Italy : Chianti

Classic Chianti Cycling

Trip code: C10TY 4.7 (26 reviews)

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

15.0Kg CO2e

Headwater
Navigation App

Optional
e-bike hire

SUMMARY

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

WHAT'S INCLUDED?

  • 10 nights accommodation
  • All buffet breakfasts and 5 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 ten night holiday has been carefully crafted to cleverly balance cultural highlights and historic treasures with natural beauty and stunningly scenic cycling. It's a perfect choice too if you like the idea of combining timeless countryside cycling with the use of local transport to explore the eternal cities of Siena and Florence on foot.

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

The hotels we've selected for this holiday are among our best, and include a magnificently restored 17th century palazzo, a wonderfully renovated, stylish watermill which dates back to the 16th century and belonged to the famous Medici family, and a family-run, traditional hotel overlooking the soaring towers of San Gimignano. As Chianti is synonymous with great food and wine, we've made sure evening meals are a celebration of local flavours throughout.

Terrain

Distances vary and parts of the countryside are fairly hilly, so take your time on the steeper climbs and admire the wonderful long distance views.

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

READ MORE

DAY-BY-DAY ITINERARY

 

Day 1: Arrive at Volterra

Arrive in Volterra where you've time for a dip in the hotel pool and a wander round the town's tangle of cobbled alleys and hidden squares before dinner.

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.

elevation

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 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 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 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 5: At Colle di Val d'Elsa: suggested day in Siena

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

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

After a fairly long day yesterday, we propose that you spend a relaxed morning in Colle di Val d'Elsa. The historic town dates back to Etruscan times with a cathedral, museums and fine Renaissance buildings. After lunch in the old square, maybe spend relax in the hotel's spa before a pre-dinner stroll along the lovely River Elsa where limestone-rich rapids come crashing dramatically downstream.

Day 7: At Colle di Val d'Elsa: suggested day in Florence

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

Day 8: Colle di Val d'Elsa to Pescille (43km/26.7mi)

Get back on your bike this morning and enjoy superb rolling views before the ride up to Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning views from its hilltop position. Take time to explore its 12th century church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps in the lovely piazza. You then wind north through wonderfully scenic countryside, the fabulous medieval towers of San Gimignano providing a formidable backdrop as you pedal on to Pescille.

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 9: At Pescille

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

Day 10: Pescille to Volterra (39km/24.2mi)

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

elevation

You stay at Hotel Pescille.

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

Day 11: Leave Volterra

You stay at Hotel La Cisterna.

hotel details

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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.

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 £674.

These flight inclusive prices are based on two people sharing. Single supplement from £674.

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 4pm 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

Wonderful holiday. The scenery was spectacular and every hotel was a great experience.

Mr Daxter, 28 Jun 2022

 

A leisurely end of season break

Mrs Tanner, 8 Oct 2018

 

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

Mrs Clucas, 29 Aug 2018

 

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

Mrs Moffat, 2 Jul 2018

 

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

Mr Lypka, 27 May 2017

 

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

Mrs Sparshott, 21 May 2016

 

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

Dr Winter, 3 Sep 2015

 

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

Mr Gilbert, 10 Aug 2015

 

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

Mr Pridmore, 9 Aug 2015

 

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

Mrs Brown, 3 Aug 2015

 

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

Mrs Downes, 5 Jul 2015

 

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



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



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



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



For anyone wanting to know here are my restaurant highlights:



Siena - La taverna de San Giuseppe

San Gim - Cum Quibus

Certaldo Alto - Fonte Antica



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

Ms Smart, 10 Jun 2015

 

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



Mr Millican, 6 Oct 2014

 

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



My husband found the food at Relais della Rovere disappointing.

Mrs Spriggs, 16 Sep 2014

 

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



Mr McDowell, 7 Sep 2014

 

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

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

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



Thank you all

Mrs Capper, 31 Aug 2014

 

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

Mrs Wall, 29 Aug 2014

 

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

Mrs Pickles, 10 Jun 2014

 

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

Mr Stead, 30 May 2014

 

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

Mrs Bird, 12 May 2014

 

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

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

Mrs Duncan, 24 Sep 2013

 

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

Mr Whitton, 2 Sep 2013

 

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

Mr Groom, 25 Aug 2013

 

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

Mrs Kimber, 10 Jul 2013

 

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

Mr Hart, 4 Jun 2013

 

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

Mrs Stonehouse, 1 Jun 2013

 


Self-guided cycling

10 nights,
hotel-to-hotel

Level: 2+
Moderate plus

15.0Kg CO2e

Headwater
Navigation App

Optional
e-bike hire

10 nights from £2289

CHOOSE A DEPARTURE

Call: 01606 720199