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Chianti Classic Walk

from $2,465.00

A 10-night walking holiday that explores the fabulously unspoilt Chianti countryside, with the chance to visit the world-famous cities of Florence and Siena too! Stay in friendly, family-run hotels, including a beautifully restored C12 abbey, and enjoy superb meals.

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  • Vacation Style Holiday Type
    Self-guided
  • Activity Level Moderate
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All about the Chianti Classic Walk.

On this self-guided 10-night walking holiday, you explore the timeless countryside between picturesque Volterra and the soaring towers of San Gimignano. You’ll feel as though you’re strolling through history as you discover sleepy hilltop hamlets crowning sun-dappled hills, verdant vineyards and panoramic picnic spots in fields ablaze with sunflowers. There’s the option too to visit the eternal cities of Siena and Florence – Tuscan favourites right on your doorstep!
You start in Volterra, a real Etruscan gem with its tangle of alleys home to alabaster workshops and secret chapels, from where you walk through the verdant Berignone Forest and up to a fantastic panoramic ridge before a final climb to Casole d’Elsa. Your journey then takes you east to mediaeval Colle di Val d’Elsa, enjoying balcony views across the Elsa Valley. As you move towards stunning San Gimignano, the mediaeval ‘Manhattan of Tuscany’, the landscape is dominated by vines so there are plenty of wine-tasting opportunities here!
Our carefully picked hotels, all with pools, are full of contrasts. From a recently renovated, elegant boutique hotel just outside the mediaeval town of Casole d’Elsa to the refined elegance of the **** Relais della Rovere in Colle di Val d’Elsa, a magnificently restored C12 abbey where you spend four nights, and which is an excellent base for day trips to the eternal cities of Siena and Florence. Chianti is synonymous with excellent food and wine and evening meals are a celebration of the local cuisine. Perhaps try pappardelle alla lepre (fresh ribbons of pasta with a hare sauce) or bruschetta (toasted bread rubbed with garlic and olive oil, topped with sun ripened tomatoes), all washed down by a glass or two of full-bodied Chianti!

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.
  • 10 nights accommodation, hotel-to-hotel
  • All continental breakfast and 6 evening meals
  • Services of your local Headwater Representative
  • Headwater Wine Collection Service
  • Route directions and maps
  • Luggage transfers between hotels
  • Walking transfers
What is not included in this tour?

Highlights

  • Quintessential Italian landscapes: rolling hills, sunflowers, endless vines and hilltop hamlets
  • Scenic walking on Etruscan trails and pilgrims’ paths; wildlife in abundance
  • Exceptionally friendly hotels, family-run, with gorgeous swimming pools
  • Mouth-watering local cuisine; world famous wines
  • Possible trips to the ‘Super Tuscans’: Florence, Siena and Pisa
  1. Day 1 Day 1 Arrive in Volterra

    We meet you at Pisa airport, and take you to your hotel (75 mins) just outside Volterra’s mediaeval gates, where you have time to relax in the pool before dinner. (Staying at Park Hotel Le Fonti, Half Board)

  2. Day 2 Day 2 Volterra to Casole d'Elsa 14km/9mi/4hr

    A short transfer (30 mins) this morning to the start of your walk. Forest trails lead east through the Berignone Nature Reserve where you may be lucky enough to see wild boar, deer and fox. As you leave the forest, the ridge opens up giving wonderful valley views out towards Casole d’Elsa where you’ll spend the next two nights. (Staying at Hotel Terre di Casole, Half Board)

  3. Day 3 Day 3 At Casole d'Elsa

    Casole d’Elsa is a picture perfect etruscan village atop a panoramic ridge. From the vermillion hued C14 castle, views stretch as far as Monte Amiata in the south of Tuscany. A leisurely lunch maybe in the mediaeval piazza, before visiting the small but intact amphitheatre and Etruscan tombs. (Staying at Hotel Terre di Casole, Half Board)

  4. Day 4 Day 4 Casole d'Elsa to Colle di Val d'Elsa 19km/12mi/5hr

    Today’s walk takes you down to the valley floor passing fields of sunflowers and orchid-sprinkled paths, before coming to the small hamlet of Quartaia, a good lunch stop. Continue through the woods along the famous pilgrim’s path, the Via Francigena, where the fossils in the stones beneath your feet bear witness to the time when this area was covered by the sea. A final easy stroll takes you along the milky-blue, limestone-rich river d’Elsa and to your stunning hotel, a beautifully converted C12 Benedictine Abbey with garden and pool. (Staying at Relais Della Rovere, Half Board)

  5. Day 5 Days 5 - 7 At Colle di Val d'Elsa

    Regular buses to Siena (30 mins) and Florence (1hr) leave from just outside the hotel grounds so you can easily explore Il Campo, the Duomo, and the treasures of the world-famous Uffizi. The historic town of Colle di Val d’Elsa dates back to Etruscan times with cathedral, museums and fine Renaissance buildings. Back at the hotel, you can relax in the pleasant gardens surrounding the sparkling outdoor pool. (Staying at Relais Della Rovere, 1st night Half Board, following days Breakfast only)

  6. Day 6 Day 8 Colle di Val d'Elsa to San Gimignano 16km/10mi/4.5hr

    Today you follow in pilgrims’ footsteps along the Via Francigena. Bright with sunflowers and fragrant apple orchards, this historic path skirts tiny hamlets and lonely chapels towards the lazy Foci River. You may like to make a short detour to take in a wine-tasting at Montauto, before retracing your steps to rejoin the Via Francigena up to San Gimignano. Time for a swim in the pool before dinner. (Staying at Relais Santa Chiara, Breakfast only)

  7. Day 7 Day 9 At San Gimignano

    Visit San Gimignano’s mystical towers this morning built by warring neighbours in the C12 to out-do one another! Or for a longer day out, hop on a local bus to Siena (30 mins), a perfectly preserved mediaeval gem with a stunning striped C14 Gothic Cathedral and beautiful square. (Staying at Relais Santa Chiara, Breakfast only)

  8. Day 8 Day 10 San Gimignano to Volterra 22km/14mi/6.5hr

    A short taxi ride (10 mins) from your hotel takes you to the start of the walk at the Castelvecchio Nature Reserve. From here you follow a woodland trail dotted with rock roses and wild strawberry plants to reach a panoramic strada bianca, where hawks soar overhead. With open views across cypress studded ochre fields to Monte Voltraio, you pass through the villages of Sensano and Ulignano, historic hamlets with C16 villas. Perhaps picnic by the Era Valley before ascending an ancient mule track back to Volterra. (Staying at Park Hotel Le Fonti, Half Board)

  9. Day 9 Day 11 Leave Volterra

    Return home after breakfast. See our Volterra to San Gimignano Walk for an 8-night version of this holiday.

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Where you stay
Park Hotel Le Fonti
The 4 star Park Hotel Le Fonti is located just below the Porta dell’Arco entrance to Volterra’s beautifully preserved mediaeval centre. It’s an easy 10 minute stroll into arguably one of Italy’s oldest towns. The hotel has over 50 comfortable rooms, all of which are furnished in a simple style with terracotta floors and elegant fabrics. All rooms have ensuite facilities. The real highlight of the hotel is the breathtaking view from the terrace and fabulous infinity pool – the sweeping panorama over the rolling Pisan hills is truly outstanding.
Hotel Terre di Casole
Just a 10-minute walk from the centre of the village, the **** Hotel Terre di Casole has recently reopened after being completely refurbished – and the end result is stunning! The hotel boasts 40 en-suite modern yet stylish rooms which come with either a garden terrace or a balcony – both have views over the pool and the lovely gardens to the rear of the hotel. The public rooms at the Terre di Casole reflect the attractive, modern decor in the bedrooms. Both the lounge/bar area and the restaurant are large, airy rooms with a white colour scheme, which lends them a stylish yet minimalist feel. Ideal for relaxing in! Your evening meal will be taken in the hotel’s restaurant. The menu features a number of classic Italian/Tuscan dishes with a modern twist, all made with herbs from the hotel’s garden! The hotel also has a resident patissier, so you’ll be really spoilt with the quality of the desserts!
Relais della Rovere
The Relais della Rovere is a stunning 4-star hotel located at the edge of Colle di Val d’Elsa. The Cellerai family have sympathetically converted this C12 Benedictine Abbey into a 31 room luxurious hotel, retaining many of the abbey’s original features. The bedrooms are split between two buildings and decorated in a contemporary style with wooden floors and beech furniture. The rooms are quite large with ensuite facilities. The hotel has a lovely outdoor pool which is surrounded by pleasant gardens.
Relais Santa Chiara
Situatued just 400m from the mediaeval walls of UNESCO listed San Gimignano lies the charming, four star Relais Santa Chiara Hotel. This elegant property is surrounded by some of Tuscany’s most beautiful scenery and enjoys countryside views over hills covered with vineyards and olive groves, not to mention its own private garden featuring a swimming pool and hydro massage pool. There is also a terrace on which you can enjoy breakfast in the morning and a selection of drinks from the hotel’s cocktail bar in the evening. All the ensuite rooms come with air-conditioning, satellite TV, minibar and hairdryer. You can also upgrade to a room with balcony and views of the surrounding vineyards and stunning countryside.
Eating and Drinking

All continental breakfast and 6 evening meals

Chianti is synonymous with excellent food and wine and evening meals are a celebration of the local cuisine. Perhaps try pappardelle alla lepre (fresh ribbons of pasta with a hare sauce) or bruschetta (toasted bread rubbed with garlic and olive oil, topped with sun ripened tomatoes), all washed down by a glass or two of full-bodied Chianti!

Italy’s most famous export is probably its cuisine and the traditional dishes of Tuscany are the most influential and revered. The region’s food is based on cucina povera, ‘poor/peasant cookery’, a rural cuisine based on available natural ingredients: olive oil, unsalted bread, pulses and vegetables, wild mushroom or porcini, and salt-cured meats such as salame and prosciutto. In particular, Tuscan olive oil is renowned for its quality and is the most important ingredient in the region’s cooking. You will find it in almost every dish – as a salad dressing, poured over vegetables and into soups and even as a replacement for butter on bread (very nice with a sprinkling of salt!).

Of course the Chianti region is best known for its regional wine (the very best ones are Chianti Classico and have a black cockerel stamped on the label). Chianti is produced in the vineyards dotted around the Tuscan hills; we actually visit the hills to the north of Siena, where the Chianti Colli Senesi wine is produced. Made from the Sangiovese grape, this is an excellent light, fruity red. Although best known for its red wine, a good white wine is also produced in the Chianti region. Made from the Vernaccia grape, the Vernaccia di San Gimignano is a crisp dry white which has greatly improved over recent years. It is best drunk young.

Activity Level: 2 (Leisurely/Moderate)
Av. daily ride: 18km (11 miles).
No. of days walking: 4
Terrain & route: The walking mainly follows flat strade bianche (white roads) with some asphalt lanes and partly shaded forest and valley trails. Walking boots and poles are recommended. Strade bianche are mainly exposed, affording excellent views – a sunhat is essential.
Vehicle Support: A representative will be there to meet you, make sure the bikes are all set up and will be on call throughout the trip should you need.

It is important that you are happy reading maps and following route notes, we make these as accurate as possible and they are regularly checked.

As this is a self-guided holiday there is no group and no leader. There maybe others on the same departure date as you, but you will not be organised together. The route notes contain an emergency assistance telephone number should you need it and in emergencies, the local representative is normally able to dispatch a taxi or pick you up themselves. They may wish to charge for this service.

You start in Volterra, a real Etruscan gem with its tangle of alleys home to alabaster workshops and secret chapels, from where you walk through the verdant Berignone Nature Reserve and up to a fantastic panoramic ridge before a final climb to Casole d’Elsa. Your journey then takes you east to mediaeval Colle di Val d’Elsa, enjoying balcony views across the Elsa Valley. As you move towards stunning San Gimignano, the medieval ‘Manhattan of Tuscany’, the landscape is dominated by vines so there are plenty of wine-tasting opportunities here!

Overall Rating
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