14-Night Chianti & Tuscany Guided Walking Holiday

Chianti - Toscana -  AdobeStock_43839304.jpeg
Duration: 14 nights
Type: European Multi-Centre
Walking Grade: 1 & 2

Explore two different regions of Italy in one holiday! In Chianti we’ll explore the romantic Tuscan hills from our base in the medieval hilltop town of Colle di Val d’Elsa, which is ideally situated for us to enjoy great walks amongst the rolling hills and vineyards of this famous wine-growing region. We’ll also explore the beautiful landscapes surrounding Colle and the medieval skyscrapers which tower above the narrow streets of nearby San Gimignano. Tuscany is equally beautiful; our base in the medieval hilltop town of San Quirico d’Orcia is ideally placed to set out on walks in the surrounding undulating terrain. We’ll also visit the picturesque and historic hilltop villages of Montepulciano and Pienza and explore the Renaissance city of Siena with a local guide.

Holiday Highlights


  • Sample the wonderful cuisine at our hotel within the walls of Colle’s old town
  • Reach San Gimignano and wander through the atmospheric alleyways
  • Discover pretty Radda and charming Castellina on our walks
  • Enjoy a well deserved glass of Chianti after leisurely walks amongst quintessentially Italian landscapes


  • 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
  • All transport to and from the walks
  • The services of experienced HF Holidays' leaders
  • "With flight" holidays include return flights from the UK and hotel transfers
  • 14 nights accommodation in en-suite rooms
  • Transport between the two destinations
  • Half Board - continental breakfast and evening meal

Trip Notes

Trip notes are detailed, downloadable PDF’s for each holiday, please click the button below to find the right trip notes for your departure date.

On our Guided Walking holidays, we believe that choice is key. Our walks descriptions will help you choose according to your interests and fitness. The walks are grouped together with care by local experts to give the best experience. While every effort will be made to adhere to the described itinerary, we may occasionally vary the sequence shown here or substitute an alternative route to suit local conditions or for other operational reasons, potentially at short notice.

Welcome to hotel Palazzo San Lorenzo.

Today both groups take a closer look at Colle di Val d'Elsa, its river and the surrounding countryside.

Option 1 - The Sentierelsa and Colle di Val d'Elsa

Distance: 6 miles (10km)

Total ascent: 350 feet (100m)

In summary: We are driven a short distance to nearby Quartaia, a village on the via Francigena long distance pilgrimage route to Rome. We use this path to reach an ancient bridge over the river Elsa and walk along its banks, crossing over it several times and enjoying its wildlife, before reaching the centre of Colle di Val d'Elsa. We have time to explore the town or stop in one of its cafes on the main square before continuing back to the hotel.

Highlight: The Cascata del Diborrrato waterfall which plunges into a 10m deep basin.

Option 2 - The Sentierelsa and the Piano delle Lame

Distance: 8½ miles (13½km)

Total ascent: 700 feet (200m)

In summary: We walk from the hotel through the historic centre and down to the lower town, perhaps stopping for a coffee in the main square, before reaching the river Elsa at the Ponte di Spugna. We walk along the river bank in the opposite direction to the other group, and leave the river after viewing the waterfall at the Ponte di San Marziale. We then walk along the via Francigena for a short time before ascending through woodland to the 'Plain of the Llamas'. Continuing our walk past sunflower fields and vineyards we arrive back at our hotel through the Porta Nova.

Highlight: A varied walk through history, along riverbank and in countryside.

We all travel by coach to Greve in Chianti, the most northerly of the six villages that make up the Chianti region, considered by many as the Gateway to Chianti. Our walks, above and around the town, finish in the triangular shaped main square with its attractive porticoes. There should be time to relax here, perhaps with a glass of Chianti, before boarding the coach for the return journey.

Option 1 - Around Greve in the hills and vineyards

Distance: 5½ miles (8½km)

Total ascent: 900 feet (270m)

In summary: We walk into Piazza Matteoti, the square that is the focal point of the town and head uphill on a quiet lane to the beautiful, small, fortified village of Montefioralle. From here, we walk through woodland and rural landscapes to Pieve di San Cresci, the oldest parish church in Chianti with its recently discovered frescoes of Twelve Saints, before heading back to Greve for well earned refreshments.

Highlight: The castle of Montefioralle dominated by massive turrets.

Option 2 - Above Greve to the Sentiero del Chianti

Distance: 8½ miles (13½km)

Total ascent: 1650 feet (500m)

In summary: We begin by walking through vineyards, to reach a wide gravel track that rises steadily past a winery and a remote hamlet and eventually emerges from woodland onto the Sentiero del Chianti: the long distance footpath between Siena and Florence. We walk on the Sentiero for a short while towards Monte Domini, on a wide crest full of wild flowers in springtime. We then descend on a quiet 'white road' down into Greve and the main square.

Highlight: Panoramic views, including of Monte San Michele, Chianti's highest mount.

Today we walk in the hills around iconic San Gimignano: Ascending into the town to discover the medieval alleyways, shops and sights beneath the competing towers.

Option 1 - Giro di San Gimignano

Distance: 5 miles (8km)

Total ascent: 900 feet (270m)

In summary: We start our walk just to the north of San Gimignano in the hamlet of Casale, from where we walk gently downhill on Chianti 'white roads' past vineyards, olive groves and villas, stopping occasionally to marvelenjoy the surrounding countryside and the view of San Gimignano with its tall towers. The sting in the tail is the final ascent into San Gimignano itself; but well worth the effort as there is plenty of time to explore and refresh before the short homeward journey.

Highlight: The medieval skyscrapers of San Gimignano

Option 2 - The Strada di Vernaccia to San Gimignano

Distance: 7 miles (11km)

Total ascent: 1400 feet (400m)

In summary: We are dropped off south east of San Gimignano and begin our walk in woodland and vineyards (Vernaccia grapes not the Sangiovese of Chianti) before ascending on to a wide ridge, with outstanding views of San Gimignano in the distance virtually all morning. We continue on quiet lanes, past villas and wineries and take the opportunity to stop at one of them for refreshment before dropping down into the valley and then tackling the ascent into town. We too have plenty of time to explore this fascinating medieval hilltop town at the end of our walk.

Highlight: The view of San Gimignano from our lunchtime stop.

Each week there is a 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. Some options for your free day may include:

A day trip to one of the tourist honey-pots of Siena (30 minutes) or Florence (one hour) is possible using the public bus service.

Lesser known Volterra, with its Roman Amphitheatre and structures from the Etruscan, Roman and Medieval periods is also within easy reach by public bus (40 minutes).

Or simply relax in Colle di Val d'Elsa and around the hotel with its well equipped wellness centre.

Both groups travel a short distance to discover the Etruscan tombs near Castellina di Chianti. Then different walks through the heart of the Chianti region finish together near the headquarters of the League of Chianti for over 400 years, in Radda in Chianti.

Option 1 - Etruscan Tombs and Medieval Villages

Distance: 4½ miles (7km)

Total ascent: 1,000 feet (300m)

In summary: We are driven to the medieval village of Volpaia and undertake a circular walk through woodland, vineyards and olive groves. We stop at a nearby winery with fabulous views, walk through its vineyards down to the Romanesque church of Santa Maria Novella, and back up to Volpaia on a wide track through an avenue of cypress trees to board the coach for the short drive to Radda, where we can join the other group and explore or relax before the journey back to our hotel.

Highlight: The Etruscan tombs of Montecalvario.

Option 2 - Castellina to Radda in Chianti

Distance: 10 miles (15½km)

Total ascent: 1,200 feet (360m)

In summary: We leave Castellina on foot to journey to Radda on a pleasant and varied route through the typical Chianti landscape of vineyards, woodland and olive groves. Walking on 'white roads', dirt tracks and narrow paths, lined with fragrant wild flowers, we reach the tiny isolated chapel at Badiola and the larger Romanesque church of San Giusto in Salcio before passing a former Convent, now a winery and small museum, before the final ascent into Radda, renowned capital of the region.

Highlight: The Palazzo del Podesta in Radda, with its 51 Coats of Arms belonging to local families.

After a short drive to different locations nearby, each group walks to the fortified castle of Monteriggioni, a fitting final destination in which to meet up and celebrate the week.

Option 1 - Along the Via Francigena to Monteriggioni

Distance: 7 miles (11km)

Total ascent: 800 feet (240m)

In summary: We start our walk near the Etruscan bathing pools of Le Caldane and follow the old pilgrim's route on wide tracks, country lanes and paths along the via Francigena. We stroll through the countryside, visiting the lovely village of Strove, where we can stop for lunch or eat our picnics, then on to Abadia Isola, before ascending into the walled castle of Monteriggioni, visible from far afield.

Highlight: Discovering the 10th Century Cistercian Abbey of San Salvatore.

Option 2 - On the Montagnola Senese to Monteriggioni

Distance: 8½ miles (13½km)

Total ascent: 1,400 feet (400m)

In summary: Our route takes us high into the wooded hills of the Montagnola Senese on good paths and tracks, past the isolated hamlet of Poggiarello, where we can stop for a break and admire the scenery. We have occasional views of some of the many places we have visited during the week as we uncover the recent history of the area; a stronghold of Italian resistance during World War II. On reaching the small hamlet of Bracciano, our final destination, Monteriggioni, is in plain sight.

Highlight: The walled medieval castle town of Monteriggioni.

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.

Chianti Itinerary Map
San Quirico Itinerary Map

Palazzo San Lorenzo Hotel & Spa, Chianti, Italy

Situated in the centre of the ancient town of Colle di Val d’Elsa, this elegant 4-star 17th century palace has been lovingly restored and now offers the perfect mix of tradition and modern comfort. The bright and spacious bedrooms offer modern furniture and real wood flooring while the restaurant produces exquisite Tuscan cuisine. The wellness centre features a sauna, small pool, relaxation area and steam bath - perfect for unwinding at the end of the day. The medieval streets of Colle di Val d’Elsa are right on the doorstep and are begging to be explored.  

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 days out walking.

Essential Information

Passport Requirements

You may need to renew your British passport if you’re travelling from 1 January 2021.

On the day you travel, you’ll need your passport to both:

  • have at least 6 months left
  • be less than 10 years old (even if it has 6 months or more left)

Use the government website to see if your passport is valid for this holiday

EHIC cards

The UK government has officially launched the Global Health Insurance Card (GHIC), which will replace the European Health Insurance Card (EHIC). UK residents can now apply for one of the GHIC cards, which will gradually replace the EHIC cards as they reach their expiry dates. Every family member travelling requires a GHIC. You can make an application for yourself and on behalf of your partner and any dependent children under the age of 16. Both cards will offer equivalent protection for emergency and medically necessary healthcare needs when in the EU on a temporary stay, which includes holiday, study and business travel. Necessary healthcare includes things like

• emergency treatment and visits to A&E
• treatment for long-term or pre-existing medical conditions
• routine medical care for pre-existing conditions that need monitoring
• oxygen and kidney dialysis

The public only need to apply for their free GHIC cards when their current EHIC expires. The process is likely to take two weeks. For more information visit https://www.nhs.uk/using-the-nhs/healthcare-abroad/apply-for-a-free-uk-global-health-insurance-card-ghic/.

The GHIC is not an alternative to travel insurance. We advise all holidaymakers to also invest in travel insurance that covers healthcare, so they are covered for other issues that may arise, as well as cancellations and lost luggage.

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. 
  • 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.
  • Camera.
  • Gaiters.

Guest Reviews

14 nights
European Multi-Centre
Walking Grade:

Fully Booked

020 3974 8865

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