Chianti Ultra Trail - Run your Chianti dream!

Από 05 Απρ 2022

Choosing a trail race outside Greece is not something simple and is determined by many factors. For others it is the "glamor" of the race, for others the wild part of the route or the challenge of its difficulty and distance. There are of course races which are internationally renowned and are held in areas of enormous natural beauty, cultural and gastronomic value! One such race is the Chianti Ultra Trail which, although relatively new in the international calendar, has managed to emerge thanks to the stubbornness, work and vision of its people. Besides, it has a huge advantage that one cannot easily find in the world and is called… Tuscany!

The area

Tuscany does not need special recommendations. It is an area of ​​Italy that one should visit regardless of any racing "obligation". If of course this visit is combined with the participation in a very important international competition… even better! A region of central Italy with Florence as its capital, it is one of the most important tourist destinations in the world. A trademark of its incredible landscapes, its cultural heritage and of course … its wines!


No lover of good wine should miss the opportunity to travel to Tuscany. Especially in Chianti, the area of ​​the race, the temptations are endless. Wineries of incredible beauty and technological superiority cause you to taste their wine and admire through guided tours their vineyards and their facilities. We visited one of them, Dievole, which is one of the main sponsors of the race to taste some of his labels and left speechless from the incredibly organized unit and the endless cellars! But for this, keep your appetite for after the race!

At the wine cellars of Dievole

Waiting to be tasted!

Shops with incredible quality and quantity of local wine labels 

It is not only the size of the Radda in Chianti or the richness of its history that will fascinate you in this small town, but the evocative atmosphere within the stone walls, the quiet little squares and the fantastic views of the landscapes that characterize this area. Radda in Chianti, the epicenter of the race, is the "homeland" of the famous red wine labeled with the Chianti Classico Black Rooster seal, located in the center of the wider Chianti area where one can wander among thousands of hectares of vineyards and medieval villages like paintings in a fairy tale.

The Black Rooster at the entrance of Radda in Chianti, trademark of Chianti Classico wines

Peaceful alley road in Castellina di Chianti

At a very short distance from Chianti one may choose among numerous destinations. San Gimignano, a small medieval walled city known for its very tall tower houses, famous among others for its world-famous ice cream; Montalcino, the capital of another famous red wine, Brunello di Montalcino, or Pienza, which is one of the six UNESCO World Heritage Sites in Tuscany; Siena famous for its monuments, such as its Gothic cathedral, its museums, its medieval atmosphere, its beautiful sloping square, its cuisine and Palio, a horse race that takes place twice a year. Obviously we are not mentioning Florence which is less than an hour drive from Radda, because it is a chapter in itself and it is worth dedicating some days exclusively to experience it.

Panorama of Montalcino...

The wonderful Siena square

Mona Lisa after a bottle of Brunello!

The destinations are truly endless, each with its own beauty and history. And between them, real magic. What you have seen in photos is not montage. Vast colorful hills of ornate vineyards were constantly alternated with dense deciduous forests, enchanting the senses and the insatiable need for exploration.

The race

The reason for all the above of course was Chianti Ultra trail. We like good wine and food but sometimes … we even run! We chose to run the marathon race (42K, + 1400m) just to be able to have more time to explore the surrounding area. A wise decision for someone who is visiting Tuscany for the first time (like me) and does not have many days at his disposal. An easy and beautiful rolling hills route without technical parts, among huge vineyards, dense deciduous forests, villages and castles of the greater Chianti area.

Vineyards all the way!

It's been a long since I last enjoyed so much running in nature. We do not always have to run in wild mountains, cliffs and steep ravines. We need the tranquility of easy trails, runnable dirt roads, open landscapes. The dominant elements from the beginning to the end of the route, the incredibly lined vines, dry due to winter, were eagerly waiting for spring to take another color to the wonderful background of the painting that appeared in front of us at every kilometer of the race.

Talking to people who ran the longest races as well as to the technical director and soul of the race, Matteo Matteuzi, they told us that they were not so easy as the incline of some trails was high and there were several parts with technical "single track" trails.

The race options left no one complaining due to the fact that this year, for the first time, a 100 km race was added, the route of which passed through a series of medieval castles in the Chianti area. The “hard” ultra trailer can collect "easy" qualifying points for other races, but also its companion can walk or run between vineyards and wineries. Details of the races from which one could choose:

  • 100Κ | +4200m
  • 73Κ | +2800m
  • 42Κ | +1400m
  • 20Κ | +850μ
  • 15Κ Run & Nordic Trail
  • 8Κ Walk & Taste – non competitive

The scenery of the route, a real painting!

Along with us, ten runners from Greece ran in the below races:


  • Orfanidis Giorgos - 15:54:41
  • Galanopoulos Dimitris - 21:15:43
  • Xenaki Maria - Stella – DNF


  • Troupis Dimitris - 5:08:09
  • Apostolidis Giorgos - 5:20:10
  • Tsogkarakis Takis - 5:21:38
  • Apostolidou Aikaterini - 6:30:54


  • Toskas Miltiadis - 2:13:39
  • Toskas Ilias - 2:13:39


  • Tsigerliotis Giorgos - 2:04:15

Marco de Gasperi, winner of 42K race

In the 42km race we had the joy and honor to run together with 2 legends of sky running, Marco De Gasperi and Elisa Desco! Marco invited us to visit his own race, the Valtelina Wine Trail, in the Lombardy area in November. An invitation that of course we gladly accepted and as you understand after that we will be ready to open a new business: Trail Running Red Wine Tasting!

See all the results at

Easy running

The organization in collaboration with Advendure offered an attractive participation package that included in addition to accommodation and participation in a race of one's choice many other goodies:

  • Wine tasting and guided tour of the Castello di Albola winery
  • After race dinner at the Chianti Classico House Wine Museum
  • Chianti Ultra Wine full package. Package that includes, among others
    • Guided tours and wine tasting in famous wineries of the area
    • Guided tour of the Chianti Classico Wine Museum
    • Buffet dinner at Casa Chianti Classico

Approaching Castello di Vertine, one of the castles along the route of the 100K race

The event was of a high level, despite the fact that it had to handle so many competitive and non-competitive events! More than 1500 runners from 40 countries took part in the 2 days of the races! The vision of the people of the Chianti Ultra Trail does not stop here. Discussing with Matteo, he told us that "We want to be a race - point of reference both in Italy and worldwide. "Our 'weapon' may be Tuscany and Chianti, but organizationally we have made leaps ahead of 2018, when the race was organized for the first time, so we have nothing to envy from more famous races". The latter we found out that is absolutely true! In the end he stated that "Next goal, to enter the UTMB World Series race by getting the stamp 'by UTMB'". The people who 'run' the race are born in Tuscany and want to project its true image. Matteo repeated the words he had written four years earlier in our first contact. "Many foreign tourism companies operate in Tuscany, projecting a wrong side of it. We want to extend the tourist season and highlight the most alternative, classic, old Tuscany… »

Enjoying a bottle of red wine while waiting for the racers of the 100K 

‘Run your Chianti dream’ which is the motto of the event takes shape in the historic and picturesque village of Radda in Chianti. Tuscany and the region of Chianti are among the areas that are definitely worth visiting and by participating in one of the races of its organization, one is given the opportunity to enjoy routes with many emotions, but also explore history, the culture, the gastronomy and the excellent wines of the region.

The next time you see any information about Chianti Ultra Trail in Advendure, do not skip it. You will lose! Viva Chianti!

View this photo set on Flickr

Τάκης Τσογκαράκης

Η αγάπη του για το βουνό ξεκινάει πολλά χρόνια πίσω με τις πρώτες αναβάσεις στην αγαπημένη του Πάρνηθα και μετέπειτα με την σχολή Ορειβασίας του ΕΟΣ Αχαρνών. Το 2007 έτρεξε τον πρώτο του αγώνα ορεινού τρεξίματος και από τότε ονειρεύεται "όλο και ψηλότερα, όλο και μακρύτερα". Ελπίζει να το κάνει για πολλά χρόνια ακόμα...



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