Active Adventure

You don't have to be a serious hiker to join this tour. On average we walk 5-6 miles every day with a comfortable pace.
Trip rating 2+ (On a base of 1=easy to 5=strenuous).

Duration: 8-day trip begins in Siena and ends in Chiusi - Chianciano Terme train station that easily connects you to Rome (South) or Florence or Milan (North).

Tour itinerary - Siena - Montalcino - Pienza with escursions

Typical Day

An average day of the trip
On a typical day you hike/walk with your guide in the morning for 3 hours, then we stop at a restaurant or farmhouse for lunch (lunch can last 1hour and half). We serve local food and wines as we believe that food plays an important role in the enjoyment of Tuscany.
In the afternoon there might be some more walking or city stroll. Around 5pm your guide will take you back to the hotel.
Before dinner you will be able to rest a couple of hours.
Dinner will be served in a restaurant in town that you will be able to easily reach on foot. At dinner the guide will not be with you. This is why we planned to have all the hotels in the town centers and pedestrian areas.
Local wine is always included for lunch or dinner. We serve vino della casa (house wine) as the quality of local house wines is very high. Not by chance this part of Tuscany is one of the most famous wine making area in Italy (Chianti Classico, Brunello, Vino Nobile di Montepulciano)

Siena, Torre del Mangia

Age range, type of group

You can sign up for this tour if you are a solo traveler or a couple, family or group of friends.

Sleeping and meals

Accommodation: 7 nights in charming accommodations with beautiful views
Meals: All meals, except 2 dinners, included

Tasting local wines (Chianti and Brunello)


There is no age restriction. You need to have the capability of walking 5-6 miles every day on a rolling hill terrain with some ascent.

Other Information

• Explore the streets, alleys and piazzas of Siena, Montalcino and Pienza.
• Walk in the beautiful countryside of Monteriggioni along a section of the Francigena Pilgrimage route that connects Canterbury (UK) to Rome.
• Hike in the scenic vineyards and olive groves of the Chianti region
• Explore San Gimignano and its many turrets. One of the most fascinating medieval towns of Italy!
• Enjoy two wine tastings and cellar visits at very small producers of Chianti and Brunello wine. You will learn about wine making directly from the owners.
• Walk to the Abbey of Sant’Antimo and listen monks singing Gregorian Chants.
• Taste the specialties such as pici hand-made pasta, ribollita soup or panzanella and experience the pride of the Tuscany people for their recipes.
• Walk to San Quirico d’Orcia through lush wheat fields and rolling hills.
• Enjoy an informal cooking class with Carmela and Samanta.
• Last but not least this tour is a private tour! It means that you can ask us to tailor the tour to your needs.

walking through Chianti vineyards
Starting at:
USD $1,925.00 per trip pp
Reservations & Information
for Tuscany Hilltop Towns Walking Tour May 8-15, 2016
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Travel Dates

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