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Hill Top Towns of Tuscany

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Homepage > Italy > Hill Top Towns of Tuscany
  • Duration: 7 Nights
  • Difficulty: Level 2
  • Tour Type: Self Guided
  • Availability: Daily from 1st April to 31st October
  • Location: Montepulciano

Hiking in The Hilltop Towns of Tuscany

Tour Details

The Tuscan landscape of the UNESCO world heritage site, Val d’Orcia will warm your heart and like a view from a postcard conveying its natural beauty. Tuscany has a natural charm all of its own that only those who have visited the area will know. As we go on this walking holiday in Italy you are in for a thrilling trip along steep valleys, dense forests, rivers and the legendary “Badlands” eroded clay slopes. During your hiking vacation in Italy, you will walk alongside picturesque farmhouses nestled amidst olive groves, vineyards and fig trees on your way to the hot spring hamlet of Bagno Vignoni and the heavenly Renaissance city of Pienza.

You shall visit captivating Palaces, Romanesque churches, thermal baths, and prestigious wineries serving the divine local red “Brunello”. Soaring up high on invigorating hilltop towns, you’ll revel in the delight of this naturally stunning area.

Starting Location


Price Includes

  • 7 night’s on Bed and Breakfast
  • 3-4 star hotels, Agriturismo and B&B’s
  • Luggage transfers
  • People transfers on days 4, 6 and 7
  • GPS Files on request
  • Navigation by Smart Phone App

Price Excludes

  • Transport before and after tour
  • Single Supplement
  • Flights
  • Public Transport
  • Entrance to attractions
  • Travel Insurance
  • Extra nights
Trip Info

Route Information

This route is quite easy, with ups and downs typical of Tuscany’s rolling hills. The whole itinerary is mostly on paths and gravel roads (strade bianche), you will find some sections on asphalted road.

Some walks can be shortened only if requested in advance


In Pieve a Salti you may stay 1km away from the main hotel in a beautiful farm area. There will be a free shuttle to and from the restaurant for dinner that you can arrange with the owner of the hotel.

Travel Insurance

It is a requirement of booking this tour with Hooked on Walking that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


Day 1Individual arrival in Montepulciano

Day 2Montepulciano to Pienza – 9.3 miles / 15 km (384m up & 504m down)

Starting from the San Biagio church you will follow a quiet trail to the peaceful village of Monticchiello where you can take a break 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; this is a great spot to indulge in local Tuscan treats!

Day 3 Pienza to Bagno Vignoni – 7.5 miles / 12 km (197m up & 418m down)

Today’s route takes you through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths and complex at Bagno Vignoni sitting on a hill above Val D’Orcia it is the perfect location to spend the afternoon soaking up the Tuscan warmth.  Perhaps a visit to the Old Baths of St. Catherine or the church of St. John the Baptist.

Day 4Transfer from Bagno Vignoni to Castelnuovo and walk to Montalcino – 8.7 miles / 13 km (450m up & 280m down).

Today first we have a transfer to Castelnuovo where we start the walk mainly on wide dirt roads. Before starting your walk visit the stunning abbey of Sant’Antimo. This is a former Benedictine Monastery which dates from the 8th century. During the walk, you will have many stunning panoramic landscapes to admire across the Orca Valley. In Montalcino why not enjoy one of the fine local wines famous from this region?

Day 5Montalcino to Buonconvento – 11.2 miles / 18 km (316m up & 619m down)

A hearty breakfast will set you up for a long but enjoyable day of walking in the famous Brunello wine region. In the first part of today’s walk you will pass through the many vineyards and olive groves; before later entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento.  Buonconvento is widely regarded as one of the most beautiful towns in Tuscany, if not Italy. 

Day 6 Loop walk to Monte Oliveto Maggiore Monastery – 8.7 miles / 14 km (382m up & 460m down)

A short day which is full of ups and downs, 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, with its Benedictine Monastery and Museum. After an early visit to avoid the crowd, walk back to Buonconvento.

Day 7Transfer to Monteroni d’Arbia, then walk to Arbia, train to Siena – 6.2 miles / 10 km (227m up & 187m down)

Today will start with a short transfer to Monteroni d’Arbia from where you start your walk to Siena. Hiking through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Enter the town through Porta Romana, one of the medieval gates and walk through the city to reach your hotel.

Once you reach Arbia train station take the train into Siena. Take in the sites of this quintessential Italian city, enjoying a refreshment in the Piazza del Campo or take a stroll along the many quaint streets around Siena Cathedral. 

Day 8Departure

Depart after breakfast.

Italy is famous for its historic medieval towns and villages often perched on hillsides, well we do find similar such trips in France, such as our Dordogne walking tour and our walking tour in the Luberon.


How to get there

By plane to Pisa, Perugia or Rome airports

There are trains to Chiusi (from Pisa 2.5 hours, Perugia 1.5 hours, Rome 1.5 hours) and then by bus to Montepulciano or a taxi (around 30,00 €)

NOTE: Please advise upon booking if you are planning to arrive by car as this will incur a small fee due to hotel change that will allow car parking for your trip.

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HillTTus (7 Nights)  from £925 Book Now
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Hilltop Town in Tuscany