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Classic Chianti Cycling

from $2,999.00

This 10-night cycling tour combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You’ll stay in high quality hotels, enjoy superb meals and relax by panoramic pools with views that extend as far as Corsica on a clear day!

  • Reviews 25 Reviews
    5/5
  • Vacation Style Holiday Type
    Self-guided
  • Activity Level Moderate plus
    6/8
All about the Classic Chianti Cycling.

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.

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.
  • 10 nights accommodation, hotel-to-hotel in a mix of *** and **** hotels
  • All buffet breakfasts and 6 evening meals
  • Services of your local Headwater Representative
  • GPS route navigation provided
  • RideWithGPS navigation app
  • RidePlus route options (more challenging routes)
  • High quality hybrid bikes (upgraded road bikes available for a supplement)
  • Luggage transfers between hotels
What is not included in this tour?
  • Flights
  • Arrival & departure transfers (available on request, inquire for supplement)
  • Single Accommodation (available on request, inquire for supplement)
  • E-Bike (available on request, inquire for supplement)
  • Room upgrades and extra nights at selected hotels
  • Tandems available (inquire for supplement)
  • RidePlus road bike (inquire for supplement)

Highlights

  • 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 Media eval art and architecture
  1. Day 1 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. (Staying at Park Hotel Le Fonti, Half Board)

  2. Day 2 Day 2 Volterra to Certaldo 36km/22.5mi

    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)

  3. Day 3 Day 3 At Certaldo

    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)

  4. Day 4 Day 4 Certaldo to Colle di Val d'Elsa 28km/17.5mi

    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)

  5. Day 5 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 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)

  6. Day 6 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 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)

  7. Day 7 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. (Staying at Relais della Rovere, Breakfast only)

  8. Day 8 Day 8 Colle di Val d'Elsa to Pescille 40km/25mi

    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)

  9. Day 9 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. (Staying at Hotel Pescille, Breakfast at the hotel and evening meal in a local restaurant)

  10. Day 10 Day 10 Pescille to Volterra 38km/24mi

    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)

  11. Day 11 Day 11 Leave Volterra
c10ty_map
Where you stay
Park Hotel Le Fonti
The 4 star Park Hotel Le Fonti is located just below the Porta dell’Arco entrance to Volterra’s beautifully preserved mediaeval centre. It’s an easy 10 minute stroll into arguably one of Italy’s oldest towns. The hotel has over 50 comfortable rooms, all of which are furnished in a simple style with terracotta floors and elegant fabrics. All rooms have ensuite facilities. The real highlight of the hotel is the breathtaking view from the terrace and fabulous infinity pool – the sweeping panorama over the rolling Pisan hills is truly outstanding.
Hotel Certaldo
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! 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* 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.
Relais della Rovere
The Relais della Rovere is a stunning 4-star hotel located at the edge of Colle di Val d’Elsa. The Cellerai family have sympathetically converted this C12 Benedictine Abbey into a 31 room luxurious hotel, retaining many of the abbey’s original features. The bedrooms are split between two buildings and decorated in a contemporary style with wooden floors and beech furniture. The rooms are quite large with ensuite facilities. The hotel has a lovely outdoor pool which is surrounded by pleasant gardens.
Hotel Pescille
The Hotel Pescille is located just 4km outside San Gimignano, in the heart of the Tuscan countryside, surrounded by olive groves and vineyards. It started life as an old farmhouse before being converted into the 3* hotel it is today. Evidence of its origins still remains however, with its ancient tower housing the hotel’s small agricultural museum. There are pleasant gardens surrounding the hotel – with lovely views of the surrounding landscape – and it also benefits from an outdoor swimming pool. All rooms at the Hotel Pescille are ensuite and are simple yet spacious with tiled floors, whitewashed walls and pristine white linen; air conditioning. satellite TV, minibar and hair dryer also all come as standard. Rooms have views onto either the timeless Tuscan countryside, or the roofs and mediaeval towers of San Gimignano itself. The hotel does not have a restaurant open for dinner, we have therefore arranged for you to have return taxi transfers to the centre of San Gimignano, where there is a wealth of restaurants to suit all budgets and tastes.
Eating and Drinking

All buffet breakfasts and 6 evening meals included.

Italy’s most famous export is probably its cuisine and the traditional dishes of Tuscany are the most influential and revered.
The region’s food is based on cucina povera, ‘poor/peasant cookery’, a rural cuisine based on available natural ingredients: olive oil, unsalted bread, pulses and vegetables, wild mushroom or porcini, and salt-cured meats such as salame and prosciutto. In particular, Tuscan olive oil is renowned for its quality and is the most important ingredient in the region’s cookery. You will find it in almost every dish – as a salad dressing, poured over vegetables and into soups and even as a replacement for butter on
bread (very nice with a sprinkling of salt!).

Classification: Self-Guided
Activity Level: 2 (Leisurely/moderate)
Average daily distance on move on days: 35.5km (22.3 miles).
No. of days cycling: 4
Terrain: Lots of the cycling is on off road strada bianca, although at times it has been necessary to use busier roads for short stretches where no alternative exists. Most of the countryside is moderately hilly, so there is every excuse to stop for a breather to admire the view!
Vehicle Support: This is a self-guided trip for those who prefer to cycle independently, but with our assistance to take out the stress of the logistics and planning. We arrange your accommodations, provide you with a map and route notes so that you can cycle at your own pace. A representative will be there to meet you, make sure the bikes are all set up and will be on call throughout the trip should you need.

It is important that you are happy reading maps and following route notes, we make these as accurate as possible and they are regularly checked.

As this is a self-guided holiday there is no group and no leader. There may be others on the same departure date as you, but you will not be organised together. The route notes contain a 24-hour emergency assistance telephone number should you need it and in emergencies, the local representative is normally able to dispatch a taxi or pick you up themselves. They may wish to charge for this service.

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.

Overall Rating
5/5
Reviewed On 24/10/2018
5/5

Mrs Tanner

A leisurely end of season break

Reviewed On 13/09/2018
5/5

Mrs Clucas

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.

Reviewed On 26/07/2018
5/5

Mrs Moffat

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!

Reviewed On 02/01/2018
5/5

Mr Lypka

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.

Reviewed On 13/06/2016
5/5

Mrs Sparshott

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

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August 17, 2020
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August 19, 2020
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August 21, 2020
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August 23, 2020
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August 25, 2020
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August 27, 2020
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August 29, 2020
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August 31, 2020
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September 2, 2020
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September 4, 2020
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September 6, 2020
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September 8, 2020
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September 10, 2020
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September 12, 2020
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September 14, 2020
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September 16, 2020
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September 18, 2020
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September 20, 2020
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September 22, 2020
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September 24, 2020
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September 26, 2020
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September 28, 2020
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September 30, 2020
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October 2, 2020
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October 4, 2020
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October 6, 2020
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October 8, 2020
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