This six-day MTB cycling Chianti tour will take you from the undulating lands of the historic Chianti vineyards to the hills of the Livornese coastline, accompanied all the way byour qualified oenologist Carlo Travagli. The tour offers a unique opportunity to discover the enchantingland and seascapes of Tuscany and to sample the region’s outstanding wines.

This fascinating area is renowned for its natural beauty and prime quality production of wine, olive oil, cheese and other gastronomic delights. Starting from the small town of Castellina in Chianti, synonymous with Chianti Classico wine, we will ride through unspoilt green landscapes, crossing into the province of Livorno, through Castellina Marittima, and finally to Bolgheri, a village whose charms have become well-known throughout Italy and beyond.

This cycling Chianti tour is a rewarding experience, taking in an area rich in history, culture, art and beautiful landscapes, seeped in tradition and shaped by the skilful work of man. We will cycle through a region dominated by vineyards, olive groves, wheat fields and thick forest, a landscape that has forever been a source of income for rural Tuscany.

Our journey will also take in some of Tuscany’s many ancient churches, castles and archaeological sites and, of course, some incredibly breath-taking scenery.

Cycling Trip in Tuscany

Starting from the small town of Castellina in Chianti, synonymous with Chianti Classico wine, we will ride through unspoilt green landscapes, cross into the province of Livorno, through Castellina Marittima, coming finally to Bolgheri, a village whose charms have become well-known throughout Italy and beyond.

Day 1 – Arrival and introductions

Meeting with participants at Florence Airport, private transfer to your hotel in Castellina in Chianti. At 6.00 pm, an introduction to the tour and our staff. After this, you will enjoy a welcome dinner, prepared and served for you in your room.

Meals: Dinner

Day 2 – Castellina in Chianti to Pietreto

This will be a challenging day, but your efforts will be well rewarded by the uniqueatmosphere of the route we will follow. Heading west along the western side of the Chianti Classico hills, just outside Castellina in Chianti we will come to the Etruscan necropolis of Fonterutoli, one of the oldest remains of civilization in the Chianti area. Not far from the necropolis we will stop at the beautiful Fonterutoli winery for a guided tour and tasting of their excellent wines. We will then pay a visit to the stunning fortress of Staggia Senese, perfectly maintained due to recent restoration. A typical lunch will be served at a local osteria before continuing along the Via Francigena towards the hamlet of AbbadiaaIsola and the Roman spa of Pietreto.

Meals: Breakfast, Lunch, Dinner

Technical details for day 2:

Grade: moderate – challenging

Terrain: undulating, varied terrain, comprising a mixture ofmetalled roads, dirt and stony tracks, single track and fords

Distance: 50km

Elevation gain: 1100m

Day 3 – Pietreto to Volterra

After cycling through unspoilt natural surroundings we will reach an important archaeological site where we will be able to take in the ancient Etruscan splendors of Volterra. Our second stop is at Montemiccioli, an ancient medieval fortress and a viewpoint over Volterra and the Berignone nature reserve. Next we head for the Carai dairy where we will witness the art of cheese-making, enjoy lunch and do some winetasting. The remaining 30 km is on well-surfaced roads with long, regular up and downhill slopes, the ideal terrain from which to enjoy the sweeping panorama that unfolds before us. This thrilling stage brings us from the rugged hills of the Chianti to the rolling landscapes of Volterra. Free dinner in Volterra

Meals: Breakfast, Lunch

Technical details for day 3:

Grade: challenging

Terrain: varied: metalled roads, dirt and stony track, and singletrack paths

Distance: 50km

Elevation gain: 1450 m

Day 4 – Volterra to Castellina Marittima.

This day’s cycling leads us towards the coast and with it the scent of fresh sea air. Setting off from thecittà delle balze, as Volterra is known, our route is gentle to begin with, becoming more demanding as we head towards Castellina Marittima. This hamlet is perched on a terrace surrounded by Mediterranean maquis with views stretching to the islands of Elba, Capraia, Gorgona and Corsica which at sunset become immersed in a sea of fire. This part of our tour is dedicated mainly to the wild natural landscape with its unique charm. Our one cultural stop will be at Montecatini Val di Cecina, a small village set on the slopes of a rugged hill, dominating the entire surrounding area.

After this you will be transferred by private vehicle to your exclusive retreat in Bibbona. Enjoy a welcome aperitif, followed by dinner and overnight stay at the hotel.

Meals: Breakfast, Lunch, Dinner

Technical details for day 4:

Grade: challenging

Terrain:mainlydirt and singletrack paths, and a general variety of metalled roads, dirt and stony tracks, and single track paths.

Distance: 35km

Elevation gain: 1350 m

Day 5 – Bibbona to Bolgheri, from history to wine.

Today’s route will start from Bibbona, a typical Tuscan village close to the Magona Park. We will cycle through the vineyards of Italy’s most prestigious wines, arriving in Bolgheri for lunch at a local Tuscan trattoria. During the afternoon we will visit the wine cellars at the Ornellaia winery, where expert oenologists will introduce us to the production of one of the world’s most famous wines. We will then return to our accommodation in Bibbona, either by bike or by private transfer. Enjoy an aperitif at sunset and dinner prepared by the chef.

Meals: Breakfast, Lunch, Dinner

.Technical details for day 5:

Grade: easy

Terrain: mainly dirt tracks and foresttrails, and a general variety of metalled roads, dirt tracks, foresttrails, loose terrain and single track paths.

Distance: 25km

Elevation gain: minimal

Day 6 – Castagneto Carducci to San Vincenzo. Poetry, wine,and the Etruscan sea.

Today we will cycle along the famous wine route known as the “Strada del Vino” as far as Castagneto Carducci, the town named after the famous Italian poet Giosuè Carducci, while the second part of our day will take us towards San Vincenzo. We will ride mountain bikes through forest for 90% of the time, where steep ascents and descents and single tracks alternate with rolling hills. At the end of the day you will be able to relax at the hotel spa before dinner. The last dinner on the tour will include local organic food from the Val di Cornia.

Meals: Breakfast, Dinner

Technical details for day 6:

Grade: challenging

Terrain: mainly dirt tracks and forest trails, and a general variety of metalled roads, dirt tracks, forest trails, loose terrain, steep climbs, and descents where it may be necessary to dismount and push our bikes downhill on foot.

Distance: 40km

Elevation gain: 650m

Rescue service available in order to make this day’s cycling accessible to everyone.

Day 7 – Departure

After a hearty breakfast in the hotel’s green surroundings, private transfer to Florence Airport and final farewells.

Meals: Breakfast




cycling chianti


BORGO PIETRAFITTA RELAIS (Castellina in Chianti)

Medieval restored hamlet with panoramic views of Chianti and its vineyards.


Palazzo San Lorenzo is a prestigious palace set in the characteristic hamlet of Colle Val d’Elsa, a medieval gem in the heart of Tuscany, where you can find history, art, nature, wine and food, all with the background of a spectacular landscape.


HISTORICAL LUXURY RESIDENCES (Borgo Vicarello di Volterra)

Vicarello of Volterra is a 15th Century hamlet, immersed in the heart of the Tuscan countryside. Set on the panoramic road which connects San Gimignano to the Etruscan town of Volterra, two of the most beautiful cities of the Region, Vicarello di Volterra benefits from a privileged position, it is in the triangle between Pisa, Florence and Siena and the gorgeous Tyrrhenian Coast. The history of the Region resounds in the hamlet through the aristochratic rooms of the 15th Century villa, nowadays converted into residences with the unique Florentine splendor.

Italy - Tuscany

Property of 1800, part of a three historical relais estate, perfectly restored, set in the undulating Tuscan countryside. The relais, immersed in the Tuscan countryside, close to Magona Natural Reservation, will give us unforgettable relaxing moments and unique experiences: all of these in a perfect Tuscan style.



Accommodation, food and transport

  • 6 nights in Luxury Hotels and Hotels of Charm
  • All breakfasts, lunches as in the program, dinners as in the program
  • 1 welcome dinner prepared especially for you in an agriturismo
  • Welcome aperitif and all other aperitifs mentioned in the itinerary
  • Private transfer from Florence Airport to tour departure point
  • Private transfer from the end of the tour to Florence Airport
  • Entrance to art locations and guided tours
  • Baggage transfer
  • Rescue service

Technical equipment and assistance

  • back up vehicle, rescue support
  • services of an oenologist, a professional trekking guide, and an MTB guide throughout the tour
  • travel insurance
  • heart rate monitor
  • mountain bike and helmet

Guided tours, winery visits and tastings

  • wine cellar tours and tastings, as described in the itinerary
  • 4 sessions of guided tastings
  • 4 tours at local wineries
  • guided tour of the Ornellaia Estate
  • Tastings of wines and local food(Overall a total of six kinds of wine and 15 different labels will be tasted. There will also be tastings of the prized dessert wine, Vin Santo, and of prime quality extra virgin olive oil).
  • Personalized data sheet summarizing tour details


  • Air fares
  • Extra Beverages
  • Personal Extras


  • We can organize transport to arrival and departure points other than those specified in the tour.
  • It is possible to arrange hotel and guided tours both in Pisa and Florence, before or after the tour.


Note: the tour is subject to variation in the event of bad weather or other unforeseen circumstances, at the discretion of the tour leader.

Cycling level



Tour leader

  • Carlo Travagli

    Carlo Travagli

    Since 2004 I have been workin freelance in the wine world. I’m a consultant for many wineries mostly in the areas of Siena and Florence, in Cerreto ...

  • IMG_0635

    Giuseppe Gaimari

    Technical manager of ITD Factory but above all a sports and nature lover. A competitive skier, I have always worn some kind of boots, whether they be ...


Length: 6 nights/7 days. WINE & MTB Experience, with enologist 24/7 with us


Per person based on 4 people in double room starting from 3500 euro


You'll ride in one of the most famous wine regions in the world , discovering the wine-making traditions and magic and unexplored corners of this region The discovery of the historical and archaeological local . You will travel through the culture and traditions of ancient people , in a mix of landscapes among the most picturesque in the world . A unique experience , which will guide you to discover the world of wine under the careful guidance of our winemaker , who will ride alongside you Km after Km

Need help?

Still curious? See all our tours of this type

Our offer includes also...