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Guided Montalcino Hiking Tour

Guided Montalcino Hiking Tour
One of the most beautiful walks of Italy is in an area called the Val d'Orcia. Lying just south of Siena, this ancient valley of gently rolling hills and scenic villages feels blissfully timeless, its rich history and natural splendor exquisitely preserved. This Tuscan walking holiday takes you on a five-day trek from Montalcino to Montepulciano. We hike on peaceful dirt roads and quiet country footpaths as we explore the best of southern Tuscany. We visit a castle, walk through vineyards, and tour wineries. We swim in the soothing thermal waters of Bagno Vignoni, a Renaissance spa. Strolling down an ancient dirt path on your way to a Renaissance village you will experience Tuscany as it should be, peaceful and astonishingly beautiful.

Day 1 Montalcino  We meet in Florence and shuttle to Montalcino, a picturesque hilltop town brimming with medieval architecture. Montalcino is best known for its Brunello wine, one of the world's best reds. We explore the castle of Montalcino, climbing its high walls for 360 degree views. Optional hike through vineyards and olive groves.

Day 2 Bagno Vignoni  We start hiking from the Sant'Antimo abbey, Tuscany's most beautiful Romanesque church. Before departing we listen to Gregorian chants. We walk past a castle and ancient quarries on our way to Bagno Vignoni, a thermal spa where you can swim or soak in hot spring waters. Your hotel has its own thermal pools.

Day 3 Pienza  The hike to Pienza takes us through rolling fields of corn and wheat. In places the path is still lined with squared-off stones laid by Romans 2,000 years ago. We pass rustic stone farmhouses surrounded by stately cypress trees. Pienza was built in three years beginning in 1459 at the behest of Pope Pius II who decided to transform his birthplace into a utopian town.

Day 4 Montepulciano  A rolling hike leads to the castle of Monticchiello. Later we arrive in Montepulciano, home to another great red, the Vino Nobile. We tour the Redi Winery and sample their best vintages. If wine is your passion two other wineries are just steps from the hotel.

Day 5 Montefollonico  A three-hour hike takes us to the perfectly preserved hamlet of Montefollonico. With its twisty cobblestone streets, Montefollonico has retained its medieval air. Your walking holiday ends in Montefollonico. On Day 6 a private shuttle takes you to the Chiusi train station (on a main north/south train line).

Reserve This Tour Detailed Itinerary

US$ 1,800 per person
($250 Single Supplement)

Tour prices are based on double room occupancy. A single supplement is required for single room occupancy. Please note that in Italy single rooms are frequently smaller than double rooms. Groups of three can book triple rooms and avoid the single supplement.

2018 Dates

October 28-November 2

6 Days, 5 Nights
Route Rating
Moderate:  3-5 miles per day of hiking with some steep ascents/descents.

Meet / Finish
Florence / Chiusi
  • Guided Brunello winery tour and tasting
  • Vino Nobile winery tour and tasting
  • Swim in the thermal baths of Bagno Vignoni
  • The charming Tuscan hill towns of Montalcino, Pienza, and Montepulciano
  • Scenic country walking trails

What's Included
  • All lodging (3-star hotels)
  • Winery visit and wine tasting
  • All breakfasts
  • Two lunches
  • Private van transfer on day one
  • Van support on hikes
  • Admission to thermal baths
  • 5 beautiful hikes
  • Friendly bilingual tour guide

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Dates don't work?
Consider one of our self-guided hiking trips. We can schedule a self-guided hiking tour whenever you want March 1 to October 31.

Have a group of four or more?
With a group of four or more we can schedule a guided tour whenever you want.