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Tours/Europe/Italy/Tuscany

Walking in Val d’Orcia: Montepulciano to Siena

Discover beautiful renaissance villages on this mesmerizing 8-day self-guided walking tour

4.7 (54 ratings)

Italy, Europe

Happiness Promise

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From $750USDBook Now

Lifetime Deposit - Lifetime deposit means if you need to cancel your booking you’ll get a credit for your full deposit to use on your next booking.

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About this tour:

8 days

Apr-Oct

Walking

Self-guided, Private

Hotels

Moderate (3/5)

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Why travellers choose this tour

At 10Adventures, we take care of the details so that our guests can focus on making memories. Enjoy these key features on this tour.

We're Canadian

Book with a Canadian company whose mission is to help you travel the world.

Meals

Don't worry about meals. 7 breakfasts are included.

Transfers

Check out the 'What's Included' tab for more info on personal transfers during your tour.

Local Support

Travel stress-free knowing in-country local support is available by regular phone or WhatsApp to support you during your tour.

Payments Made Easy

Enjoy the flexibility and ease of staggered payments in your own currency using your choice of credit card.

Route Resources

Route notes, maps, and/or a trail app make navigation on this tour a breeze.

Park Entrance Fees

Included where possible! Check the 'What's Included' tab for more info on park entrance fees during your tour.

Luggage transfers

Take a load off, with optional or included luggage transfers. Check inclusions for further details.

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.

Hotels on Standard Tour

Night 1

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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.

Night 2

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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

Night 3

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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.

Night 4

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Hotel Il Giglio in Montalcino

This romantic hotel is located within the heart of Montalcino. Enjoy cozy rooms and tasty breakfast.

Night 5-6

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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.

Night 7

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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.

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Walking in Val d’Orcia: Montepulciano to Siena Tour Details

Overview

Itinerary

Walking in Val d’Orcia: Montepulciano to Siena Itinerary

Day 1

Day 1: Arrival in Montepulciano

Overnight Location - Hotel in Montepulciano | Distance - None | Meals - None

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.

Day 2

Day 2: Walk to Pienza

Overnight Location - Hotel in Pienza | Distance - 4 hours, 14 km, 384m elevation gain | Meals - Breakfast

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.

Day 3

Day 3: Walk to Bagno Vignoni

Overnight Location - Hotel in Bagno Vignoni | Distance - 4 hours, 12 km, 197m 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.

Day 4

Day 4: Walk to Sant’Antimo

Overnight Location - Hotel in Montalcino | Distance - 5 hours, 13 km, 450m 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.

Day 5

Day 5: Walking to Buonconvento

Overnight Location - Hotel in Buonconvento | Distance - 5 hours, 16.5 km, 316m 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.

Day 6

Day 6: Monte Oliveto Maggiore Loop

Overnight Location - Hotel in Buonconvento | Distance - 5 hours, 14 km, 382m 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.

Day 7

Day 7: Monteroni d’Arbia to Siena walk

Overnight Location - Hotel in Siena | Distance - 7 hours, 10 km, 227m 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.

Day 8

Day 8: Departure from Siena

Overnight Location - None | Distance - None | Meals - Breakfast

Savour a final breakfast in Siena before the official end of the Walking in Val d’Orcia: Montepulciano to Siena Tour.

Tour Highlights

What's Included

Dates & Prices

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	$1,625USD	$1,325USD	$1,025USD	$895USD

Optional Extras
Pick up from Arbia Train Station and transfer to Siena (1-4 travellers):$150USD
Printed trip documents:$50USD

Accommodation

Map

Reviews (54)

Tour Booking Process

FAQ

FAQ for Walking in Val d’Orcia: Montepulciano to Siena

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.

Tour Difficulty

From $750USD

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Walking in Val d’Orcia: Montepulciano to Siena

What travellers are saying about 10Adventures

Why travellers choose this tour