This ten night holiday has been carefully crafted to cleverly balance cultural highlights and historic treasures with natural beauty and stunningly scenic cycling. It's a perfect choice too if you like the idea of combining timeless countryside cycling with the use of local transport to explore the eternal cities of Siena and Florence on foot.
Your holiday starts in Volterra, a real Etruscan gem with its tangle of alleys home to alabaster workshops and secret chapels, in the heart of the Era Valley. You'll pedal through the archetypal Tuscan countryside, cypress dotted rolling hills, olives, vines, sunflowers, and on, via postcard-pretty Certaldo, to Colle di Val d'Elsa where you'll spend four nights. From here, you can enjoy day trips to the great art cities of Florence and Siena before pedaling on through panoramic wine country to the tiny hamlet of Pescille, a short cycle from mediaeval San Gimignano. Your route then takes you through the Castelvecchio Nature Reserve (great for bird spotting) giving you a real sense of achievement as you loop back to Volterra for your final night.
The hotels we've selected for this holiday are among our best, and include a magnificently restored C12 abbey, a wonderfully renovated, stylish watermill which dates back to the C16 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.
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. (Staying at Park Hotel Le Fonti, Half Board)
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. (Staying at Hotel Certaldo, Breakfast only)
Explore stunning Certaldo, Boccaccio's birthplace. Split into two distinct halves, the mediaeval centre of Certaldo Alto with its fabulous ancient buildings, is accessed by funicular and offers spectacular views across the Val d'Elsa. On the other hand, Certaldo Basso is the more modern part of the town with shops, bars and restaurants. You could also spend time today, relaxing by the hotel pool. (Staying at Hotel Certaldo, Breakfast only)
Today's route explores the panoramic wine country between Certaldo and Colle di Val d'Elsa. You'll follow the official, mainly off-road, Chianti Wine Route where you'll find lots of tasting opportunities - don't forget, we can collect any purchases for you! It's then on to the old town of Poggibonsi, a perfect stop for lunch and to visit the ruins of its unfinished C15 fortress. The day ends with gentle pedalling through tree-lined meadows and a valley of poppy and sunflower fields to Colle di Val d'Elsa. (Staying at Relais della Rovere, Half Board)
There is so much to see and do in and around Colle di Val d'Elsa that you really will be spoiled for choice. However, today we recommend hopping on the local bus (from just outside the hotel) for the 30min ride to the great mediaeval city of Siena. Visit the Palazzo Pubblico with its impressive pre-Renaissance frescoes and climb the Torre del Mangia for the best views of the town and surrounding Sienese countryside. For lunch, or simply a drink, there is no better place than Siena's beautiful shell-shaped Piazza del Campo. (Staying at Relais della Rovere, Half Board)
After a fairly long day yesterday, we propose that you spend a relaxed morning in Colle di Val d'Elsa. The historic town dates back to Etruscan times with a cathedral, museums and fine Renaissance buildings. After lunch in the old square, maybe spend some time by the pool before a pre-dinner stroll along the lovely River Elsa where limestone-rich rapids come crashing dramatically downstream. (Staying at Relais della Rovere, Breakfast only)
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. (Staying at Relais della Rovere, Breakfast only)
Get back on your bike this morning and enjoy superb rolling views before the ride up to Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning views from its hilltop position. Take time to explore its C12 church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps in the lovely piazza. You then wind north through wonderfully scenic countryside, the fabulous mediaeval towers of San Gimignano providing a formidable backdrop as you pedal on to Pescille. (Staying at Hotel Pescille, Breakfast at the hotel and evening meal in a local restaurant)
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. (Staying at Hotel Pescille, Breakfast at the hotel and evening meal in a local restaurant)
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. (Staying at Park Hotel Le Fonti, Half Board)
During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking. If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day.
NEARBY: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.
Room upgrades: Deluxe Room with Terrace, Junior Suite or Suite.
Deluxe rooms with terrace have their own terrace overlooking the pool. Junior suites are much larger than a standard room, with a sitting area. The suite is situated in the tower, and is larger than a junior suite. It has a balcony and a jacuzzi.
Extra nights: Please contact us for details.
Located on the fringe of Certaldo Basso, on the River Elsa, the stunning 4* Hotel Certaldo dates back to the 1500s when it belonged to the infamous and all powerful Medici family. It started life as a water mill and signs of its original use are still in evidence, including its mighty water wheel. Over the 20C, the mill was used as a power turbine and produced enough electricity to service the entire town of Certaldo up to the 1950s!
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.
NEARBY: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.
Room upgrades: Luxury (Double Only), Junior Suite or Suite.
Luxury rooms are located in the Renaissance Villa and feature antique furniture and prints, and precious tapestries and ceilings with encased beams and parquet flooring. Large windows with a view over the historical centre of Colle Val D'Elsa. Bathroom with whirlpool bath, courtesy kit, bathrobe and slippers. Junior Suites are located in the Benedictine Convent and in the farmhouse. They comprise an entrance hall with living room and one double bedroom, and feature modern, solid oak furniture. They have beamed ceilings and parquet flooring. One/two bathrooms, one with shower, the other with whirlpool bath, courtesy kit, bathrobe and slippers. Suites are in the Benedictine Convent and in the Villa. They are larger with an entrance hall, living room and sofa bed and a double bedroom, with two bathrooms. Some have modern decor with solid oak furniture, beamed ceilings and parquet flooring. Others feature antique furniture and prints, and precious tapestries, ceilings with encased beams and parquet flooring.
NEARBY: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.
Room upgrades: Double with view of San Gimignano.
Rooms with balcony offer wonderful views of San Gimignano.
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.
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.
Extra nights: Please contact us for details.
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.
Extra nights: Please contact us for details.
NEARBY: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.
Extra nights: Please contact us for details.
Transfers included from Pisa airport at 10:30, and back to Pisa airport at 09:00.
Please call our sales team on 1-800-267-3347 or email firstname.lastname@example.org to arrange connecting flights.
Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.
Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.
A leisurely end of season break
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.
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!
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.
don't under-estimate how hilly/undulating Tuscany is.
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.
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.
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.
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.
This is a great way to explore Tuscany with a good physical challenge and lots of wonderful gastronomic experiences thrown in.
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
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
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.
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.
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
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.
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!
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!
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.
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
Very well organised. Excellent reps on site. Excellent choice of hotels
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
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.
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
we loved cycling in Chianti country - the climbs up to the hilltop towns were always rewarded with fantastic pistacchio gelati!
You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.
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Over 2 and under 12 sharing with 2 adults.
Self-guided cycling Managed locally by Headwater appointed rep.
Every two days from 13th Apr 2019 to 22nd Oct 2019, for 10 nights.
All buffet breakfasts and 6 evening meals
It is possible to hire electric bikes for this holiday at a supplement of £275 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment. Please call us for further details.
Transfers included from Pisa airport at 10:30, and back to Pisa airport at 09:00.
Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for Classic Chianti Cycling. 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 an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.
Alternatively, you can call our sales team on 1-800-267-3347 to discuss your requirements in more detail.
We've been creating high-quality relaxed activity holidays since 1985 and our wealth of experience means we're able to build the perfect tailor-made tour for you. Our 'Gold Trusted' rating on Feefo, the independent review site, underlines our exceptional levels of customer service, and our ATOL bonding and ABTA membership guarantees your holiday is safe with us.