14-Night Chianti & Cinque Terre Guided Walking Holiday

Scenic aerial view of ocean and harbor in colorful village Vernazza, Cinque Terre
Duration: 14 nights
Type: European Multi-Centre
Walking Grade: 1, 2 & 4

Two fantastic destinations to see different sides of Italy in one holiday! Explore the romantic Tuscan hills from our base in the medieval hilltop town of Colle di Val d’Elsa, ideally situated for us to enjoy great walks amongst the rolling hills and vineyards of the famous Chianti wine region. We’ll also explore the beautiful landscapes surrounding Colle and the medieval skyscrapers which tower above the narrow streets of nearby San Gimignano. Moving on to the Cinque Terre coast, we’ll walk on the spectacular coastal path with visits to all five of the area’s famous villages. Here we’ll immerse ourselves in the history of the area as we explore the narrow streets lined with preserved architecture. Enjoy panoramic views from the vineyard terraces and take a boat trip from Portovenere.

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

Cinque Terre

  • Visit the five enchanting villages of the Cinque Terre, each with their own unique character
  • Stop for the quintessential Italian gelato
  • Head away from the coast to peaceful countryside, covered in vineyards and olive groves
  • Enjoy a boat trip to view the spectacular coastline from the sea
  • Stay in the charming resort of Bonassola linked to Cinque Terre by coastal train


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
  • 7 nights' accommodation in en-suite rooms
  • 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.

Introductory walks either explore the villages above Bonassola, or head along the coast to the neighbouring resorts of Levanto and Monterosso. Both walks take in narrow streets, mule tracks, and pathways through woodland, and have splendid views down the sweep of the coast below. We learn something of the history of Bonassola and the surrounding communities.

Option 1 - Above Bonassola: Headland of the Hare, Montaretto and San Giorgio

Distance: 5 miles (8km)

Total ascent: 1,400 feet (420m)

In summary: The goal for today’s walk is the magnificently situated hillside village of Montaretto high above Bonassola. The morning will be spent gradually winding our way up there, via a spectacular headland and on through olive and vine terraces. There is the opportunity for lunch in a café before returning to the hotel via waterfalls, a church and Bonassola’s castle.

Highlight: Enjoy the company of our local interest guide who will give us a great insight into the local flora, fauna and history of the area.


Option 2 - Over two saddles: Bonassola to Monterosso

Distance: 7 miles (11km)

Total ascent: 1,900 feet (570m)

In summary: We too walk from the hotel, but go up and over the headland to the south to reach the popular resort of Levanto. From here we continue out through the medieval quarter and up to a ridge for extensive views as we reach the open saddle between Levanto and Monterosso. We enjoy more great views as we follow a section of the Cinque Terre high level route over the next headland and steeply down into Monterosso and our train back to Bonassola.

Highlight: Views of the valley and hilltop villages.


Both groups start the day with a train journey and explore the Cinque Terre villages.

Option 1 - Cinque Terre Villages: Vernazza to Corniglia, Manarola & Riomaggiore

Distance: 6 miles (9½km)

Total ascent: 1,000 feet (300m)

In summary: After alighting the train at Vernazza we head off along the famous Cinque Terre Coastal Path to reach the charming village of Corniglia perched on its headland. Our route continues with a visit to Manarola and walk down to the harbour. Then onwards we go to Riomaggiore with its tempting cafés and train back.

Highlight: Soak up the atmosphere in Manarola, with its brightly coloured houses set above the rocky cove.  


Option 2 - Vineyards & Villages: (Riomaggiore to) Manarola, Volastra, Corniglia and Vernazza

Distance: 7.5 miles (12km)

Total ascent: 1,900 feet (580m) 

In summary: We take the train to Manarola. From here, we head up to a medieval village high on the hillside above. After absorbing the stunning views down to the sea from a path contouring through terraced vineyards, we drop down to Corniglia and take the train back to Manarola.

Highlight: Visiting peaceful Volastra, as well as 3 Cinque Terre villages.


Today we explore the area to the northwest of Bonassola, around the villages of Framura. Framura is actually not one place but a collection of settlements as we’ll discover by winding our way up through them. On reaching a broad ridge above Framura there is an opportunity to have a simple meal with local wine on a farmhouse terrace. After lunch we head into some of the best preserved woodland in the area, contouring around Monte Serra on a delightful path. 

Option 1 - Framura Villages and Monte Serra Circuit

Distance: 6 miles (9½km)

Total ascent: 1,300 feet (390m)

In summary: We take the train to Framura which lies just beyond the headland to our north. We’ll spend the morning walking up through the villages to a farm/restaurant where we can enjoy a locally produced lunch. We return on a broad track overlooking first the hills of the interior and then the sea before descending to the small harbour at Framura.

Highlight: Sampling the delightful home-cooked and locally sourced lunch at the Agriturismo including their own olive oil and wine.


Option 2 - Bonassola to Framura Villages and Monte Serra Circuit

Distance: 9 miles (14½km)

Total ascent: 2,100 feet (630m)

In summary: We start our walk from the hotel heading over the headland to Salto della Lepre (Leap of the Hare) with its breathtaking views along the coast, before passing through woodland and cultivated terraces to reach Framura. From here we follow the same route as the easier group, meeting up with them for lunch.

Highlight: Our local interest guides deep knowledge of wild herbs, flowers and fauna provides a fascinating insight into the local culture. 


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 include:

Cinque Terre villages: You may enjoy re-visiting some of the Cinque Terre villages that you have seen previously on the walks. Each village has its own railway station and the frequent trains mean that it is possible to visit all five villages in one day.

Genoa: The largest port in Italy, was designated European Capital of Culture in 2004. After a fairly lengthy train journey along the coast, you’ll find a number of attractions including the cathedral, a magnificent street of palaces, opera house and museums, plus a regenerated dock area and a vast ornate cemetery with its very own bus network! Alternatively, you may just prefer to wander through the famous caruggi (narrow alleyways) in the old town.

Portofino: The chic resort of Portofino is approximately two thirds of the distance to Genoa. This is a picturesque town where you can admire the expensive yachts and Italy’s rich and famous. You might also take a boat along the splendid coastline to Santa Margherita.

Today we travel south along the Cinque Terre and enjoy some spectacular walking with views over the naval port of La Spezia, the Gulf of the Poets, and, as we walk down to it, the village of Portovenere at the tip of the peninsula. From here, if sea conditions permit, we take a boat back along the coast seeing the Cinque Terre harbours from the sea.

Option 1 - Campiglia Ridge Walk to Portovenere

Distance: 6 miles (9½km)

Total ascent: 700 feet (210m)

Total descent: 2,200 feet (660m)

In summary: Today’s walk begins with a chance to enjoy the views from the pretty village square of Campiglia before heading through woodland to a great picnic spot high on a ridge. Our route then winds gently along the peninsula for more fine vistas, followed by a long steep section of rugged path and steps leading down to Portovenere at the tip of the peninsula. From here if sea conditions permit, we take a boat back along the coast seeing the Cinque Terre villages.

Highlight: Relax on the afternoon boat trip to enjoy the stunning coastline with its colourful, tumbling villages from a different perspective. 


Option 2 - Riomaggiore Ridge and Coast Walk to Portovenere

Distance: 8 miles (13km)

Total ascent: 2,100 feet (630m)  

In summary: Our walk starts from Riomaggiore ascending to the 14th century Sanctuary of the Madonna of Montenero. From this popular viewpoint we ascend to the col known as Telegrafo and follow the ridge to the pretty square in Campiglia for a spot of lunch. We then take a spectacular coastal path high above the sea before descending steeply down the ridge to Portovenere to meet our boat.

Highlight: Dramatic views from the spectacular coastal path.


Vernazza is arguably the prettiest of the five Cinque Terre villages with its colourful houses winding down to its natural harbour, protected by a rocky headland. Today we walk from Vernazza to Monterosso. Both walks use the final section of the coast path which links the five villages of the Cinque Terre.

Option 1 - Monterosso to Vernazza Coastal Path

Distance: 4 miles (6½km)

Total ascent: 1,100 feet (330m)

In summary: From Monterosso old town we wind our way to many viewpoints and head along a section of the elevated coastal path. The path ascends through lemon groves and descends through woodland to Vernazza. Here there is plenty of time to explore before heading to the station for our train back to Bonassola.

Highlight: Enjoy the perfume as you descend through lemon groves into Monterosso old town, with views of the coast stretching as far as the eye can see. 


Option 2 - Vernazza to Monterosso Monastery Trail

Distance: 6 miles (9½km) 

Total ascent: 1,800 feet (540m) 

In summary: Our route winds its way up from Vernazza past a series of viewpoints to the Sanctuary of the Madonna di Reggio. After a chance to enjoy a rest in the shade of this tranquil spot we continue up the hillside to the Sanctuary of Soviore a great spot for a picnic lunch. From here a path descends to the old town of Monterosso.

Highlight: Popping in to visit the centuries old monastery and Madonna surrounded by ancient oak trees and olive groves. 


Depart after a leisurely breakfast.

Bonassola Itinerary Map
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.  

Hotel Delle Rose - Cinque Terre

The 3-star Hotel Delle Rose is a charming family-run hotel, owned and run by two brothers, Roberto and Enrico Bernardin. The hotel is located close to the seafront in Bonassola and within easy walking distance of all the local facilities. A handful of cafés and bars can all be found within a couple of minutes’ walk from the hotel.  Offering a warm welcome and a personal and friendly service, the Hotel Delle Rose has been welcoming HF Holidays' guests for over 15 years. 

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:
1 & 2

Fully Booked

020 3974 8865

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