Prices
Is this tour for me?
Get In Touch
Highlights
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!
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!
Read more
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
Distance: None
Meals: None
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
Distance: 4 hours, 14 km, 384m elevation gain
Meals: Breakfast
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
Distance: 4 hours, 12 km, 197m elevation gain
Meals: Breakfast
Day 4 Walk to Sant’Antimo
Today you will walk mainly on wide dirt roads. As you arrive in the village Castelnuovo dell’Abate take your time to enjoy the stunning beauty Sant’Antimo Abbey, a former Benedectine monastery dating back to the 8th century A.C. The first part of the route to Montalcino is extremely panoramic, with fabulous views over the Orcia valley while the last few km are in the woods. As you arrive in Montalcino, relax and enjoy one of the exquisite local wines.
Overnight Location: Hotel in Montalcino
Distance: 5 hours, 13 km, 450m elevation gain
Meals: Breakfast
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
Distance: 5 hours, 16.5 km, 316m elevation gain
Meals: Breakfast
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
Distance: 5 hours, 14 km, 382m elevation gain
Meals: Breakfast
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
Distance: 7 hours, 10 km, 227m elevation gain
Meals: Breakfast
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: None
Distance: None
Meals: Breakfast
Departure on April 1st – October 31st, 2023:
- Solo traveler: EUR1309
- Single room (group of 2+): EUR1043
- Sharing a double/twin room: EUR813
- Sharing a triple room: EUR685
Departure on April 1st – October 31st, 2024:
- Solo traveller: EUR1463
- Single room (group of 2+): EUR1166
- Sharing a double/twin room: EUR911
- Sharing a triple room: EUR783
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.
What’s included in the Walking in Val d’Orcia: Montepulciano to Siena Tour?
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
- How hard is the Walking in Val d’Orcia: Montepulciano to Siena Tour?
- Do I need a Visa to travel to Italy?
- Are meals included on the Walking in Val d’Orcia: Montepulciano to Siena Tour?
- I’ve never been on a self-guided trip! How does it work?
- Do I need insurance?
- How do I get to Montepulciano to start this tour?
- Is the Walking in Val d’Orcia: Montepulciano to Siena Tour guided?
- Where does the Walking in Val d’Orcia: Montepulciano to Siena Tour end?
- Can I rent any equipment?
- Do I need special vaccines to travel to Italy?
- Are there any travel restrictions for Italy?
We rate this tour as a 3 / 5. You will walk long distances daily, but paths are generally flat and easy to follow.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
7 breakfasts are included.
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.
Yes. You will need to acquire travel insurance that covers hiking/walking. Get your Travel Insurance.
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.
No, you will be provided with maps, route guides, notes, and 24/7 telephone support to complete your self-guided tour.
The tour ends in Siena, where you can take the bus or train to the airport.
No, you will need to bring any personal or walking gear needed for the duration of the trip.
Check with your family doctor.
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.
Customer Ratings
S-Cape Travel is a boutique tour operator focused on sharing the best walking, cycling, cultural and food & wine tours in Europe. Book one of their self-guided tours to live La Dolce Vita for a week or two, as you walk or cycle around Europe, enjoying incredible views and amazing food and wine.
