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Tuscany – San Gimignano and Volterra

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Homepage > Italy > Tuscany – San Gimignano and Volterra
  • Duration: 4 or 7 Nights
  • Difficulty: Level 2-3
  • Tour Type: Self Guided
  • Availability: Daily 1st April to 30th October
  • Location: San Gimignano

San Gimignano and Volterra

Tour Details

Time to enjoy a wonderful self-guided cycling in Tuscany based from two fabulous towns. San Gimignano is a treasure on the hill and a 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. On this cycling holiday, you will ride over clouds of sunflower fields under the Tuscan sun and along cypress-lined country roads through olive groves and vineyards, which produce some of the world’s finest olive oil and wine. You shall savour the flavour of these ingredients in the outstanding local cuisine. Travel to Etruscan and Roman times, from one picturesque hilltop to the next, each with its own history and charisma. Then you cycle to Volterra, the Etruscan centre of Tuscany, again a hilltop town but lessor known than other famous towns in this region.

Starting Location

San Gimignano

Price Includes

  • 4 or 7 nights bed and breakfast
  • 1 dinner on day of arrival
  • Information Pack
  • Navigation by Smart Phone App
  • Luggage transfers
  • People and bike transfer to and from Colle Val d’Elsa ( 7 Night tour only)

Price Excludes

  • Transport before and after tour
  • Flights
  • Travel Insurance
  • Hybrid Bike Rental
  • E-Bike Rental
  • Extra nights
  • Single Supplement
  • City Tax
Trip Info

Route Characteristics

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 busier which is unavoidable.

Accommodation: Subject to Change

San Gimignano                  – Hotel La Cisterna

Volterra                                – Albergo Etruria  

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


The 4-night program includes day 1, 2, 5, and 7 of the 7-night program

Day 1Arrival in San Gimignano

Arrive to San Gimignano and unwind and get ready for your Tuscan adventure. Breathe in the wonderful country air and maybe head out to explore San Gimignano.

Day 2Vineyards of Ulignano, Certaldo Alto & Barberino 22-32 miles 35-51 km

Today you will cycle through prestigious vineyards towards Ulignano and the charming hilltop village of Certaldo, the 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.

Day 3San Gimignano and Poggio del Comune 23 miles 37 km

This day offers a lovely circle tour around the highest hill in the immediate area, Poggio del Comune. Before setting out stop at  Castel San Gimignano at the local bar for a delicious sandwich (panino). Continue through a nature reserve of woods and cow pastures as you return to San Gimignano for a glimmering ride and a refreshing drink.

Day 4Colle Val d’Elsa, Monteriggioni, Lilliano & Castellina in Chianti 25 miles 40km

Today a morning transfer to Colle Val d’Elsa. The  you 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 San Gimignano.

Day 5Ride to Volterra 23 miles 36km

Today to cycle to the Etruscan centre 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.  This truly is what you imagine Tuscany to be like. One more solid climb before you arrive at your marvellous hotel, a former convent set inside in the gates of the old city centre.

Day 6 Volterra to Montecatini Val di Cecina 24 miles 38km

Head out on your bikes today where you shall be greeted with an exhilarating downhill ride into the valley below. You then cycle through the lovely Val d’Era and over stretches of ‘strade bianche’, typical Tuscan white roads (fine gravel). The route winds through the lovely landscape filled with remote farmsteads and villas, and hills covered with vines and olive groves, this is true bliss! Grand views of the vast infinitely undulating terrain will accompany you throughout the entire day.


Day 7Loop ride via Lajatico & Teatro del Silenzio 23-28 miles 37-45 km

Today you cycle from Volterra, with more typical Tuscan landscapes which seem to envelop you in an expanse of green and golden hills that are scattered with cypresses and farmhouses. Now a short stretch of asphalt takes you to the village of Lajatico, known for being the birthplace of tenor Andrea Bocelli. Along your way, the stunning “Theatre of Silence”, a quaint lake adorned with pieces of contemporary art that once a year turns into an open-air amphitheater for a much-awaited Bocelli concert. After a short rest continue on your way along plain cart roads and nice asphalted roads, with a final challenging uphill stretch that brings you can back to Volterra.

Day 8Departure

Depart after breakfast.


How to get there

By Plane
To Pisa/Florence airport and the by train to Siena and then by bus or by bus from Florence direct to San Gimignano. From San Gimignano short taxi ride to accommodation.

Book Now

2024 Prices – For a complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
SanGim-4 (4 Nights)  from £542 Book Now
SanGim-7 (7 Nights)  from £868 Book Now
Tour Images
Tuscany in the sun