Tuscany Guided Walking Holiday

Tuscany at sundown - countryside road with trees and house
Duration: 7 nights
Type: Centre Based
Walking Grade: 1 & 2
from £1,249pp with flights

Explore the beautiful setting of San Quirico d'Orcia with walks in undulating terrain. Visit the historic hilltop villages of Montepulciano and Pienza, and explore the Renaissance city of Siena with a local guide.  The medieval town of San Quirico d’Orcia lies in the heart of the Orcia valley, amidst a wonderful landscape of green and golden hills for which Tuscany is famous. Due to its position in the middle of the main Via Francigena pilgrimage route, it has long been a staging post for wayfarers, pilgrims and merchants on the way to Rome. San Quirico is just one of the many hilltop towns and villages that dominate the skyline of this part of Tuscany. During our stay we’ll visit a number of these, including beautiful Pienza, Montalcino and Montepulciano. These fortified villages contain a wealth of architectural treasures and offer an insight into the turbulent history of the Republic of Siena and the legacy of Etruscan and Roman settlement. On one day we make a sightseeing excursion to Siena, whilst your free day offers opportunities to explore San Quirico or further afield. Tuscany’s rural countryside, where traditional farming methods can still be seen, offers a variety of enchanting walks amidst scented woodlands and vine-clad hillsides. The hilltop towns and the forested slopes of Monte Amiata provide wonderful backdrops. Walks are amongst gently undulating hills. Conditions are generally good underfoot, but can be a little muddy after rain showers. Some steeper ascents are also required to reach some of the beautiful hilltop towns.

Holiday Highlights

  • Gentle countryside walks through classic Tuscan countryside crowned with historic towns
  • The beautiful Renaissance city of Siena makes a fascinating sightseeing day
  • Ridge walk to get a beautiful view of Rocca
  • Sample the natural hot springs at Bagno Vignone
  • Finish your walk with a coffee or ice cream in the enchanting hilltop villages

What’s included

  • A full programme of guided walks with 2 options every walking day plus 1 full sightseeing day
  • All transport to and from walks
  • The services of experienced HF Holidays' leaders
  • "With flight" holidays include return flights from the UK and hotel transfers
  • 7 nights' accommodation in en-suite rooms
  • Half board - continental breakfast and evening meal

Trip Notes

Trip notes are detailed, downloadable PDFs for each holiday.

Download Trip Notes

Welcome to Hotel Albergo Palazzuolo. Unpack and settle in.


The hot springs at Bagno Vignoni have been known since Etruscan times. Santa Caterina of Siena and Lorenzo the Magnificent were amongst those to have taken advantage of the therapeutic values of the waters. The Medici family built the splendid arcaded pool which sits in the middle of the village where you would expect to find the main square.

Option 1 - A New Route to The Spa

Distance: 4 miles (6½km)

Total ascent: 400 feet (120m)

In summary: We start our week with an exploration of San Quirico, a fascinating town in its own right with some spectacular views from the town walls. We then head south out of town through beautiful countryside to Vignoni Alta with its truncated tower. Our route continues descending towards Bagno Vignoni accompanied by great views to Rocca d’Orcia.

Highlight: Explore Bagno Vignone with its hot springs and interesting history.

Option 2 - A Castle and a Spa

Distance: 6 miles (9½km)

Total ascent: 700 feet (210m)

In summary: After exploring San Quirico with the easier group, we too head south, taking a loop out to the west via Forn del Chigi and Poggio Grande. We then head east past the ruins of the old bridge, swept away in 1929, and up the side of the calcite cliffs, past bathing pools, to arrive in Bagno Vignoni to join the easier group.

Highlight: Views to Monte Amiata, which forms the southern backdrop to the Val d’Orcia.


Montalcino is a Tuscan hill town with a full circuit of walls. It was permanently settled in 1,000AD by fugitives from the Saracens and their family groups, the Borghetto, Pianello, Ruga and Travaglio. To this day you will see rival flags outside the houses and they compete against each other in an archery competition. The final destination of both walks is the Abbey of San Antimo with time to explore before enjoying refreshments in the village of Castelnuovo dell Abate.

Option 1 - From the Castle to the Abbey

Distance: 6 miles (9½km)

Total ascent: 600 feet (180m)

In summary: Our walk starts with a bus ride to Montalcino where we can explore the town and enjoy a drink before re-joining the coach to take us to the start of our walk a couple of miles south. Our route takes us through forests, vineyards and farmlands as we make our way to our objective of the day, the Abbey of San Antimo. Our coach then picks us up at the edge of Castelnuovo dell Abate.

Highlight: Visit the attractive town of Montalcino.

Option 2 - Montalicino to San Antimo

Distance: 8 miles (13km)

Total ascent: 700 feet (210m)

In summary: The harder walk begins at Montalcino where, after a chance to look around, we head off towards the Abbey of San Antimo through undulating countryside, woodland and farmland.

Highlight: Villa a Tolli, an ancient hamlet of Etruscan origin.


The city of Siena is a magnet for visitors to this region of Italy. At the heart of the walled city lies the Campo, where the famous ’Palio’ horse race takes place. The surrounding central core is entirely medieval in plan and appearance. The 320 feet Torre del Mangia bell tower dominates the scene and you can ascend its many steps to get a bird’s eye view over the city. The Museo Civico, in the Palazzo Publico, contains 13th century frescoes. In the Piazza del Duomo, the Museo dell Opera is worth a visit, housing elaborate frescoes and works by Simone Martini and an unusual work of art – the Maesta, a huge altar piece painted by Duccio in the 1270s. An additional bonus, if you go into the museum, is ascending the ‘new nave’, arguably a better viewpoint than the more famous Torre del Mangia. The Duomo itself is incredible both inside and out: the black and white marble decoration, the unique marble floor panels and sculptures are all breathtaking. While the Duomo will be crowded, a far quieter place to visit is the Ospedale di Santa Maria Della Scala, across the square, recently converted into a museum. The church itself is very airy and then inside the old hospital is a wonderful cycle of frescoes, which depict entirely secular scenes and are described in English. As well as visiting these principal sights there will also be opportunities to relax in the pavement cafés, or to wander through some of the city’s quieter corners.


Pienza was once a small village named Corsignano, where Pope Pius II was born. When he became Pope in 1459 he commissioned the most famous architect of his day, Bernardo Rossellini, to create a city fit for a Pope on the site of his birthplace. Pius died within three years of the completion of the city, which was largely ignored by future Popes, leaving us with a beautifully preserved renaissance city not much bigger than a village.

Option 1 - Montichiello to Montepulciano

Distance: 6 miles (9½km)

Total ascent: 900 feet (270m)

In summary: After looking around the beautiful city of Pienza we reboard our coach for Monticchiello where our walk starts. We leave this beautiful walled hilltop town across rolling countryside past the pilgrimage church of San Biagio to Montepulciano for a well-earned drink.

Highlight: Monticchiello is a delightful walled village with a crooked watch tower and a 13th century parish church.

Option 2 - Pienza to Montepulciano

Distance: 10 miles (16km)

Total ascent: 1,600 feet (480m)

In summary: Our walk starts from Pienza. After a spot of sightseeing we head east out of town towards Monticchiello where we pick up the route of the easier walk to Montepulciano where we can join them for refreshments.

Highlight: Pienza is an historical town with Romanesque architecture.


Each week there is a free day when no guided walks are offered. This is an ideal opportunity to relax around the hotel, walk independently or visit local places of interest. If there is sufficient demand, leaders can organise a visit to San Gimignano.

San Gimignano: This is a fascinating hilltop town with a breathtaking skyline of towers. You can enter the town through the Porta San Giovanni and then head to the Piazza del Duomo. The Duomo has an exotic interior containing fresco cycles of the Old and New Testament stories. It is worthwhile visiting the Rocca and ramparts which offer extensive views across the countryside. The church of St. Augustine is well away from the crowds and has frescoes on the life of Saint Francis. On the return to San Quirico you could stop at the heavily fortified small town of Monteriggioni, once the border of the Florence and Siena republics.

Pienza: Pay a return visit to Pienza to visit the Piccolomini Palace, the Diocesan Museum and the medieval Pieve di Corsignano church where Pope Pius II was baptised.

Villa La Foce: Visit this villa and its gardens, made famous by Iris Origo’s book War in the Val d’Orcia – An Italian Diary 1943-44.


Today we travel south to the castle keep of Tentennano, known locally as Rocca d’Orcia. The harder walk is circular, starting and finishing at the Rocca and taking in three castles. The easier walk takes in a beautiful stretch of the Via Francigena heading for the little village of Gallina which sits on the 43rd Parallel. Both groups walk through undulating farmland and woodland where wild game, such as deer and boar have been seen. At the end of both walks there will be the opportunity to climb the tower of the castle keep and/or take refreshments at the café nearby before we return to the hotel.

Option 1 - From the Rocca to the 43rd Parallel along the Via Francigena

Distance: 7 miles (11km)

Total ascent: 400 feet (120m)

In summary: Today’s walk begins with a circuit of the beautiful village of Castiglione d’Orcia before walking through Rocca d’Orcia village and picking up the Via Francigena which we walk almost all the way to Gallina. After a short refreshment stop we will board the coach to return to our starting point and meet up with the harder walkers at Rocca d’Orcia.

Highlight: Castiglione d’Orcia is an ancient settlement first referenced in 714AD.

Option 2 - Rocca D’Orcia Circular – A Three Castles Walk

Distance: 9 miles (14½km)

Total ascent: 1,600 feet (480m)

In summary: The walk starts by wandering through the medieval streets of Rocca d’Orcia village. An old road, now just a track takes us down to the Orcia River with views of Ripa d’Orcia. We follow the river for a while before gaining height to join a ridge with stunning views of Monte Amiata to the south. The return allows us to explore the village of Castiglione d’Orcia and its castle – the Rocca Aldobrandesca. Finally we return to Rocca d’Orcia to join the easier party with time to explore the castle and/or take refreshments.

Highlight: Take in views of three medieval castles.


We hope to see you again soon.


San Quirico Itinerary Map

Hotel Albergo Palazzuolo - Tuscany

The 3-star Hotel Albergo Palazzuolo is set in a peaceful location in the countryside surrounding the village of San Quirico, and is very convenient for the local amenities. This family owned hotel was originally an attractive farmhouse, extended on both sides to incorporate the bedrooms. The property has excellent views to the rolling hills of Montalcino and offers good standards of service and comfort with a relaxing atmosphere after your day’s walking.

Rooms

The hotel has 42 comfortable bedrooms, all en-suite with shower. 

All bedrooms also have:

  • TV
  • Telephone
  • Air conditioning
  • Fridge
  • Hairdryer

Facilities

Hotel Albergo Palazzuolo facilities consists of:

  • Lounge
  • Bar
  • Terrace
  • Attractive gardens
  • Outdoor swimming pool (swimming hat is required)

Food & Drink

Our holidays at Hotel Albergo Palazzuolo are on a Half Board basis and include breakfast and evening meal.

Breakfast

The self-select continental breakfast includes cereal, cheese and cooked meats, bread, croissants and home-produced honey. Tea and coffee is available.

Lunch (payable locally)

You can buy a picnic lunch from the hotel (order the night before). Alternatively ingredients can be bought in local shops, including a supermarket five minutes' walk away. On some days it may be possible to eat in a café during a walk or excursion; your leaders will advise you of all the options.

Evening meal

The five course set menu features many Tuscan specialities, using homemade pasta and locally-produced oil, meat and cheese. An alternative is available for vegetarians; however we recommend that those with special diets discuss their requirements with the manager or chef.

Drinks

There is a well-stocked bar serving beer, wine and spirits.

Your Evenings

The friendly atmosphere of our holidays continues into the evening.

Enjoy a glass of wine or local beer before hearing about the next day's activities, then join your fellow guests for a leisurely meal.

One evening our guests can learn more about olive oil and take part in a tasting session, very popular with our guests.

Your leader will be checking out for other local events going on nearby, or you may prefer to relax on the terrace enjoying the panoramic view or in the bar with a drink.

Italy - Tuscany - Hotel Albergo Palazzuolo -camera con vista piano superiore 3.jpg

Getting to Hotel Albergo Palazzuolo - Tuscany

Find out more about this location including travel details and room types.

More Information

What to Bring

Essential Equipment

To enjoy walking/hiking comfortably and safely, footwear, clothing and equipment needs to be suitable for the conditions. Safety and comfort are our priorities, so our advice is to come prepared for all eventualities.

  • Footwear with a good grip on the sole (e.g.Vibram sole) is the key to avoiding accidents.
  • Walking/hiking boots providing ankle support and good grip are recommended (ideally worn in), and specialist walking socks to avoid blisters.
  • Several layers of clothing, which can be added or removed, are better than a single layer (include spares).
  • Fabrics (lightweight and fast drying) designed for the outdoors are recommended.
  • Waterproof jacket and waterproof over trousers.
  • Warm hat and gloves. Gaiters are an optional but useful extra.
  • Denim jeans and capes are not suitable on any walks.
  • Rucksack with a waterproof liner.
  • Thermos flask for hot drink.
  • Water bottle (at least 2 litre).
  • Spare high-energy food such as a chocolate bar.
  • Small torch.
  • First aid kit – your leader’s first aid kit doesn’t contain any medication or blister kits (such as Compeed).
  • Sun hat and sunglasses
  • Sun cream.

Optional Equipment

  • Walking poles are useful, particularly for descents.
  • Insect repellent.
  • Sunglasses.
  • Camera.

Guest Reviews

All holidays are subject to availability and prices are subject to change.
Non-member associate fee: £10 per person.

These departure dates can be booked with flights or as land only holiday options. All packages that include flights are ATOL protected. Advertised flight prices are based on UK flights departing from London. Regional departures and/or connections to London, if available, can be requested. Cabin upgrades may also be available on request.

Date (Start/ End) Version Price Status Trip Notes Book
2019
07 Sep / 21 Sep 2019 Itinerary £1,249 Unavailable
14 Sep / 21 Sep 2019 Itinerary £1,324 Unavailable
21 Sep / 05 Oct 2019 Itinerary £2,149 Unavailable
28 Sep / 05 Oct 2019 Itinerary £1,249 Holiday Guaranteed to run - book now - few places left Book Now
05 Oct / 12 Oct 2019 Itinerary £1,249 Holiday Guaranteed to run - book now - few places left Book Now
2020
25 Apr / 09 May 2019 Itinerary £1,349 Available Book Now
02 May / 16 May 2019 Itinerary £2,449 Available Book Now
09 May / 16 May 2019 Itinerary £1,349 Available Book Now
16 May / 30 May 2019 Itinerary £1,349 Available Book Now
23 May / 30 May 2019 Itinerary £1,349 Available Book Now
05 Sep / 19 Sep 2019 Itinerary £2,449 Available Book Now
12 Sep / 26 Sep 2019 Itinerary £2,449 Available Book Now
19 Sep / 03 Oct 2019 Itinerary £2,449 Available Book Now
26 Sep / 10 Oct 2019 Itinerary £2,449 Available Book Now
03 Oct / 17 Oct 2019 Itinerary £1,349 Available Book Now
Date (Start/ End) Version Price Status Trip Notes Book
2019
07 Sep / 21 Sep 2019 Itinerary £1,849 Unavailable
14 Sep / 21 Sep 2019 Itinerary £899 Unavailable
21 Sep / 05 Oct 2019 Itinerary £1,849 Unavailable
28 Sep / 05 Oct 2019 Itinerary £899 Holiday Guaranteed to run - book now - few places left Book Now
05 Oct / 12 Oct 2019 Itinerary £899 Holiday Guaranteed to run - book now - few places left Book Now
2020
25 Apr / 09 May 2019 Itinerary £2,149 Available Book Now
02 May / 16 May 2019 Itinerary £2,149 Available Book Now
09 May / 16 May 2019 Itinerary £1,049 Available Book Now
16 May / 30 May 2019 Itinerary £2,149 Available Book Now
23 May / 30 May 2019 Itinerary £1,049 Available Book Now
05 Sep / 19 Sep 2019 Itinerary £2,149 Available Book Now
12 Sep / 26 Sep 2019 Itinerary £2,149 Available Book Now
19 Sep / 03 Oct 2019 Itinerary £2,149 Available Book Now
26 Sep / 10 Oct 2019 Itinerary £2,149 Available Book Now
03 Oct / 17 Oct 2019 Itinerary £2,149 Available Book Now

Important Information

  • Double room for sole occupancy: £23 per night
  • With flight holidays include flights from Heathrow. Flight supplement from Manchester: £60
  • Independent travellers can join our transfer from Pisa Airport: £53.50 single
Duration:
7 nights
Type:
Centre Based
Walking Grade:
1

7 nights from £1,249pp with flights

...or call 020 3974 8865

For group bookings of 10+ people click here

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