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Self-Guided Montalcino Hiking Tour

Self-Guided Montalcino 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 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.
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.

Day 2 Bagno Vignoni  A private shuttle takes you to the Sant'Antimo abbey, Tuscany's most beautiful Romanesque church. We can schedule your shuttle so you can hear Gregorian chants at the abbey. 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.

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  Hike to the castle of Monticchiello for lunch. Later arrive in Montepulciano, home to another great red, the Vino Nobile. Tour the Redi Winery and sample their best vintages. To visit a second winery head to the Cantina Contucci.

Day 5-6 Montefollonico  A three-hour hike takes you to the perfectly preserved hamlet of Montefollonico. With its twisty cobblestone streets, Montefollonico has retained its medieval air. Your tour ends in Montefollonico. 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).

Reserve This Tour Detailed Itinerary

US$ 1,200 per person
(Single Supplement)

Traveling alone?
Join a self-guided tour that has already been scheduled. We can't run self-guided trips for one person, but we may have already booked a self-guided tour that works for you. More info

Group of three?
Tour prices are based on double room occupancy. Groups of three on self-guided trips have two options:
Option 1: Request a triple room. With a triple there is no single supplement. Option 2: Pay a single supplement (US$ 50/night) for the single room.


Any date from March 1 to October 31
6 Days, 5 Nights
Route Rating
Moderate to Challenging: 5-9 miles (8-15 km) per day of hiking with some steep ascents/descents.

Start / Finish
Montalcino / Montefollonico
  • Thermal Baths, Bagno Vignoni
  • Winery tours
  • Montalcino castle
  • Gregorian chants, Sant'Antimo
  • The town of Pienza
  • The hill town of Montepulciano

What's Included
  • All lodging
  • All breakfasts
  • Luggage transfer from hotel to hotel
  • Private shuttle on Day 2 to Sant'Antimo
  • 5 beautiful hikes
  • Route notes and map

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
What if it rains?

On self-guided hiking tours there is no van support. However, we do move your luggage from hotel to hotel. In the event of rain you can catch a ride with us when we move your bags. You can call in the morning and make arrangements for a lift.

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.