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The Heart of Tuscany: Montepulciano to Siena

Walk in the Heart of Tuscany: Montepulciano to Siena


Of all Italy’s beautiful regions, Tuscany is by no doubt the most iconic one. Your route in the heart of Tuscany winds through the hills, vineyards and olive groves of Val d’Orcia as you walk between Medieval hill-top towns, taking in Montepulciano, Pienza, Bagno Vignoni, Montalcino, Buonconvento, and finally Siena. You will also be able to sample the genuine Tuscan kitchen in its entire variety, from the precious white truffles to the tasty pici of Siena, washed down with a glass of the divine local red Brunello.


  • The fascinating Val d’Orcia countryside with its vineyards and picturesque rolling hills
  • Medieval villages and Renaissance towns
  • The thermal baths at Bagno Vignoni
  • Charming, family-run accommodations offering delicious Tuscan culinary specialities

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Day 1: Arrival Montepulciano

Your Tuscan walking holiday begins in the medieval and Renaissance hill town of Montepulciano. Montepulciano is easily accessible via Rome, Florence or Pisa; catch the train to Chiusi, then take a local bus or a short taxi ride to Montepulciano. Admire the impressive views over the rolling Tuscan landscape you’ll explore over the next week.

  • Accommodation: hotel in Montepulciano (Hotel Il Duomo or similar). If you arrive by car, we will book for you Hotel San Biagio (or similar) that has a parking lot

Day 2: Montepulciano to Pienza | 15 km

Starting from the San Biagio church, you follow a quiet track to the peaceful village of Montichiello, where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing to Pienza. Pienza is a UNESCO World Heritage site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles; it is a great spot to indulge in Tuscan treats.

  • Walking for the day: 15 km, 4-5 hrs, ↑380 m ↓500 m
  • Accommodation: B&B in Pienza (Il Giglio B&B or similar)

Day 3: Pienza to Bagno Vignoni | 12 km

Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths complex at Bagno Vignoni Is the perfect location to spend the afternoon soaking up the Tuscan warmth. What in traditional towns is the main square, in Bagno Vignoni is a huge thermal pool, but you can’t jump in there! Try the Parco dei Mulini for a free bath just steps away. The thermal baths of Bagno Vignoni, probably well known even in Etruscan times, were enjoyed by the Romans, who consecrated these waters to the Nymphs (as a plaque located under the arcade of the church of Santa Caterina testifies).

  • Walking for the day: 12 km, 3-4 hrs, ↑200 m ↓418 m
  • Accommodation: B&B in Bagno Vignoni (La Locanda del Loggiato or similar)

Day 4: Bagno Vignoni to Sant’Antimo/Montalcino | 14 km

A bit more challenging but rewarding day’s walking awaits as you follow dry riverbeds to Sant’Antimo, an isolated abbey situated in a Pastoral landscape. After exploring the abbey, the car will pick you up at 16:00 h, and you will be transferred to Montalcino (~15 min/10 km).

Day 5: Montalcino to Buonconvento | 18 km

A hearty breakfast will set you up for a long but enjoyable day of walking in the famous Brunello wine region, passing vineyards and olive groves, and then again entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento. Once you cross the gate of the walls, entering the fine old town centre of the village, you will discover why its name means “happy, fortunate place”: you walk through the picturesque streets, where life is lived quietly following the slow rhythms of a provincial village, and if you love art, you will be able to admire the works of some of the most famous Sienese painters in the Museum of Sacred Art of the Val d’Arbia.

  • Walking for the day: 18 km, 5 hrs, ↑316 m ↓619 m
  • Accommodation: Agriturismo just outside Buonconvento (Fattoria Pieve a Salti or similar)

Day 6: Monte Oliveto Maggiore Monastery Walk | 14 km

A short walking day but full of ups and downs awaits you, beginning with a transfer to the monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick and set in the rugged Tuscan landscape. After an early visit to avoid the crowd, walk back to Buonconvento.

  • Walking for the day: 14 km, 4-5 hrs, ↑380 m ↓460 m
  • Accommodation: Agriturismo just outside Buonconvento (Fattoria Pieve a Salti or similar)

Day 7: Monteroni d’Arbia to Arbia/Siena | 10 km

Today you will start with a short transfer to Monteroni d’Arbia, from where you start the walk towards Siena. Hike through a landscape of rolling hills, and small hamlets as the unmistakable silhouette of Siena appears in the distance. Once you reach Arbia train station, take the train into Siena (10 min; train fare EUR 1-3 pp not included; you can also optionally book a private transfer with us). Your luggage will be waiting for you at the hotel. Enjoy the magnificent beauty of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo (Cathedral), an architectural treasure, and the numerous imposing medieval palaces.

  • Walking for the day: 10 km, 3-4 hrs, ↑227 m ↓197 m
  • Accommodation: 3-star hotel in Siena (Hotel Chiusarrelli or similar)

Day 8: Departure

Departure on your own or extension upon request.

What to Expect


Accommodation is in charming 3-star hotels, B&Bs and agriturismi*. Some of the places chosen have a swimming pool. All rooms have en-suite facilities. All places have been carefully hand-picked by us, and their quality is regularly monitored. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Click to view default hotels

*What is an agriturismo? A combination of the words for “agriculture” and “tourism” in Italian is a farm-stay, but it’s also much, much more. Typically, an agriturismo is an independently-owned farm that the owners have decided to use partially for accommodation purposes, in a way similar to English or American bed and breakfasts. One of the best parts of staying in a traditional agriturismo? The food. An Italian agriturismo will usually serve guests food that was prepared from raw materials – vegetables, fruit, eggs, meat, and often wine and olive oil – produced on the farm or from other local merchants.

Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.


Breakfast is included every day. Throughout the trip, there are plenty of opportunities to taste both the great local food and a wide range of the region’s prestigious wines.

Difficulty & terrain

The route is relatively easy, with ups and downs typical of Tuscany’s rolling hills. A good level of fitness is required for enjoying the walks to the maximum (read more about difficulty grades). The itinerary is mostly on paths and gravel roads (strade bianche), even if you find some sections on asphalted roads. Some walks are long but can be optionally shortened using local transport or private transfers. We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime.

When to go

You can start your holiday every day between the beginning of April and the end of October. Spring and autumn months are a preferred travel period if you want to avoid the summer heat of July and August (If you’d like to catch the famous Palio di Siena, you will have to travel in July or August, however). In September – October, you will enjoy pleasant temperatures and might also be able to catch the regional wine harvest.

Getting there

FCO up-to-date travel advice

Click to view travel options

By plane

Our recommended arrival airports for this holiday are Florence, Pisa and Rome Fiumicino. Other Italian airports are also well connected to the area.

By train or bus

From all airports, you can take a train to Montepulciano (usually changing at Chiusi). If you prefer, from Chiusi, you can opt to take a local bus or taxi the short distance to Montepulciano (25 min, payable locally). Up-to-date train timetables are available at www.trenitalia.com, or you can use the Omio planner above.



  • 7 nights in charming B&Bs, small hotels and agriturismi
  • 7 breakfasts
  • Luggage transfer on all walking days (only 1 piece per person up to 15 kg; there is a supplement for each additional bag)
  • Transfer from Castelnuovo dell’Abate to Montalcino (Day 4 at 16:00 h)
  • Transfer from Buonconvento to Monte Oliveto Maggiore Abbey (Day 6)
  • Transfer from Buonconvento to Monteroni d’Arbia (Day 7)
  • Holiday information pack including GPS-checked and regularly updated route notes and maps (digital copy sent by email and a hard copy delivered at the first hotel)
  • 24/7 phone support by our local office/representative


  • Airfare and connecting land transfers
  • Lunches and dinners, drinks and snacks
  • Travel insurance (required – get a quote online)
  • Personal expenses
  • Local tourist tax & entry fees (payable on the spot)
  • Any items not specifically mentioned as ‘Included’ in the programme

Options, extras & supplements

  • Supplement applies to members of a group who require a single room / single use of a double room
  • This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
  • Extra nights
  • Private transfer from Arbia to Siena on Day 7
  • If you arrive by car in Montepulciano, we will book Hotel San Biagio (or similar) with a parking lot – please advise at the time of booking.