the ideal location for a walking wine tour through the Chianti vineyards, tasting all the different Chianti wines, learn about the techniques of production and meeting the producers personally.
    HIGHLIGHTS: taste Chianti wine in different cellars and vineyards; walk through Tuscany countryside and enjoy the beautiful view from the hills; follow the Etruscan trails; visit Castellina in Chianti, Radda in Chianti, Gaiole in Chianti and many more medieval villages scattered through the Chianti hills.
  • SAN GIMIGNANO and MONTERIGGIANO. These two towns are the perfect example of Medieval Italian towns, walled and with many towers still preserved to our days. San Gimignano rises on top of a hill, it has still 13 towers of the 72 built in the fourteenth century, and it has become UNESCO heritage. Monteriggiano is amazing for its walls, the central square and the romantic and historical atmosphere you can breath while walking in the narrow streets of the village. It has become stage number 32 of Via Francigena and the best way to discover these places is to choose one of the numerous paths in the countryside and admire the beauty of the landscapes characterized by vineyards, forests, poppy fields and cypress trees. This area is also famous for Vernaccia wine and olive oil production.
    HIGHLIGHTS: walk along the Via Francigena; taste Vernaccia wine at one of the many family-run vineyards; walk along Elsa river; Colle Val D’Elsa famous for crystal production; discover medieval villages; and much more… contact us to find out all the possibilities.
  • CORTONA and MONTEPULCIANO. These two beautiful medieval towns are located on the two opposite sides of Val di Chiana, a valley situated between the provinces of Arezzo and Siena in Tuscany, and between Perugia and Terni in Umbria. Cortona is considered the best “borgo” in Tuscany, also thanks to the 180°  breathtaking view over the countryside beyond Umbria border. Also from Montepulciano hill you can enjoy an amazing view over Sibillini mounts and, in particularly limpid days, over Gran Sasso National Park in Abruzzo. This area is famous also for the production of DOC wine such as Nobile and Sirah. Take a relaxing walk in thorough vineyards and olive groves to fully recharge with the sounds of nature.
    HIGHLIGHTS: meet the producers and taste DOC wine; discover the traditions of olive oil production and taste the local olive oil; visit Cortona and Montepulciano, Montefollonico, Torrita di Siena, and Lucignano; Lake Chiusi (Tuscany) and Lake Trasimeno (Umbria), and much more.. 

    Extra activities in the same area:

We can personalize your walking tour and help you decide the best itinerary for your interests and level of difficulty. Contact us to find out all the options and ask for a tailor-made tour.