Imagine beautiful architectural examples, great wine, surrounded by the lovely landscape of the Tuscan hills…
You will wake up in the morning immersed in the oldest and most hidden medieval towns of Tuscany’s countryside. And then, cycle across the Chianti hills, accompanied by a support vehicle, a mechanic, and an architect; go through the old roads, which tell the ancient history of pilgrimages and memorable bike races that coast historic farmhouses and cross marvelous medieval towns. You will explore a new scenic wine cellar every day, combining the pleasure of a tasting with the chance to admire the works of art of mankind. And again, visit, taste the best wines of the region, enjoy a unique and relaxing atmosphere, sleeping in exclusive old towns and historic villas, which will improve your stay thanks to the culinary specialties they will prepare especially for you.
We will organize many cultural events like a wonderful jazz concert, which will take place in the historic house surrounded by the hills around the city of Siena where you will be staying.

Stefano Corazzini, our expert guide and passionate architect, will accompany you throughout the whole tour, and will enrich your experience unveiling the unique relationship that ties wine and architecture together, creating a rare work of art.
This trip is inherently unique. Suited to the architecture lovers, the wine and Tuscan countryside fans, this tour combines diverse experiences under a common denominator: exploring and living these magical places in the deepest way possible.

The bike will not only serve as a mean of transportation, but also as a better mean to take advantage of the emotions that this experience will offer you.

Day 1: Arrival

Arrival at the International Airport of Pisa, where you will meet your guide. Transfer to Florence to our Hotel with private transportation. During the afternoon, there will be the possibility to join a walking urban tour of Florence. First dinner and preview of the tour; bike and technical material checking. Dinner and night stay at the Hotel.


  • Dinner

Day 2: Antinori Wine Cellar, Bargino, Project: ARCHEA ASSOCIATI

In order to get used to the cycling rhythms, today we will limit ourselves to 25km, cycling across the Tuscan landscape, stopping by small historical towns, until we reach our “agriturismo”, immersed in the nature.
During the day, we will be able to visit one of the most interesting and recent wine cellars, with its impressive architecture perfectly inserted in the hilly landscape. We will have lunch here and taste fine wines. Our dinner will be accompanied by a tasting event with a sommelier.


  • Breakfast
  • Lunch
  • Dinner

Technical Data:

  • Length: 25km/15.5 m
  • Difference in altitude: 500m
  • Path: paved ways and white roads
  • Rescue Service with water and nutritional support

Day 3: Brolio Castle, Ricasoli Baron, Gaiole in Chianti

On our third day we will mainly focus on the “History of Wine”, cycling on panoramic roads on the Chianti hills until we reach one of the wine cellars that has contributed the most to making the wine of this region famous and unique.
We will leave early from our agriturismo in the direction of the Brolio Ricasoli Baron Castle, where we will be welcomed as guests with a guided tour, wine tastin, and a lunch featuring local products and recipes. After lunch, we will move to Sinalunga by private transport, where we will settle in an exclusive little medieval neighbourhood, transformed into a luxury Hotel with a typical Tuscan style.
Dinner with tasting of “grappa” liquor. Night stay at the hotel.


  • Breakfast
  • Lunch
  • Dinner

Technical Data:

  • Length: 41km/25 m
  • Difference in altitude: 700 meters
  • Path: paved ways and white roads
  • Rescue Service with water and nutritional support

Day 4: Pienza/Montepulciano, Cantina Icario, Project: Studio Valle

On our fourth day we will visit one of the most beautiful towns of Italy, rich in history and delicatessen. Cycling on old fascinating roads, we will be hosted by a small wine cellar close to Montepulciano. We will then bike toward Pienza and Montepulciano following the ancient Via Francigena and some traits of dirt road that is part of the “Eroica” (a cycling event on the Chianti dirt roads, still honoured to date with bikes and traditional clothes).
We will arrive to the surroundings of Pienza where we will enjoy a tasting of local cheese and then visit the city of Pienza.
Next is Montepulciano, where we will participate in a tasting event at the wine cellar Icario.
We will finally reach our medieval town, where a Jazz and Cheese event will entertain us, followed by a dinner featuring typical local products.
Night stay.


  • Breakfast
  • Lunch
  • Dinner

Technical Data:

  • Length: 42km/26 m
  • Difference in altitude: 500m
  • Path: paved ways and white roads
  • Rescue Service with water and nutritional support

Day 5: Tenuta Castel Giocondo, Montalcino, Project: Piero Sartogo

Today we pass by bagno Vignoni, famous town known since the time of the Medici family for the curative qualities of its waters. We will continue toward Montalcino, until we reach one of the most famous cellars of the region.
We will arrive at the property Castel Giocondo Montalcino, where, after a visit and tasting, we will have lunch immersed in the beautiful frame of the surrounding countryside. After lunch, we will move to our luxury Hotel. We will be able to reach it comfortably by mini van or for those who wish so, by bike across splendid hilly roads. The hotel offers a SPA facility with thermal baths and pool. We will also book a massage for you in order to relax after the tiring day.
Dinner will be served à la carte in the restaurant of the hotel, with a selection of local wines.
To conclude, we will distribute the technical data sheets and gadgets.


  • Breakfast
  • Lunch
  • Dinner

Technical Data:

  • Length: Option1:48km/30 m. Option2: 69km/43m
  • Difference in altitude: Opt1:500m Opt2: 700meters
  • Path: paved ways and white roads
  • Rescue Service with water and nutritional support

Day 6: Departure

Transfer to the airport after breakfast according to the flight schedule


  • Breakfast

Villa La vedetta   5 Stelle Luxury Hotel 

Built in the second half of the 1800s, this romantic Villa of the renaissance is today a refined luxury hotel. Situated near Piazzale Michelangelo, not far from Ponte Vecchio,Villa la Vedetta has a breathtaking view upon Florence and will welcome you in the warm atmosphere of its living rooms and wonderful rooms.




Agritourism Fonte dei Medici  Ancient hamlet located in “Chianti classico” lands 

The hamlet of Fonte de’ Medici dates back to 1400 and is located in the heart of the Chianti Classico region. Around the village lie the vineyards belonging to the Antinori Family, which produce two of their best-known wines: Tignanello and Solaia. It takes its name from a fresh water spring, which served as a resting place for pilgrims on their way from Florence to Rome.




Locanda dell’amorosa  Charming hamlet dating to 1300

Once upon a time, in the distant 1300s, there was a tiny little hamlet called Amorosa… today, the ancient stables have been converted in charming restaurant, the old cellars filled with an excellent selection of wines and, in the villa, romantic bedrooms and luxurious suites created.





Borgo di Castelvecchio  Ancient hamlet located in the heart of Val d‘Orcia 

Set in a large Italian-style garden, the Villa dates back to the XIth century and dominates the Borgo di Castelvecchio with discreet, refined authority. Within its walls reigns a genuine, unspoilt atmosphere, offering guests maximum comfort combined with great peacefulness. …




Castello di Velona  Resort Thermal Spa & winery 

Situated between Val d’Orcia, a UNESCO world heritage site in the heart of Tuscany, and Mount Amiata, Castello di Velona Resort, Thermal SPA & Winery is a centuries-old residence that offers its guests unique sensory emotions.








What’s included

Accommodation, meals, transportation

  • 5 nights in luxury accommodation facilities immersed in nature
  • All Breakfast, lunches as per program, and dinners as per program
  • Transport from the airport of Pisa or Firenze to the starting point of the tour
  • Transport from the ending point to the airport
  • Transfer, loading and unloading of baggage

Technical support and Nutrition

  • Travel insurance
  • Bikes appropriate for the tour
  • Helmet
  • Garmin trip computer with cardio armband to control the heartbeat and calories
  • Local expert guide for architecture and wine tasting present throughout the trip
  • Gps files that you can download
  • Support car for mechanical issues and rescue services
  • Nutritional support

Events and visits

  • Jazz and Cheese event
  • Tasting events with sommelier
  • 4 visits to wine cellars with tasting
  • Visit to a cheese factory with tasting
  • Massage at the Castle of Velona’s thermal baths


  • Flight rates
  • Extra drinks
  • Personal Extras

Extra Services

  • Hotel booking and guided tour of Florence or Pisa for an extra day before the beginning of the tour or after the end

Note: the tour could potentially be subjected to changes based on the weather conditions, and on the discretion of the guide.


Cycling level



Tour leader

  • 20130407_185726

    Stefano Corazzini

    Laureato in architettura, vive e lavora a Firenze dove si sposta ogni giorno con la sua adorata bicicletta. Questa magnifica città gli ha insegnato ...


5 nights/6days For all level: focus on wine and architecture


Per person based on 4 people in double room starting from 5200 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 For totally luxury experience .... by Hotels luxury superior, to sophisticated restaurants and the activities most exclusive The classic image of Tuscany postcard . For an experience totally Tuscan-style Cycling or walking along the famous "Via Francigena" , the old pilgrim route from Canterbury to Rome Experiences which will be given special attention to the world of wine from the vineyards , cellars and tasting , the dishes combined with the finest wines

Need help?

Still curious? See all our tours of this type

Our offer includes also...