Walking in Val d’Orcia: Montepulciano to Siena

Val d'Orcia walking tour

Walking in Val d’Orcia: Montepulciano to Siena


From $695USD




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Discover beautiful renaissance villages on this mesmerizing 8-day self-guided walking tour

Explore the Val d’Orcia, one of the most beautiful natural areas in Tuscany.

Trek through cypress-lined hills, rolling vineyards, and sunset-lit fields on your journey.

Walk through ancient medieval towns and learn about the region’s impressive history.

Stay in family-run accommodations and dine on world-renowned Tuscan cuisine.

The Walking in Val d’Orcia: Montepulciano to Siena walking tour is an excellent way to immerse yourself in Tuscany’s most beautiful landscapes and get in touch with Tuscan culture, history, and cuisine through walking and trekking.

The Walking in Val d’Orcia: Montepulciano to Siena Tour begins in Montepulciano, a Renaissance town with exciting history. Make sure to take in the views of the countryside before walking to Pienza, a UNESCO World Heritage site. Here, Renaissance architecture and delicious cheeses and truffles welcome you. After your first taste of Tuscan delicacies, you’ll walk to Bagno Vignoni, a region of picturesque rolling hills and cypress trees.

Next, your self-guided walking tour through the Val d’Orcia takes you to Sant’Antimo, where you can explore an isolated abbey in a unique setting. Next, walking through the famed Brunello wine country takes you to Buonconvento. The classic Tuscan landscape makes every view incredible, and the final hike to Siena is inspiring in its beauty.

The Val d’Orcia walking tour from Montepulciano to Siena is full of inspiring beauty and Tuscan charm, so don’t wait to book your visit!

Walking in Val d’Orcia: Montepulciano to Siena Tour Itinerary

Day 1 Arrival in Montepulciano

This walking tour through Tuscany begins in the idyllic Renaissance hill town of Montepulciano. A first look at the iconic Tuscan views can be enjoyed over dinner at one of the great restaurants.

Overnight Location
Hotel in Montepulciano

Day 2 Walk to Pienza

Take a moment to admire the San Biagio church before following a calm trail out of the village. Once you make it to Montichiello, take some time to enjoy lunch or a cup of cappuccino before completing the walk to Pienza.

Overnight Location
Hotel in Pienza
4 hours, 14 km, 384m elevation gain

Day 3 Walk to Bagno Vignoni

Pienza is a UNESCO World Heritage site, so make sure you fully immerse yourself in the Renaissance architecture. Sample truffles and pecorino before departing to Bagno Vignoni. The walk through this region is picturesque, with oak woods, rolling hills, and lovely villages. Bagno Vignoni also has a thermal bath area, which is perfect for a dip on nice days.

Overnight Location
Hotel in Bagno Vignoni
4 hours, 12 km, 197m elevation gain

Day 4 Walk to Sant’Antimo

Today’s walk through the Tuscan countryside is a little more strenuous but passing through the untamed countryside to reach Sant’Antimo is an exciting journey. Sant’Antimo is an isolated abbey, and you can explore the historical setting to your satisfaction before being transferred to Montalcino for the night.

Overnight Location
Hotel in Montalcino
6 hours, 14 km, 227m elevation gain

Day 5 Walking to Buonconvento

The famed Brunello wine region is the site of today’s walk! Pass through postcard-worthy olive groves and vineyards as you make your way towards Buonconvento, where you should most definitely sample a glass or two with dinner.

Overnight Location
Hotel in Buonconvento
5 hours, 16.5 km, 316m elevation gain

Day 6 Monte Oliveto Maggiore Loop

You’ll begin today with a transfer to Monte Oliveto Maggiore, a grand abbey of red brick. Beat the crowds to explore the site before strolling back to Buonconvento for dinner. The classic Tuscan countryside is a wonderful view the entire way back.

Overnight Location
Hotel in Buonconvento
5 hours, 14 km, 382m elevation gain

Day 7 Monteroni d’Arbia to Siena walk

A quick morning transfer to Monteroni d’Arbia begins the final day of your Walking in Val d’Orcia: Montepulciano to Siena Tour. Rolling hills and tiny hamlets mark the way. Siena is known for its Palio horse race, and it’s absolutely worth seeing the Piazza del Campo, the shell-shaped square where the race is held. Then, make sure to stop by the architectural marvel of the Duomo on your way to any of the countless medieval palaces in the city.

Overnight Location
Hotel in Siena
7 hours, 10 km, 227m elevation gain

Day 8 Departure from Siena

Savour a final breakfast in Siena before the official end of the Walking in Val d’Orcia: Montepulciano to Siena Tour.

Overnight Location

Walking in Val d’Orcia: Montepulciano to Siena Tour Price and Dates

This self-guided Walking in Val d’Orcia: Montepulciano to Siena walking tour is always run as a custom tour for your group only, therefore the price depends whether you are staying in single, double, or triple room.

Prices below are per person:

  • Solo traveller in a single room: $1,450USD
  • Price per person staying in single room (group of 2+): $1,175USD
  • Price per person sharing a double/twin room: $925USD
  • Price per person sharing a triple room: $775USD
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Accommodation on the Walking in Val d’Orcia: Montepulciano to Siena Tour

This tour is based in hotels and bed and breakfasts. Hotels on this trip are 2-4-star hotels along with smaller “agriturismo” farmhouse inns. They offer a great location, atmosphere, excellent food, and welcoming staff.

In some cases, the accommodation listed below may need to be substituted for other, comparable accommodations.

Single Rooms and Solo Travelers
Solo travellers must pay a supplement (please check Dates and Prices for more info). However, it’s definitely possible to match single travellers up.

Hotel Albergo Il Duomo in Montepulciano

This hotel is centrally located, with rooms that feature minibars, air conditioning, and TVs. The breakfast is a great buffet, and the location (right next to Piazza Grande) is unbeatable.

Camere il Giglio in Pienza

Enjoy relaxing in the sauna in this classically Tuscan hotel, which is outfitted with air conditioning, kitchenettes, free Wi-Fi, and charming décor.

B&B La Locanda del Loggiato in Bagno Vignoni

This top-rated B&B is romantic, and it offers modern conveniences with plenty of character. The rooms are well air-conditioned, the staff is friendly, and the breakfast is served across the plaza in a lovely tearoom.

B&B Le Scalette di Piazza in Montalcino

B&B Le Scalette di Piazza offers fantastic views of the countryside and the town square. The rooms come with air conditioning, kitchenettes, TVs, private bathrooms, and complimentary toiletries.

Agriturismo Pieve a Salti in Buonconvento

This farmhouse B&B is within walking distance of some of Buonconvento’s top destinations. The rooms are beautifully decorated in rustic Tuscan style.

Hotel Chiusarelli in Siena

This hotel is in the centre of Siena, and the recently renovated rooms offer air conditioning, Wi-Fi, and TVs.

Hotels on Standard Tour

What’s included in the Walking in Val d’Orcia: Montepulciano to Siena Tour?


7 breakfasts are included.


Accommodation for 7 nights is included.

Transportation during the Tour

This tour includes two transfers (day 6 and day 7) and all luggage transfers from day 2 until day 7.

Also Included

  • Route guides and notes
  • Maps and detailed information packs
  • 24/7 telephone guidance and support

Not included

  • Travel insurance
  • All transfers, not mentioned as ‘included’
  • Lunches and dinners or drinks and snacks not previously mentioned
  • Tourist taxes (€0.7 – 2 EUR per person daily)
  • Personal equipment

Optional Extras

  • Airport transfers
  • Any additional nights before or after the tour

Frequenty Asked Questions about Walking in Val d’Orcia: Montepulciano to Siena

How hard is the Walking in Val d’Orcia: Montepulciano to Siena Tour?

We rate this tour as a 3 / 5. You will walk long distances daily, but paths are generally flat and easy to follow.

Do I need a Visa to travel to Italy?

Check with your local country about visa requirements. You could also try this website, though you should verify with your government.

Are meals included on the Walking in Val d’Orcia: Montepulciano to Siena Tour?

7 breakfasts are included.

I’ve never been on a self-guided trip! How does it work?

Self-guided travelling is not difficult! For many, it is a preferred type of travel as you are in charge of your own time and pace. You are provided all the information on which direction you need to go daily. You don’t need to carry lots of things with you and can only carry your daypack, as your luggage will be picked up from your hotel daily in the morning and delivered to your destination hotel.

Do I need insurance?

Yes. You will need to acquire travel insurance that covers hiking/walking. Get your Travel Insurance.

How do I get to Montepulciano to start this tour?

The best airports to arrive at are Rome (FCO), Florence (FLR), or Pisa (PSA). From each airport, you can take a train to Montepulciano. You will also be able to take the train from Siena to your airport at the end of the tour. Check train schedules here.

Is the Walking in Val d’Orcia: Montepulciano to Siena Tour guided?

No, you will be provided with maps, route guides, notes, and 24/7 telephone support to complete your self-guided tour.

Where does the Walking in Val d’Orcia: Montepulciano to Siena Tour end?

The tour ends in Siena, where you can take the bus or train to the airport.

Can I rent any equipment?

No, you will need to bring any personal or walking gear needed for the duration of the trip.

Do I need special vaccines to travel to Italy?

Check with your family doctor.

Are there any travel restrictions for Italy?

Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.


All tours on 10Adventures are operated by highly vetted local tour operators and guides.

Having local tour operators and guides means you get a more authentic experience, and your booking creates jobs in the local communities you visit.

Details of the local tour operator will be listed on your booking invoice. If you have questions about the local operator prior to booking, please click the “Ask a Question” button below.

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From $695USD




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Tour Difficulty

We rate this tour as a 3 / 5. You will walk long distances daily, but paths are generally flat and easy to follow.

Read about our scale for Tour Difficulty Ratings.

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