Headwater - Chianti Classic Self-Guided Walk

11 days
from
£1,459
View Trips
Excl. Flights
Add to wishlist View Dates & Prices
Loading...
Leisurely / Moderate
 Learn more
Trip code: 
W10TY
Way to Travel:
Self-Guided
Activity:
Walking & Trekking
Min age:
8

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!

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!

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

Key information

  • 10 nights hotel-to-hotel accommodation
  • 4 Days walking
  • 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's included

  • All accommodation
  • Services of your local Headwater Representative
  • Headwater Wine Collection Service 
  • Route directions and maps 
  • Luggage transfers between hotels 
  • Walking transfers

What's not included

  • Travel insurance
  • Single accommodation (available on request -compulsory supplement)
  • Visas or vaccinations

OPTIONAL UPGRADES

  • Flights from Heathrow to Pisa with British Airways, including local transfers
  • Other flights, including regional departures
  • Business/club/first class fares on request
  • Room upgrades and extra nights at selected hotels
  • City break add-ons in Pisa, Florence, Siena and Lucca
  • Option to shorten to 8 nights
Call for general departures:
020 8772 3936
Call for tailormade trips:
020 8772 3874
Email us >
Request a brochure >
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

View Trip Notes
Add your photos

4

Days of Walking & Trekking
Terrain:

The walking mainly follows flat strade bianche (white roads) with some asphalt lanes and partly shaded forest and valley trails.

Day by day breakdown
Day 214.0km/9.0miles
Day 419.0km/12.0miles
Day 816.0km/10.0miles
Day 1022.0km/14.0miles

Responsible Travel

At Exodus we believe in the power of Responsible Travel.

Every time we travel, we are part of a global movement that creates jobs, builds more sustainable societies, encourages cultural understanding and safeguards common natural and cultural heritage. To learn more about what Responsible Travel means to Exodus click here…

Itinerary

Include flights Expand all
Volterra
to
Volterra

  • 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)

    Meals included: Dinner

  • Day 2

    Volterra to Casole D'Elsa

    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)

    Meals included: Breakfast Dinner

  • 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)

    Meals included: Breakfast Dinner

  • Day 4

    Casole D'Elsa to Colle Di Val D'Elsa

    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)

    Meals included: Breakfast Dinner

  • Day 5

    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)

    Meals included: Breakfast Dinner

  • Days 6-7

    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)

    Meals included: Breakfast

  • Day 8

    Colle Di Val D'Elsa to San Gimignano

    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)

    Meals included: Breakfast

  • 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)

  • Day 10

    San Gimignano to Volterra

    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)

    Meals included: Breakfast Dinner

  • Day 11

    Leave Volterra

    Return home after breakfast.

    Meals included: Breakfast
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

View Trip Notes
Show map

Essential Info

Visas

Italy

No visa required for British passport holders.
Please note in Italy it is compulsory to carry ID with you at all times.

Vaccinations

Italy

There are no specific health risks.

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 cookery. 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.

Weather

April and May departures can expect warm days and although rain is possible, it seldom lasts long. Nights may still be rather cool. We strongly recommend a fleece-lined jacket or warm sweater in these months. June sees the start of summer and July and August can become quite hot by mid afternoon, so this time is kept free for lunch. Although rain is unusual, torrential cloudbursts are not unknown. September and October are cooler and wetter, yet visibility is often better. Swimming is usually still possible at this time.

Is this trip for you?

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 mediaeval 'Manhattan of Tuscany', the landscape is dominated by vines so there are plenty of wine-tasting opportunities here!

Call for general departures:
020 8772 3936
Call for tailormade trips:
020 8772 3874
Email us >
Request a brochure >
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

View Trip Notes

Accommodation

Hotels

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.

Call for general departures:
020 8772 3936
Call for tailormade trips:
020 8772 3874
Email us >
Request a brochure >
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

View Trip Notes

Expert Blog Entries

Reviews

Add your own review

Be the first to post your review! If you have recently returned from an Exodus adventure and want to help other travellers with your feedback then simply use the link below to post your holiday review.

See all reviews

Dates & Prices

An overview of flight options

Exodus is committed to making joining our tours as easy as possible, wherever you live. We generally only block book seats from London, but this certainly does not mean that you need to fly from there. Depending on the route and airlines available, there will usually be various options available for those who want to fly from their local airport.

This page aims to provide a useful overview of the options available to our clients. However, the best flight arrangements should be tailored to your personal requirements, so please contact our Sales team for expert advice.

 

What kind of options do I have ?

1. We can book for you: Flights from anywhere in the world - not via London  

Depending on the route, this may be direct or via an overseas hub like Amsterdam, the Middle East or elsewhere. On short haul routes there may be direct flights with low cost airlines, charter flights or scheduled airlines. Exodus can book most, but not all, of these for you. The most appropriate airline may be different to that which we use for the group flight from London, but many people now travel on different airlines and meet up with their fellow passengers at the destination.

Pros Cons
  • May be the most direct route
  • Often the extra fare compared to the London flight is minimal.
  • As you will be in the hands a single airline for your entire journey, the airline will be responsible for your bags and your connections.
  • You may not be able to join the group transfers. However, we can usually arrange private transfers, or book your flights to try and coincide with the group transfers. See notes on transfer arrangements below.

 

2. We can book for you: Connecting flights from your local airport to London

Exodus can book connecting flights to London so you can join the group flight there. Connecting times will be followed according to airline advice, or as requested by clients. There are two types of fares we can use for this option: a 'through-fare' or a 'published fare'.
 
a) A 'through-fare' is where you will be in the main airline's care throughout. You change planes, but your bags are checked all the way through to your final destination. 

b) A 'published fare' ticket is completely seperate from your onward ticket from London. It is usually cheaper than a through-fare but will need to be paid for and issued as soon as it is booked. This can be a problem if your tour has not yet reached minimum numbers. On 'published fares' neither airline is aware that you have connecting flights, so Exodus is responsible for timing your connection, not the airlines involved. The tickets are also usually non changeable and non refundable.

Pros Cons
  • Depending on the fare type, Exodus or the airline is responsible for flight connections.
  • Through fare tickets can be expensive.
  • On a published fare, tickets must be issued immediately; tickets on published fares can be very difficult to change if onward flight times change; bags are not checked though to your final destination.
  • Published fares are non-refundable.

 

3. Booking some or all of the flights yourself

You can also book connecting air travel yourself, either to London, or all the way to the start point. There may be certain airlines or routes we don't have access to, so this is always an option. However, if you make your own travel arrangements you become liable for any delays, cancellations or missed connections, and Exodus is not required to offer refunds if you have trouble reaching the start of your trip.

Pros Cons
  • You might find cheaper fares, or routes not available to Exodus.
  • You are responsible for any delays or missed connections, and the cost of the tour is not protected should you miss your flight be cancelled.

 

 Notes on transfer arrangements

Sometimes it is possible to travel on a different airline to the group flight from London. Where this is the case, we need to think about ensuring you meet up with the group with minimum extra cost and hassle.

  • On certain trips, it is easy to arrive on a different flight and still meet the group at the hotel with time in hand. We can usually arrange private transfers (at extra cost) or offer advice on taking a taxi to the start hotel.
  • On other trips (especially in Europe), the transfer meets the group flight and then travels some distance to the first night's accommodation. Where this is the case, our Sales team will try to arrange flights that arrive before (and depart after) the group. However, we do have to make it clear in your final documentation that if your flights are delayed, the transfer cannot wait for you. While Exodus or our local operators will do what we can to help you reach the start point of the tour, any additional costs must be paid by the client. 

 

Next steps? 

Call our Sales team on: 0203 733 0698

Email your query: [email protected]

Call us on 020 8772 3936
Chat with us online