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, tour a cheese farm, 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.
​Highlights
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Pecorino cheese farm tour with farm to table lunch
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Guided Brunello winery tour and tasting
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Vino Nobile winery tour and tasting
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Swim in the thermal baths of Bagno Vignoni
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The charming Tuscan hill towns of Montalcino, Pienza, and Montepulciano
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Scenic country walking trails
Price
US$ 1,800 per person, double occupancy
Dates
Email us your dates. We can schedule the tour when you want.
Single Supplement
+ US$ 250 for single room occupancy
Length
6 Days, 5 Nights
Meet / Finish
Florence / Chiusi
Route Rating
Moderate: 4-8 miles (6-13 km) per day of hiking with some steep ascents/descents.
Terms and Conditions >
Daily Itinerary
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.
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Day 2: Bagno Vignoni
We start hiking from the Sant'Antimo abbey, Tuscany's most beautiful Romanesque church. We walk past a castle and ancient quarries on our way to Bagno Vignoni, a thermal spa. Our hotel has a spa center and two thermal pools. Italians believe the hot mineral waters have therapeutic effects.
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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 the perfect Renaissance town.
Day 4: Montepulciano
A scenic hike leads to a family-run pecorino cheese farm. We tour the farm and learn how full cream ewe's milk is lovingly transformed into artisinal cheese. After a farm to table lunch, we hike to the castle of Monticchiello before arriving in Montepulciano. Montepulciano is home to another great red, the Vino Nobile. We tour the Cantucci Winery and sample their best vintages. If wine is your passion two other wineries are just steps from the hotel.
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Day 5 and 6: Montepulciano
A two-hour hike takes us to the perfectly preserved hamlet of Montefollonico. With its ancient stone gates and twisty cobblestone streets, Montefollonico has retained its medieval air. After lunch in a family-run trattoria, we will shuttle you back to Montepulciano in our van. On the last morning of the tour we will drive you to the Chiusi train station which has good connections to Rome and Florence.
Daily Distance
Lodging
Hotel Dei Capitani
Montalcino (1 night)
Situated in the historical center of Montalcino, this 18th Century building has a panoramic pool. Rooms are air-conditioned and offer breathtaking views.
hotel website >
Hotel Posta Marcucci
Bagno Vignoni (1 night)
The main attraction of the hotel is their spa center and two thermal hot springs pools with breathtaking views of the countryside and a castle.
Hotel Corsignano
Pienza (1 night)
The Hotel Corsignano has breathtaking views of the Orcia Valley and offers a terrace with a hot tub. Rooms are quiet, spacious and modern.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Mueble il Riccio
Montepulciano (2 nights)
The Mueble Il Riccio is a small family-run inn just steps away from the town's main piazza. The hotel has a roof top terrace with majestic views.
hotel website >
What's Included
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All lodging (three and four star hotels)
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Winery visit and wine tasting
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Cheese farm tour with lunch
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All breakfasts
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Two lunches
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Private van transfer on Day 1
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Van support on hikes
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Admission to thermal baths
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Five beautiful hikes
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Friendly bilingual tour guide
Departure from Montepulciano
End of Tour
On the last day of the tour you will be driven to the train station in Chiusi (included in your tour price). Chiusi is on a main north/south rail line. Train travel times to Florence and Rome are:
Chiusi to Florence: 1 hr 50 min
Chiusi to Rome: 1 hr 50 min
Want to Save?
Consider one of our self-guided hiking trips. We can schedule a self-guided hiking tour whenever you want March 1 to October 31.
Our Dates Dont Work?
We may be able to offer the dates you want. Email us with the dates you prefer.