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Tuscany: Siena, Chianti, Florence 8-day Self-guided Cycling Tour Level 3

  • 8days
  • Italy

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Cycling Tours Europe

Siena, Chianti, Florence Self-guided Cycling Tour 

The landscape of Tuscany is one of the most beautiful and evocative in Europe, with rolling hills laced with verdant vineyards and cypress trees lining the roads. You’ll pedal from one incredible view to the next, getting to know the lands of many great artists of the past, such as Leonardo da Vinci and Michelangelo. You’ll have the chance to visit the superb medieval town of Siena, as well as to admire Florence, the cradle of Renaissance. Last but not least, in this tour you’ll discover also picturesque villages where you’ll be tempted by the excellent Tuscan cuisine.

Tour character: Level 3

Heavy, with sloping landscapes dotted with steeper inclines, but not overwhelmingly so. The daily distance is about 40km. Though the daily routes are not too long, they can be strenuous, so we do recommend being in reasonably food physical condition for this tour. 

Included in the Tour:

  • 7 nights hotel accommodation in 3*
  • Breakfast buffet
  • Luggage transportation
  • Travel Guide + Roadbook + Maps
  • 7-days Hotline service

Not Included in the Tour:

  • Local taxes (approx 10-15 EUR)


  • Saturdays Only

If you would like to hire a bike (85 EUR) or e-bike (195 EUR) or helmet (15 EUR), please contact our office when booking: [email protected]

Slow Tours offers a number of other Cycling Tours in Europe

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  • Day 1


    Individual arrival at hotel

  • Day 2

    Siena – Radda in Chianti 45km

    From Siena head north towards the beautiful village of Radda in Chianti. The remains of its ancient walls show the significance that this town had in the competition between Florence and Siena.

  • Day 3

    Radda in Chianti – Greve 40km

    The route brings you to Greve over the rounded hills with beautiful views.

  • Day 4

    Greve – Florence 40km

    You will cycle to Florence, capital of Tuscany, and admire the world famous artworks of Leonardo and Michelangelo.

  • Day 5

    Florence – Tavarnelle 40km

    The village of Tavarnelle Val di Pesa has Roman origins. It is named after the ancient taverns offering accommodation and refreshment located along the road which linked Florence to Siena and thence to Rome.

  • Day 6

    Tavarnelle – Colle Val d’Elsa 45km

    From Tavarnelle you cycle to Colle Val d’Elsa, which lies in the heart of Tuscany, in a strategically favourable position near the towns of Siena and Florence. It is situated on the via Francigena that connects Rome with the North. On the way you pass Certaldo, whose upper part has remained as it was in the Middle Ages. Further on you come across San Gimignano, which rises on a hill dominating the Val d’Elsa with its towers.

  • Day 7

    Colle Val d’Elsa – Siena 40km

    From Colle Val d’Elsa you will cycle to the beautiful town of Siena, which is not only one of the most fascinating towns in Tuscany but is also in a particularly beautiful position, with lovely surroundings.

  • Day 8


    Departure after breakfast

    Due to organisational reasons, weather conditions or provisions issued by local authorities, the itinerary may be subject to some changes before and/or during the holiday. Along the way you may find temporary deviations (for example road works) which cannot be foreseen

  • Day 9

    in this case each rider can decide autonomously how to deal with these stretches.

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Please enquire for dates

Car rental in Italy

If you would like to drive yourself before or after your tour, ask us for a quote on any brand new Renault, Peugeot or Citroen vehicle for driving in Europe.

Pick up your vehicle from most capital cities in Europe and return it to your drop off destination. Top insurance cover. Email [email protected] for a competitive quote

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