Feefo - Independent reviews
  Contact Us

Request a Brochure | Newsletter

Secrets of San Gimignano Cycling

Secrets of San Gimignano Cycling

1-800-267-3347 Email us
  • Holiday typeSelf-guided cycling
  • Duration8 nights
  • Accommodationhotel-to-hotel
  • Activity level
  • From $2549per person, tour only
  • Departures
    Every two days from 30 Jun '19 to 20 Oct '20
  • What your holiday price includes
  • 8 nights hotel-to-hotel accommodation in a mix of and hotels
  • All continental breakfasts and 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 Pisa, Siena and Lucca
  • RidePlus road bike
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history, swimming opportunities, couples
      from 44 reviews

Mrs Walden says...
Fantastic rep who couldn't have been more helpful. Helpful office staff in the UK. Mixed bag of accommodation. Most was very good. One definitely let ...
Read reviews »

Italy: Tuscany

Secrets of San Gimignano Cycling

  • Exhilarating cycling through open and totally unspoilt countryside
  • San Gimignano's soaring towers; Volterra's Etruscan treasures; great art cities of Florence, Pisa and Siena
  • Fabulous hotels all with stunning pools; superb cuisine and fine wines
  • Cypress-studded hills, sun-drenched olives, row upon row of sunflowers and world-famous vineyards
  • Pretty hamlets, hidden chapels, timeless vermilion villas

This eight night holiday is, quite simply, outstanding in every way - think rich scenery, fantastically contrasting hotels, superb local cuisine and exceptional wines.

You'll start off in Volterra, a beautifully preserved hilltop gem whose eclectic mix of Etruscan, Roman and Renaissance art and architecture has inspired artists and writers for centuries. From here, you pedal north east along quiet, rolling country lanes as you coast towards honey-coloured Pancole, nestled in the Tuscan hills. The cycling is truly glorious as you continue, via fortified towns and hill villages, to medieval Colle, from where you can also head to Florence and Siena for day trips. Then it's on to Pescille, which is perfectly positioned overlooking San Gimignano. Your final stretch takes you through a timeless and kaleidoscopic landscape of ochre-coloured hills and verdant vineyards, giving you a real sense of achievement as you loop back to Volterra for your final night.

Superb 3-star and 4-star contrasting hotels, all with sparkling swimming pools, are an added highlight of this holiday. In Colle di Val d'Elsa, you stay in a fabulously restored 12th century Benedictine abbey, complete with original frescoes, whilst in Volterra, your 4-star hotel has a panoramic infinity pool, with stunning, sweeping views over the Tuscan countryside. Of course, you're in the heart of some of Europe's finest wine country too, so you'll never be short of tasting opportunities.

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.

Read more about this holiday in The Sunday Times.

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 pool and a wander round its myriad of cobbled alleys and hidden squares before dinner.
You stay at the Park Hotel Le Fonti (breakfast and evening meal)

Day 2: Volterra to Pancole 41km/ 26mi

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, 12th century 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 where you can stop for a gelato before your final climb through olive groves and vineyards to the hamlet of Pancole.
RIDE PLUS - 75km / 47mi Leaving Volterra drop down into the valley heading north, passing the Theatre of Silence and the family home of Andrea Bocceli. Ride past rich green meadows and stunning countryside and on to the pretty spa town of Gambassi Terme. A long downhill ride lets you roll into Certaldo before a short climb to your peaceful hotel Le Renaie for the next two nights.
You stay at the Hotel Le Renaie (breakfast and evening meal)

Day 3: At Pancole

If you fancy a day off from cycling, the pool here is simply gorgeous and nice lunches are served on the geranium-scented terrace. There's also a small shop where you can buy olive oils, produced by the owners, and Tuscan wines. The more energetic might want to cycle past orchards and vines to visit Boccaccio's birthplace, stunning Certaldo. Take the funicular to its medieval centre for spectacular views across the Val d'Elsa.
You stay at the Hotel Le Renaie (breakfast and evening meal)

Day 4: Pancole to Colle di Val d'Elsa 33km/ 20.5mi

Today's route explores the panoramic wine country between Pancole and Colle di Val d'Elsa. You'll first retrace your route to Certaldo and then 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 15th century 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 - 92km / 57mi (shorter routes available) Today you head into wine country on a beautiful ride with vines as far as the eye can see and passing through beautiful hamlets and interesting wine towns. With the climbing over you pass two of the famous Chianti towns, Castellina and Radda, both offer great wine tasting chances and good restaurants. Heading down to the valley you pass the stunning walled villa
You stay at the Relais Della Rovere (breakfast and evening meal)

Day 5: At Colle di Val d'Elsa

There's masses of choice today: explore the medieval old town which dates back to Etruscan times; take the bus to Siena (30 mins) or to Florence (60 mins); take in the medieval town of Monteriggioni, an easy cycle or short bus ride away; or simply laze by your hotel's sparkling swimming pool, surrounded by lovely gardens.
You stay at the Relais Della Rovere (breakfast and evening meal)

Day 6: Colle di Val d'Elsa to Pescille 43km/ 26.5mi

It's easy pedalling this morning as you head south past the old town of Colle di Val d'Elsa, gradually climbing 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 12th century church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps, in the lovely piazza. You then wind north, gently uphill, through wonderfully scenic countryside against the backdrop of the impressive medieval towers of San Gimignano 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 that are well off the beaten track. Maybe lunch late in walled Caole d' Elsa, then pass Castel San Gimignano and fin
You stay at the Hotel Pescille (breakfast at the hotel, evening meal at a local restaurant)

Day 7: At Pescille

San Gimignano is just a short cycle away; explore its myriad of narrow streets and many hidden cobbled squares before returning 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 8: Pescille to Volterra 39km/ 24mi

It's a short ride to San Gimignano today before a climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers. Enjoy the 16km, mainly downhill run into the Era Valley. There's a real sense of achievement on your final climb through open countryside and you'll enjoy spectacular views before heading 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 and passing through the surrounding wine country. Head uphill through vineyards and then enjoy a long downhill with views of the Volterra. Finishing with a climb into Volterra, pass through the town and ride back to your hotel for the last night.
You stay at the Park Hotel Le Fonti (breakfast and evening meal)

Day 9: 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

Swimming Pool IconHair dryer iconNEARBY:

The 4 star Park Hotel Le Fonti is located just below the Porta dell'Arco entrance to Volterra's beautifully preserved medieval 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 Le Renaie, Pancole

Swimming Pool IconHair dryer iconNEARBY:

Hotel Le Renaie is a lovely family run 3 star hotel run by the Sabatini family in the pretty hamlet of Pancole, midway between San Gimignano and Certaldo.

The hotel started life as a restaurant but over time, it has grown into the charming 25 room hotel it is today.

The bedrooms are spacious and decorated in a traditional style. All have ensuite bathroom facilities.

Surrounding the hotel is a pretty terrace with bright flowers and scented gardens. There is an outdoor pool, a tennis court and a shop which sells wine as well as the family's own home grown and produced olive oil.

Room upgrades: Double Room with a Balcony.
Deluxe rooms have a private balcony.

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

Relais della Rovere, Colle di Val d'Elsa

Swimming Pool IconHair dryer iconNEARBY:

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 12th century 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

Swimming Pool IconHair dryer iconNEARBY:

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 star 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 Alessandro della Spina, Pisa

Hair dryer iconNEARBY:

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.

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

Hotel Chiusarelli, Siena

Hair dryer icon

Hotel Chiusarelli is located just beyond Siena's medieval 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 La Luna, Lucca

Hair dryer icon

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.


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 Walden, 16/05/2019

Fantastic rep who couldn't have been more helpful. Helpful office staff in the UK. Mixed bag of accommodation. Most was very good. One definitely let everything down. Same with food - some truly excellent some distinctly average. Route information very good but could have done with slightly longer routes. If you happen to have bad weather as we did for a couple of days you can end up quite stranded with very little to do - especially in Pancole. Taxis are very expensive but often no alternative form of transport. This was very nearly a truly excellent holiday. Just needs a couple of tweaks with some of the accommodation and meal options to have given it full marks.

Mrs Driver, 06/10/2018

Great cycling - some challenging- in a beautiful area. Fabulous reps - Paul and Phaedra who were helpful, informative and assisted in every way they could. Siena and San Gimignano were good places to explore on the rest days.

Mrs O'Donnell, 28/06/2018

Phaedra and Paul made us so welcome, and were very helpful (returning our key one day when we rode off with it). They gave us some very useful tips about the routes and hotels, and they set the tone for a lovely week right from the start. The bikes are easy to ride, good quality and very smooth. We were provided with water bottles and a cage each, so we could drink on the go. That helped a lot - do not underestimate the heat and the hills - those rest days are needed! We're reasonably fit, regular road cyclists and we found the hills quite challenging in the heat.

We saw some beautiful countryside in Tuscany, met some very friendly people and ate some good food. We will go back - but maybe not in June!

Mr O'Keeffe, 11/06/2018

We had a fantastic trip, a great mix of cycling in spectacular surroundings and relaxation, sightseeing and indulging in the local food and wine. For people of average fitness, the cycling is challenging in parts, not because of the distances involved, but because of the hills in some sections. The lovely reps, Phaedra and Paul, were friendly, helpful, professional, available and unobtrusive. The bikes were sparkling clean/new and well equipped with water cage, phone holder and panniers. Remember to bring a helmet as these are not supplied. GPS worked well. The accommodation was varied and generally good and we really appreciated having a pool at every stop. We did not meet any other Headwater holiday makers on the trip, so it very much felt like an intimate private holiday.

Mr Moody, 17/10/2017

Overall an excellent holiday in a region new to us .... Headwater Reps excellent ...

Mrs Bennett, 13/10/2017

Wonderful way to see Tuscany. The fitter you are though, the more you will enjoy it.

Miss Perry, 22/09/2017

Lovely way to see the country and get fitter

Mrs Anderson, 19/09/2017

This is the second holiday we have taken with Headwater and both have been excellent. Two years ago we did the Gastronomic Barollo cycling holiday. Both were really enjoyable. Tuscany was stunning, the hotels excellent and our reps really friendly and helpful. On balance we preferred the Barollo holiday, but only because the cycling is on less busy roads and it is slightly less touristy, but I don't think we could find fault with either holiday.

Ms Bates, 11/09/2017

Stunning scenery, stunning locations - a holiday to remember! We weren't really sure what to expect with the 2+ rating for cycling - I would say on average the cycling ranged between enjoyable undulating roads & exhilarating descents which were interspersed with some really (really!) tough climbs - beware of the Strava Biancas & just enjoy the scenery on route - the pain is quickly forgotten & the achievement of arriving at each destination makes it all worthwhile! I truly memorable holiday - thank you Headwater!

Mr Hughes, 05/07/2017

We left Manchester in pouring rain to spend a week climbing Tuscan hills at 34c. The theme of the accommodation is Tuscan hill towns so every morning was an easy start but you soon realise every days ride finishes with a picturesque uphill! The hotels were always a good standard and a couple of the swimming pools were simply amazing. Eating outside in the courtyard at the 'Relais della Rovere' was particularly special. We had researched eating out in San Gimignano beforehand which proved well worthwhile and it is definitely wiser to book ahead from UK if you can.

The first day is quite a challenge so carry plenty of water. We hadn't realised that Headwater don't supply the water bottles anymore but luckily our local reps found us a couple of spares from last year. Phaedra and Paul were kind and attentive keeping in touch by text if we needed them. The bikes were reliable and comfortable to ride. The routes do get easier after the first day and it is worth carrying a small picnic most days as the cafes tend to be towards the end of the ride. There are some good sights to see on the rest days or else there are the lovely pools just to lounge by instead.

It was a great holiday and the hills made sure you felt fitter coming home.

Thanks again Headwater

Mr Campbell, 29/06/2017

The route was generally disappointing, lots of detours through small hamlets where there was nothing, very few places to stop for a coffee. May just be that the topography dictates the route but I would have hoped Chianti could have yielded more places of interest. This was our 3rd Headwater holiday and I'd place this route 3rd by some margin. The hotels were generally excellent, Le Fonti in Volterra was very professional with good views, La Renaie in Pancole was the highlight, excellent family run hotel with nice feel and really good food. Relais della Rovere was Ok but needs to employ some gardeners, the grass everywhere hadn't been cut for weeks, bushes badly trimmed etc all contributing to an unkempt appearance. The catering being separate from the hotel was unusal and contributed to the disjointed feel. This should be a fantastic hotel but needs a lot of work to get there. Pescille was really good with great views of San Gimignano.

The bikes were new so in perfect condition, should have had a bottle cage on each bike rather than 2 on one bike and none on the other. We would have brought our own water bottles if we'd known these were no longer provided, contrary to what your literature said.

Headwater response:
Dear Mr Campbell,
Thank you for taking the time to provide your post-holiday feedback. We were pleased to read you had an enjoyable holiday. We were however sorry to read there were areas of your holiday that you felt required improvement. Please be assured all of the feedback we receive, whether positive or constructive is valued and used to help improve our holidays for the future. With this in mind, we were sorry to read you felt the gardens at Relais della Rovere required maintenance. This is the first time we have received constructive feedback for this hotel. We have discussed your comments with the hotelier; we expect to see an immediate improvement. We are sorry for any disappointment this may have caused.
We were pleased to read you found the bikes in perfect condition; our Reps receive extensive training in this area and do pride themselves on providing well-serviced bikes. They do not provide water bottle cages to our low framed bikes; this is due to past customer feedback, where customers advised us they were banging their legs on the cages, our Reps will provide water bottle cages if requested. Again, due to customer feedback we discontinued providing our water bottles, customers advised they preferred to use their own. Our Reps may have a surplus if required. This information is included in our pre travel information booklets; we are sorry you were unaware and hope this did not cause you an inconvenience.
In closing, we would like to thank you for your continued loyalty and look forward to welcoming you on another of our holidays in the future.
Kind regards,
Headwater Customer Service team

Mr Bill, 21/06/2017

Great time, hills in Tuscany are not hills....So get in shape, but scenery worth the ride...amazing! We were able to meet the locals and enjoy ourselves without any pressure when and when not to ride...

Mr Haxton, 19/06/2017

The holiday provided a wonderful experience of cycling in this most scenic of Tuscan landscapes. Some of the cycling was tough in the hot weather but the excellent hotels were perfect for relaxing after the cycle rides

Mr Mcgeoch, 16/06/2017

Great combination of challenging cycling, breathtaking views, a range of different hotels with excellent food and wine

Mrs Pincott, 14/10/2016

The Secrets of San Gimignano holiday was fantastic. Eleanor and Luke, the reps, simply could not have been more helpful, the cycling was excellent (but hard work - Tuscany is hilly) and the hotels and food amazing.

Mr Dick, 21/09/2016

The cycling routes and notes were excellent, the food was gorgeous and the scenery beguiling. Luke & Eleanor were more than welcoming and helpful. When I reported a small technical issue with one of our bikes, it was changed within an hour. The restaurant suggestions were lovely for the nights not on half board.

The opportunity to take a day in Sienna or Florence should not be missed.

Mrs Craig, 17/09/2016

I was initially somewhat trepidatious about attempting a' two and a half cycle' difficulty holiday with my younger, fitter, regular cyclist husband and so ,probably, was he. I am dog walking fit and that's about it. Some of the hills were fairly challenging but the bikes supplied have plenty of gears and the views from the top and the downhills are well worth the effort involved getting up and I was never that far behind him in the end! We went in September during the grape harvest, a lovely time of year. I'm not sure I would have coped with the cycling quite so well in July or August! The reps were very helpful but not intrusive and the hotels were all good. My husband is a map man and thought the quality of maps supplied was poor so we used the written instructions which were accurate and detailed. You don't need to be an olympic athlete to get the most out of this holiday, you have all day to complete the 40k between hotels, just take your time and enjoy those views!

Mr Davies, 04/08/2016

This was my fourth holiday with Headwaters and have enjoyed them all

Mis Aplin, 13/07/2016

This is a lovely cycling holiday but quite challenging with regard to the hills especially when its 34C! An early start is recommended to avoid the hottest part of the day. The hotels are all good and food at the Della Rovere is excellent. Nice pools at all the hotels. Plenty to do on the off days. The walled town of Monteriggioni is a relatively easy cycle from the Della Rovere. Worth booking an extra night at the end of the holiday in Volterra. Beautiful town with lots of little shops, cafes and alleyways. Thanks to Luke and Eleanor who were excellent reps.

Mr Precious, 06/07/2016

This was our first Headwater Cycling Holiday and our first visit to Tuscany, we felt that we were able to get up close and personal with the beautiful countryside. We would recommend this type of activity to anyone, we had a wonderful time and we look forward to booking another trip soon.

Mrs Payne, 29/06/2016

We were surprised at how strenuous the cycling actually was! The distances were not long, and so we really expected to complete the routes much quicker than we did.Very big hills, but the bikes have good gears and we managed to cycle to the top of them all. The downs were brilliant. Roads were mainly very quiet.

The hotels were all lovely and we enjoyed having non cycling days to explore the interesting hill top towns.

Lots of great food and wine was had.

Mrs Ryan, 27/06/2016

This holiday delivered on great food, amazing scenery, friendly staff along the route and comfortable hotels. We thoroughly enjoyed the whole experience

Mr Wightman, 10/06/2016

We really enjoyed this first cycling holiday, we loved the Tuscan countryside and the rustic food, delicious wine! We regularly enjoy our bicycles at home but are not 'cyclists'. So the 'undulating hills' and ' steady climbs' mentioned in the brochure were a lot more challenging than we expected. Having said this, we completed the route with a great sense of achievement and looked forward each day to a new adventure !

Mrs Prentis, 09/06/2016

I was a little sniffy with the 40km every other day distance. However the hills more than make up for it. We are both very fit and did manage the hills but it was warm and quite a few are long and on the stranda bianca which are unmade up and with the wrong size of stones which makes cycling quite difficult at times. The area is lovely and the reps were delightful and extremely helpful.

Ms Woodall, 06/06/2016

Great holiday. Good challenging cycling days and a region with great food and wine for lunch and dinner. Headwater looked after us well again in Italy.

Mrs Thomas, 06/06/2016

Don't be put off by the two and a half star rating of this holiday. We are two averagely fit 50+ couple that managed all the hills and they were well worth it for the fantastic views. Each hotel was unique and individual and the welcome you received at the end of a days cycling was lovely. The standard of food for most was good. We thoroughly enjoyed our holiday and have come back invigorated and amazingly pounds lighter! The reps Luke and Eleanor were very helpful and couldn't do enough for you - even texting us to see if we were alright on the only rainy day we had.

Mr Flett, 28/05/2016

A fabulous way to explore the beauty of rural Italy. The exercise during the day is balanced by delightful food and wine in the evenings. Self-guided cycling with Headwater offers independence, but with the comfort and reassurance of excellent local Reps. This was our second holiday with Headwater and is unlikely to be our last.

Ms Vipond, 20/10/2015

Beautiful cycling! Great route and some excellent hotels.

Ms Morris, 18/09/2015

Everybody was so professional, friendly and helpful from our first phone call to the office to our final goodbye to the reps. The routes were great - enough cycling to feel we'd earned our lovely hotel, pool and dinner but not too much to feel disheartened. There was plenty of time built in to sight see with excellent suggestions for rest days. We visited some great places that we'd never have found on our own as well as some more main stream destinations. A lovely combination and so well organised.

Mr Elliott-Jones, 14/09/2015

A fantastic package, great value for money in superb, friendly & family-run hotels. Great cycling routes through some challenging terrain, very good, sensibly built bikes. Reps & Headwater office staff were very helpful, couldn't do enough to make sure we were sorted.

Mr Quick, 02/09/2015

Our most scenic Headwater cycling holiday to date and well worth the physical effort!

Mrs Firth, 25/08/2015

We found the holiday provided a good mix of cycling and relaxation. The cycling in July was very hot and the hills quite challenging while the hotels were very comfortable and quiet. Enough choice of things to do from the hotels or simply relax by the pool.

Cycle routes were very well mapped, cycles were properly geared for the climbs and well maintained.

Transfers from the airport to the hotel were well organised and on cycling days our luggage was promptly transferred between hotels.

Mrs Stockton, 14/08/2015

An excellent first holiday with Headwater. We chose a 2+ cycle standard which was tougher than we expected, however the heart had a large effect on our ability. All the hotels were beautiful my only complaint was the air conditioning could of been a lot more powerful. The scenery was just breathtaking on the rides and over all i would highly recommend this trip.

Mis Barrie, 11/06/2015

A fun way to exercise in a beautiful location

Mr Hill, 13/10/2014

The scenery is spectacular - typical Tuscany -but beware the cycling is not for the inexperienced. The region is hilly and you do cycle on some busy roads. Good location for visits to Sienna and other famous hill top villages We very much enjoyed the holiday

Mrs Holman, 04/08/2014

Excellent service from Kate and Jim starting with a postcard before hand saying that they were looking forward to meeting us. Excellent combination of sight seeing and cycling

Mrs Marks, 26/06/2014

This was our third holiday with Headwater and as always everything was great, the guides, accommodation, trip routes, bikes, excellent and memorable holiday

Mis Wilson, 17/06/2014

A solitary bat swinging from the arched roof of an underground Marmini Etruscan tomb. Lizards posing on sun bleached steps or rustling through the undergrowth as you cycle past. The call of frogs, the flash of jays. An abundance of flowers, butterflies, insects and birds and stunning panoramic views. Loads of local colour and culture. Pasta, gnocchi, pecorino cheese with a honey and pine nut dip, ricotta cheesecake, pizza al taglio, gelato. Buongiornos and waves from Italian cyclists. Enjoy those downhill whizzes because there are also some climbs - but you will survive to tell the tale!

Mr Fletcher, 29/09/2013

A very good holiday. All the hotels were good and the local reps were fantastic.

Ms McLellan, 28/09/2013

Helpful reps and decent kit with good route notes but accommodation and food variable; slightly disappointing overall. 50 euro 'cash back' for dinner in San G when hotel restaurant closed was a bit tight based on what the hotel charged for a 3 course meal (but did mean that we had a good night out in San G and the best meal of the holiday by far!). Cycling tough at times, more road work than expected and would have struggled if it had been in the height of the summer heat but rewarding and some memorable views.

Mrs Lee, 18/09/2013

Overall, very enjoyable with delicious local food and beautiful scenery. The thrilling downhill sections made up for the uphill challenges. Volterra is a gem and a wonderful place to celebrate your cycling achievements on the final night.

Mr Thomas, 02/08/2013

Our Tuscany Holiday (Secrets of San Gimignano) was totally brilliant and was enjoyed by the whole family ( 6 of us) - age range 24 to fit 70!.Our reps made life very easy for us and were incredibly helpful. The hotels were varied and all really lovely and well chosen by Headwater. The food was excellent - and being Italy, there were plenty of options for my vegetarian daughter ( no meat or fish). There was plenty to do on our non-cycling days which is always important.

Mr Alexander, 09/07/2013

Beautiful countryside, gorgeous hilltop towns, good accommodation, superb reps; cuisine (in and out of hotels) generally somewhat disappointing - ordinary and predictable (except Relais della Rovere) - this is more a comment on the region than on the Headwater aspects.

Mrs Gillison, 02/06/2013

A well organised holiday with very helpful reps onsite. We haven't needed them in past holidays but had saddle trouble this time which was fixed in a trice (with a lift up one of the VERY steep hills as well!). Although we discussed this holiday on the phone before booking we didn't get a clear picture of difficulty from the brochure, so be very clear about how good a cyclist your are!!!

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 8 night self-guided cycling holiday includes:

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

All continental breakfasts and 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.

  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
Jun 2019Tour only Availability
30th Jun US$2779 Check availability
Jul 2019Tour only Availability
2nd Jul US$2779 Check availability
4th Jul US$2779 Check availability
6th Jul US$2779 Check availability
8th Jul US$2779 Check availability
10th Jul US$2779 Check availability
12th Jul US$2779 Check availability
14th Jul US$2779 Check availability
16th Jul US$2779 Check availability
18th Jul US$2779 Check availability
20th Jul US$2779 Check availability
22nd Jul US$2849 Check availability
24th Jul US$2849 Check availability
26th Jul US$2849 Check availability
28th Jul US$2849 Check availability
30th Jul US$2849 Check availability
Aug 2019Tour only Availability
1st Aug US$2849 Check availability
3rd Aug US$2849 Check availability
5th Aug US$2849 Check availability
7th Aug US$2849 Check availability
9th Aug US$2849 Check availability
11th Aug US$2849 Check availability
13th Aug US$2849 Check availability
15th Aug US$2849 Check availability
17th Aug US$2849 Check availability
19th Aug US$2849 Check availability
21st Aug US$2849 Check availability
23rd Aug US$2849 Check availability
25th Aug US$2849 Check availability
27th Aug US$2849 Check availability
29th Aug US$2849 Check availability
31st Aug US$2849 Check availability
Sep 2019Tour only Availability
2nd Sep US$2849 Check availability
4th Sep US$2849 Check availability
6th Sep US$2849 Check availability
8th Sep US$2849 Check availability
10th Sep US$2849 Check availability
12th Sep US$2849 Check availability
14th Sep US$2849 Check availability
16th Sep US$2849 Check availability
18th Sep US$2849 Check availability
20th Sep US$2849 Check availability
22nd Sep US$2779 Check availability
24th Sep US$2779 Check availability
26th Sep US$2779 Check availability
28th Sep US$2779 Check availability
30th Sep US$2779 Check availability
Oct 2019Tour only Availability
2nd Oct US$2549 Check availability
4th Oct US$2549 Check availability
6th Oct US$2549 Check availability
8th Oct US$2549 Check availability
10th Oct US$2549 Check availability
12th Oct US$2549 Check availability
Apr 2020Tour only Availability
13th Apr US$2779 Check availability
15th Apr US$2779 Check availability
17th Apr US$2779 Check availability
19th Apr US$2779 Check availability
21st Apr US$2779 Check availability
23rd Apr US$2779 Check availability
25th Apr US$2779 Check availability
27th Apr US$2779 Check availability
29th Apr US$2779 Check availability
May 2020Tour only Availability
1st May US$2779 Check availability
3rd May US$2779 Check availability
5th May US$2779 Check availability
7th May US$2779 Check availability
9th May US$2779 Check availability
11th May US$2779 Check availability
13th May US$2799 Check availability
15th May US$2799 Check availability
17th May US$2799 Check availability
19th May US$2799 Check availability
21st May US$2799 Check availability
23rd May US$2799 Check availability
25th May US$2799 Check availability
27th May US$2799 Check availability
29th May US$2799 Check availability
31st May US$2799 Check availability
Jun 2020Tour only Availability
2nd Jun US$2799 Check availability
4th Jun US$2799 Check availability
6th Jun US$2799 Check availability
8th Jun US$2799 Check availability
10th Jun US$2799 Check availability
12th Jun US$2949 Check availability
14th Jun US$2949 Check availability
16th Jun US$2949 Check availability
18th Jun US$2949 Check availability
20th Jun US$2949 Check availability
22nd Jun US$2949 Check availability
24th Jun US$2949 Check availability
26th Jun US$2949 Check availability
28th Jun US$2949 Check availability
30th Jun US$2949 Check availability
Jul 2020Tour only Availability
2nd Jul US$2949 Check availability
4th Jul US$2949 Check availability
6th Jul US$2949 Check availability
8th Jul US$2949 Check availability
10th Jul US$2949 Check availability
12th Jul US$2949 Check availability
14th Jul US$2949 Check availability
16th Jul US$2949 Check availability
18th Jul US$2949 Check availability
20th Jul US$2949 Check availability
22nd Jul US$2979 Check availability
24th Jul US$2979 Check availability
26th Jul US$2979 Check availability
28th Jul US$2979 Check availability
30th Jul US$2979 Check availability
Aug 2020Tour only Availability
1st Aug US$2979 Check availability
3rd Aug US$2979 Check availability
5th Aug US$2979 Check availability
7th Aug US$2979 Check availability
9th Aug US$2979 Check availability
11th Aug US$2979 Check availability
13th Aug US$2979 Check availability
15th Aug US$2979 Check availability
17th Aug US$2979 Check availability
19th Aug US$2979 Check availability
21st Aug US$2979 Check availability
23rd Aug US$2979 Check availability
25th Aug US$2979 Check availability
27th Aug US$2979 Check availability
29th Aug US$2979 Check availability
31st Aug US$2979 Check availability
Sep 2020Tour only Availability
2nd Sep US$2979 Check availability
4th Sep US$2979 Check availability
6th Sep US$2979 Check availability
8th Sep US$2979 Check availability
10th Sep US$2979 Check availability
12th Sep US$2979 Check availability
14th Sep US$2979 Check availability
16th Sep US$2979 Check availability
18th Sep US$2979 Check availability
20th Sep US$2979 Check availability
22nd Sep US$2949 Check availability
24th Sep US$2949 Check availability
26th Sep US$2949 Check availability
28th Sep US$2949 Check availability
30th Sep US$2949 Check availability
Oct 2020Tour only Availability
2nd Oct US$2679 Check availability
4th Oct US$2679 Check availability
6th Oct US$2679 Check availability
8th Oct US$2679 Check availability
10th Oct US$2679 Check availability
12th Oct US$2679 Check availability
14th Oct US$2679 Check availability
16th Oct US$2679 Check availability
18th Oct US$2649 Check availability
20th Oct US$2649 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

Please contact us for child prices.

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

Every two days from 30th Jun 2019 to 20th Oct 2020, for 8 nights. All dates are subject to availability, please contact us to check.

All continental breakfasts and evening meals

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £210 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 £165 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 £288 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.

We are ATOL registered We are an ABTA member
Independent customer reviews and ratings

If you would like to subscribe to our emails in accordance with our Privacy Policy, please tick this box.

+ Add More Passengers

We can often obtain preferential rates with our travel partners. We can often obtain preferential rates with our travel partners.

We can call you when it's most convenient for you, or contact you by email if you'd prefer. During busy periods we cannot always guarantee a specific call time but we promise to try our very best.

By clicking the 'Enquire now' button, you confirm that you have read and understood our Privacy Policy and consent to our use of your information.

You may also like