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Classic Chianti Cycling

Classic Chianti Cycling

1-800-267-3347 Email us
  • Holiday typeSelf-guided cycling
  • Duration10 nights
  • Accommodationhotel-to-hotel
  • Activity level
  • From $2879per person, tour only
  • Departures
    Every two days from 28 Jun '19 to 20 Oct '20
  • What your holiday price includes
  • 10 nights hotel-to-hotel accommodation in a mix of and hotels
  • All buffet breakfasts and 6 evening meals
  • Services of your local Headwater Representative
  • Headwater Wine Collection Service
  • GPS route directions and maps
  • RideWithGPS navigation app
  • High quality hybrid bikes
  • RidePlus route options
  • Standard transfers at the start/end of the trip
  • Luggage transfers between hotels
  • Optional Upgrades
  • Electric bikes available
  • Tandems available
  • Room upgrades and extra nights at selected hotels
  • City break add-ons in Lucca, Siena and Pisa
  • RidePlus road bike
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history, swimming opportunities, solo travellers, couples
      from 25 reviews

Mrs Tanner says...
A leisurely end of season break
Read reviews »

Italy: Tuscany

Classic Chianti Cycling

  • 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

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.

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.

The hotels we've selected for this holiday are among our best, and include a magnificently restored 12th century abbey, a wonderfully renovated, stylish watermill which dates back to the 16th century and belonged to the famous Medici family, and a family-run, traditional hotel overlooking the soaring towers of San Gimignano. As Chianti is synonymous with great food and wine, we've made sure evening meals are a celebration of local flavours throughout.

This holiday can be booked as a RidePlus option - see itinerary details for routes and distances. Details of the upgraded bikes available and the supplement payable are in the dates and prices section. At time of booking, just request the RidePlus option for the number of people wanting it and before departure you will be sent your route details, with access to downloadable GPX files for you to add to your own Garmin device.

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Day-by-day itinerary

cycling elevations

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

Rideplus is available on this holiday (see daily route options below) and includes additional route directions and GPX files for you to download to your own route navigation device (Garmin, Wahoo, Bryton, etc). Simply request the Rideplus option at the time of booking. Upgraded bikes are also available, see the dates and prices for further details.

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.
You stay at the Park Hotel Le Fonti (breakfast and evening meal)

Day 2: Volterra to Certaldo 36km/22.5mi

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 mediaeval Certaldo.
RIDE PLUS - 75km / 47mi Leaving Volterra your route drops down into the valley before heading north, passing the Theatre of Silence and the family home of Andrea Bocceli and then passing through rich green meadows and stunning countryside. On to the pretty spa town of Gambassi Terme and then a long downhill ride into medieval Certaldo, to your hotel for the next two nights.
You stay at the Hotel Certaldo (breakfast included)

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.
You stay at the Hotel Certaldo (breakfast included)

Day 4: Certaldo to Colle di Val d'Elsa 28km/17.5mi

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.
RIDE PLUS - 100km / 62mi (shorter routes available) 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.
You stay at the Relais della Rovere (breakfast and evening meal)

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.
You stay at the Relais della Rovere (breakfast and evening meal)

Day 6: At Colle di Val d'Elsa: suggested day exploring locally

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.
You stay at the Relais della Rovere (breakfast included)

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.
You stay at the Relais della Rovere (breakfast included)

Day 8: Colle di Val d'Elsa to Pescille 40km/25mi

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.
RIDE PLUS - 87km / 54mi (shorter routes available Heading to the south of the region today you are rewarded with beautiful peaceful scenery, with mountain vistas as you pass meadows, small forests and lines of cyprus trees. You pass small villages which are well off the beaten track. Maybe lunch late in walled Caole d' Elsa, then pass Castel San Gimignano and finish
You stay at the Hotel Pescill (breakfast at the hotel, evening meal at a local restaurant)

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.
You stay at the Hotel Pescille (breakfast at the hotel, evening meal at a local restaurant)

Day 10: Pescille to Volterra 38km/24mi

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.
RIDE PLUS - 59km / 37mi 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.
You stay at the Park Hotel Le Fonti (breakfast and evening meal)

Day 11: Leave Volterra

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking. If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Park Hotel Le Fonti, Volterra

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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.

Room upgrades: Deluxe Room with Terrace, Junior Suite or Suite.
Deluxe rooms with terrace have their own terrace overlooking the pool. Junior suites are much larger than a standard room, with a sitting area. The suite is situated in the tower, and is larger than a junior suite. It has a balcony and a jacuzzi.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Certaldo, Certaldo

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Located on the fringe of Certaldo Basso, on the River Elsa, the stunning 4* Hotel Certaldo dates back to the 1500s when it belonged to the infamous and all powerful Medici family. It started life as a water mill and signs of its original use are still in evidence, including its mighty water wheel. Over the 20C, the mill was used as a power turbine and produced enough electricity to service the entire town of Certaldo up to the 1950s!

The mill was lovingly restored and converted into a hotel in 2007 and now boasts 30 modern and stylish rooms with all the amenities you would expect of a comfortable 4* hotel. There is also a pleasant garden (with pool) and terrace area overlooking the river, and a lounge area with tv and books where you can relax after a day's exploring.

Room upgrades: Superior Room, Deluxe Room or Junior Suite.
Superior rooms are larger than standard rooms and have a minibar and free wifi. Deluxe rooms are larger than the superior rooms, they also have a minibar and free wifi. The Junior Suites are larger than all the other room types, they have a minibar and free wifi.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Relais della Rovere, Colle di Val d'Elsa

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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.

Room upgrades: Luxury (Double Only), Junior Suite or Suite.
Luxury rooms are located in the Renaissance Villa and feature antique furniture and prints, and precious tapestries and ceilings with encased beams and parquet flooring. Large windows with a view over the historical centre of Colle Val D'Elsa. Bathroom with whirlpool bath, courtesy kit, bathrobe and slippers. Junior Suites are located in the Benedictine Convent and in the farmhouse. They comprise an entrance hall with living room and one double bedroom, and feature modern, solid oak furniture. They have beamed ceilings and parquet flooring. One/two bathrooms, one with shower, the other with whirlpool bath, courtesy kit, bathrobe and slippers. Suites are in the Benedictine Convent and in the Villa. They are larger with an entrance hall, living room and sofa bed and a double bedroom, with two bathrooms. Some have modern decor with solid oak furniture, beamed ceilings and parquet flooring. Others feature antique furniture and prints, and precious tapestries, ceilings with encased beams and parquet flooring.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Pescille, Pescille

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The Hotel Pescille is located just 4km outside San Gimignano, in the heart of the Tuscan countryside, surrounded by olive groves and vineyards. It started life as an old farmhouse before being converted into the 3* hotel it is today. Evidence of its origins still remains however, with its ancient tower housing the hotel's small agricultural museum. There are pleasant gardens surrounding the hotel - with lovely views of the surrounding landscape - and it also benefits from an outdoor swimming pool.

All rooms at the Hotel Pescille are ensuite and are simple yet spacious with tiled floors, whitewashed walls and pristine white linen; air conditioning. satellite TV, minibar and hair dryer also all come as standard. Rooms have views onto either the timeless Tuscan countryside, or the roofs and mediaeval towers of San Gimignano itself.

The hotel does not have a restaurant open for dinner, we have therefore arranged for you to have return taxi transfers to the centre of San Gimignano, where there is a wealth of restaurants to suit all budgets and tastes.

Room upgrades: Double with view of San Gimignano.
Rooms with balcony offer wonderful views of San Gimignano.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel La Luna, Lucca

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The Hotel La Luna is a friendly hotel, tucked away in a quiet side street, just off the atmospheric Via Fillungo, the most sophisticated and exclusive street in Lucca's historic centre.

The original part of the hotel dates back to the 1200s when it was built elsewhere and then 'moved' about a century later to its present location. It now comprises of 2 buildings, with the 29 en suite rooms divided between the two. Breakfast is taken in the buffet breakfast room in the reception building, where there is also a small bar.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Chiusarelli, Siena

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Hotel Chiusarelli is located just beyond Siena's mediaeval walls and a ten-minute walk away from town's main square, Il Campo. Its position on the edge of the historical centre is perfect as the hotel is spacious and quiet but still within walking distance of all the sights and restaurants. There is even a small garden to the front with palm trees and a quiet (except on Sunday afternoons when you will have a grandstand view of AC Siena's matches!) veranda to the rear of the hotel.

The en-suite rooms have recently been renovated and are quite simple but comfortable.

In order to give the best available rate, prices are on request. Please contact us for a quote.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Alessandro della Spina, Pisa

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The Hotel Alessandro della Spina is located just 500m from Pisa central train station and just a 10 minute walk from most of the city's main monuments. This modern and cosy property welcomes its guests with an elegant, warm atmosphere, enhanced by its charming garden, and friendly staff that are always on hand to ensure you a relaxed stay.

Hotel facilities include internet and wi-fi access in the lobby and a bar and comfortable seating area. Guest rooms are spacious, furnished with wood and marble and have air conditioning, a safe and satellite TV. Buffet breakfast includes homemade bread and croissants.

Extra nights: Please contact us for details.


Transfers included from Pisa airport at 11:45 (10:30 Saturdays), and back to Pisa airport at 09:00 (07:45 Saturdays).

Call now to speak to our specialist team at 1-800-267-3347 or email us at usa@exodustravels.com for enquiries or to book your trip.


Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Mrs Tanner, 23/10/2018

A leisurely end of season break

Mrs Clucas, 12/09/2018

Very well organised holiday, local reps were excellent, and great hotels. Good quality bikes and easy to follow route instructions (Ride GPS worked well). This is a stunning area, with beautiful views and interesting historic towns. The cycling is challenging in places as Tuscany is hilly!! However, the views, hotels and food/wine availbale compensate for the effort required.

Mrs Moffat, 16/07/2018

Excellent holiday, lovely hotels and good food. Cycling was quite tough but we still enjoyed the routes and the countryside was beautiful. One problem we had was when going by bus to Siena no one told us that in Italy you need to validate your ticket on the bus. As a result we ended up with a €120 fine!

Mr Lypka, 13/06/2017

Cycling around the hills of Tuscany is challenging and you need to be in good shape to take them on. Its worth it though for the views and the downhill stretches. I particularly enjoyed the four night stop allowing for visits to Florence and Siena. The highlight though for me was San Gimignano.

Mrs Sparshott, 03/06/2016

don't under-estimate how hilly/undulating Tuscany is.

Dr Winter, 20/09/2015

Well organised and professional service - headwater deliver what they promise and the holidays are excellent. A reasonable degree of fitness is required for the cycling holidays - not suitable for beginners or irregular cyclists.

Mr Pridmore, 26/08/2015

A challenging holiday but thoroughly enjoyable. The views were amazing and the rides took you through beautiful places. The use of the word undulating in the notes was over used, hill was closer! Had such a sense of achievement at the end of the holiday! Would love to do this again.

Mr Gilbert, 24/08/2015

We were initially slightly worried by the directions and unknown roads etc, however the notes proved to be excellent and only got momentarily lost once during the whole holiday. Take plenty of food, water and sun cream on the rides as shops and shelter can be few and far between.

Mrs Brown, 17/08/2015

I have found Headwater holidays to be consistently excellent over the three occasions that I've used them. You find some amazing places for us to stay in and provide really useful information on local places to visit. It's lovely to get off the usual tourist tracks and really get to see the countries in more detail, experiencing far more of the areas we visit. The views were spectacular which made up for the challenging sections of the rides, and we were entertained by a golden eagle only metres away from us on the first and last cycle days.

Mrs Downes, 21/07/2015

This is a great way to explore Tuscany with a good physical challenge and lots of wonderful gastronomic experiences thrown in.

Ms Smart, 23/06/2015

A challenging (take note) cycling tour taking you to some beautiful places in Tuscany. The bike was great and despite having to get off a few times in a few places I was mostly very happy with the km and the routes. If I could change any part of the route it would be the strada biancha on day 1 as that really is a bit tough with no views for most of it. The rest of the routes were fine and took you to beautiful scenery.

I was sorely disappointed with the hotel in Siena and would strongly recommend that Headwater change this option as it spoilt my trip a bit. The other hotels were great - my favourite was Pescile. Hotel Revere was good if the weather was ok but I can imagine this is a bit gloomy if its raining as there are limited places to sit inside.

The food was mostly good - breakfasts can be a bit 'Italian' but on the whole not too bad. The biggest let down for food was being sent to two Pizzerias two nights in a row in Certaldo. There is a huge choice of restaurants in Certaldo Alto and I would have preferred paying for my own meal and being given options.

A highlight was a tour of Montalcino (can be done from hotel Revere) and finding some amazing restaurants in San Gim (better at night to avoid the day trippers) and Siena.

For anyone wanting to know here are my restaurant highlights:

Siena - La taverna de San Giuseppe

San Gim - Cum Quibus

Certaldo Alto - Fonte Antica

Overall very happy and am missing the cycling now I am back in the UK

Mr McDowell, 02/11/2014

We had a wonderful holiday and will have plenty of fond memories and photo's. It was a nice mix of exercise,visiting some lovely cities and villages and relaxation.The beauty about cycling is that you get time to appreciate the views, the Tuscan countryside is absolutely amazing. Our reps were extremely pleasant and helpful which went a long way towards our holiday enjoyment. We would definitely do another cycling holiday or even a walking one, but would not want to cycle on another Strada Bianca! It was a very well organised holiday from start to finish. Thank-you Headwater

Mr Millican, 21/10/2014

The cycling was challenging, much more difficult than we expected from the rating. We would not have made it without the help and assistance from the reps Katy and Jim. They were excellent. There were downhill parts of the route that were dangerous for moderate cyclists. I know the area is hilly, however some of the climbing was more akin to a cycling race than a holiday.

Mrs Spriggs, 30/09/2014

Beautiful countryside, tough cycling you would need to do some cycling at home prior to a 2 bike plus. We feel the hotels are much more cosmopolitan than in the past. Whilst they are of a very good standard we miss the more authentic accommodation with more local traditionally prepared food and eating together as a group.

My husband found the food at Relais della Rovere disappointing.

Mrs Capper, 13/09/2014

Excellent holiday, very well organised. Will definitely take another holiday with headwater

A special thank you to the reps Kate and Jim Illingworth who went far over and above there duty to make our holiday outstanding

A special thank you to headwater for the 2 bottles of wine we received for our 30th wedding anniversary

Thank you all

Mrs Wall, 11/09/2014

Excellent! Not a cheap holiday, but worth every penny. Good hotels, excellent food. Bikes were good. Friendly helpful service from the reps who went out of their way to meet the needs of individual guests.

Mr Stead, 10/07/2014

This was our first holiday with Headwater and we thoroughly enjoyed the whole experience. The cycling was challenging and we would advised others choosing this holiday to be prepared for the 'undulations' also known as long, steep hills! However, saying that if you are of a competitive nature they only added to the enjoyment when you reach the top. On the whole the accommodation was fantastic especially the Relais della Rovere where nothing was too much trouble and Le Renaie whose family atmosphere was lovely. We're now looking forward to choosing from next year's brochure - roll on next summer!

Mrs Pickles, 25/06/2014

Tuscany is wonderful. Beautiful countryside and enchanting hilltop towns. However the cycling routes are long and steep, and hard work in the very high temperatures we experienced. It's a glorious holiday if you're fit!

Mrs Bird, 01/06/2014

Katie and Jim looked after all our needs and we are grateful to them for making our holiday work. We found the cycling very tough, but were able to switch to the walking holiday with their help. We probably over estimated our ability but the grading of the holiday was a little misleading to us. Some of the other guests agreed that they had found it tougher than they had expected. Overall, the holiday was enjoyable and we would use Headwater Holidays again.

Mrs Duncan, 09/10/2013

good mix of cycling and rest days. Profile maps giving an indication of the heights gained and lost would be of interest. We cycled an extra day whilst at H della Rovere, and some information about possible routes might have been useful. In fairness, we hadn't told the reps we intended to do this as it was a last moment decision. Hotel Rovere room 404 was noisy as it was opposite reception and trundling suitcases early and late were noisily intrusive. Don't book this room or ask the hotel to lay down a rubberised pathway... The room was also quite dark.

Reps were excellent and helpful setting up and checking the bikes.. Rattly rear mudguards over the via bianchi and uneven road surfaces needed a bit of first aid. A bike bottle holder on the bike frame would have been nice

Mr Whitton, 16/09/2013

Very well organised. Excellent reps on site. Excellent choice of hotels

Mr Groom, 09/09/2013

Very well organised allowing us the opportunity to have many splendid days to enjoy both countryside and town alike. Accommodation, with one notable exception, excellent. Scenery, sights and sounds will all remain locked in the memory for a long time to come - would happily recommend the holiday

Mrs Kimber, 25/07/2013

Fabulous way to see Tuscany. Excellent service from the reps and they were reliable with delivrng luggage and had super local knowledge. All the hotels were friendly and had lovely pools which we needed when we arrived. A great holiday that I would thoroughly recommend.

Mr Hart, 20/06/2013

generally excellent holiday. I think however, we over estimated our capabilities on the bike ride in tuscany. But enjoyed it nevertheless, esp. the scenery. We would certainly book with headwater again but be more careful on the bike ride we choose in future

Mrs Stonehouse, 18/06/2013

we loved cycling in Chianti country - the climbs up to the hilltop towns were always rewarded with fantastic pistacchio gelati!

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.

Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

This 10 night self-guided cycling holiday includes:

Hotel-to-hotel accommodation in a mix of and hotels

All buffet breakfasts and 6 evening meals

Services of your local Headwater Representative

Headwater Wine Collection Service

GPS route directions and maps

RideWithGPS navigation app

High quality hybrid bikes

RidePlus route options

Standard transfers at the start/end of the trip

Luggage transfers between hotels

How to book:

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

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18th Sep US$3149 Check availability
20th Sep US$3149 Check availability
22nd Sep US$3099 Check availability
24th Sep US$3099 Check availability
26th Sep US$3099 Check availability
28th Sep US$3099 Check availability
30th Sep US$3099 Check availability
Oct 2019Tour only Availability
2nd Oct US$2879 Check availability
4th Oct US$2879 Check availability
6th Oct US$2879 Check availability
8th Oct US$2879 Check availability
10th Oct US$2879 Check availability
12th Oct US$2879 Check availability
Apr 2020Tour only Availability
13th Apr US$3199 Check availability
15th Apr US$3199 Check availability
17th Apr US$3199 Check availability
19th Apr US$3199 Check availability
21st Apr US$3199 Check availability
23rd Apr US$3199 Check availability
25th Apr US$3199 Check availability
27th Apr US$3199 Check availability
29th Apr US$3199 Check availability
May 2020Tour only Availability
1st May US$3199 Check availability
3rd May US$3199 Check availability
5th May US$3199 Check availability
7th May US$3199 Check availability
9th May US$3199 Check availability
11th May US$3199 Check availability
13th May US$3199 Check availability
15th May US$3199 Check availability
17th May US$3199 Check availability
19th May US$3199 Check availability
21st May US$3199 Check availability
23rd May US$3199 Check availability
25th May US$3199 Check availability
27th May US$3199 Check availability
29th May US$3199 Check availability
31st May US$3199 Check availability
Jun 2020Tour only Availability
2nd Jun US$3199 Check availability
4th Jun US$3199 Check availability
6th Jun US$3199 Check availability
8th Jun US$3199 Check availability
10th Jun US$3199 Check availability
12th Jun US$3299 Check availability
14th Jun US$3299 Check availability
16th Jun US$3299 Check availability
18th Jun US$3299 Check availability
20th Jun US$3299 Check availability
22nd Jun US$3299 Check availability
24th Jun US$3299 Check availability
26th Jun US$3299 Check availability
28th Jun US$3299 Check availability
30th Jun US$3299 Check availability
Jul 2020Tour only Availability
2nd Jul US$3299 Check availability
4th Jul US$3299 Check availability
6th Jul US$3299 Check availability
8th Jul US$3299 Check availability
10th Jul US$3299 Check availability
12th Jul US$3299 Check availability
14th Jul US$3299 Check availability
16th Jul US$3299 Check availability
18th Jul US$3299 Check availability
20th Jul US$3299 Check availability
22nd Jul US$3399 Check availability
24th Jul US$3399 Check availability
26th Jul US$3399 Check availability
28th Jul US$3399 Check availability
30th Jul US$3399 Check availability
Aug 2020Tour only Availability
1st Aug US$3399 Check availability
3rd Aug US$3399 Check availability
5th Aug US$3399 Check availability
7th Aug US$3399 Check availability
9th Aug US$3399 Check availability
11th Aug US$3399 Check availability
13th Aug US$3399 Check availability
15th Aug US$3399 Check availability
17th Aug US$3399 Check availability
19th Aug US$3399 Check availability
21st Aug US$3399 Check availability
23rd Aug US$3399 Check availability
25th Aug US$3399 Check availability
27th Aug US$3399 Check availability
29th Aug US$3399 Check availability
31st Aug US$3399 Check availability
Sep 2020Tour only Availability
2nd Sep US$3399 Check availability
4th Sep US$3399 Check availability
6th Sep US$3399 Check availability
8th Sep US$3399 Check availability
10th Sep US$3399 Check availability
12th Sep US$3399 Check availability
14th Sep US$3399 Check availability
16th Sep US$3399 Check availability
18th Sep US$3399 Check availability
20th Sep US$3399 Check availability
22nd Sep US$3349 Check availability
24th Sep US$3349 Check availability
26th Sep US$3349 Check availability
28th Sep US$3349 Check availability
30th Sep US$3349 Check availability
Oct 2020Tour only Availability
2nd Oct US$3099 Check availability
4th Oct US$3099 Check availability
6th Oct US$3099 Check availability
8th Oct US$3099 Check availability
10th Oct US$3099 Check availability
12th Oct US$3099 Check availability
14th Oct US$3099 Check availability
16th Oct US$3099 Check availability
18th Oct US$3079 Check availability
20th Oct US$3079 Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Over 2 and under 12 sharing with 2 adults.

Holiday type
Self-guided cycling Managed locally by Headwater appointed rep.

Every two days from 28th Jun 2019 to 20th Oct 2020, for 10 nights. All dates are subject to availability, please contact us to check.

All buffet breakfasts and 6 evening meals

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £275 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

It is possible to hire tandem bikes for this holiday at a supplement of £195 per bike. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

Customers wishing to include the free RidePlus option should request this at the time of booking. RidePlus holidays include additional route directions as GPX files for you to download to your own route navigation device (Garmin, Wahoo, Bryton, etc). Not all RidePlus routes are suitable for our standard hybrid bikes so you may need to bring your own road bike or hire one - please call for details.

Rideplus bike upgrades
Road bikes (Willer Ultegra) are available at a supplement of £329 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

Tailor-made travel

Tour only

Transfers included from Pisa airport at 11:45 (10:30 Saturdays), and back to Pisa airport at 09:00 (07:45 Saturdays).

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

Call now to speak to our specialist team at 1-800-267-3347 or email us at usa@exodustravels.com for enquiries or to book your trip.

Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for . Simply complete the form below (fields marked * are mandatory) and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.

Alternatively, you can call our sales team on 1-800-267-3347 to discuss your requirements in more detail.

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We've been creating high-quality relaxed activity holidays since 1985 and our wealth of experience means we're able to build the perfect tailor-made tour for you. Our 'Gold Trusted' rating on Feefo, the independent review site, underlines our exceptional levels of customer service, and our ATOL bonding and ABTA membership guarantees your holiday is safe with us.

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