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!
Highlights of the Walking in Val d’Orcia: Montepulciano to Siena
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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
The departure is available on any day of the week. Prices below are per person:
Departure on April 1st – October 31st, 2023:
- Solo traveler: $1,475 USD
- Single room (group of 2+): $1,175 USD
- Sharing a double/twin room: $925 USD
- Sharing a triple room: $775 USD
Departure on April 1st – October 31st, 2024:
- Solo traveller: $1,650 USD
- Single room (group of 2+): $1,325 USD
- Sharing a double/twin room: $1,025 USD
- Sharing a triple room: $875 USD
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.
Hotels on Standard Tour
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.
Piccolo Hotel La Valle in Pienza ★★★
Enjoy a stay in a cozy small hotel in an oldtown of Pienza.
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.
Hotel Il Giglio in Montalcino ★★★
This romantic hotel is located within the heart of Montalcino. Enjoy cozy rooms and tasty breakfast.
Agriturismo Pieve a Salti in Buonconvento ★★★
This farmhouse B&B is just a few kilometres away from some of Buonconvento’s top destinations. The rooms are beautifully decorated in rustic Tuscan style.
Hotel Chiusarelli in Siena ★★★
Hotel Chiusarelli*** is in the city center of Siena and finds its natural setting in a neoclassical villa built around 1870.
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
Frequently Asked Questions about Walking in Val d’Orcia: Montepulciano to Siena
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.
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