Italy : Tuscany

Secrets of San Gimignano Cycling

Trip code: C08TY 4.8 (56 reviews)

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

15.0Kg CO2e

Headwater
Navigation App

Optional
e-bike hire

SUMMARY

  • 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; 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 accommodation
  • All continental breakfasts and 4 evening meals
  • Bike fitting and briefing at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • Luggage transfers between hotels

TRIP DESCRIPTION

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'll pedal through the archetypal Tuscan countryside, cypress dotted rolling hills, olives, vines, sunflowers, and on, via postcard-pretty Certaldo. The cycling is truly glorious as you continue, via fortified towns and hill villages, to medieval Colle di Val d'Elsa, 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, are an added highlight of this holiday. In Colle di Val d'Elsa, you stay in a fabulously restored 17th century palace, whilst in Volterra, your 4-star hotel is located right in the heart of the historical centre with panoramic views of the medieval town. 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.

Terrain

Distances vary and parts of the countryside are fairly hilly, so you can take your time on the steeper climbs and admire the wonderful long distance views. As part of your journey, you'll transverse the iconic Strade Bianche of Tuscany. While these renowned white gravel paths add a unique charm to your trip, they can also be a bit strenuous.

Read more about this holiday in The Headwater Blog and The Sunday Times.

READ MORE

DAY-BY-DAY ITINERARY

 

Day 1: Arrive at Volterra

Arrive in Volterra where you've time for a wander round its myriad of cobbled alleys and hidden squares before dinner.

You stay at Hotel San Lino.

hotel details

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Hotel San Lino, Volterra

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Hotel San Lino is set within the medieval walls of Volterra, a 5-minute walk from Piazza dei Priori. Originally built as a convent in 1480, Hotel San Lino has been attentively renovated to preserve the original architectural features that celebrate its historical charm.

Rooms here are spacious and bright, exquisitely decorated in Tuscan style, with traditional terracotta floors and wooden furniture. All rooms are equipped with ensuite bathroom, TV, air conditioning and Wifi.

A buffet breakfast is served in the main dining room, and includes homemade cakes, cured meats, yogurt and cereals.

The property also benefits from a garden with outdoor swimming pool and panoramic terrace.

Day 2: Volterra to Certaldo (40km/24.9mi)

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 stay for the next two nights.

elevation

You stay at Hotel Certaldo.

hotel details

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Hotel Certaldo, Certaldo

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Located on the fringe of Certaldo Basso, on the River Elsa, the stunning 4 star 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 20th century, 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 star 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.

Day 3: At Certaldo

Explore stunning Certaldo, Boccaccio's birthplace. Split into two distinct halves, the medieval 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.

Day 4: Certaldo to Colle di Val d'Elsa (29km/18.0mi)

Today's route explores the panoramic wine country between Certaldo 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! 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.

elevation

You stay at Palazzo San Lorenzo & Spa.

hotel details

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Palazzo San Lorenzo & Spa, Colle di Val d'Elsa

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The Palazzo San Lorenzo and Spa is located in the upper part of the medieval town of Colle di Val d'Elsa, better known as the old village of the “town of lead crystal-glass”. The building dates back to the 17th century when it started life as a hospital, whilst today, the public spaces are decorated with statues and crystal chandeliers.

The spacious rooms come with free Wi-Fi, Flat screen TV, free mineral water in the minibar and air conditioning. They have parquet floors and marble bathrooms. Headwater customers get the Superior rooms as standard.

A buffet breakfast is served in the breakfast room, a wonderful 'winter garden' completely lit by natural light, where you can find a large range of sweet and savoury delicacies. Your evening meals (when included), will be taken in the hotel’s restaurant which serves traditional Tuscan dishes.


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 enjoy the spa facilities of your hotel.

elevation

Day 6: Colle di Val d'Elsa to Pescille (43km/26.7mi)

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.

elevation

You stay at Hotel Pescille or Hotel La Cisterna.

hotel details

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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 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, a short walk will be leading you to a local restaurant.

Room upgrades: Superior room
Superior rooms are much larger than standard rooms

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Hotel La Cisterna, San Gimignano

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Enjoy your stay at this picturesque 14th century building hotel nestled in the heart of San Gimignano.

La Cisterna offers beautifully decorated rooms in both Florentine and modern style all of which are equipped with air conditioning, free Wifi and a flat-screen satellite TV.

A continental buffet breakfast is served at the on site restaurant Le Terrazze, where you can enjoy panoramic views over the historical square whilst your sip on your morning caffé.

The advantageous position of this property will allow you to easily reach shops, points of interest and a vast choice of restaurants in the town centre.

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 (39km/24.2mi)

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.

elevation

You stay at Hotel San Lino.

hotel details

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Hotel San Lino, Volterra

HOTEL WEBSITE      TRIP ADVISOR

Mastercard
AmEx
Pool
Hairdryer
WiFi
TV
Minibar
Aircon
Safe


Hotel San Lino is set within the medieval walls of Volterra, a 5-minute walk from Piazza dei Priori. Originally built as a convent in 1480, Hotel San Lino has been attentively renovated to preserve the original architectural features that celebrate its historical charm.

Rooms here are spacious and bright, exquisitely decorated in Tuscan style, with traditional terracotta floors and wooden furniture. All rooms are equipped with ensuite bathroom, TV, air conditioning and Wifi.

A buffet breakfast is served in the main dining room, and includes homemade cakes, cured meats, yogurt and cereals.

The property also benefits from a garden with outdoor swimming pool and panoramic terrace.

Day 9: Leave Volterra

Extending your holiday

If you'd like to extend your trip with extra hotel nights we recommend: Hotel Cosimo De Medici, Florence; Hotel La Luna, Lucca; Hotel Alessandro della Spina, Pisa; Hotel Chiusarelli, Siena.

hotel details

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Hotel Cosimo De Medici, Florence

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This 3-star hotel is beautifully decorated, with rooms in individual styles - some are traditionally Tuscan whilst others are funky and modern. Parts of the the building actually date back to the 18th century, and the reception and public rooms are designed with this in mind, with Persian rugs, stained glass windows and wrought iron doors in evidence.

Although just off the main Via Nazionale, only 2 minutes' walk from the central station and 5 minutes from the Duomo, the hotel faces an internal courtyard for peace and quiet. All the rooms are double glazed, and all have air-conditioning so there is absolutely no reason not to have a good night's sleep!

There is no restaurant at the hotel, but there is plenty of choice nearby.

Extra nights: Please contact us for details.

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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.

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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.

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Hotel Chiusarelli, Siena

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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 Robur 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.

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These tour only prices are based on two people sharing. Single supplement from £558.

These flight inclusive prices are based on two people sharing. Single supplement from £558.

OPTIONAL UPGRADES
  • Flights from Heathrow to Pisa with British Airways
  • Other flights, including regional departures
  • Alternative flights, including regional departures
  • Business/club/first class fares
  • Electric bikes
  • Room upgrades and extra nights at selected hotels
TRAVEL DETAILS

Our aim is to provide holidays that are unbeatable for choice and flexibility. We've listed our most popular travel options below, however you aren't limited to these - we can tailor-make virtually any holiday to suit.

Air prices include our standard flights/transfers
Out: British Airways Heathrow to Pisa transfer to hotel 75 minutes Return: Transfer to airport 75 minutes British Airways Pisa to Heathrow

Business/club/first class seats are available on request.

Alternative Air Travel
Alternative flights, onward rail to your holiday area, and connecting private transfers can be arranged from most UK airports. If you would like to use one of the many 'low cost' airlines, we can book these on your behalf. We can also book UK shuttles to connect with your onward flight, please call for details and prices.

Self drive
We can arrange various channel crossings for you. Please call for details and prices.

Alternative transfers
If you require alternative transfers (because you will be arriving at a different time to our standard flights), then we can usually arrange these for you (there may be an additional charge).

To find out more about the travel options available call our sales team on 01606 720199, use our live webchat (we're open until 10pm today) or email sales@headwater.com

Should you require overnight airport accommodation, airport parking or even a uniformed chauffeur to take your car from your departure terminal and park it for you, we can arrange this for you through Holiday Extras. You can book airport parking, airport hotels and executive lounges through their website or contact us for further details. Early booking is recommended to obtain the best availability and prices.

REVIEWS

Great holiday. Well organised. Lovely hotels. Routes all well planned & easy to follow.

Sandra Goddard, 17 May 2024

 

Cycling in Tuscany was a great way to see the superb scenery and enjoy local food and wine. Headwater organised everything exceedingly efficiently and everyone involved was reliable and friendly.

Valerie Harris, 27 Apr 2024

 

An excellent holiday. Proved to be tougher than envisaged. The final road into Certaldo was concerning at times, sharing with very large cement transporters. Hotels were truly excellent.

Diane Hall, 26 Sep 2023

 

Travel and adventure made easy. A great experience end to end seeing an area of Italy at our pace and mostly alone. Hassle free

Stephen Power, 26 Jun 2023

 

The itinerary has clearly been well thought out to showcase some of the loveliest places in Tuscany, both the historic towns and routes through beautiful countryside. We had had misgivings about the bikes before the trip as we had looked them up and found that they were very heavy. However they had great gears and tyres which negotiated the hills and Strada Bianca's very well. Overall well suited to the task. Only one hotel was really disappointing, although the staff were great. Room was tiny with no air conditioning, even though we had upgraded. Food at the linked restaurant wasn't good and we paid ourselves for somewhere else on our return night there. The other three hotels were really exceptional. Highlights were the restaurant in the Certaldo hotel and Zaferano ( restaurant by Il Pescille). Great experience.

TWIGG, 31 May 2023

 

The beautiful views of the Tuscan landscape never failed to draw a smile whether it was a daytime view across fields of sunflowers or an evening sunset over the vineyards. The wine tasting experiences were first class and we have many beautiful memories thanks to the passion of the wine makers and their families. The cycling was fun and not difficult for anyone in moderate physical condition.

Mr Jones, 6 Jul 2022

 

Fantastic scenery and lovely villages to visit

Can be very hot and is constantly uphill or downhill for cycling with some very steep sections and some busy roads

Mr Yellen, 29 May 2022

 

We have travelled with Headwater many times and holidays obviously vary. Frankie the rep was excellent and had good practical knowledge of e-bikes. We found the roads were rather busy and not suitable for families. We realised the choice of routes was limited. Our first night coincided with two coach loads of visitors, the food was poor and we were not happy to be asked to vacate our table immediately at the end of our meal. The places we visited were all fascinating and the bus trip to Sienna was brilliant.



Mr Jenkinson, 30 Sep 2019

 

Tuscany is indeed hilly, be prepared for some pretty hard cycling. You will be rewarded with some fantastic views though and some great food along the way. Our rep Frankie was incredibly helpful and offered some great advice. All of the places we visited along the way were very friendly and our stop off at the end in Pisa was a great addition.

Mr Metcalf, 16 Sep 2019

 

Fabulous scenery, food and wine. Some of the gradients were challenging for those less used to cycling, but the views were worth the effort.

Mr Oliver, 6 Sep 2019

 

Our holiday experience was everything we had hoped it would be.

Ms Harris, 16 Jul 2019

 

What a great way to see part of Tuscany - electric bikes such a help up the many hills. Hotels chosen for us were great - varied but consistently good service and most of the meals were excellent. GPS app so helpful - made navigating so easy. Had a few technical hitches on two days, but Frankie our Rep was at the other end of the phone and found us promptly to sort us out. All in all a great holiday. Not a cheap holiday but worth it for the great organisation by Headwater which allowed us to really relax and focus on enjoying the experience. Would thoroughly recommend.

Mrs Hardy, 18 Jun 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 Walden, 3 May 2019

 

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 Driver, 24 Sep 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!

Mrs O'Donnell, 16 Jun 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 O'Keeffe, 27 May 2018

 

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

Mrs Bennett, 2 Oct 2017

 

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

Mr Moody, 22 Sep 2017

 

Lovely way to see the country and get fitter

Miss Perry, 6 Sep 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!

Ms Bates, 27 Aug 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.

Mrs Anderson, 25 Aug 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 Hughes, 10 Jun 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 Haxton, 8 Jun 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.

Mr Campbell, 31 May 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 Bill, 27 May 2017

 

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

Mr Mcgeoch, 21 May 2017

 

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.

Mrs Pincott, 2 Oct 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.

Mr Dick, 9 Sep 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!

Mrs Craig, 6 Sep 2016

 

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

Mr Davies, 20 Jul 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.

Mis Aplin, 21 Jun 2016

 

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

Mrs Ryan, 16 Jun 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.

Mr Precious, 8 Jun 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 Payne, 4 Jun 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.

Mrs Prentis, 29 May 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.

Ms Woodall, 25 May 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.

Mrs Thomas, 25 May 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 !

Mr Wightman, 21 May 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.

Mr Flett, 17 May 2016

 

Beautiful cycling! Great route and some excellent hotels.

Ms Vipond, 8 Oct 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.

Ms Morris, 4 Sep 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 Elliott-Jones, 2 Sep 2015

 

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

Mr Quick, 21 Aug 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 Firth, 30 Jul 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.

Mrs Stockton, 29 Jul 2015

 

A fun way to exercise in a beautiful location

Mis Barrie, 29 May 2015

 

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

Mr Hill, 2 Oct 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 Holman, 22 Jul 2014

 

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

Mrs Marks, 4 Jun 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!

Mis Wilson, 2 Jun 2014

 

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.



Ms McLellan, 14 Sep 2013

 

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

Mr Fletcher, 14 Sep 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.

Mrs Lee, 6 Sep 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 Thomas, 20 Jul 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.

Mr Alexander, 24 Jun 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!!!

Mrs Gillison, 21 May 2013

 


Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

15.0Kg CO2e

Headwater
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Optional
e-bike hire

8 nights from £2019

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Call: 01606 720199

 

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