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This trip is the result of over 20 years of experience riding in Tuscany and will give you the opportunity to ride with Danilo Di Luca and its bikes.

Explore the quintessential Tuscany moving from South to North on some of its most iconic roads, challenge yourself on the training grounds of cycling legends seeing beautiful scenery and participating in its lively cycling scene with an insider’s perspective.

Ride through UNESCO World heritage site Orcia Valley and stay 2 nights in the magnificent Valley.

Climb Mount Amiata, the tallest mountain in southern Tuscany. Ride the unforgettable “Crete Senesi” to visit the magnificent medieval city of Siena. Pedal through the Chianti region and its charming forests and fortified villages.



This cycling trip is a joyous feast for the legs and for the eyes. Join to Danilo Di Luca.. finally time to ride with him is arrive !

About Danilo Di Luca: 54 professional race won.

A jorney that began at the age of 8.

It is also thanks to the immense teamwork and the people who have always accompanied me on this adventure that I managed to reach important milestones such as the Giro d'Italia in 2007, the Liegi Bastogne Liegi, the Giro di Lombardia, the Amstel Gold Race and the Flèche Wallonne.


This bike tour explores the magic of the Tuscan region.

We will ride in 2 different and wonderful areas: Val d’Orcia and Chianti Classico. Rolling hills, ancient villages, vineyards and towers: the Val d'Orcia is a very special land, a corner of the Siena countryside where nature and man's work have come together over the centuries to create a panorama unique in the world. A Unesco World Heritage Site.

Crossed by the Orcia river, this splendid area of southern Tuscany extends along the provinces of Siena and Grosseto. Chianti is the wine region of Tuscany.

It extends between the provinces of Florence and Siena, covers the entire area between the two cities and extends east towards the Valdarno and west of the Val d'Elsa.

Chianti offers a unique landscape, with green, rolling hills covered by vast fields of vineyards and olive groves.

Chianti is a priceless treasure for all travelers interested in discovering the food and wine culture of Tuscany.


On this trip, you will:

  • Ride some of the most distinctive, and scenic roads in Tuscany on mostly car-free country roads.
  • Explore the largely still agrarian culture and tradition of the Tuscanian farmer and the rich verdant countryside.
  • Relax in some of the most beautiful and relaxing accommodations. Taste the Brunello and Chianti Classico.
  • Sample the hearty cuisine from the region, from the elegant fine dining to the home-cooked meal.



16th June


We will transfer you to the first hotel, in the Val d’Orcia, an area so beautiful that UNESCO designated it a World Heritage Site and the movie Gladiator’s famous wheat field scene was filmed here.

After a fitting, we’ll take our high-end bikes on a warm-up loop ride to the town of Pienza, an architectural gem thanks to its namesake, Pope Pius II, who made it a pet project to turn his hometown into the ideal Renaissance city.

After a taste of some famous local Pecorino cheese, it’s time to complete the loop home to our hotel, and relax in its award-winning spa.


Ride : 50 - 60 km 1200 mt elevation gain
Visited : Pienza, Montalcino
Hotel : 5 stars accommodation in Val d’Orcia area
Meals : welcome lunch and dinner


17th June


Today an absolutely epic ride awaits you, as you set off today for Tuscany’s pre-eminent climb: Monte Amiata, a dormant volcano from the top of which you can see central Italy for hundreds of Kilometers.

Our first stop is the interesting Roman baths in Bagno Vignoni. The riding here is superb as it passes through the typical Tuscan scenery of the Val d’Orcia.

After the stop, the riding gets a bit more challenging as we ride up Monte Amiata on a regular but very long 20+ km climb. We will reach the clouds on the top at 1700 mt elevation.

Not too bad for the Apennines! Enjoy a well-earned, scenic lunch in the restaurant at the top before the long descent and the final climb back to our castle.

Tonight we’ll celebrate with a glass of Brunello di Montalcino in an intimate tasting at our friends’ local winery.


Ride : 100 km 1800 mt elevation
Visited : Monte Amiata, Sai Quirico, Castiglione
Hotel : 5 stars accommodation in Val d’Orcia area
Meals : B,L,D


18th June


Say goodbye to the Val d’Orcia as we ride through the mystic morning light that bathes the Romanesque Abbey of Sant’Antimo and towards Siena.

Spin through forests and pastures before the landscape opens up as we enter the magnificent Crete Senesi, an absolute classic must-do ride for anyone visiting Tuscany.

Crete Senesi are literally ‘Sienese clays’, and the distinctive gray coloration of the soil gives the barren landscape an appearance often described as lunar.

We will continue to cycle past Siena and into the region just beyond it, il Chianti, where the bare clays will give way to forest and vineyards and castles, and where the most famous wine is made.

Our hotel, a Relais & Chateaux property is located in the middle of its own extensive vineyards.

Rest your legs with a well-deserved massage, before we head out into the medieval city of Siena to explore and dine there tonight at one of our favourite local restaurants.


Ride : 75km 1300 mt elevation
Visited : Crete Senesi, Chianti Classico, Siena
Hotel : 5 stars accomodation in Chianti area
Meals : B, L, D


19th June


Today we will ride into the beautiful area of Chianti Classico, a word that conjures images of a well-known wine, revered around the world.

Nestled in the hills between Florence and Siena, Chianti is blanketed with oak forests where native Tuscans and wild boars alike search out portabella mushrooms and chestnuts each fall.

These lush woods open into deep valleys full of vineyards, castles, and noble estates. Almost car-free roads, lined with short stone walls and olive trees lead from charming town to charming town.

Our loop ride will follow much of the same loop the pros rode in the time trial on Stage 9 of the 2016 Giro d’Italia. In Gaiole or Radda there are some great places to stop for Lunch to taste “Pici cacio e pepe” at a local trattoria, and maybe to buy a “Chianti Classico” bike jersey as a keepsake.

Tonight we dine in the most exclusive and interesting Chianti winery and taste their precious vintages.


Ride : 60 – 100 – 125 km variable elevation
Visited : Castelnuovo Berardenga, Radda, Gaiole, Eroica route, Pianella
Hotel : 5 stars accomodation in Chianti area
Meals : B, L, D


20th June


Grab one last cappuccino on the terrace of the hotel or stroll through the streets of Chiantishire for some last few gifts, before we transfer you to Florence and your next destination.

Date: 16th - 20th June 2022
Accomodation: 5 stars hotel
Group size: Max 14 guests (3 guides)
Cost: Euro 3450 in double accomodation (Single supplement on request)


If you decide to buy the bike at the end of the tour Danilo

will give you 20% of discount!