Discover beautiful renaissance villages on this mesmerizing 8-day self-guided walking tour
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!
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.
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.
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.
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.
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.
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.
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.
Savour a final breakfast in Siena before the official end of the Walking in Val d’Orcia: Montepulciano to Siena Tour.
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:
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.
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.
Enjoy relaxing in the sauna in this classically Tuscan hotel, which is outfitted with air conditioning, kitchenettes, free Wi-Fi, and charming décor.
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 offers fantastic views of the countryside and the town square. The rooms come with air conditioning, kitchenettes, TVs, private bathrooms, and complimentary toiletries.
This farmhouse B&B is within walking distance of some of Buonconvento’s top destinations. The rooms are beautifully decorated in rustic Tuscan style.
This hotel is in the centre of Siena, and the recently renovated rooms offer air conditioning, Wi-Fi, and TVs.
7 breakfasts are included.
Accommodation for 7 nights is included.
This tour includes two transfers (day 6 and day 7) and all luggage transfers from day 2 until day 7.
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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27 total ratings, 0 with reviewsStephen L.
I’ve been using 10Adventures route guides for a while, but had never booked a tour. My wife and I booked a self-guided hike in Greece and were so impressed with how we were able navigate the route without a guide with the detailed and easy to follow itinerary. We enjoy travelling independently, and 10Adventures made that happen.
Melinda S.
I was going through a tough time and really needed a getaway so I decided to book a tour through 10Adventures. My trip to Peru changed my life in so many positive and eye-opening ways. I am so thankful for the kind, empathetic team at 10Adventures.
Lina K.
I’ve adventured around a lot of Canada and the US, but I’ve always wanted to explore other parts of the world. I felt a bit scared before booking my trip to Israel, but my conversations with the team at 10Adventures helped ease any worry. I can’t wait to explore more of the world!
Gabriela H.
Travel companies have had to go through a lot during the pandemic but 10Adventures were super flexible and accommodating nonetheless. I had to cancel my tour in France due to the pandemic. 10Adventures was great and let me reschedule for a later date!
Mikael V.
My wife Sarah and I had a great experience booking our 7-day cycling trip through Portugal via 10Adventures. The communication between us and Nadine leading up the trip was top-notch!
Alexandra D.
Communicating with 10Adventures feels like talking with a family-run business. I love to explore and travel, and exploring with the comfort of knowing I can talk to the team at 10Adventures with almost immediate feedback helps to ease any stress that comes with adventuring!
Eric S.
Whenever I’m looking for my next adventure 10Adventures never fails. Their routes all over England are my main go to for exploring and I have only had great experiences booking both guided and self-guided trips in Europe and South America with them. I am looking into Africa next.
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I tend to have a lot of questions before travelling and was so happy to find that the team at 10Adventures responded to every single one of my inquiries in a timely fashion. I was never left waiting and waiting for a response. This was much appreciated!
Isabella N.
I have horrible dietary issues making it super hard to book a pre-planned trip sometimes, but the communication through 10Adventures helped me navigate this situation! I am so grateful for all of their help. I cant wait to book with them again!
Erika S.
I just got back from backpacking in the Sierra Nevada, and WOW. What an unreal journey! The alpine meadows, waterfalls, and the lakeside camping spot were memorable highlights! I wonder what other tours 10Adventures has to offer. That one went so well that I am now convinced I need to book another!
Robert D.
I'm not a big fan of traveling because of my fear of flying, but my girlfriend convinced me to go on the Aurora Borealis Tour in the Yukon. I will never forget the mesmerizing northern lights. Such a romantic (and cold) getaway. I would highly recommend it.
Monica L.
Wow! I am so happy with the experience I had with booking through 10Adventures for my tour in Italy! I worked with Nadine and she was super easy-going and helpful when it came to tweaking the itinerary provided on the website. 10/10 would book through 10Adventures again.
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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