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San Gimignano Hike

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Trip at a Glance

  • Company

    Local Florence

  • Locations

    San Gimignano, Tuscany, Italy

  • Activities

    Adventure, Hiking Trekking

  • Price
    €695 EUR per trip
  • Duration

    10 hours

  • Avg Distance

    Max 20 km

  • Departure Day(s) and Time(s)

    On demand

  • Starting Location

    Florence, Siena, port of La Spezia

  • Price Includes

    Private transfer and guide included in price; museum tickets, food and wine extra.


  • Private tour or small group (max 15 hikers) - Private transfer by minivan or minibus with professional driver- Brilliant guide
  • Sightseeing itinerary for non-hikers: Tuscan Medieval villages, including San Gimignano and Monteriggioni
  • San Gimignano town - Medieval Manhattan; Castelvecchio ghost village abandoned during the plague of 1348 Picturesque hamlets
  • Best gelato in Tuscany! Vernaccia white wine Visit of local wine producers and wine tasting on demand
  • Varied landscape: Tuscan forest, vine and olive groves, hilly terrain Frescos by Benozzo Gozzoli, Domenico Ghirlandaio and many others Torture museum




Trip Info

This is a trip to the heart of Tuscany from Florence, Siena, Pisa or the ports of La Spezia and Livorno.

Difficulty: full day, hilly, varied terrain (forest trail, vineyards, gravel roads, short stretch on asphalt)
Length: ca 20 km or shorter depending on our wishes
Duration: 10 hours, breaks and transfer included
To bring: waterproof non-slippery hiking boots or sneakers, rain gear, packed lunch, water enough for the day.

We begin our hike at the brim of a thick Tuscan forest, whose heart conceals ruins of a medieval town abandoned during the plague; we explore its stone walls, towers and dwellings, stroll through the main street and discover a church with remains of original frescos. Having learned what happened here in 1348, we follow in the footsteps of village dwellers through vineyards and olive groves towards San Gimignano, a town known for its unique skyline dotted with Medieval stone towers. Fourteen of the original 72 towers are still standing today. San Gimignano is a perfectly preserved town from the IX-XXII centuries, whose churches boast frescos by Domenico Ghirlandaio, Benozzo Gozzoli and many other artists. It thrived on the major medieval trade and pilgrimage route, the via Francigena, which led from France to Rome, to Brindisi and the Holy Land. We will discover San Gimignano in late afternoon, as tourist crowds begin to leave, and will enjoy one of the most spectacular gelato of Tuscany in its main square.

The hiking itinerary will be adjusted to weather.

Your adventure awaits!

Local Florence

Benvenuti alla Dolce Vita! Brilliant licensed art and history guide, PhD, with a decade guide experience in Florence, Cinque Terre, Tuscany, and Sicily - all the regions connected in culture and history, a combination of sea and land - I enjoy sharing my love for them with others. I'll plan your itinerary, arrange skip-the-line museum tickets, a minivan with private driver and a boat ride, show you the hidden beauties of Florence, take you to my favorite local restaurant and on the most panoramic hike, talk art, history, Italian life and politics, and can even cook for you a Sicilian meal. Pleasure in life must be holistic - and Italy is an ideal country for this. My tours of Florence are outstanding - my experiences of Tuscany and the Cinque Terre sublime - and my Sicily is breathtaking. I am driven by passion for local Italy, my home over the past 17 years. Here, I studied in Rome and Florence, worked in Parma, the Cinque Terre and Tuscany, and of course fell in love - in Sicily. It's this pleasure, careful research and local knowledge that I'm happy to share on tour. What to expect from my tours? Expect more and better! A watermelon popping out from my backpack in the middle of a spectacular hike, a memorable love abduction story from a Medieval monastery, a delicious seafood meal, a marble quarry worthy of Michelangelo, and a wine tasting in the villa of Mona Lisa. Guiding is one of the most creative activities, where each guest is a chance to discover the place anew. I enjoy creating your custom itinerary, preparing each detail, adding local insight, taking you to places as varied as a trail above Portofino, a Medici villa, the Uffizi, Vasari corridor or a prehistoric village in Sicily. And in winter I indulge in another creative and passionate pleasure: writing, now working on my second book. For an even more unique and local experience, please ask about my vacation homes for rent: a real Medieval tower in the heart of Florence, a panoramic home with infinity swimming pool in Taormina and a beach home in Sicily. Welcome to the Dolce Vita!


  1. 5 out of 5


    A not-to-miss hike of most beautiful views in Tuscany with a knowledgeable and experienced guide. Having your lunch while enjoying the views of the vineyards, stopping for a glass of wine tasting… but do not underestimate that it is also a good workout considering all those steep paths. All in all, a great day spent!

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