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Find your perfect trip!
Tuscany San Giminiano & Chianti short
style :
Level :
Duration :
5 days
Comfort :
Mar Apr May Jun Jul Aug Sep Oct
E-Bikes Cycling
price in double room from: € 506
Tuscany San Giminiano & Chianti short

Tuscany San Giminiano & Chianti short

The Chianti at its best

  • Explore San Gimignano, a UNESCO world-heritage town
  • Stay in a charming Tuscan farmhouse with a pool
  • Quiet roads and quintessential 'strade bianche'
  • Wonderful landscapes with vineyards, cypress-lined roads and olive groves
  • Authentic country towns and villages: Siena, Volterra, Certaldo, Casole d'Elsa, Colle Val d'Elsa, Monteriggioni
  • Friendly people and great traditional Tuscan culinary specialties
Map cycling routes san gimignano and chianti
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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.

Day 1: Arrive in San Gimignano
Day 2: Colle Val d’Elsa, Monteriggioni, optional extention to Castellina (40 km)
Day 3: Ulignano and Certaldo Alto, extention to Barberino (47.3 km)
Day 4: Cycle from Volterra back to San Gimignano (43.5 km)
Day 5: Arrivederci San Gimignano!

Day 1:    Arrive in San Gimignano

Arrive at the farmhouse near San Gimignano and unwind, as this shall be your comfortable Tuscan home for the next week. Breathe in the wonderful country air as you explore the tiny medieval village of San Donato and take a stroll along the classic green rolling hills, marvelling at the breathtaking views of the surrounding countryside. Immerse yourself in tranquility.

Day 2:    Colle Val d’Elsa, Monteriggioni, optional extention to Castellina (40 km)

Today you choose the ride that suits you best. 

A morning transfer takes you 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 3:    Ulignano and Certaldo Alto, extention to Barberino (47.3 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, 47.3 km, 1070m ascent, 985m descent, optional extention to Barberino 19km 1 hour

Day 4:    Cycle from Volterra back to San Gimignano (43.5 km)

Transfer to the magical and mysterious Ancient Etruscan city of Volterra, where you can explore its alabaster artisanry shops, Roman theater, superb palaces and alluring city walls. Then hop on your bike for an exhilarating downhill ride into the valley, through a patchwork of wheat fields and impressive villas, followed by a delightful ascent to return to San Gimignano.

Challenge: 3.5 hours, 43.5 km, 882m ascent, 1127m descent

Day 5:    Arrivederci San Gimignano!

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.

Agriturismo Fattoria Voltrona (San Gimignano)
Agriturismo Fattoria Voltrona (San Gimignano)

Agritourism Fattoria Voltrona is located 6km from the center of San Gimignano. Immersed in the Tuscan countryside, it is surrounded by a large garden. Rooms are decorated in a rustic style with tiled floors and offer free Wi-Fi, a private bathroom and heating. You can access the outdoor pools and the Vespa rental. Breakfast buffet is plentiful and tasty, the restaurant offers typical Tuscan quality recipes.


practical info

You can start on any day of the week, subject to availability, between March 22nd and October 27th.

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.

Once in San Gimignano, you need to catch a taxi from the bus stop to Fattoria Voltrona (approx. 5 km).


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.



  • 4 nights accommodation with breakfast
  • Dinner on DAY 1
  • Bike delivery to San Gimignano, theft insurance and collection from San Gimignano
  • Private transfer (+ bikes) from San Gimignano to Colle and back after ride on DAY 2
  • Private transfer (+ bikes) from San Gimignano to Volterra on DAY 4
  • Digital detailed route notes and maps in English
  • Access to the trip on our navigation app
  • 24-hour telephone assistance

Not included

  • Travel insurance
  • Touristic city taxes
  • Bike Rental
  • Travel to/from San Gimignano - Località San Donato
  • 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: hybrid / e-bike
  • Helmets
  • Single Room Supplement(s)
  • Solo Traveller Supplement
  • Transfer from airport to San Gimignano - Località San Donato
  • Transfer from San Gimignano - Località San Donato to airport
  • Shipment of printed documents to the first accommodation

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