• Duration

    5 days / 4 nights

  • Location

    From Montalcino to Montepulciano

  • Length

    40 Km of classic Tuscany

  • Price

    From 500 € / Person

The Val D’Orcia is a marvelous landscape of never-ending hills, grain fields, and streams, with rich clay and tufa soils; it is today the real icon of Tuscany, a natural setting of extraordinary beauty that has become known all over the world as the classic Tuscan landscape.

This tour will take you to a 40 km of route framed by medieval villages, churches and Abbeys, hilltop towns with narrow streets and beautiful landscapes, inviting local food and superb wines.


Departure from Montalcino

Start your visit to Montalcino at La Rocca. The fortress commanding the town, from which views are spectacular.

Rolling sunny hills, picturesque olive groves, scenic country roads and vineyards as far as the eyes can see.
Take a stroll in the historic centre, its churches, stairways and alleys will take you back in time to distant fascinating periods.
Wine is present in every corner and aspect of Montalcino, from cellars to room wines, restaurants and shops, you will smell the floral, fruity, spicy and wood odors of the Brunello wine everywhere.
Enjoy a gourmet dinner with local delicious fresh products and afterwards, relax in your charming room, have a nice hot shower and a good night’s rest before your tour starts.

Extra night! Add an extra night in Montalcino and visit the Sant’ Antimo Abbey

Day 2 – Montalcino to San Quirico d’ Orcia

Visit the historical center of Montalcino and explore the local crafts and products, you can also stop at the old town wine shop for a tasting of the superb wines of the areA. The hike from Montalcino to San Quirico will be between vineyards and grain fields.

The perfect trail for quiet contemplation that will provide a wonderful frame of outstanding natural beauty. In San Quirico, and after a rest, visit this small, absolutely charming town with its beautiful buildings and fortified walls, shops, restaurants and cafés. There is a lot to see, the Collegiata Church, Palazzo Chigi, Church of San Francesco, Santa Maria Assunta and Horti Leonini just to mention a few..


11.5 Km / 7.5 Mi


Day 3 – San Quirico to Pienza

On route Vignoni Alto and Bagno Vignoni. The hike from San Quirico to Pienza will be absolutely stunning, you will first get to Vignoni Alto, a small fortified borgo dating back to XI Century, from here you will admire a breathtaking panorama of the whole Val D’orcia.

Following the route to Pienza, you will make another stop at Bagno Vignoni, esteemed thermal locality, a place of extreme beauty with a characteristic small chapel dedicated to St. Catherine built in the center of the porch overlooking a termal pool.

In Pienza, one of the most famous and beautiful hill top towns of the entire Tuscany, Visit the square and historical buildings, Palazzo del Comune, Palazzo Vescovile, Palazzo Piccolomini and the Duomo, after this hike, it will be necessary a super dinner at a nice, local Osteria.


13.5 Km / 8.6 Mi


Day 4 – Pienza to Montepulciano

This hike will get you passing through typical Tuscan farmhouses, beautiful open landscapes towards Mount Amiata.

Stop at Monticchiello, a small borgo perched on top of a hill and known as the balcony of the Valdorcia, it retains a truly gothic fascination. After Monticchiello, straight to Montepulciano, a town built along a narrow ridge of limestone, surrounded by an imposing city wall, famous for its renaissance architecture.

You will visit the Piazza Grande, Duomo, Palazzo Pubblico and others. Have also time to taste the “Nobile di Montepulciano”, the town’s winemaking symbol.


12.8 Km / 7.2 Mi


Day 5 – Departure

Before you leave Montepulciano make sure you put the cherry on the top of your Walking Tour of Tuscany.
After this tour you will enjoy recovering your energy. With a glass of a good red “Nobile di Montepulciano” in your hand, take the pleasure of a hydromassage in the thermal waters, whose therapeutic and healing properties have been enjoyed since Roman times.

Then let the memories of this Tour come back to your mind… A unique, unforgettable experience!

We hope you enjoyed your Tour !


  • 6 people
  • 500
    per person
  • 4 nights accommodation with breakfast
  • Luggage transfer
  • Detailed map and travel information
  • GPS data
  • Taxes and VAT
  • 4 people
  • 550
    per person
  • 4 nights accommodation with breakfast
  • Luggage transfer
  • Detailed map and travel information
  • GPS data
  • Taxes and VAT
  • 2 people
  • 590
    per person
  • 4 nights accommodation with breakfast
  • Luggage transfer
  • Detailed map and travel information
  • GPS data
  • Taxes and VAT




  1. :

    What is included in the price of the tour?
    – 4 night accommodation with breakfast
    – Luggage transfer
    – Detailed map and travel information
    – GPS data
    – Taxes and VAT

  2. :

    Are all taxes included in the prices?
    Yes – there are no hidden extras.

  3. :

    How can I make a reservation and when should I book?
    You can make a reservation on this website. Our tour depart any day from March 15th to Oct 31st. We recommend to book in advance, however, reservations must be made at least 7 days before departure date.

  4. :

    Can I pay when I get to Italy, direct to your company representative ?
    No, the total expense of the Tour must be paid before the tour start

  5. :

    Can you book a hotel for me before or after my tour?
    Yes, contact us

  6. :

    How many people will I be travelling with?
    Our walking tours are designed for a minimum of 2 people and multiples of 2 travelling.
    It will be your personal Tour and therefore you will be on your own.

  7. :

    Do you accept groups ?
    Yes, we are happy to accept groups on our tours. Discounts are available, check out the prices table or email for more information.

  8. :

    Where does the tour depart from?
    The Tour is scheduled to depart from Montalcino and arrive to Montepulciano. In the event that you need to invert arrival/departure points, that will be possible.

  9. :

    How do I get to the Tour departure point and leave from the arrival point ? Do you pick up from airports, train stations or hotels ?
    You should get to the departure point and leave from the arrival point by yourself, however, if you need a transfer, please email us to get our prices.

  10. :

    How much luggage can we bring on the tours ?
    Your luggage will be transfered from one hotel to another, it is allowed one full-sized suitcase per person, extra pieces will have extra charges.

  11. :

    Can we leave our extra luggage with you?
    Yes, we have a secure deposit for our clients to leave their extra luggage, please email us to get our prices.

  12. :

    Will it be easy for me to get an evening meal?
    Your accommodation will be within easy walking distance of a Trattoria or Restaurant so you’ll be able to taste the renowed wines and delicious tuscan cuisine.

  13. :

    What should we wear?
    For most of the time, you will be biking amidst nature, we recommend you bring suitable clothing and footwear for your tour, including waterproof clothing when touring during spring and autumn

  14. :

    Should we take out travel insurance?
    Yes, We highly recommend it.

  15. :

    What is your cancellation policy?
    Click here to view full terms and conditions.

  16. :

    I’ve missed my tour, can I get a refund?
    Like other tour operators we cannot be responsible if you miss your tour and full cancellation charges will apply.

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