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Tuscany: San Gimignano & Volterra
Tuscany: San Gimignano & Volterra
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8 days
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Apr May Jun Jul Aug Sep Oct
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price from € 793
Tuscany: San Gimignano & Volterra
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Tuscany: San Gimignano & Volterra


Bike Tour: Tuscany: San Gimignano & Volterra - 8 days

San Gimignano is a treasure on the hill and jewel of Tuscany, wonderful for cycling and exploring. With its thirteen outstanding medieval towers, it is clear why the town is on the UNESCO world heritage list. Riding under the Tuscan sun you will pedal on quiet cypress-lined country roads passed sunflower fields, olive groves and vineyards; producing some of the world’s finest olive oil and wine by. Savour the flavour of these ingredients and that of the local produce in the outstanding local cuisine. Then cycle to the former Etruscan centre of Volterra, a unique hilltop town with its own history and charisma. Get pinched, this is the real thing.

Day 1: Arrive in San Gimignano
Day 2: Vineyards of Ulignano, Certaldo Alto & Barberino
Day 3: San Gimignano and Poggio del Comune
Day 4: Colle Val d’Elsa, Monteriggioni, optional extention to Castellina
Day 5: Cycle from San Gimignano to Volterra
Day 6: Volterra to Montecatini Val di Cecina
Day 7: Loop ride via Ulignano
Day 8: Arrivederci Volterra!

Day 1:    Arrive in San Gimignano

Arrive at the hotel in San Gimignano and unwind, as this shall be your comfortable Tuscan home for the next few days. Breathe in the wonderful country air and take a stroll along the classic green rolling hills, marvelling at the breath-taking views of the surrounding countryside. Immerse yourself in the tranquillity.

Day 2:    Vineyards of Ulignano, Certaldo Alto & Barberino
35 km

Today you will cycle through prestigious vineyards towards Ulignano and the charming hilltop village of Certaldo, hometown of the renowned Italian writer Boccaccio. The ascent to Certaldo is either by funicular or by a very steep climb. After visiting its ceramic-decorated main square and stunning churches, you can choose an extended ride to Barberino and Tavernelle in the Chianti Classico area, offering magnificent views.

Challenge: 35/51 km, 580/970 m ascent, 580/970 m descent

Day 3:    San Gimignano and Poggio del Comune
36 km

This day offers a lovely loop ride around the highest hill in the surrounding area, Poggio del Comune. Before you start to pedal along country lanes we recommend you make a stop at the local bar by the Castel San Gimignano, and pick up a delicious sandwich (panino) for along the way. Continue through a nature reserve of woods and cow pastures as you return to San Gimignano for a glimmering ride and a refreshing drink

Challenge: 36.5km, 826 m ascent, 826 m descent

Day 4:    Colle Val d’Elsa, Monteriggioni, optional extention to Castellina
40 km

Morning transfer to Colle Val d’Elsa. Cycle along the undulating hills of the Val d’Elsa to the perfectly preserved medieval hamlet of Monteriggioni. Continue uphill, past abundant vineyards and stimulating woods, either towards Lilliano or directly up to Castellina in Chianti, where the views are spellbinding. Afternoon transfer from Colle Val d’Elsa back to the accommodation. 

Challenge: 40 km, 640 m ascent, 640 m descent
Optional extention to Castellina: + 14 km, 315 m ascent, 315 m descent

Day 5:    Cycle from San Gimignano to Volterra
35 km

Today, you will leave San Gimignano behind and cycle to the ancient Etruscan town of Volterra. Through a patchwork-like landscape dotted with wheat fields, olive groves and villas, you reach the base of the imposing hill upon which the town is set. One more solid climb before you arrive at your marvellous hotel, a former convent set inside in the gates of the old city centre.

Challenge: 35.9 km, 922m ascent, 649m descent

Day 6:     Volterra to Montecatini Val di Cecina
38 km

After an exhilarating downhill ride into the valley, you cycle through the lovely Val d’Era and over stretches of ‘strade bianche’, typical Tuscan white roads. The itinerary winds through the landscape filled with remote farmsteads and villas, and hills covered with vines and olive groves. Grand views on the vast infinitely undulating terrain will accompany you throughout the entire day.

Challenge: 38.3 km, 840 m ascent, 840 m descent

Day 7:    Loop ride via Ulignano
37 km

An easy yet very scenic ride today in the surroundings of Volterra. Erosion caused by rain water have artistically sculpted the landscape creating cracks and gullies of a majestic beauty. After descending from Volterra you will venture off the beaten track on unpaved tracks to then return on the very panoramic Strada del Cornocchio.

Challenge: 37 km, 920 m ascent, 920 m descent


Day 8:    Arrivederci Volterra!
The trip and our services end after breakfast, unless you have booked a transfer to the airport or other supplementary services.

Nights in 3-star hotels with breakfast


Available on request


Front and rear lights included


Padlock included


1 rear bag, 1 phone holder and 1 odometer included


Repair kit included

Wilier Triestina GTR

  • Frame: Carbon RACE monocoque 46TON
  • Brakes: Shimano Ultegra
  • Rear derailleur: Shimano Ultegra

Tandem Cannondale Touring

  • Frame: MTB Tandem USA handmade
  • Rear derailleur: Shimano XT
  • Shifters: Shimano Deore


Winora Y420.X Yamaha

  • Motor: Yamaha PW motor 250W, 36V
  • Battery pack: Yamaha battery, 36V, 400Wh, lithium ion
  • Frame: 6061 aluminium hydro formed
  • Brakes: Shimano Deore, aluminum lever, hydraulic disc brake, 180mm (front disc), 160mm (rear disc) 

Cube Touring One

  • Frame: AluminiumSuperlite Trekking Comfort Double Butted
  • Rear Derailleur: Shimano RD-M360, 8-Speed
  • Brake System: Shimano BR-M315, Hydr. Disc Brake (160/160)

Practical info

7 nights included


3 Star Hotels

Breakfast included

Tourist information on all the places of interest

Bike rental available

7-days a week service-hotline

Luggage transport included

Poggibonsi/San Gimignano Train station

GPS-tracks available


Medical and luggage travel insurance

Arrival info

Florence (FLR), Pisa (PSA) and Bologna (BLQ) Airports are served by major and low cost international flight carriers.

Rome Airport (FCO) is a bit farther away.

Arrival in San Gimignano

From any airport, reach Florence Santa Maria Novella train station by either train or bus.

From there, you can reach Poggibonsi by either bus or train. From Poggibonsi, take a direct bus to San Gimignano.

You can find more information about timetables and train tickets heretrenitalia.it

Italian Bike Tours

Borgo Allegri 16R
50122 Firenze FI
+39 055 2340736 

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