Secrets of San Gimignano Cycling

From $1936 per person

****# Based on 35 customer reviews
(C) Getty Imanges
  • 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

What's included?

  • 8 nights, hotel-to-hotel
  • Departs Every two days from 11 May '17 to 14 Oct '17
  • All continental breakfasts and 6 evening meals included
  • Managed locally by Headwater employed representative
  • Sustainability rating: 80%
  • Headwater wine service
  • Route notes and maps provided
  • High quality bikes provided
  • Luggage transfers between hotels

Excellent for...

Secrets of San Gimignano Cycling

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 mediaeval 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 C12 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.

Read press reviews of this holiday in The Sunday Times.

Day-by-day itinerary

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.

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, 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 where you can stop for a gelato before your final climb through olive groves and vineyards to the hamlet of Pancole.

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 mediaeval centre for spectacular views across the Val d'Elsa.

Day 4 - Pancole to Colle di Val d'Elsa 32km/ 20mi

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 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.

Day 5 - At Colle di Val d'Elsa

There's masses of choice today: explore the mediaeval old town which dates back to Etruscan times; take the bus to Siena (30 mins) or to Florence (60 mins); take in the mediaeval 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.

Day 6 - Colle di Val d'Elsa to Pescille 40km/ 25mi

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 C12 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 mediaeval towers of San Gimignano as you pedal on to Pescille.

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.

Day 8 - Pescille to Volterra 38km/ 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.

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. You can call our sales team on 1-800-567-6286 to discuss accommodation options.

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. Please contact us on 1-800-567-6286 for further details.

Park Hotel Le Fonti, Volterra   (4 Star)

Park Hotel Le Fonti, Volterra

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Swimming pool
  • Hairdryer
  • Internet access
  • Television
  • Minibar
  • Air conditioning

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Hotel Le Renaie, Pancole   (3 star)

Awimming pool at Le Renaie

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Swimming pool
  • Hairdryer
  • Internet access
  • Television
  • Minibar
  • Air conditioning

Nearby facilities:

  • Shops
  • Banking / cheques cashed

Relais della Rovere, Colle di Val d’Elsa   (4 Star)

Swimming pool Relaos della Rovere

The Relais della Rovere is a stunning 4-star hotel located at the edge of Colle di Val d'Elsa. The Cellerai family have sympathetically converted this C12 Benedictine Abbey into a 31 room luxurious hotel, retaining many of the abbey's original features.

The bedrooms are split between two buildings and decorated in a contemporary style with wooden floors and beech furniture. The rooms are quite large with ensuite facilities.

The hotel has a lovely outdoor pool which is surrounded by pleasant gardens.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Market
  • Mastercard accepted
  • American Express accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Air conditioning

Nearby facilities:

  • Banking / cheques cashed

Hotel Pescille, Pescille   (3 star)

Birds eye Hotel Pescille

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Diners Club card accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Television
  • Minibar
  • Air conditioning

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Hotel Palazzo San Lorenzo, Colle Val d'Elsa   (4 star)

The Palazzo San Lorenzo is a luxury hotel in an old Val d’Elsa medieval building which has been meticulously renovated respecting its original architecture, so that guests can enjoy the unique and suggestive atmosphere of the old residence. Modern technology was added and today it is a luxury charm hotel offering visitors a wide range of exclusive services.

Palazzo San Lorenzo is in the mediaeval village of Colle di Val d'Elsa. It offers rooms with modern-style décor, 32” LCD TV and hydro-massage bath or shower.The spacious rooms come with free Wi-Fi, free mineral water in the minibar, and air conditioning. They have parquet floors and marble bathrooms.

The elegant San Lorenzo palace dates back to the 17th century. Public spaces are decorated with statues and crystal chandeliers. Covered by a glass ceiling, the central court has lots of natural light. A buffet breakfast is served here. The hotel’s restaurant serves Tuscan dishes.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Diners Club card accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Air conditioning
  • Safe

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine



Extra nights and stop over hotels

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.

Relais Santa Chiara, San Gimignano   (4 Star)

Swimming pool Relais Santa Chiara

Situatued just 400m from the mediaeval walls of UNESCO listed San Gimignano lies the charming, four star Relais Santa Chiara Hotel. This elegant property is surrounded by some of Tuscany’s most beautiful scenery and enjoys countryside views over hills covered with vineyards and olive groves, not to mention its own private garden featuring a swimming pool and hydro massage pool. There is also a terrace on which you can enjoy breakfast in the morning and a selection of drinks from the hotel’s cocktail bar in the evening.

All the ensuite rooms come with air-confitioning, satellite TV, minibar and hairdryer. You can also upgrade to a room with balcony and views of the surrounding vineyards and stunning countryside.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Television
  • Minibar
  • Air conditioning
  • Safe

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Hotel Alessandro della Spina, Pisa   (3 Star)

Hotel Alessandro della Spina, Pisa

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Banking / cheques cashed
  • ATM / Cash machine
  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Air conditioning
  • Safe

Nearby facilities:

  • Market

Hotel Chiusarelli, Siena   (3 Star)

Hotel Chiusarelli, Siena

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine
  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Air conditioning
  • Safe

Hotel La Luna, Lucca   (3 Star)

double room, Hotel La Luna

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine
  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Television
  • Minibar
  • Air conditioning
  • Safe

Travel options

Transfers included from Pisa airport at 12:00, and back to Pisa airport at 09:45.

Please call our sales team on 1-800-567-6286 or email info@breakaway-adventures.com to arrange connecting flights.

Customer reviews

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, of course, an overall rating and comments about their holiday.

Any feedback collected is posted straight to our website - totally unedited. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Reviewed by Mrs Pincott on 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.

Reviewed by Mr Dick on 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.

Reviewed by Mrs Craig on 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!

Reviewed by Mr Davies on 04/08/2016

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

Reviewed by Mis Aplin on 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.

Reviewed by Mr Precious on 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.

Reviewed by Mrs Payne on 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.

Reviewed by Mrs Ryan on 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

Reviewed by Mr Wightman on 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 !

Reviewed by Mrs Prentis on 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.

Reviewed by Ms Woodall on 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.

Reviewed by Mrs Thomas on 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.

Reviewed by Mr Flett on 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.

Reviewed by Ms Vipond on 20/10/2015

*****
Beautiful cycling! Great route and some excellent hotels.

Reviewed by Ms Morris on 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.

Reviewed by Mr Elliott-Jones on 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.

Reviewed by Mr Quick on 02/09/2015

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

Reviewed by Mrs Firth on 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.

Reviewed by Mrs Stockton on 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.

Reviewed by Mis Barrie on 11/06/2015

*****
A fun way to exercise in a beautiful location

Reviewed by Mr Hill on 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

Reviewed by Mrs Holman on 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

Reviewed by Mrs Marks on 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

Reviewed by Mis Wilson on 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!

Reviewed by Mr Fletcher on 29/09/2013

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

Reviewed by Ms McLellan on 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.

Reviewed by Mrs Lee on 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.

Reviewed by Mr Thomas on 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.

Reviewed by Mr Alexander on 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.

Reviewed by Mrs Gillison on 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!!!

Reviewed by Mrs Wright on 30/10/2012

*****
All arranged at very last minute and your staff were up to the challenge. Thanks especially to Karen Ross in the office,particularly as we added an extra day in the middle to our itinerary. Also appreciated being able to discuss this 'upper 2 bikes' holiday with Catherine Crone as she and her husband had done it previously - helped us decide we would be able to manage it! Routes very varied with lots of scenic and historic interest. Hotel Le Renaie at Pancole was the best one for us - delightful staff, gorgeous evening meals and lovely setting. We wouldn't have managed this in the heat of the summer but late Sept/early Oct the weather was pleasant especially as we managed not to get caught in any of the thunderstorms. Great to have all swimming pools still open as we used them all. We ended our holiday with a great sense of achievement and we can't wait to go back to Italy. Charles and Ruth aged 50 something and only moderately fit.

Reviewed by Ms Meadows on 06/10/2012

***#.
We could write pages about a lovely combination of cycling and walking but the best recommendation that we can give is that at the end of the holiday we were thinking about how we could just stay in Tuscany and do the holiday all over again

Reviewed by Mrs Melhuish on 24/09/2012

*****
we thoroughly enjoyed all aspects of our holiday.

Reviewed by Mis Lording on 29/08/2012

*****
The Secrets of San Gimignano is definitely an upper two bike holiday! There were plenty of hills going up but the rewards were the breath taking scenery, excellent hotels and lovely places that could be visited. Thank you Headwater for another great holiday. I can't wait until 2013 to book the next one!

Reviewed by Mr Park on 23/06/2012

***#.
Great hotels, lovely scenery

From our postbag

In addition to comments received on our post-holiday questionnaires, we've also been sent the following comments from our satisfied customers.

Mrs A Godsall travelled to Chianti in 2011

Thank you for another lovely holiday. We are already looking forward to next year!

Departure dates & prices

May 2017 departuresTour only 
May 11$2155
May 13$2155
May 15$2155
May 17$2155
May 19$2155
May 21$2155
May 23$2155
May 25$2155
May 27$2155
May 29$2155
May 31$2155
June 2017 departuresTour only 
Jun 2$2155
Jun 4$2155
Jun 6$2155
Jun 8$2155
Jun 10$2155
Jun 12$2275
Jun 14$2275
Jun 16$2275
Jun 18$2275
Jun 20$2275
Jun 22$2275
Jun 24$2275
Jun 26$2275
Jun 28$2275
Jun 30$2275
July 2017 departuresTour only 
Jul 2$2275
Jul 4$2275
Jul 6$2275
Jul 8$2275
Jul 10$2275
Jul 12$2275
Jul 14$2275
Jul 16$2275
Jul 18$2275
Jul 20$2275
Jul 22$2310
Jul 24$2310
Jul 26$2310
Jul 28$2310
Jul 30$2310
August 2017 departuresTour only 
Aug 1$2310
Aug 3$2310
Aug 5$2310
Aug 7$2310
Aug 9$2310
Aug 11$2310
Aug 13$2310
Aug 15$2310
Aug 17$2310
Aug 19$2310
Aug 21$2310
Aug 23$2310
Aug 25$2310
Aug 27$2310
Aug 29$2310
Aug 31$2310
September 2017 departuresTour only 
Sep 2$2310
Sep 4$2310
Sep 6$2310
Sep 8$2310
Sep 10$2310
Sep 12$2310
Sep 14$2310
Sep 16$2310
Sep 18$2310
Sep 20$2310
Sep 22$2310
Sep 24$2275
Sep 26$2275
Sep 28$2275
Sep 30$2275
October 2017 departuresTour only 
Oct 2$2015
Oct 4$2015
Oct 6$2015
Oct 8$2015
Oct 10$2015
Oct 12$2015
Oct 14$2015

Holiday details

Holiday type

Self-guided cycling, hotel-to-hotel. Managed locally by Headwater employed rep.

Departures

Every two days from 11 May '17 to 14 Oct '17, for 9 days (8 nights). This holiday departs every 2 days, however non-standard arrivals and altered itineraries may be possible - please call for prices.

Meals

All continental breakfasts and 6 evening meals included.

Other details

Please see our Planning your holiday and What's included in the price? pages for additional information. Please call us for single room supplements, room upgrade options and child prices.

Starting your tour

Transfers included from Pisa airport at 12:00, and back to Pisa airport at 09:45.

Enquire about this holiday

Simply complete the form below and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and additional information.

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We can call you when it's most convenient for you, or contact you by email if you'd prefer. Morning calls will be between 9:00-13:00, afternoon calls between 13:00-17:00, and evening calls after 17:00.
Let us know any queries you might have about departure dates, similar holidays or tailor-made options.

 

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  • ATOL Protected (No. 9957)
  • IATA Registered
  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

We love to chat about our holidays

call us: 1-800-567-6286 or email: info@breakaway-adventures.com

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