Tuscan Colors Road Cycling Holiday

An 8 Day Road Cycling Holiday Through Tuscany.

Cycling Holidays in Tuscany

If you love road cycling there’s no better place to take your cycling holiday.  Quiet roads, smooth tarmac and famous climbs.  Our guided holiday takes away all the hard work of baggage transfers, cafe stops and preparing lunch and leaves you to just enjoy your cycling.  We’ll be with you all the way.

Tuscany or Toscana needs no introduction, it’s full of history and probably the best known and appreciated Italian region in the world.  The history, culture, art and food are interwoven and perfectly depicts the Italian people.

The Tuscan lands are crisscrossed by countless roads and paths that connect the inner areas of the coast to the Tyrrhenian Sea and the north of Europe to the city of Rome. Roads and paths like the Via Francigena are still used as the main routes for pilgrims and traders.

Our trip crosses the hills and valleys of Tuscany, often on unpaved roads, following the famous route of “Strade Bianche” (dirt roads) and the “Eroica” paths.  As many of you will be aware the Strade Bianche is part of the UCI professionals’ World Tour!

On our travels we’ll  enjoy the landscape of Siena, the Chianti area and also the Val d‘Orcia, a Unesco World Heritage site.  If this has got you interested and you’d like to know more take a look at the highlights of the trip below or contact us using this button:

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Val d’Elsa, a land with art, as they call it here.

Chianti, with its 13,000 hectares of vineyards.

Siena and his baggage of history.

Le Crete Senesi, whose hills covered by grain, show us an ancient geology.

The Val d’Orcia almost a coffer that preserves the beauty of country life.

The Amiata Mount, a green land of lumberjacks, miners and coal miners.

Tour Information

Price – € 2.200,00

Single Room Supplement – € 380,00

Accommodation – 3 / 4 stars Hotel

When – 27th April to 6th May • 23rd – 30th May •5th – 12th September • 26th September – 3rd October

Category – Road Cycling Holiday

Grade – C  (Read our Grades of difficulty)

Start/End – Casole d’Elsa / Casole d’Elsa

Suggested Airports Start/End – Pisa

Duration – 8 Days

Days Riding – 6 Days

Terrain – Hilly and Mountainous

Kind of Tour – Point to Point

Guided Tour – One cycling guide every 8 riders and another guide driving the support vehicle

Support Vehicle  We always have a van supporting the group.

What’s Included

  • 7 nights in 3 / 4 stars Hotels
  • All breakfasts, 3 pic-nic lunches, 2 lunches in restaurant, 3 dinners
  • Full tour service including 2/3 guides with deep knowledge of the area, skilled and equipped with any indispensable tools to ensure the safety of the group
  • Support Vehicle. Luggage transportation all along the tour and the scheduled stages. Bike mechanic assistance. Refreshments during the rides
  • All guides qualified in First Aid
  • Airport collections / drop-offs from local airport on scheduled arrival and departure days
  • Stretching and yoga classes at the end of the ride

What’s Not Included

  • Personal clothing and equipment
  • Travel insurance
  • Bar bills, telephone calls, souvenirs, etc.
  • Bike hire (available if required).
  • Flights & charges for travelling with your bike
  • Airport transfers on days other than the scheduled arrival / departure days
  • Laundry services at the accommodations

Tuscan Colors Itinerary 




Casole d’Elsa Arrival


2 Radda in Chianti Val d’Elsa to Chianti 70 km / Ascent 1400 mt

B  L


Radda in Chianti Chianti North Loop 87 km / Ascent 2000 mt B  L  D
4 Siena Radda in Chianti to Siena 50 km / Ascent 750 mt



Pienza Siena to Pienza 84 km / Ascent 1600 mt B  L  D
6 Pienza Val d’Orcia & Mount Amiata 115 km / Ascent 2340 mt

B  L


Casole d’Elsa Val d’Orcia to Val d’Elsa 120 km / Ascent 1800 mt B  L  D
8 Departure

Tour Description Day by Day.

Day 1.  Arrivals and transfer to Casole d’Elsa.

On your arrival at the airport you will be met by the Wild Trails team and transferred to your first accommodation Hotel Terre di Casole, located in Casole d’Elsa, a typical Tuscan town, overlooking the valley and hills of Val d’Elsa, 1,30 min. far from Pisa airport. We will set some time aside to learn all about your week of road biking and fit the bikes. After we will enjoy a drink at the pool before a dinner.

Hotel in Casole d’Elsa.

Day 2.  Val d’Elsa to Chianti.

Distance 70 km   •   Total Ascent  1400 mt

We are leaving the Valdelsa today, riding to north direction to San Gimignano, an UNESCO World Heritage, famous for its medieval towers that still stand out on its landscape, which have earned him the nickname of Manhattan of the Middle Ages. Between the 72 towers and tower houses, existing in the heyday of the town, today there are sixteen. After 20 km on our bike we’ll enter in the land of ancient wine traditions, the Chianti. The landscape is still undulating, through an endless panorama of vineyards, olive groves, oak forests and centuries-old stone farmhouses. Yes, there are a few hills (this is Tuscany after all) but remember you are on holiday, just follow your pace and enjoy the ride!

Our accomodation it’s in the meddle of this area, not far from Radda in Chianti, where you can taste the Chianti Classico.

Hotel in Radda in Chianti area.

Day 3.  Chianti North Loop.

Distance 87 km   •   Total Ascent  2000 mt

Another hilly raid! We get on the saddle from the hotel, going to north direction to explore the roads and the villages of Chianti. The borders of Chianti are still confused and fiercely contested but include all the hilly area between the provinces of Florence, Siena and Arezzo. From the historical point of view the municipalities of Gaiole, Radda and Castellina, were the old Chianti League. Here we ride! In the heart of Chianti. We will have the opportunity to know the valleys and hills where was born a wine industry more environmentally friendly.

Hotel in Radda in Chianti area.

Day 4.  Radda in Chianti to Siena.

Total distance:  50 km   •    Total ascent:  750 mt

In the morning we will continue to explore the Chianti area and the first stop will be at the village of Gaiole in Chianti, home of the famous competition “Eroica” a cycling event since 1997, which has the distinction of recall of a cycling time, with routes are mostly on dirt roads (Strade Bianche) riding antique bicycles, usually it held the first Sunday of October.

In order to participate you must have a bike with steel frame, gear levers on the down tube of the frame, brake wires coming out of the levers and pass outside the handlebar, pedals with cage and wheels with minimum 32 spokes and rims.

Continuing south we will arrive in the afternoon in Siena, Tuscany’s pearl, has a prominent place in the cultural history and Italian art. Siena is an extraordinary medieval city. The city is a masterpiece of dedication and inventiveness in which buildings are designed to be adapted to the entire design of the urban structure, and also to form a whole with the surrounding cultural landscape. For almost a century, between XII and XIII century, Siena was the star of the European scene thanks to its merchant nobility that laid down the law in the fairs of Champagne and the intense banking activities.

Hotel in Siena.

Day 5.  Siena to Pienza.

Total distance:  90 km    •    Total ascent:  1650 mt

Today we’ll go away from Siena, initially to enter into a new area of Tuscany, the Crete Senesi, southeast of Siena. The name is derived from clay, present in the soil, giving the landscape the characteristic bluish-gray color and appearance often described as lunar. This feature clay, mixed with rock salt and gypsum, called “mattaione”, represents the sediments of the Pliocene sea that covered the area between 2.5 and 4.5 million years ago. The landscape is characterized by treeless and gently rolling hills, oak and cypress trees lonely, isolated farms on top of hills, stretches of forest in the valleys.

If you are daring you take an Eroica stretch through the Crete on dirt roads on the ridges, offering magnificent views and visions that are renewed at every turn.

In the afternoon we’ll enter in another area, the Val d’Orcia to arrive in Pienza where not to far there’s our accomodation.

Hotel in Pienza area.

Day 6.  Pienza loop – Val d’Orcia and Amiata Mount.

Total distance: 115 km   •    Total ascent: 2300 mt

Crossed by the Orcia river in the middle, which gives its name, it is characterized by pleasant landscape views and a number of medieval villages, two of which are well known as Pienza and Montalcino, with its typical foods and wines, like Pici (a type of hand-made pasta, similar to spaghetti but larger), the Cinta Senese salami, Pecorino di Pienza and the Brunello di Montalcino wine.

The valley is also an important park, nature, arts and culture, and from 2004 has been recognized by UNESCO World Heritage, for the excellent state of preservation of the landscape, as well as produced by an intelligent work of human settlement.

But our goal today is the top of the massif of Mount Amiata, in addition to a summit of 1738 meters. This mountain is an ancient volcano, now extinct, with attendance of rocks and volcanic lakes.

Hotel in Pienza area.

Day 7.  Val d’Orcia to Val d’Elsa.

Distance 122 km   •   Total Ascent  2000 mt

Left the town of Pienza still be riding on the hills of the Val d’Orcia, the perfect setting for a movie, remember the Gladiator of Ridley Scott? Some scenes were filmed between the wheat fields of this valley.

We will pass San Quirico d’Orcia, the ancient baths of Bagno Vignoni, where in the past some Pope was staying, then Montalcino where we decide to have lunch or stop for a visit. Continuing our ride we will enter again in the area of the Crete Senesi and then into more wooded areas to get back where he started this nice tour of Tuscany, Casole d’Elsa.

Hotel in Casole d’Elsa.

Day 8.  Departure.

Transfers will be arranged depending on your flight times.