Chianti & the Val d’Elsa Guided Walking Holiday

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Duration: 7 nights
Type: European Centre Based
Walking Grade: 1 & 2

Explore the romantic Tuscan hills from our base in Colle di Val d’Elsa, which is ideally situated for us to enjoy great walks amongst the rolling hills and vineyards of the famous Chianti wine region, as well as the beautiful landscapes surrounding Colle and the medieval skyscrapers of nearby San Gimignano.

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

What’s included

  • A full programme of guided walks with 2 options every walking 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' en-suite accommodation
  • Half board – 7 buffet breakfasts and 7 evening meals

Trip Notes

Trip notes are detailed, downloadable PDFs for each holiday.

Download Trip Notes

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.

We hope to see you again soon.

Chianti 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.  


The hotel’s 48 well-appointed bedrooms feature:

  • Air conditioning
  • Television
  • Room safe
  • Fridge
  • Telephone
  • Toiletries
  • Free Wi-Fi


The Palazzo San Lorenzo has a fabulous wellness centre, a fully stocked bar with ample seating areas, restaurant and café serving local delicacies and goodies.

Food & Drink

Breakfast is an extensive buffet with a range of hot and cold options including sliced meats, cheeses and pastries served in the hotel restaurant.

Lunch (payable locally)
The hotel can provide picnic lunches for an additional charge but must receive your order the day before. Alternatively you can purchase ingredients for lunches at the local shops. Your leaders will inform you of the best options.

Evening Meal
The hotel provides a 3-course meal each night, served to your table with options for each course. There is always a vegetarian option available and all dietary requirements can be catered for with advance notice.

Your Evenings

In Europe, our walking holidays continue into the evening. Enjoy a glass of wine or local beer whilst listening to your leaders outlining the next day's walks.

After a relaxed evening meal take advantage of the warm evenings and chat with your fellow guests drinking a cocktail in the hotel bar.

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Getting to Palazzo San Lorenzo Hotel & Spa, Chianti, Italy

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

More Information

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

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

7 nights
European Centre Based
Walking Grade:

Fully Booked

020 3974 8865

For group bookings of 10+ people click here

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