Tuscany – San Gimignano

Cycling in Tuscany, around the beautiful town of San Gimignano

Under the Tuscan sun, you’ll cycle on quiet cypress-lined country roads past olive groves, sunflower fields and vineyards that produce some of the world’s finest wines and olive oils. During this trip, you’ll experience the cultural and gastronomic secrets of Tuscany.
You will stay in the famous villages of San Gimignano and Volterra. San Gimignano is truly the jewel of Tuscany! With its many outstanding medieval towers, it is obvious why the city is on the UNESCO World Heritage List.
The cycling is mostly on quiet country roads with little traffic. We rate the difficulty of this trip as 4 out of 5, mainly because the landscape is quite hilly. If you or someone in your party is unsure of their fitness level, we recommend an electric bike, it works great!
A cycling trip in Tuscany is definitely a memory you carry with you for a long time to come!

Choose to travel either 8 days/ 7 nights or 5 days/ 4 nights.

Highlights

  • Delicious local culinary specialities and wines
  • Wonderful landscapes with large open fields, vineyards and olive groves
  • The medieval village of San Gimignano, the jewel of Tuscany and a UNESCO World Heritage Site
  • Volterra with its rich Etruscan background, and the Roman theatre, Palazzo dei Priori

Quick facts

Travel duration: 8 days/ 7 nights, 5 days/ 4 nights
Travel period: 1/4 - 31/10
Grade:
Challenging. Average 40-75 km/ 500-1200 m per day. Day by day trip grading, see "program" on each trip.
4
Accommodations:
Trip type: Self guided cycling holidays
Price example: From €480
Meals: Breakfast and 1st dinner

Prices per person in EUR

This trip is available from 01 April – 31 October, with any arrival date.

5 days/ 4 nights hotel *** From €480 Book your trip

Period TRP - Triple Room Double Room - shared bed Twin Room - separate beds SGL - Single Room
2026-04-01 2026-06-20 €490 €600 €600 €790
2026-06-21 2026-07-13 €480 €580 €580 €770
2026-07-14 2026-07-27 €490 €600 €600 €790
2026-07-28 2026-08-24 €480 €580 €580 €770
2026-08-25 2026-10-17 €490 €600 €600 €790
2026-10-18 2026-10-31 €480 €580 €580 €770
Book your trip

8 days/ 7 nights hotel *** From €700 Book your trip

Period TRP - Triple Room Double Room - shared bed Twin Room - separate beds SGL - Single Room
2026-04-01 2026-06-20 €720 €870 €870 €1,180
2026-06-21 2026-07-13 €700 €840 €840 €1,150
2026-07-14 2026-07-27 €720 €870 €870 €1,180
2026-07-28 2026-08-24 €700 €840 €840 €1,150
2026-08-25 2026-10-17 €720 €870 €870 €1,180
2026-10-18 2026-10-31 €700 €840 €840 €1,150
Book your trip
Prices are per person and include
  • Accommodation 4 or 7 nights
  • Breakfast
  • 1st dinner on the first evening
  • Luggage transport for hotel changes
  • Detailed cycling maps
  • Mobile app with:
    • Digital maps
    • Destination information
    • Practical information
    • Detailed cycling descriptions day by day
    • GPX files, for GPS maps on your mobile phone or GPS
  • 24 h emergency phone for urgent matters
Not included
  • Transport to/from the destination
  • Transfer to/from the airport
  • Local ‘City Tax,’ so called ‘Tassa di Soggiorno’ in San Gimignano and Volterra. The tax is paid on site and the cost varies, about 1-3 EUR per person per night.
  • Bike hire
* Single room rates
  • Single room rates apply when travelling in the company of others. If you are travelling on your own, in most cases there is an extra charge due to more expensive luggage transport. Please contact us for prices.
Optional extras
  • Bike hire: 5 days – 90 Euro, 8 days – 140 Euro. 21 geared hybrid bikes includes repair kit, map holder, bottle cage, odometer and bike bag (front or side bag). You can also rent a helmet for 10 Euro.
  • Electric bike – E-Bike: 5 days trip – 160 Euro, 8 days trip – 250 Euro.
  • Printed maps and tour descriptions, price 30 Euro, can be picked up at the reception of the first hotel.
  • Private transfer from Florence or Pisa airport can be booked. Contact us for price information.

Itinerary

5 days/ 4 nights

Day 1 Arrival in San Gimignano

Arrive at the hotel in San Gimignano. Breathe in the air, unwind and enjoy the village, the breathtaking views and the hotel where you will stay for the next 2 nights.

Day 2 Cycling around San Gimignano - 35 km (51 km)

Today’s ride takes you through vineyards towards Ulignano and the charming hilltop village of Certaldo, home to the famous Italian writer Boccaccio. After visiting Certaldo with its pottery-adorned square and stunning churches, you can choose between a shorter variant or a longer ride to Barberino and Tavernelle, in Chianti Classico.
35,3 km, +580 m (51 km, 970 m)

Day 3 Cycling from San Gimignano to Volterra – 36 km

Today you will leave San Gimignano and cycle towards the ancient Etruscan city of Volterra. Through a landscape of wheat fields, olive groves and villas, you then reach the mighty mountain, on top of which Volterra is located. A fairly steep climb up the mountain and then you arrive at your cosy hotel.
35,9 km, +922 m / -649 m

Day 4 Cycling around Volterra & Montecatini Valle di Cecina – 38 km

After an exhilarating descent into the valley, you’ll cycle through the beautiful Val d’Era and over the ‘Strade bianches’, typical Tuscan white roads. The route winds through a landscape of remote farms and villas, and hills covered with vineyards and olive groves. Glorious views of endlessly undulating terrain follow the rest of the day’s cycling.
38 km, +/- 840 m

Day 5 Departure day

We at EverTrek hope you have had a great trip!
We hope to see you again.

8 days/ 7 nights

Day 1 Arrival in San Gimignano

Arrive at the hotel in San Gimignano. Breathe in the air, unwind and enjoy the village, the breathtaking views and the hotel where you will stay for the next 4 nights.

Day 2 Cycling around San Gimignano - 35 km (51 km)

Today’s ride takes you through vineyards towards Ulignano and the charming hilltop village of Certaldo, home to the famous Italian writer Boccaccio. After visiting Certaldo with its pottery-adorned square and stunning churches, you can choose between a shorter variant or a longer ride to Barberino and Tavernelle, in Chianti Classico.
35,3 km, +580 m (60 km, +/- 970 m)

Day 3 Cycling around Poggio del Comune – 36,5 km

This day offers a lovely walk around Poggio del Comune, the highest hill in the neighbourhood. Take the opportunity to buy a panino from the local bar in Castel San Gimignano, before continuing the tour. The cycle continues through a nature reserve with woods and pastures before returning to San Gimignano, where you can stop for an ice cream in the piazza.
36,5 km, +/-826m

Day 4 Cycling around Colle Val d’Elsa, Monteriggioni, Lilliano, Chianti – 65 km (40 km)

Today you can choose between two different tours, one 40 km and one 54 km. The day starts with us driving you to Colle Val d’Elsa. From there you cycle along the rolling hills of Val d’Elsa, to the fortified medieval village of Monteriggioni. Continue up, passing large vineyards, either towards Lilliano or straight up to Castellina in Chianti, where the views are magical. The day’s cycling ends at Colle Val d’Elsa, where we drive you back to San Gimignano. 40 km, +/- 640 m

Day 5 Cycling from San Gimignano to Volterra – 36 km

Today you will leave San Gimignano and cycle towards the ancient Etruscan city of Volterra. Through a landscape of wheat fields, olive groves and villas, you then reach the mighty mountain, on top of which Volterra is located. A fairly steep climb up the mountain and then you arrive at your cosy hotel.
35,9 km, +922 m / -649 m

Day 6 Cycling around Volterra & Montecatini Valle di Cecina – 38 km

After an exhilarating descent into the valley, you’ll cycle through the beautiful Val d’Era and over the ‘Strade bianches’, typical Tuscan white roads. The route winds through a landscape of remote farms and villas, and hills covered with vineyards and olive groves. Glorious views of endlessly undulating terrain follow the rest of the day’s cycling.
38 km, +/- 840 m

Day 7 Cycling from Volterra & Cozzanao - 37 km

Today’s tour is relatively easy and offers beautiful views of the surrounding Volterra. Erosion caused by rainwater has sculpted the landscape with cracks and ravines in majestic beauty. Once you have descended Volterra, you continue on smaller paths, and then return back towards Volterra on the beautiful ‘Strada del Cornocchio’.
37 km, +/- 920 m

Day 8 Departure day

We at EverTrek hope you have had a great trip!
We hope to see you again.

Accommodations

During this trip you will stay in 3-star hotels including breakfast. 1 three-course dinner (excluding drinks) is included on the day of arrival.

8 days/ 7 nights

NightPlaceAccommodation
Night 1San GimignanoHotel ***
Night 2San GimignanoHotel ***
Night 3San GimignanoHotel ***
Night 4San GimignanoHotel ***
Night 5VolterraHotel ***
Night 6VolterraHotel ***
Night 7 VolterraHotel ***

5 days/ 4 nights

NightPlaceAccommodation
Night 1San GimignanoHotel ***
Night 2San GimignanoHotel ***
Night 3VolterraHotel ***
Night 4VolterraHotel ***

Route map

Getting to the destination

Plane

The nearest airports to fly to are Pisa (PSA) and Florence (FLR).

Transfers

Private transfers from Pisa or Florence can be booked. Please contact us for prices.

Local transports

You can travel by train and bus to San Gimignano via Poggibonsi or from Volterra. For more information, see Trenitalia.

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