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Northern Tuscany on Wheels: Pisa to Florence 25

San Gimignano & Volterra Cycling Break


Riding under the Tuscan sun, you will pedal through the heart of Tuscany on quiet cypress-lined country roads past 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 a jewel of Tuscany, wonderful for cycling and exploring on a short 5-day active holiday. With its thirteen outstanding medieval towers, it is on the UNESCO world heritage list. You will spend the second part of the trip in the former Etruscan centre of Volterra, a unique hilltop town with its own history and charisma. To add up to this purely Italian experience, you will be able to enjoy the outstanding local cuisine fully.


  • 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 alleys, 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

Click to view map


Day 1: Arrive in San Gimignano

Arrive at your hotel in San Gimignano. Breathe in the wonderful country air and take a stroll along the classic green rolling paths, marvelling at the breath-taking views of the surrounding countryside. Immerse yourself in the Tuscan tranquillity.

Day 2: Vineyards of Ulignano, Certaldo Alto & Barberino | 35 or 60 km

Today you will cycle through many vineyards towards Ulignano and the charming hilltop village of Certaldo, the hometown of the renowned Italian writer Boccaccio. You can get to Certaldo, either by a funicular train or by cycling on a steep section. 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.

  • 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
  • Accommodation: 3-star hotel in San Gimignano (Hotel La Cisterna or similar)

Day 3: San Gimignano to Volterra | 36 km

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 on which the town is located. It takes one more solid climb before you arrive at your marvellous hotel, a former convent set inside in the gates of the old city centre.

  • Cycling for the day: 36 km, 4 hrs, ↑925 m ↓650 m
  • Accommodation: 3-star hotel in Volterra (Albergo Etruria or similar)

Day 4: Volterra Loop Rides | 37 or 39 km

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 undulating terrain will accompany you throughout the entire day.

Option 2: Loop ride via Ulignano

An easy and very scenic ride in the surroundings of Volterra. Erosion caused by rainwater has 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, returning on the very panoramic Strada del Cornocchio.

  • 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
  • Accommodation: 3-star hotel in Volterra (Albergo Etruria or similar)

Day 5: Departure

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

What to Expect


Standard accommodation for this trip is in comfortable 3-star 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.

Click to view default hotels

Hotel La Cisterna in San Gimignano

The hotel overlooks the ancient Piazza della Cisterna used to welcome pilgrims from all over the world and the 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.

Albergo Etruria in Volterra

The hotel is situated in an 18th-century palazzo, located in the heart of the historic centre of Volterra, on the main pedestrian shopping street and just 100 yards from the Piazza dei Priori. The bus station and a guarded toll parking are only 150 meters away from the hotel. The private garden looks out over the rooftops of Volterra. All the rooms are individually decorated and furnished, but all of them are with their own private bathroom with shower, free WiFi, TV and telephone.

*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 in the town where you stay overnight.

Difficulty & terrain

The trip is graded 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 well travelled. 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). Before you arrive, you will be sent a 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 working with.

When to go

You can start your holiday every day between the beginning of April and the end of October. Spring and autumn months are a preferred travel period if you want to avoid the summer heat of July and August. In September – October, you will enjoy pleasant temperatures and might also be able to catch the regional wine harvest.

Getting there

FCO up-to-date travel advice

Click to view travel options

By plane

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

By train or bus

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 www.trenitalia.com
  • Check bus timetables on www.busfox.com/timetable/

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



  • 4 nights in private rooms as per the itnerary
  • 4 breakfasts
  • Dinner on Day 1 in San Gimignano
  • Luggage transfer from San Gimignano to Volterra on Day 3
  • A detailed information pack, route notes and maps with tracks on
  • 24/7 phone support by our local office/representative


  • Flights and connecting land transfers
  • Lunches, 3 dinners, drinks & snacks
  • Bike rental
  • Travel insurance (required – get a quote online)
  • Personal expenses
  • Local tourists tax & entry fees (payable on the spot)
  • Any items not specifically mentioned as ‘included’ in the programme

Options, extras & supplements

  • Supplement applies to members of a group who require a single room / single use of a double room
  • This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
  • Bike rental, including bike insurance, delivery to San Gimignano and collection from Volterra – see details below
  • Extra nights in San Gimignano or Volterra

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; front and backlights, puncture repair kit, front and back lights, phone holder.

You are expected to know the 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)