Self-Guided
Montalcino Hiking Tour
A hiking tour in Italy should include beautiful trails, charming hotels, a dash of history, and great local food. Our Self-Guided Montalcino Hiking Tour combines all of these ingredients to create an exceptional walking holiday in southern Tuscany. Quiet trails lead to a 14th Century castle, a Renaissance thermal spa, and a walled medieval hamlet. Along the way you enjoy traditional Tuscan cuisine made from the freshest local ingredients. Wild boar sauce, spelt soup, and beef brazed in red wine are among the local specialties. Hike through the vineyards that produce some of Italy’s finest red wines, the Brunello di Montalcino and the Vino Nobile di Montepulciano. The trails have few tourists and offer spectacular views of the countryside. Strolling on quiet paths you will experience the best of Tuscany.
​Highlights
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Thermal baths at Bagno Vignoni
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Winery tours
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Montalcino castle
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Hiking quiet unpaved farm roads and trails
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Breathtaking scenery
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Optional pecorino cheese farm visit
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The hill towns of Montalcino, Pienza, and Montepulciano
Price
US$ 1,450 per person, double occupancy
Dates
Any date, Mar 1 to Dec 1
Single Supplement
+ US$ 250 for single room occupancy
Length
6 Days, 5 Nights
Start / Finish
Montalcino / Chiusi
Route Rating
Moderate to Challenging: 2-8 miles (3-13 km) per day of hiking with some steep ascents/descents.
Terms and Conditions >
Daily Itinerary
Day 1: Montalcino
Travel on your own to Montalcino (busses depart from Siena). Montalcino is best known for its Brunello wine, one of the world's best reds. 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
A private shuttle takes you to the Sant'Antimo abbey, Tuscany's most beautiful Romanesque church. Hike past a castle and ancient quarries on your way to Bagno Vignoni, a thermal spa. Swim or soak in the soothing hot waters. Your hotel has its own thermal pools.
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Day 3: Pienza
Your walk to Pienza takes you 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. Walk past 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
Visit a pecorino cheese farm (optional). Hike to the castle of Monticchiello for lunch. Later arrive in Montepulciano, home to another great red, the Vino Nobile. Tour the Tolosa Winery and sample their best vintages. To visit a second winery head to the Cantina Contucci.
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Day 5 and 6: Montepulciano
A four-hour loop hike takes you to the perfectly preserved hamlet of Montefollonico. With its twisty cobblestone streets and ancient gates, Montefollonico has retained its medieval air. Your tour ends in Montepulciano. On Day 6 a private shuttle (included in the tour price) takes you to the Chiusi train station (on a main north/south train line).
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 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.
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.
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.
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.
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
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All breakfasts
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Luggage transfer from hotel to hotel
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Private shuttle on Day 2 to Sant'Antimo
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Private shuttle to Chiusi train station at tour's end
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Five beautiful hikes
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Route notes and map
Departure from Montefollonico
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
Self-Guided Hiking in Italy
Explore Southern Tuscany at your own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates. We take care of the details.
Can I really start any date I want?
Yes! You can start your tour any day of the week, March 1 through December 1. We have complete flexibility with the starting dates.
Why Southern Tuscany?
Southern Tuscany is quieter than Chianti. You can tour ancient wineries, soak in thermal waters, and visit a cheese farm.