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Hike & Wine

Hiking experience with wine tour in the best wine regions of Tuscany and Umbria, hiking in their stunning nature and tasting the best wines.


Spend a day hiking through the rolling Tuscan hills and visiting a small and family-run winery. Enjoy the lunch enjoying beautiful views and pairing with delicious Tuscan wines and olive oil.




  • Private hiking experience in Tuscany and Umbria suitable for anyone
  • Guided tour by an English speaking guide
  • Private winery visits, private tastings and bespoke experiences with the local producers
  • Enjoy a traditional Tuscan lunch in a winery with wines pairing and extra virgin olive oil tasting
  • The stunning rolling hills and the picturesque hill towns





Hiking in Tuscany and Umbria is an extraordinary lifetime experience to enjoy the stunning views of the wine country and for enjoying some of the best Italian wines.


From the hiking in the Chianti wine country in between Florence and Siena, to a trekking experience in the Brunello wine region in Montacino following the Francigena itinerary. From hiking in the Montepulciano wine region to the Cortona wine country, up to the Trasimeno lake wine district and the Umbrian wine regions of Montefalco and Orvieto. These are the wine regions where we offer guided hiking experiences with wine and food tours.


After meeting your tour guide in the morning, tour begins following your guide along the itinerary studded with farms, vineyards and olive trees groves, you will lose yourself in spectacular landscapes discovering gorgeous views of the most beautiful countryside with plenty of stops for photos and for recharging the energies.


Going up and down the Tuscan hills, we will then stop visiting a small and family-run winery that produces excellent extra virgin olive oil too. Cellar tour will give you the chance to learn all about the winemaking activities and aging methods, for then passing to taste the extra virgin olive oil and their wines pairing with a delicious lunch based on a traditional menu, enjoying authentic Italian cuisine.


Siesta! Time to rest now breathing the family-style atmosphere of the winery and retaining the best memories of your hiking adventure in Tuscany.

Activity available in:

  • The hiking experience with wine tour is a private activity available in Montalcino, Montepulciano, Cortona, Chianti near Florence, Chianti near Siena, San Gimignano, Pienza, Val d’Orcia area, Arezzo, Perugia, Assisi, Orvieto, Trasimeno lake area and with transportation from all the main tourist sites of Tuscany and Umbria.



  • approximately 6-8 hours



  • English speaking tour guide
  • Head office assistance and insurance coverage
  • Complimentary water
  • Winery visit with wine and olive oil tasting
  • Traditional Tuscan lunch at the winery (vegetarian menu is also available)
  • Transportation with qualified and professional English speaking driver and luxury vehicle Mercedes-Benz or equivalent (optional)

Via Francigena: It is an ancient road and pilgrimage route running from Canterbury in England, through France and Switzerland, to Rome. In medieval times it was an important road and pilgrimage route for those wishing to visit the Holy See and the tombs of the apostles Peter and Paul. Today people still follow the ancient itinerary and travel on foot, on horseback or by bicycle on the Via Francigena; the part in Tuscany is considered one of the most beautiful and enjoyable for seeing the iconic Tuscan countryside, with soft rolling hills scattered with cypresses, gravel roads stretching as far as the eye can see and a  horizon filled with more and more beautiful landscapes.


Tuscany Wine Regions: Located in central Italy along the Tyrrhenian coast, Tuscany is home to some of the world’s oldest and most famous wine regions: Chianti, Brunello di Montalcino and Vino Nobile di Montepulciano primarily made with Sangiovese grape whereas the Vernaccia grape is the basis of the white Vernaccia di San Gimignano. Tuscany has forty-one Denominazioni di origine controllata (DOC) and eleven Denominazioni di Origine Controllata e Garantita (DOCG). In the 1970s a new class of wines known in the trade as “Super Tuscans” emerged. These wines were made outside DOC/DOCG regulations but were considered of high quality and commanded high prices. Many of these wines are based on a “Bordeaux-blend” and became cult wines. Others very well reputed Tuscan wine regions and Tuscan wines are Cortona, Morellino di Scansano and Carmignano. Tuscany is also known for the dessert wine Vin Santo, made from Trebbiano and Malvasia grapes.

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