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Tuscany: San Gimignano & Chianti
Tuscany: San Gimignano & Chianti
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Duration :
8 days
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Mar Apr May Jun Jul Aug Sep Oct
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price from € 664
Tuscany: San Gimignano & Chianti
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Tuscany: San Gimignano & Chianti


Bike Tour: Tuscany: San Gimignano & Chianti - 8 days

San Gimignano is a treasure on the hill and jewel of Tuscany, wonderful for cycling and exploring. With its thirteen outstanding medieval towers, it's clear why the town is on the UNESCO world heritage list. You will ride over clouds of sunflower fields under the Tuscan sun along cypress lined country roads and through olive groves and vineyards which produce some of the world's finest olive oil and wine, which you shall savor the flavor of. 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.

Day 1: Arrival in San Gimignano
Day 2: Vineyards of Ulignano, Certaldo Alto & Barberino (47.3 km, 66.7 km)
Day 3: Ride around the Poggio del Comune (39.3 km)
Day 4: Colle Val d'Elsa, Monteriggioni & Lilliano, extension to Castellina (40 km)
Day 5: Free day to relax and go sight seeing
Day 6: Ride from Volterra to San Gimignano (43.5 km)
Day 7: Transfer to Casole d'Elsa ride back to San Gimignano (28 km)
Day 8: Arrivederci San Gimignano!

Day 1:    Arrival 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 2:    Vineyards of Ulignano, Certaldo Alto & Barberino (47.3 km, 66.7 km)

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 across the Elsa and Pesa valleys.

Challenge: 4.5/5 hours, 47.3/66.7 km, 1070/1500m ascent, 985/1500m descent


Day 3:    Ride around the Poggio del Comune (39.3 km)

With this trip you will become familiar with the area as you make a full circle around the Poggio del Comune hill. From San Donato you go towards Castel San Gimignano passing by an unexpected sight for this very agricultural area, it is a prison. In Castel San Gimignano there is a great little bar where you can buy very good panini (sandwiches), then on in the direction of Volterra. Once you leave the asphalt road you enter the nature reserve which is mostly woods and some cow pastures, something rare in Italy. Leaving the forest behind you, you reach San Gimignano and you cycle straight through the old town centre stopping for a refreshing drink.

Challenge: 3.5 hours, 39.3 km, 1000m ascent, 1000m descent


Day 4:    Colle Val d'Elsa, Monteriggioni & Lilliano, extension to Castellina (40 km)

Today you choose the ride which suits you best. Transfer to Colle Val d'Elsa and cycle through the gentle, 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.

Challenge: 3 hours, 40 km, 226m ascent, 106m descent, optional extention to Castellina: 12 km, 2 hours


Day 5:    Free day to relax and go sight seeing

On this rest day, 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 marveling at the magnificent palaces, churches and squares. Alternatively, visit the Duomo, the Ponte Vecchio Bridge, and experience the unforgettable Renaissance splendor of Florence.


Day 6:    Ride from Volterra to San Gimignano (43.5 km)

Transfer to the magical and mysterious Ancient Etruscan city of Volterra, where you can explore its alabaster artisanry shops, Roman theater, 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.

Challenge: 3.5 hours, 43.5 km, 882m ascent, 1127m descent


Day 7:    Transfer to Casole d'Elsa ride back to San Gimignano (28 km)

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

Challenge: 2.5 hours, 28 km, 532m ascent, 554m descent


Day 8:    Arrivederci San Gimignano!
The trip and our services end after breakfast, unless you have booked a transfer to the airport or other supplementary services.
Prices & dates

Starting dates:

Daily from March 22 till October 27.

Price pp
Single room, breakfast 2020-03-22 - 2020-04-03 719.02
2020-04-04 - 2020-05-02 720.00
2020-05-03 - 2020-06-24 719.02
2020-06-25 - 2020-08-31 720.00
2020-09-01 - 2020-10-26 719.02
Double room, breakfast 664.00
Rental bike
Hybrid 100.00
E-bike 195.00
Extra services
Bike helmet per piece 2.00

Wilier Carbonio Ultegra 22v


Whether you race or not, the GTR TEAM is aimed for the rider who needs a bike for multiple uses. Light and responsive for the racer, yet comfortable and versatile for those who enjoy cycling without stress.

  • Drivetrain: Ultegra
  • Wheelset: Shimano RS010
  • Frame: Carbon RACE monocoque 46TON
  • Fork: Carbon monocoque 46TON
  • Rear derailleur: Shimano Ultegra
  • Front derailleur: Shimano Ultegra
  • Shifters: Shimano Ultegra
  • Cassette: Shimano Ultegra, 11S 11/28T
  • Crankset: Shimano Ultegra, 50/34T 

Tandem Cannondale Touring

Most everything in life is better with a partner in crime. That’s no less true with Cannondale’s tandems. Get out and ride and take someone with you. You’ll love it.

  • Frame: MTB Tandem USA handmade
  • Fork: SI Fatty Ultrastrong Tandem 26"
  • Rear derailleur: Shimano XT
  • Shifters: Shimano Deore
  • Wheelset: SUN Rhyno lite / DH2-N35/DT Swiss 540
  • Cassette: Shimano Ultegra, 11S 11/28T

Touring Elettrica Winora

The Y420.X is the top model with the Yamaha electric motor. It has a software with 4 levels of assistance which ensure a battery usage from 50 km up to 130 km per charge.

  • Motor: Yamaha PW motor 250W, 36V
  • Battery pack: Yamaha battery, 36V, 400Wh, lithium ion
  • Display: Yamaha LCD multifunction display with operating element and pushing aid
  • Frame: 6061 aluminium hydro formed
  • Fork: Suntour NCX-D LO lockout, Suspension: steel spring / elastomer Travel: 63mm
  • Derailleur: Shimano Deore XT
  • Crankset: WinoraAlu 48/36 teeth
  • Cassette: 11-36 teeth
  • Brakes: Shimano Deore, aluminum lever, hydraulic disc brake, 180mm (front disc), 160mm (rear disc) 

Touring Cube

The Touring ONE has everything you need for fun, hassle-free cycling – no more no less. Enjoy the ride.

  • Frame: AluminiumSuperlite Trekking Comfort Double Butted
  • Rear Derailleur: Shimano RD-M360, 8-Speed
  • Cassette: Shimano CS-HG31, 11-34T
  • Front Derailleur: Shimano FD-TX800, Topswing, 31.8 mm
  • Brake System: Shimano BR-M315, Hydr. Disc Brake (160/160)
  • Weight: 16,16 kg
  • Wheels: CUBE SX20, 36H, Disc
Practical info

7 nights included

3/4 Star Hotels

Breakfast included, Halfboard optional

The possibility of renting our bikes

7-days a week service-hotline

Poggibonsi/San Gimignano Train station

Parking possibilities at the hotel

GPS-tracks available

Arrival info

Florence (FLR), Pisa (PSA) and Bologna (BLQ) Airports are served by major and low cost international flight carriers.

Arrival in San Gimignano

From any airport, reach Florence Santa Maria Novella train station by either train or bus.

From there, you can reach Poggibonsi by either bus or train. From Poggibonsi, take a direct bus to San Gimignano.

Check train timetables on www.trenitalia.com.

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