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Tour Description

  • 11 days
  • selfguided
  • tour

This self-guided bike tour tackles the rolling backroads of Tuscany. The Chianti Wine Route is the star of the ride, but you’ll also get to sweep through medieval hilltop towns and day-trip to Florence and Siena. The character hotels are the cherry on top.

Operates: Every 2 days from 11 May - 14 Oct 18.

Difficulty level: 2+.

Whats Included:

•    All buffet breakfasts and 6 evening meals included.
•    Managed locally by Headwater representative
•    Headwater wine carrying service
•    Route notes and maps
•    Bikes provided
•    Luggage transfers between hotels

Map key:
Show map key

Looking for something totally unique?
Our Italy Experts can create completely bespoke itineraries. Give them a call with your requirements and they can tailor-make a trip to suit you.

Call our experts today and turn your ideas into a dream holiday


01293 762410 *

At a glance

•    Chianti Wine Route
•    Secretive medieval cities like Certaldo
•    Ride up to towering San Gimignano
•    Day trips to Florence and Siena
•    Stay in converted watermills and abbeys

 

Suggested Itinerary

Day 1: Volterra

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 1: Volterra

Check in to the Park Hotel le Fonti (or similar) as early as possible. That leaves plenty of time to explore the ancient walled town of Volterra, which sits right above the hotel in a tangle of theatres, temples and alabaster workshops dating back to 500 BC.

Day 2: Era Valley, Castagno, Gambassi Terme and Certaldo

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 2: Era Valley

Zoom down the hill from Volterra and into the Era Valley. This is behind-the-scenes Tuscany, where sloping countryside views come crowd-free. Pedal up and out of the valley to grab a coffee in a café in sleepy Castagno. 
Gambassi Terme is up next – a red-roofed spa town perched on a flat-cap hill. Roll downhill to Hotel Le Renaie (or similar).

 

Day 3: Certaldo

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 3: Certaldo

Spend today exploring Certaldo. Modern Certaldo Basso lies along the river, while a funicular slides up to the hilltop old quarter, Certaldo Alto (AKA Castello). This neighbourhood writes an architectural ode to the Middle Ages with its Priori Palace and the Church of Saints Jacob and Philip. Boccaccio – author of The Decameron – is buried here, too.

Day 4: Chianti Wine Route, Poggibonsi and Colle di Val d’Elsa

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 4: Chianti Wine Route

You’ll dive deep into Chianti country today, veering off-road along the Chianti Wine Route. Wine tastings, boutiques and photo stops are all on the agenda. Scoot downhill to 12th-century Poggibonsi in time for lunch.
Sunflower and poppy fields parade along the route out of Poggibonsi. It brings you to the medieval hilltop town of Colle di Val d’Elsa. Your hotel for the next four nights is the Relais Della Rovere (or similar) – a converted Benedictine abbey.

 

Day 5: Siena

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 5: Siena

We recommend catching the bus to Siena on this free day. This medieval city is packed with history, from the Roman-era Piazza del Campo to Gothic Siena Cathedral. White-capped Torre del Mangia can be spied for miles – and in turn serves up broad views of the Tuscan countryside.

Day 6: Colle di Val d’Elsa

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 6: Colle di Val d’Elsa

Colle di Val d’Elsa was once an Etruscan stronghold, dating back to at least the 9th century BC. That said, the town is really a showcase for medieval and Renaissance architecture. Skinny lanes thread past grand gates, golden palazzos and an auburn cathedral. Meanwhile, workshops magic up the local speciality – crystal glass.
Fancy peeping outside the town walls? Follow the footpaths to the mini rapids along the River Elsa.
 

Day 7: Florence

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 7: Florence

Spend another day exploring Colle di Val d’Elsa – or head off on a day trip to Florence.
The city is considered the Renaissance gem of Tuscany, thanks to a heady hit of art galleries and museums. It’s really walkable, too. Admire Il Duomo di Firenze, browse the jewellery shops along Vecchio Bridge, see masterpieces at the Uffizi Gallery, or stroll around the Boboli Gardens.
Best of all, the bus from Colle di Val d’Elsa to Florence stops right outside your hotel.

 

Day 8: Casole d’Elsa and Pescille

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 8: Casole d’Elsa and Pescille

It’s back to your bike today. Swoop down into the valleys and then up to Casole d’Elsa village. Its 12th-century church and fortress pair up with a pretty piazza. Plus, you’ll be treated to 360-degree views of the rippled Tuscan hills. Grab lunch in Casole d’Elsa or throw together a picnic to take on your next rural route. 
San Gimignano is always on the skyline, watching over your path through the gold-green vineyards and orchards to Hotel Pescille (or similar). This converted Tuscan farmhouse offers a pool and hill-view sun terraces.

 

Day 9: San Gimignano

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 9: San Gimignano

Cycle to your neighbour, San Gimignano, whose skyline is a zigzag of 14 medieval towers. Scale any one of the towers for some of the best views in Tuscany. Down below, the snarl of cobbled piazzas and skinny streets is best explored on foot.

Day 10: Era Valley and Volterra

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 10: Era Valley and Volterra

Swoop down and up again, through the Tuscan valleys below Pescille and San Gimignano. Vineyards, sunflowers and olive groves patch the countryside. Skim down the hills and back into the serenely scenic Era Valley.
After that, you’re on to your final leg – a ride through wide-open countryside that ends in a climb to cobbled Volterra. Tonight, you’re back in the Park Hotel le Fonti (or similar).

 

Day 11: Volterra

Please call one of our Italy experts to discuss your accommodation choices

 

Map of Day 11: Volterra

Have an Italian breakfast before departing Chianti country.

 

**Cycling helmets**

In countries where cycling helmets are not a legal requirement, including Italy, we strongly recommend that all customers wear helmets whilst on one of our cycling tours. You are expected to bring your own helmet as we cannot guarantee the availability of helmets for hire or purchase at your destination. If you do decide to hire or purchase a helmet at your destination the choice of helmet and its suitability are at your discretion and Headwater will not be responsible for any issues or problems with helmets or other protective headwear. If you choose to ignore our advice to wear a helmet or other protective headwear you understand that you do so at your own risk and that such action may affect the validity of your travel insurance.

Cycling of all kinds has its dangers and accidents can happen from time to time. Please ensure that you are properly prepared for the riding you are going to undertake.

Call to discuss and book your tour 01293 762410 *

Flight Information

The majority of international flights arrive into Pisa airport (PSA). Direct flights to Pisa are available from Belfast, Bristol, East Midlands, Edinburgh, Glasgow, Leeds Bradford, Liverpool, London Gatwick, London Heathrow, London Luton, London Stansted, Manchester and Newcastle and take approximately 2 hours.