From Florence to Siena, Pathways of Tuscany

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From Florence to Siena, Pathways of Tuscany

Tour Highlights

Pathways of Tuscany from Florence to Siena. A great journey that connects two centers of ancient origins that have marked the history and Italian art.

From the center of Florence in the center of Siena, passing through the most significant places of Chianti and Siena countryside. This area is covered by vineyards and abandoned villages that rise out of the hills surrounded by cypresses. They are places that have always fascinated travellers from all over the world. It is not surprising to learn that this is the area of Italy with the highest percentage of English-speaking and Teutonic residents.

Among the rolling hills and valleys, the scenery never ceases to amaze, thanks in part to the lack of difficulty of the course that always allows a lively attention to and observation of the places met along the way.

We will cross woods, valleys and small villages, some of which are today famous for the production of Chianti Classico, in an old-style journey that will amaze every corner, enriched by the kitchen and Tuscan wines, which need no introduction, and that will liven up our evenings rewarded us by fatigue of the path.  Follow us on Facebook!

Tour Itinerary

  • Title

    Arrival in Florence airport and transfer to  hotel. Check in and, according to the arrival time,  brief exploration of this wonderful city. Introductory talk and explanation of trip. Dinner at restaurant. Overnight hotel.


    Breakfast  at hotel. The first steps will take us to a wonderful views of Florence from the height of the Florence hills; on the way, we will stop to visit the Certosa del Galluzzo, magnificent Church built in the 1341 and held by the cistercencians monks; then we will slowly head toward the hills of Impruneta, famous hometown of the “cotto”, the red tile brick used for pavement. We will end our first day in Piazza Buondelmonti, right in front of the Basilica di Santa Maria. Pic nic lunch. Dinner and overnight hotel.

    14.5kms, total ascent 300m, descent 140m,  5.30h


    Breakfast  at hotel. Left the magnificent and rich Impruneta we head to the rolling hills of the world famous Chianti, in a landscape where cypress tree sign the border of vineyards and oak woods, until we reach the small village of Greve. Along the way, jewels of the Romanic art such as the church of Santo Stefano a Campoli dated back to 903, the towered Badia Vallombrosana di Passignano built in 1049 and the hamlet of Montefioralle, dominated by the ancient church of Santo Stefano. Pic nic lunch. Dinner free. Overnight hotel.

    18.5kms, total ascent 420m, descent 460m, 7h



    Breakfast hotel. Today we will walk along a landscape slightly different from the vineyards that made Chianti famous worldwide; we will walk along the wide edge of the hills, along meadows and abandoned churches, abbeys and ruins of the roman civilization; we will have our lunch at the foot of the wonderful ruined abbey of Monte Domini; then, keeping our walk, suddenly from the wood will appear the splendid Medieval town of Volpaia, before heading to the tranquil village of Radda. Pic nic lunch. Dinner at restaurant. Overnight hotel.

    17.5kms, total ascent 730m, descent 600m, 6.30h


    Breakfast at hotel. We are still in the Chianti region, but the landscape seems to be very different. Once we leave the weel cultivated area, we reach the medieval hamlet of Vagliagli walking across wooded and solitary environments. The nowadays look dates back to the 1860 even if the origin are much more ancient, dating back to the XIth Century A.D.
    Pic nic lunch. Dinner at restaurant. Overnight in a “agriturismo” (farmhouse).

    10kms, total ascent 200m, descent 200m, 3.30h


    Breakfast at hotel. Leaving the small medieval hamlet of Vagliagli we follow the white tracks that snake their way through fields and forests to the ancient, well renowned town of Siena, founded by the Etruscans in the V century BC. and today worldwide famous for the Palio, the horserace, and for its spectacular medieval appearance. To arrive in Siena sign the end of our journey trough some of the best landscape and places of Tuscany.
    Dinner at restaurant. Overnight hotel.

    16kms, total ascent 520m, descent 610m, 5h


    Breakfast at hotel. Free day for visiting Siena (including inside visit of Duomo) and shopping.
    Dinner at restaurant. Overnight hotel.



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  • Visits to Florence, Siena, Chianti hills
  • Walking through vineyards and rolling hills
  • Visits to Abbeys and ruined churches


  • Traditional fresh pasta: Pici, Fiorentine, Sagnarelli, Testaròli
  • Wines and liqueurs: Chianti, Vermentino, Vernaccia di San Gemignano, Alkermes, Grappa di Chianti Classico
  • Olive oil, salame di cinta senese, zampogne chiantigiano, marzolino del chianti