Walking in Val d’Orcia: Montepulciano to Siena
Discover beautiful renaissance villages on this mesmerizing 8-day self-guided walking tour
Lifetime Deposit
Self-Guided
Walking in Val d’Orcia: Montepulciano to Siena Overview
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!
Trip highlights
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.
Day By Day Itinerary
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
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
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
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
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
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
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
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
Tour Map
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Inclusions
Included
- 7 breakfasts are included.
- Accommodation for 7 nights is included.
- This tour includes three transfers (day4, 6 and day 7) and all luggage transfers from day 2 until day 7.
- Route guides and notes
- Maps and detailed information packs
- 24/7 telephone guidance and support
- Luggage Transfers
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
Reviews
These reviews reflect all trips offered by this local tour partner on 10Adventures, not just the tour you’re viewing.
These reviews reflect all trips offered by this local tour partner on 10Adventures, not just the tour you’re viewing.
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FAQ
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.
Why book Walking in Val d’Orcia: Montepulciano to Siena with 10 Adventures?
Self-guided Specialists
Combine the freedom of travelling on your own with the confidence that all of the logistics are taken care of.
Packed with Inclusions
Accommodations, luggage transfers, gear rentals, and more - all taken care of so you can focus on making memories.
World Class Support
Have peace of mind for when travel plans change with our hassle-free booking process and unbeatable support.
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