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Find your perfect trip!
Find your perfect trip!
Tuscany San Gimignano & Volterra short
style :
Level :
Duration :
5 days
Comfort :
Apr May Jun Jul Aug Sep Oct
Cycling E-Bikes
price in double room from: € 549
Tuscany San Gimignano & Volterra short

Tuscany San Gimignano & Volterra short

The Chianti at its best & ancient Etruscan culture

  • 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, friendly Tuscans


Map cycling routes tuscany san gimignano and Voleterra
View map

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.

Day 1: Arrive in San Gimignano
Day 2: Vineyards of Ulignano, Certaldo Alto & Barberino (35 - 60 km / 22 - 37 mi)
Day 3: Ride from San Gimignano to Volterra (36 km / 22 mi)
Day 4: Selection of rides from: (38.3 - 37 km / 24 - 23 mi)
Day 5: 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 - 60 km / 22 - 37 mi)

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 / 22 - 37 mi, 736 / 1221 m ascent, 736 / 1438 m descent


Day 3:    Ride from San Gimignano to Volterra (36 km / 22 mi)

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, 36 km / 22,5 mi, 922 m ascent, 649 m descent


Day 4:    Selection of rides from: (38.3 - 37 km / 24 - 23 mi)

Volterra to Montecatini Val di Cecina  

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.

Loop ride via Ulignano  

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 / 3.5 hours, 38.3 - 37 km / 24 - 23 mi, 692 / 924 m ascent, 805 / 1101 m descent


Day 5:    Arrivederci Volterra!

The trip and our services end after breakfast, unless you have booked a transfer to the airport or other supplementary services.



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


Albergo Etruria (Volterra)
Albergo Etruria*** (Volterra)

The hotel Albergo Etruria is a small Bed & Breakfast located in the center of Volterra, 100m from the know Piazza dei priori square. This family-run accommodation offer the guest with a warm welcome 



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.


The rental includes: phone holder, rear bag, odometer, repair kit, padlock and lights

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



The rental includes: phone holder, rear bag, odometer, repair kit, padlock and lights

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.



  • 4 nights' accommodation with breakfasts
  • Dinner on DAY 1
  • Bike delivery to San Gimignano, theft insurance and collection from Volterra
  • Luggage transfer from San Gimignano to Volterra on DAY 3
  • Digital detailed route notes and maps in English
  • Access to the trip on our navigation app
  • 24-hour telephone assistance

Not included

  • Travel insurance
  • Tourist taxes
  • Bike rental 
  • Helmet (2€ per person/ tour)
  • 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 or hybrid bike (phone holder, 1 rear bag, odometer, 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
  • Shipment of printed documents to the first accommodation

There are no reviews for this trip yet.


We had a great vacation in Toscana. San Gimignano, Certaldo and Volterra are really great places to have the feeling of how people lived in the medieval era.

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