Urban Trekking Grand Tour

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Terms and Conditions

  • WHEN From Monday to Friday
  • STARTS8:30 am
  • DURATION 12 h approx
  • LIVE GUIDE English, Italian
  • CONFIRMATION within 48h
  • PRIVATE GROUPMax 5 people

Wear your most comfortable shoes and let your qualified local guide lead you to a full day urban trekking , in the heart of Tuscany, starting from Florence! After a walking tour of Florence you will experience the journey by local transport to the charming village of Certaldo. Still by local transport we will reach Siena where the historical city centre, Piazza del Campo and the Duomo awaits us. 



  • Qualified local guide
  • Train tickets reservation
  • Funicular railway ticket
  • Siena Duomo entrance ticket
You will meet your local guide in Piazza Duomo in Florence, this is where your incredible urban trekking will start. Heading towards the train station your guide will recount anecdotes, legends and mysteries of this fascinating city.  
At the Santa Maria Novella train station you will take a regional train direction Certaldo passing through countryside and villages. 
Certaldo is a walled town also known as Castello (castle), this medieval town in the heart  of Tuscany is the hometown of Boccaccio. Without doubt a must for lovers of historical settlements
First stop in the village is in one of the typical characteristic bars where you can enjoy a delicious cornetto (typical Italian pastry) and a cappuccino. A funicular railway will then take you up to the medieval town and to Palazzo Pretorio, once a home of the Alberti counts. 
The views surrounding the medieval walls and windy alleys are outstanding. After you have visited the town there will be time to indulge in a traditional, local lunch accompanied by an exceptional glass of local wine.
Next stop of your urban trekking is Siena, home of the Palio, once again travelling with the regional train. 
Along with your guide you will visit the Cathedral of Santa Maria Assunta (Siena Duomo), a remarkable example of Romananesque Gothic architecture, undoubtedly one of the most precious treasures of the city of Siena.
Walking along the alleys and roads you can see and feel the medieval characteristics, symbols of times gone by. Eventually you will arrive at the landmark Piazza Del Campo, the heart of this historical city and venue for the famous Palio.
The regional train will take you back to Florence.





A hight amount of walking is involved

Comfortable shoes and clothing recommended

Not wheelchair accessible: Due to uneven surfaces at the sites visited may be difficult for those with walking disabilities or using a wheelchair


Children under the age of 10 not admitted
In any case they must be used to walk


For a full refund, cancel at least 3 working days in advance of the start date of the experience.


8:30 amMeeting point Piazza Duomo

10:10 amTrain to Certaldo

11:00 am Arrival in Certaldo, stop at the bar

11:30 amFunicolar railway to the borgo

12:30 pm Free time for lunch or wine tasting

2:03 pm Train to Siena

2:38 pm Arrival in Siena, stop at the bar for a break

5:41 pm Train to Florence

7:32Back to Florence train station

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