Headwater - Classic Chianti Self-Guided Cycling

11 days
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This 10-night cycling tour combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena.

This ten night holiday has been carefully crafted to cleverly balance cultural highlights and historic treasures with natural beauty and stunningly scenic cycling. It's a perfect choice too if you like the idea of combining timeless countryside cycling with the use of local transport to explore the eternal cities of Siena and Florence on foot. 


RidePlus is available on this tour, meaning that on most days you have the option to do a more challenging RidePlus route. Each option comes with GPS navigation and route maps to ensure you get to your destination easily, and you’ll stay at the same hotel regardless of which route you take, although RidePlus cyclists will be provided with an upgraded lightweight road bike. If you’re travelling as a group you can split up for the day to ride independently – so everyone has their perfect day. Find out more about RidePlus here and more about the routes for this holiday in the Itinerary section.



  • Quintessential, Italian landscapes: rolling hills, endless vines, beautifully preserved honey-hued hamlets
  • Mostly 4-star hotels; gorgeous swimming pools; superb local cuisine
  • Scenic cycling through olive groves, fruit orchards and sunflowers
  • Spend 4 nights in Colle di Val d'Elsa: charming piazze, Sienese frescoes, easy access to Florence and Siena
  • Etruscan, Roman, Renaissance and Mediaeval art and architecture

Key information

  • 10 Nights, hotel-to-hotel
  • Departs Every two days from 13 Apr '19 to 22 Oct '19
  • Headwater wine service 
  • Route notes and maps provided 
  • High quality bikes provided
  • Luggage transfers between hotels

What's included

  • All accommodation
  • All buffet breakfasts and 6 evening meals 
  • Headwater wine service 
  • Route notes and maps 
  • High quality bikes 
  • Luggage transfers between hotels

What's not included

  • Travel insurance
  • Single accommodation (available on request)
  • Visas or vaccinations
Call for general departures:
074 340 4587
Call for tailormade trips:
+44 (0)20 8772 3874
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.


Days of Cycling

Lots of the cycling is on off road strada bianca, although at times it has been necessary to use busier roads for short stretches where no alternative exists. Most of the countryside is moderately hilly, so there is every excuse to stop for a breather to admire the view!

Day by day breakdown
Day 236.0km/23.0miles
Day 428.0km/18.0miles
Day 840.0km/25.0miles
Day 1038.0km/24.0miles

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… 


  • Day 1

    Arrive at Volterra

    Arrive in Volterra where you've time for a dip in the hotel pool and a wander round the town's tangle of cobbled alleys and hidden squares before dinner. (Staying at Park Hotel Le Fonti)

    Meals included: Dinner
  • Day 2

    Volterra to Certaldo

    Option: 1

    Today it's a downhill whizz out of hilltop Volterra and into the pretty Era Valley where spectacular views of the surrounding timeless Tuscan countryside open up as you pedal. After climbing out of the valley, you'll soon pass through the pretty hamlet of Castagno where we suggest a well-deserved coffee stop in the local bar. Your route continues on to Gambassi Terme, a well-preserved spa town with cobbled streets, C12 church and lovely shaded gardens. Lunch here perhaps in one of the many trattorie then, soon after leaving the town, you'll pick up the famous Via Francigena for the gentle, mainly downhill stretch to medieval Certaldo. (Staying at Hotel Certaldo)


    Option: 2

    Distance - 67km, elevation +986m / -1238m

    Leaving Volterra we drop down into the valley heading north passing the Theatre of Silence and the family home of Andrea Bocceli, then passing through rich green meadows and before climbing into the stunning countryside, and onto the pretty spa town of Gambassi Terme. A long downhill ride takes you into medieval Certaldo, to your hotel for the next 2 nights.

    Meals included: Breakfast
  • Day 3

    At Certaldo

    Explore stunning Certaldo, Boccaccio's birthplace. Split into two distinct halves, the mediaeval centre of Certaldo Alto with its fabulous ancient buildings, is accessed by funicular and offers spectacular views across the Val d'Elsa. On the other hand, Certaldo Basso is the more modern part of the town with shops, bars and restaurants. You could also spend time today, relaxing by the hotel pool. (Staying at Hotel Certaldo)

    Meals included: Breakfast
  • Day 4

    Certaldo to Colle di Val d'Elsa


    Option: 1

    Today's route explores the panoramic wine country between Certaldo and Colle di Val d'Elsa. You'll follow the official, mainly off-road, Chianti Wine Route where you'll find lots of tasting opportunities - don't forget, we can collect any purchases for you! It's then on to the old town of Poggibonsi, a perfect stop for lunch and to visit the ruins of its unfinished C15 fortress. The day ends with gentle pedalling through tree-lined meadows and a valley of poppy and sunflower fields to Colle di Val d'Elsa. (Staying at Relais della Rovere)


    Option: 2

    Distance - 100.3km, elevation: +1571m / -1616m

    Today you head up to Pancole and then into wine country - a beautiful ride, with vines as far as the eye can see,  passing through beautiful hamlets and interesting wine towns. With the climbing over, you pass two of the famous Chianti towns, Castellina and Radda, both offering great wine tasting opportunities and good restaurants. Heading down to the valley you pass the stunning walled village of Monteriggioni and onto Colle Val d’Elsa for your next two nights.

    Meals included: Breakfast Dinner
  • Day 5

    At Colle di Val d'Elsa: Suggested Day in Siena

    There is so much to see and do in and around Colle di Val d'Elsa that you really will be spoiled for choice. However, today we recommend hopping on the local bus (from just outside the hotel) for the 30min ride to the great mediaeval city of Siena. Visit the Palazzo Pubblico with its impressive pre-Renaissance frescoes and climb the Torre del Mangia for the best views of the town and surrounding Sienese countryside. For lunch, or simply a drink, there is no better place than Siena's beautiful shell-shaped Piazza del Campo. (Staying at Relais della Rovere)

    Meals included: Breakfast Dinner
  • Day 6

    At Colle Di Val D'elsa: Suggested Day Exploring Locally

    Option: 1

    After a fairly long day yesterday, we propose that you spend a relaxed morning in Colle di Val d'Elsa. The historic town dates back to Etruscan times with a cathedral, museums and fine Renaissance buildings. After lunch in the old square, maybe spend some time by the pool before a pre-dinner stroll along the lovely River Elsa where limestone-rich rapids come crashing dramatically downstream. (Staying at Relais della Rovere)


    Option: 2

    Meals included: Breakfast
  • Day 7

    At Colle di Val d'Elsa: Suggested Day in Florence

    No trip to Tuscany would be complete without a visit to the charming city of Florence, arguably the most beautiful city in the world! It's just an hour on the local bus (which leaves from just outside the hotel) giving you plenty of time to explore the Uffizi (closed Mon), Duomo and Baptistery. If you want to escape the crowds, we suggest you cross the Ponte Vecchio to the quieter side of the Arno to visit the Boboli Gardens. (Staying at Relais della Rovere)

    Meals included: Breakfast
  • Day 8

    Colle di Val d'Elsa to Pescille


    Option: 1

    Get back on your bike this morning and enjoy superb rolling views before the ride up to Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning views from its hilltop position. Take time to explore its C12 church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps in the lovely piazza. You then wind north through wonderfully scenic countryside, the fabulous mediaeval towers of San Gimignano providing a formidable backdrop as you pedal on to Pescille. (Staying at Hotel Pescille, Breakfast at the hotel and evening meal in a local restaurant)


    Option: 2

    Distance - 87.4km, elevation: +1693m / -1542m

    Heading to the south of the region today, you are rewarded with beautiful scenery, quiet roads with vistas of mountains and hills as you pass pleasant meadows, small forests and lines of cyprus trees. You pass small villages and towns that are well off the beaten track. Maybe take a late lunch in walled Casole d’ Elsa, then pass Castel San Gimignano and finish through the vines to Hotel Pescille for the next two nights.

    Meals included: Breakfast Dinner
  • Day 9

    At Pescille

    San Gimignano is just a short cycle away, its towers giving this hilltop town a distinctive Manhattan-style skyline. Explore its myriad of narrow streets and many hidden cobbled squares before popping back to your tranquil hotel for a refreshing dip in the sparkling swimming pool. (Staying at Hotel Pescille, Breakfast at the hotel and evening meal in a local restaurant)

    Meals included: Breakfast Dinner
  • Day 10

    Pescille to Volterra


    Option: 1

    It's a short downhill ride to San Gimignano before a gentle climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers. It's then an almost entirely downhill cycle into the pretty Era Valley. There's a real sense of achievement on your final pedal through open countryside, enjoying spectacular views, before your last climb back to the ancient cobbled streets of Volterra. (Staying at Park Hotel Le Fonti)


    Option: 2

    Distance - 59.4km, elevation: +1078m / -943m

    From the hotel you head towards San Gimignano, circling the 'town of towers' for 360 degree views of the surrounding area. Pass through wine country before an uphill stretch, followed by a long downhill with views of Volterra. Finish with a climb into Volterra itself, passing through the town and back to your hotel for the last night.

    Meals included: Breakfast Dinner
  • Day 11

    Leave Volterra

    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.

Essential Info



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



There are no specific health risks.

Eating and Drinking

All buffet breakfasts and 6 evening meals included.

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!).


Italy has a good all year round climate, with plenty of sunshine and warm temperatures from the spring through to autumn. Summer departures will usually have hot weather, with temperatures reaching the low to mid 30s centigrade. April-June and September-November departures are likely to be cooler with a slightly higher chance of rain. In late summer there is the possibility of heavy thunderstorms (generally in the afternoons), but these are usually short-lived.

Is this trip for you?

Classification: Self-Guided
Activity Level: 2 (Leisurely/moderate)
Average daily distance on move on days: 35.5km (22.3 miles). 
No. of days cycling: 4
Terrain: Lots of the cycling is on off road strada bianca, although at times it has been necessary to use busier roads for short stretches where no alternative exists. Most of the countryside is moderately hilly, so there is every excuse to stop for a breather to admire the view!
Vehicle Support: This is a self-guided trip for those who prefer to cycle independently, but with our assistance to take out the stress of the logistics and planning. We arrange your accommodations, provide you with a map and route notes so that you can cycle at your own pace. 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 may be others on the same departure date as you, but you will not be organised together. The route notes contain a 24-hour 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.

Your holiday starts in Volterra, a real Etruscan gem with its tangle of alleys home to alabaster workshops and secret chapels, in the heart of the Era Valley. You'll pedal through the archetypal Tuscan countryside, cypress dotted rolling hills, olives, vines, sunflowers, and on, via postcard-pretty Certaldo, to Colle di Val d'Elsa where you'll spend four nights. From here, you can enjoy day trips to the great art cities of Florence and Siena before pedaling on through panoramic wine country to the tiny hamlet of Pescille, a short cycle from mediaeval San Gimignano. Your route then takes you through the Castelvecchio Nature Reserve (great for bird spotting) giving you a real sense of achievement as you loop back to Volterra for your final night. 

Call for general departures:
074 340 4587
Call for tailormade trips:
+44 (0)20 8772 3874
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.



The hotels we've selected for this holiday are among our best, and include a magnificently restored C12 abbey, a wonderfully renovated, stylish watermill which dates back to the C16 and belonged to the famous Medici family, and a family-run, traditional hotel overlooking the soaring towers of San Gimignano.

Call for general departures:
074 340 4587
Call for tailormade trips:
+44 (0)20 8772 3874
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.

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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 074 340 4587