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Tuscany – San Gimignano

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

This particular biking vacation in Italy is a fixed location cycle tour based just outside San Gimignano in a wonderful Tuscan farmhouse and estate. 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. 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. Get pinched, this is the real thing.

Starting Location

San Gimignano

Price Includes

  • 4 or 7 nights bed and breakfast
  • 1 dinner on day of arrival
  • Information Pack
  • Routes Instructions & Maps
  • People and bike transfer to and from Colle Val d’Elsa on day 4
  • People and bike transfer to Volterra on day 6
  • People and bike transfer to Casole d’Elsa on day 7

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.


You stay in a family-run accommodation located 5km from San Gimignano, it is a wine and oil-producing Tuscan farmhouse. It is situated around 5km from the medieval town of San Gimignano.

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, 4, and 6 of the 7-night program

Day 1Arrival 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 the tranquillity.

Day 2Vineyards of Ulignano, Certaldo Alto & Barberino 26-42 miles 42-67 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 25 miles 40 km

This day offers a lovely circle tour around the highest hill in the immediate area, Poggio del Comune. Pedal along country lanes to Castel San Gimignano where we recommend a stop 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  25-42 miles 40-67 km

Today you choose the ride that suits you best. 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.

Day 5Rest Day

Today, you can choose to visit the nearby cities of Siena or Florence, both easy to reach with public transportation. Famous for its “Palio” horse race, promenade the narrow streets of Siena marvelling at the magnificent palaces, churches and squares. Alternatively, visit the Duomo, the Ponte Vecchio (OldBridge) and experience the unforgettable Renaissance splendour of Florence.

Day 6  Volterra to San Gimignano.  27 miles, 43 km

Transfer to the magic and mysterious Ancient Etruscan city of Volterra, where you can explore its Alabaster artisan shops, Roman Theatre, 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.

Day 7Casole d’Elsa and the Montagnola to San Gimignano 19 miles 29 km

The romantic landscape between Castel San Gimignano and Casole d’Elsa is mostly open pasture used for sheep grazing and wheat cultivating. The essence of the Montagnola area shall captivate you with its quiet, peaceful countryside. Cross kilometres of beautiful rolling green hills and marvel at the small local churches and quintessential Tuscan farmhouses.

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

2022 Prices – For 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 £611 Book Now
SanGim-7 (7 Nights)  from £828 Book Now
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