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Northern Tuscany on Wheels: Pisa to Florence 25

Cycling in Tuscany: San Gimignano & Volterra


Riding under the Tuscan sun, you will pedal through the heart of Tuscany on quiet cypress-lined country roads passed sunflower fields, olive groves and vineyards, producing some of the world’s finest olive oil and wine. San Gimignano is a treasure on the hill, and the region is wonderful for cycling and exploring on a week-long active holiday. With its thirteen outstanding medieval towers, it is on the UNESCO world heritage list. Then cycle to the former Etruscan centre of Volterra, a unique hilltop town with its own history and charisma.


  • Visit the natural, artistic, and cultural treasures of the hamlet of San Gimignano, a UNESCO 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 and olive groves
  • Incredibly well preserved Medieval and Renaissance villages, and quaint hill-top towns
  • Peaceful country roads, friendly Tuscans and delicious regional culinary specialities


Day 1: Arrive in San Gimignano

Arrive at your 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.

Accommodation for the day: Hotel La Cisterna*** or similar

Day 2: Vineyards of Ulignano, Certaldo Alto & Barberino

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.

  • Accommodation for the day: Hotel La Cisterna*** or similar
  • Cycling for the day (option 1): 35 km, 4 hrs, ↑736 m ↓736 m
  • Cycling for the day (option 2): 60 km, 5 hrs, ↑1221 m ↓1438 m

Day 3: San Gimignano and Poggio del Comune

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.

  • Accommodation for the day: Hotel La Cisterna*** or similar
  • Cycling for the day: 37 km, 4 hrs, ↑1000 m ↓1000 m

Day 4: Colle Val d’Elsa, Monteriggioni, Lilliano & optional extension to Castellina in Chianti

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.

  • Accommodation for the day: Hotel La Cisterna*** or similar
  • Cycling for the day: 40 km, 3 hrs, ↑225 m ↓110 m ( optional extension to Castellina 12 km, 2 hours)

Day 5: San Gimignano to Volterra

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.

Day 6: Volterra Loop Rides

Today you can choose between two options:

Option 1: 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.

Option 2: 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.

  • Accommodation for the day: Ostello Chiostro delle Monache or similar
  • Cycling for the day (option 1): 39 km, 3 hrs, ↑695 m ↓805 m
  • Cycling for the day (option 2): 37 km, 4 hrs, ↑925 m ↓1100 m

Day 7: Loop ride via Ulignano

An easy yet very scenic ride today in the surroundings of Volterra. Erosion caused by rainwater have artistically sculpted the landscape creating cracks and gullies of 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.

Day 8: Departure

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


Standard accommodation for this trip is in comfortable 3* hotels, in double/twin en-suite rooms. All places have been carefully hand-picked by us and their quality is regularly monitored. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Sample hotels*:

Hotel La Cisterna*** in 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. The staff is welcoming and helpful.

Ostello Chiostro delle Monache in Volterra

Not so far from the attractive Etruscan walls of Volterra, The Chiostro delle Monache is an ancient Franciscan convent, that was built together with the Church of San Girolamo in 1445 ad by the municipality and then assigned to the Franciscan order. Restored as a Hostel, The Chiostro delle Monache offers now some well-furnished private rooms, all with en-suite facilities.

*Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal or higher value and quality level. We will provide exact accommodation details to you upon booking confirmation.


Welcome dinner is included on day 1 in San Gimignano, and breakfast is included each morning. When no restaurant is available on the route, lunches and snacks can either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before. Dinner is available either from the restaurant in your accommodation or the restaurants in the town where you stay for overnight.


Our recommended arrival/departure airports for this holiday are the ones in Florence (FLR)Pisa (PSA) and Bologna (BLQ), all served by major and low cost international flight carriers..


By Train

From any airport, it is best to reach Florence Santa Maria Novella train station by either train or bus. From there, you can reach Poggibonsi by either bus or train, and take a direct bus to San Gimignano.

  • Check train timetables on
  • Check bus timetables on

By Car

Local public garages cost approx. €15 per day, payable locally, no reservation possible.

Country Info

  • Language: Italian. In big cities and resorts, many people speak English, but in remote areas, this might not be the case. However, most of the hotel personnel where we stay speak English and are ready to help you. Many people also speak German. You can always call our 24/7 helpline if there are any problems.
  • Electric supply and plugs: 220V, 50hZ, two-pin round plugs.
  • Currency: We strongly advise taking sufficient cash for your daily requirements. Banks and ATMs are available, and credit/debit card payments are widely accepted in towns and cities and big petrol station chains but might be limited at some of the villages we visit.
  • Up-to-date travel advice on Italy is available here.
  • Detailed travel information and hints will be provided in your holiday information pack.

Trip Info

Difficulty Grade: Moderate

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. Daily distances vary between 35 km and 60 km and daily elevation gains between 700 m and 1000 m. The trip is suitable for regular cyclists who have an active lifestyle (read more about difficulty grades).

Bike Rental

If you have rented a bike with us, you can pick it up the next day of your arrival at the bike shop in town, near your accommodation. Our adult hybrid-bikes are equipped with comfortable seats, reliable components, 21 gears and Shimano Alivio components. All bikes, before being handed out are cleaned and overhauled.

Both our standard and E-bikes are equipped with a padlock and key that must be used at all times when not riding the bike, luggage pannier attachments at the rear and 1 rear side bag per bike, 1 front bag and map compartment, front and back lights, puncture repair kit, pump and spare inner tube, all of which you should know how to use.

You are expected to know the vary basics of bike mechanics and how to mend a puncture or change a tire. If something more serious happens to the bike that you cannot repair on the spot, call the shop and they will help you fix it or suggest the best and fastest solution.

Sample models: Specialized Crossover, Specialised Sirrus Elite Carbon Disc and Winora Y420.X Yamaha (e-bike)

Route Navigation

Before you arrive you will be sent detailed information package in digital form, including a destination manual, route notes, maps and GPS tracks, which you can load on any Garmin device or smartphone application that you are used to work with.

When to Go

This trip is available from April until October, departing on any day of the week (subject to availability).


  • 7 nights in selected 3* Hotels
  • 7 breakfasts
  • Dinner on day 1 in San Gimignano (3-course meal, drinks excluded)
  • Private transfer (+ bikes) from San Gimignano to Colle and back after the ride on Day 4
  • Luggage transfer from San Gimignano to Volterra on Day 5
  • A detailed information pack, route notes and maps with tracks on
  • 24/7 telephone support 

Options and Extras

  • Single-room supplement (this applies to members of a group who require single-room accommodation)
  • Solo traveller supplement (includes single room accommodation)
  • Bike rental, including bike insurance, delivery to San Gimignano and collection from Volterra
  • Additional nights in San Gimignano or Volterra


  • Flights and connecting land transfers
  • Lunches, dinners, drinks & snacks
  • Travel insurance
  • Personal expenses such as phone calls, extra transfers, tips, etc.
  • Any items not specifically mentioned as ‘included’ in the programme
  • Local tourist taxes


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Cycling Tuscany: San Gimignano & Volterra
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by Chester on King Ludwig Way

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