Tuscany Bike Tour (7 days / 6 nights)

Val D’Orcia – Crete Senesi – Chianti Region 

Discover by bike all that Tuscany has to offer, with the people who know it best. Enjoy a real cycling adventure in Tuscany, experience the rolling hills and medieval hill top towns.

Leaded by guide born and raised in Tuscany, you will cycle through the paradise of the Tuscan landscape as you explore the region including Val d’Orcia, Pienza, Montalcino and Chianti.

Learn the secret of tuscan cuisine, taste the fantastic tuscan dishes and world famous wines.

On the first part of the week you will cycle surrounded by the beautiful landscape of Val d’Orcia, UNESCO protected site, and you can visit some nice towns including Pienza, Montepulciano and Montalcino.

On the second part you will cycle through the Crete Senesi region to Chianti, famous for its wine. The last day you can also decide to join Florence by bike, extend your stay in Tuscany and visit this beautiful city.

The Tuscany bike tour is a perfect mix of bike, history, wine tasting and cooking class, for an unforgettable holiday.

We work in collaboration with Ride Tuscany of Anima Toscana for organization and technical support.


Day 1 – Welcome to Tuscany

Meet our staff at Chiusi train station and private transportation to the Hotel Casanova, located at San Quirico d’Orcia, in the heart of Val d’Orcia. Otherwise you can join the hotel on your own.

During your stay you can take a relax break from the cycling journey and enjoy the SPA light package, an hydroterapic circuit in salted water with natural microcomponents from 9.00 to 20.00.

Briefing and delicious dinner in typical restaurant of San Quirico d’Orcia.

Day 2 – Pienza – Montepulciano – Monticchiello (56 km – elevation gain: 910 meters)

The landscapes of the Val d’Orcia region, one of the most beautiful place in Tuscany and UNESCO world heritage site.

Visit of Pienza, the “ideal” city of the Renaissance time, also famous for its Pecorino cheese.

A quick stop at Montepulciano, with its winding streets and squares.Monticchiello, a small medieval and charming town.

Light lunch with Pecorino cheese tasting in typical farm and dairy.Take a relax break from the cycling journey and enjoy the SPA before dinner.

Day 3 – Montalcino and Bagno Vignoni (51 km – elevation gain: 990 meters 81 km)

Climbing up to Montalcino, town of Brunello wine.

Visit of Montalcino, medieval town surrounded by vineyards and beuatiful view on the valley.

The Abbey of Sant’Antimo, one of the most beautiful romanic church in Italy.

Climbing again towards Castiglione d’Orcia and Rocca d’Orcia, the beautiful landscapes will compensate the challenging ascent.

Lunch at Bagno Vignoni, cute medieval town where the main square of the village is a big thermal pool which contains the original source of thermal water.

Take a relax break before a cooking class where you can discover the secret of tuscan dishes.

During the lesson you will make a complete menu and the end, dinner is served with what was prepared during the lesson.

Day 4 – the Crete Senesi (56 km – elevation gain: 700 meters)

An unforgettable ride surrounded by the views of the Crete Senesi to the edge of the Chianti.

The Crete Senesi region, where badlands and biancane characterize the landscape in this part of Tuscany.

A short break at Asciano with its churches and museums.

Lunch and wine tour and tasting in a Chianti winery located at Castelnuovo Berardenga.

Dinner and accommodation at Villa Curina Resort.

Day 5 – the Chianti region (50 km – elevation gain: 1080 meters)

Castelnuovo Berardenga and its landscape museum.Villa a Sesta and San Gusmè, cute town in Chianti.

The Castle of Brolio, symbol of Chianti and good wines to taste.Gaiole, town where L’Eroica was born in 1997.

Radda in Chianti with its small street and a wonderful view on the vineyards.

Dinner and accommodation at Borgo di Pietrafitta.

Day 6 – Monteriggioni and san Gimignano (49 km – elevation gain: 630 meters)

Castellina in Chianti, the most medieval of the Chianti towns.Monteriggioni with its walls and the ring of towers that dominate the hill.

Climbing uo to San Gimignano, the towers of the town can be seen for miles around and the historic town centre is a UNESCO World Heritage Site.

Light lunch and Vernaccia wine tasting before the transfer back with our van.Dinner and accommodation at Borgo di Pietrafitta

Day 7 – Goodbye

Check-out and transportation back to the starting point of the tour or to Florence (hotel of the city center, train station or airport.

Otherwise you can decide to join Florence by bike, where you can add more day at your stay and discover this beautiful city.

Here below the itinerary.

PANZANO AND GREVE IN CHIANTI ON THE ROAD TO FLORENCE (55 km – elevation gain: 800 meters)

Stage completely set in the Chianti Fiorentino.Panzano in Chianti and Cecchini steak!

The triangular square of Greve in Chianti, with the archied loggias that line its three side.

Triumphant arrival at Florence’s Piazzale Michelangelo, last highlights of the Tuscany bike tour.

Arrivederci in Florence, where you can extend your stay and visiti this beautiful city.


  • 7 days / 6 nights



  • Hard



  • all year long


PRICES LIST (per person in double room)

  • 2   people: € 2.900,00
  • 4   people: € 2.110,00
  • 6   people: € 1.800,00
  • 8   people: € 1.660,00


  • 6 Nights with breakfast
  • 5 Dinners, drinks not included
  • 1 Cooking class with dinner
  • 1 Light lunch with cheese tasting
  • 2 Wine tour and tasting with lunch in wineries
  • 2 Lunches
  • Baggage transportation between the hotels
  • Maps and information for your daily stage
  • Van support each day with water, fruits and power bars
  • Expert bike guide
  • Private transfer on day 1 and 7



  • Tourist city tax
  • Drinks
  • Medical/baggage insurance

OPZIONAL SERVICES (prices on request)

  • Medical/baggage insurance
  • Rental bike (hybrid, road bike, electric bike)
  • Flights
  • Activities for non-cyclist (cooking class, truffle hunting, guided tours, horse back riding, trekking…)
  • Discount for private transfer on day 1, if you arrive with your car.

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