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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
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!
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.
Trip map
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Why book with 10 Adventures?
We know adventure
Founded by experienced travellers, active and adventure vacations are all we do.
Experience the trip of a lifetime organized by a team of travel specialists who combine knowledge and passion for adventure travel.
Self-guided specialists
With over 600 tours across 30+ countries, we specialize in self-guided tours.
Combine the freedom of travelling on your own with the confidence that all of your logistics are taken care of.
Packed with value
Get everything you need for your next vacation with one easy booking.
We take care of accommodations, luggage transfers, gear rentals, and more - so you can focus on making memories.
World Class support
Get unbeatable support at every step of your journey.
Whether you are planning or travelling, no matter what your question, a real human is always a call or click away.
Hassle free bookings
Have peace of mind for when travel plans change.
Explore our flexible booking, payment, and cancellation options, as well as our Lifetime Deposits program.
Solo Traveller
Single Room (2+)
Double/Twin Room
Triple Room
| Dates | Solo Traveller | Single Room (2+) | Double/Twin Room | Triple Room |
|---|---|---|---|---|
| Apr 1, 2025 to Oct 31, 2025 | $1,795USD | $1,450USD | $1,125USD | $975USD |
| Optional Extras | ||||
| Pick up from Arbia Train Station and transfer to Siena (1-4 travellers):$150USD | ||||
| Printed trip documents:$50USD | ||||
Meals
7 breakfasts are included.
Accommodations
Accommodation for 7 nights is included.
Transportation during the Tour
This tour includes three transfers (day4, 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
Accommodation for Walking in Val d’Orcia: Montepulciano to Siena
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.
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.