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8-day Self-guided Art & Architecture Cycling Tour in Tuscany

  • 8days
  • Italy

Single bed room:
Twin bed room:
Double bed room:
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Cycling Tours Europe

Tuscany Cycling Tour of Art and Architecture

Do you want to experience the romantically wonderful Tuscany? Well, here's your chance! Get ready to discover one of the most famous Italian regions. This area is famous for its wines, its cities rich in art and the warm welcome you get from its inhabitants: the best combination of emotions, scents and traditions perfectly combined and ready to be discovered by bike. From Piazza della Signoria to Piazza dei Miracoli passing Siena, San Gimignano, Volterra.

After a short visit of Florence, the first part of the tour brings you into the heart of  Tuscany, along the "road of wines", production area  of the famous Chianti, where you will be able to have a break during the stage and have a tasting in the numerous local wine cellars.

After Siena, the tour continues towards Colle Val d' Elsa, the "Bohemia of Italy", then San Gimignano, famous for its towers and Volterra, the city of the alabaster. Finally you arrive in Pisa, the city of the leaning Tower. 

Tour character: Level 3

Terrain characteristics: hilly land, with some sweet climbs and descents (last stage mostly in descent). Global height of the tour: between 100 and 550 mt a.s.l., average duration of the stages: from 27 to 54 km per day. Roads: 70% asphalted, few country roads not asphalted

Included in the Cycling Tour: 

  • accommodation in 3* hotels double en-suite rooms (4* available on request for supplementary charge)
  • 7 breakfasts
  • luggage transport
  • App with tour map and itinerary (With points of interest, services and GPS position. The App provides GPS tracks that can also be used offline).
  • One handlebar mobile holder

Not included in the tour:

  • journey to/from Italy, meals (except for breakfasts)
  • drinks
  • bike rental
  • transfer by train Pontedera-Pisa
  • entrance fees
  • insurance
  • tourist taxes (15 to 18€ depending on the category)
  • everything extra and anything not specified as “Included”
  • paper road book is available with supplement of 15€ (to be booked in advance)

Rental bikes:

  • Suppl. bike rental - EUR90
  • Suppl. E-bike rental - EUR200
  • Suppl. helmet rental - EUR15

Please book your bikes when you book the tour: [email protected]

General information:

  • Briefing: at 09.00 am on 2nd day clients get route book, practical information on the tour and bikes (if rented)
  • Return transfer: private transfer from Pisa to Florence is possible on request. Pisa to Florence centre or airport costs € 70,00 per pax (min 2 pax, own bikes included) Transfer must be required with the reservation and paid in advance
  • Minimum 2 people
  • Departures on Saturdays April to October

Slow Tours offers a number of other Cycling Tours in Europe

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  • Day 1


    Individual arrival in Florence, jewel of the medieval and Renaissance art. Overnight in Florence.

  • Day 2

    Florence – Greve in Chianti 44 km

    Today your adventure leads you through the heart of the Tuscany which is rich in art, scents and traditions. Departure by bike from Florence to Impruneta, city of the terracotta art, where you can visit ancient villas and the Basilica. After approximately 10 km you will reach Mercatale, a small town surrounded by Chianti hills, you will be able to taste three wine varieties and other products at the wine cellar of Palagio castle. Overnight in Greve in Chianti (Standard cat.) / Greve countryside (Deluxe cat.).

  • Day 3

    Greve in Chianti – Radda in Chianti (31 km)

    Today you will discover one of the best known Tuscany areas: "the road of wines". Departure from Greve in Chianti with its main public square irregular triangle shaped. You continue across the fortified medieval village of Montefioralle dominating Greve, and then, after the splendid villages of Panzano, you reach Radda in Chianti. The Classic Chianti, situated between Florence and Siena, appears like a hilly landscape varied and colourful. Here the famous wine was born during the Etruscan age. In Radda in Chianti it is possible to admire the Pretorio Palace and the remain of its walls and of the medieval towers. Overnight in Radda in Chianti countryside (standard cat.) / Radda village (Deluxe cat.).

  • Day 4

    Radda in Chianti - Siena (41 km)

    Today the tour moves from Radda in Chianti until Siena. The first stop will be at the Meleto’s Castle, an ancient fortification transformed into a magnificent typical villa of the Tuscan countryside Cycling over the fortified village of Castagnoli you’ll continue until the famous Castle of Brolio which is rich in suggestions coming from ancient times. Here you can have a tasting in the Ricasoli wine cellar. In the afternoon you’ll reach Siena, famous for its Palio and laying down on a cross road of hills creating a colourful scenery. While visiting the city you will meet some of the most remarkable monuments in Italy: Piazza del Campo and the Public Palace, Buonsignori Palace with the National Pinacoteca (where you can admire pictures of Duccio, Lorenzetti, S. Martini etc), the Cathedral built from the XII sec and covered from white and dark-green marbles. (And also) the Piccolomini Library, the Baptistry and the Museum of the Metropolitan Work). Overnight in Siena.

  • Day 5

    Siena – Colle Val d’Elsa (27 km)

    Leaving from Siena and cycling through sweet small hills you’ll cross some little villages as Sovicille. Before reaching Abbadia a Isola, the ancient Francigena Way flanks the Mount Maggio. Along the way you can have a sight of Monteriggioni’s castle, whose "cerchia tonda", approximately 570 m its diameter, was already noticed by Dante. Then you’ll arrive at Abbadia a “Isola”,(which means “Island”) whose name belongs to its geographical position in the past: the town was an important place of rest along the Francigena Way and it was famous also for its church, similar to the entrance of the church of the Holy Sepulchre in Jerusalem. You’ll continue then until Colle Val d' Elsa, the so called "Italy’s Boemia". Colle val d’Elsa is an ancient Etruscan citizen allied since 1100 to Florence against Siena. It has seen a great development from 1400 when the most flourishing fabrication of the glass began, taking advantage from the engine force of river Elsa. Possible visit to an handicraft laboratory of crystal manufacture. Overnight in Colle Val d’Elsa.

  • Day 6

    Colle Val d’Elsa - Volterra (46 km)

    From Colle val d’Elsa you’ll cycle to San Gimignano. The town, up on a hill, dominates the Val d' Elsa: it is a splendid example of well-preserved Medieval city. It's fame is mostly due to the numerous towers still adorning it. For its particularity it has been declared universal patrimony from the Unesco. The village, locked up in its walls, consists of two aces that are intersected to cross: from east to the long west the axis that goes from the Hill of the Tower to the Hill of Montestaffoli, from north to long south the axis that goes from Saint Giovanni Door to Saint Matteo Door where also the Francigena Way passes through. In the late afternoon you’ll arrive in Volterra, a city with about 3000 years of history. Volterra is well known for its laboratories where alabaster is worked and you can visit the Acropoli, the roman theatre and the walls around the historical centre. Overnight in Volterra.

  • Day 7

    Volterra - Pisa (54 km)

    Departure from Volterra to Ghizzano, the village encircled from vineyards. After approximately 2 hours cycling you’ll reach Calcinaia, and after some kilometres more you arrive in Pontedera. Train transfer to Pisa, the city of the hanging Tower. Overnight in Pisa.

  • Day 8


    After breakfast the tour ends. Free time to visit the city: the Cathedral, the Baptistery and the famous hanging Tower.

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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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