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Tuscany San Gimignano & Volterra
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Duration :
8 days
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Apr May Jun Jul Aug Sep Oct
E-Bikes Cycling
price from € 740
Tuscany San Gimignano & Volterra

Tuscany San Gimignano & Volterra


  • Visit the natural, artistic, and cultural treasures of San Gimignano, a UNESCO world-heritage site 
  • Discover the rich Etruscan past of remote Volterra with its Roman theatre, Palazzo dei Priori, and alabaster handicraft 
  • Wonderful landscapes, wide open fields, cypress lined avenues, vineyards, olive groves plus delicious cuisine full of Tuscan specialities
  • Incredibly well preserved Medieval and Renaissance villages, and quaint hill-top towns
  • Peaceful country roads and friendly Tuscans
Map cycling routes tuscany Saj Gimignano and Volterra
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The rides are along well-asphalted country lanes, secondary roads with little traffic, and 1/3 of the time on good dirt roads. Near larger towns, the roads are well travelled.

Start: San Gimiano                 Finish: Volterra

Day 1: Arrive in San Gimignano
Day 2: Vineyards of Ulignano, Certaldo Alto & Barberino (35 km, 60 km)
Day 3: San Gimignano and Poggio del Comune (36.5 km)
Day 4: Colle Val d’Elsa, Monteriggioni, optional extention to Castellina (40 km)
Day 5: Cycle from San Gimignano to Volterra (35.9 km)
Day 6: Volterra to Montecatini Val di Cecina (38.3 km)
Day 7: Loop ride via Ulignano (37 km)
Day 8: Arrivederci Volterra!

Day 1:    Arrive in San Gimignano

Arrive at Relais 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, 60 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: 4/5 hours, 35/60 km, 736/1221m ascent, 736/1438m descent


Day 3:    San Gimignano and Poggio del Comune (36.5 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: 3.5 hours, 36.5 km, 1000m ascent, 1000m descent


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

Today you can choose the ride that best suits you. 

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: 3 hours, 40 km, 226m ascent, 106m descent, optional extention to Castellina 12 km, 2 hours


Day 5:    Cycle from San Gimignano to Volterra (35.9 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: 4 hours, 35.9 km, 922m ascent, 649m descent


Day 6:    Volterra to Montecatini Val di Cecina (38.3 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: 3 hours, 38.3 km, 692m ascent, 805m 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: 3.5 hours, 37 km, 924m ascent, 1101m 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.


'standard' hotels

All accomodations are carefully selected because of their location, atmosphere and/or unique services. All rooms are en-suite.

We choose comfortable 3* hotels, farmhouses and B&Bs where all rooms have private en-suite bathroom.

You can find below the standard hotels of this trip. If a hotel is fully booked, then we will book a similar one for you and inform you about the alternative booked. 

Extra overnight:You can book additional night(s) at any of the accommodations along the way.

Hotel La Cisterna (San Gimignano)
Hotel La Cisterna*** (San Gimignano)

The hotel is both overlooking the ancient Piazza della Cisterna used to welcome pilgrims from all over the world and charming hills of San Gimignano. This stately home is in an excellent position, into the heart of San Gimignano. The rooms are simple and modern with air conditioning, free Wi-Fi, TV and bathroom. Breakfast is very good although not particularly plentiful. The staff is welcoming and helpful

Hotel Foresteria Volterra (Volterra)
Hotel Foresteria Volterra*** (Volterra)

Hotel Foresteria is just 1 km walk from the historic center of Volterra. Rooms are simply furnished, offer TV, private bathroom, balcony and are fully equipped for disabled guests. Breakfast buffet is plentiful and tasty, the staff very helpful and kind.

practical info

You can start on any day of the week, subject to availability, between April and October.

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.

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.


Specialised Sirrus Elite Carbon Disc

  • Shifters: Shimano Sora Rapidfire 
  • Wheeelset: AXIS Classic Disc
  • Frame: Specialized Sirrus FACT 9r carbon, Fitness Geometry, Zertz 
  • Fork: Specialized Sirrus FACT 9r carbon, Fitness Geometry, Zertz, 1-1/8" headtube 
  • Brakes: Tektro Gemini, hydraylic disc


Specialized Crossover

  • Frame: Specialized A1 Premium Aluminum
  • Fork: SR Suntour, coil spring, 65mm travel 
  • Brakes: die cast alloy V-brake 


Wilier Triestina GTR

  • Shifters: Shimano Ultegra  
  • Wheelset: Shimano RS010  
  • Frame: Carbon RACE monocoque 46TON  
  • Fork: Carbon monocoque 46TON  
  • Brakes: Shimano Ultegra



Winora Y420.X Yamaha

  • Motor: Yamaha PW motor 250W, 36V 
  • Battery pack: Yamaha battery, 36V, 400Wh, lithium ion
  • Frame: 6061 aluminium hydro formed 
  • Fork: Suntour NCX-D LO lockout, Suspension: steel spring / elastomer Travel: 63mm
  • Brakes: Shimano Deore, aluminum lever, hydraulic disc brake


GPS tracks are available on request.



  • 7 Nights in selected B&Bs, hotels and agriturismo
  • 7 Breakfasts
  • Dinner on DAY 1
  • Bike delivery to San Gimignano, theft insurance and collection from Volterra
  • Private transfer (+ bikes) from San Gimignano to Colle and back after ride on DAY 4
  • Luggage transfer from San Gimignano to Volterra on DAY 5
  • Detailed information pack, route notes and maps with tracks on
  • 24/7 telephone support 

Not included

  • Travel insurance
  • Touristic city taxes
  • Bike rental
  • Helmet
  • Travel to/from San Gimignano
  • Trains, busses or boats wherever necessary
  • Lunches & Dinners not specifically mentioned
  • Drinks and snacks
  • Personal equipment


  • Additional nights before, during or after the walk
  • Bike rental: e-bike & hybrid bikes (map holder, front bag, 1 rear bag, 1 odometer every 2 bikes, 1 repair kit, 1 padlock, lights)
  • Helmet 
  • Single Room Supplement(s)
  • Solo Traveller Supplement
  • Transfer from airport to San Gimignano
  • Transfer from San Gimignano to airport

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