Tour Description
30 Sept – 8 Oct 2027 – ENQUIRE TODAY
Tuscany is a region for the senses. So, there is no better way than to experience it by bike! We have designed a memorable tour following the landscapes and most picturesque towns and cities of Tuscany: Radda in Chianti, Volpaia, Gaoile in Chianti, Siena, Pienza, Montalcino, San Gimignano and Florence. Picture yourself cycling routes through historic villages, rolling hills and vineyards. There will also be the mandatory stops for a macchiato coffee and pastry in the small plazas!
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When it comes to road cycling the region is visited frequently by the Giro d’Italia and Strade Bianche professional road races. The Chianti wine region is also home to the unique L’Eroica vintage gran fondo event which you will ride in 2027! You will traverse some of the most scenic sections of ‘strada bianca’ as the roads are well compacted and in good condition for road bikes.
You will also immerse yourself in all things Tuscany including its diverse districts and traditions, superb food and fine wine: Viva la Toscana!
Daily Tour Overview
Day 1 – Florence to Chianti wine region
We will collect you from Florence Airport during the morning and transfer you to Chianti in the heart of Tuscany. After the official tour welcome the bikes will be set-up and a picturesque warm-up ride through the vineyards awaits. Tonight you will enjoy dinner with the tour guides.
Distance: 50km / Meals: Dinner Included / Sleep: Chianti
Day 2 – Cycling through Chianti wine region
Sunday is a big day of Gran Fondo gravel action so it will be time to start familiarising yourself with the local landscapes and the riding on offer. The Chianti region is loved for its natural beauty, postcard perfect small towns, friendly locals, quality wine and fresh produce!
The riding is brilliant as you pedal along winding roads past old agricultural estates and manor houses. The gravel roads surrounding the Castello di Brolio region are first class. The Ricasoli family are the original owners of this Tuscan jewel and the extensive vineyards on-ground are actually Italy’s oldest winery. Amazingly, this family has been fine-tuning their craft since way back in 1141!
The beautiful views and wine tradition of the region will have you captivated. We will also be pleased to organise a wine tasting event this afternoon.
Distance: 75km / Meals: Breakfast Included / Sleep: Chianti
Day 3 – Volpaia ‘hamlet’
There will be more time to practise on the ‘strada bianca´ today as we will also hit-up some gravel roads on the outskirts of Radda. The perfect ride to have you fit and ready for l’Eroica. Today you will finish your ride up at the small mountain hamlet of Volpaia.
Later in the afternoon you will visit the l´Eroica event village. Here you will collect a vintage (pre-1985) steel bike ahead of tomorrow´s gran fondo cycling event. The village includes close to 100 stalls with cycling gear from yesteryear.
Distance: 70km / Meals: Breakfast & Dinner Included / Sleep: Chianti
Day 4 – l’Eroica Gran Fondo – 46km, 75km or 135km??
Today you ride Italy´s version of the Paris Roubaix! The l´Eroica Gran Fondo was born from a pure passion for cycling with the aim of rediscovering the authentic roots of a truly beautiful sport! The ride is through the ´Chianti Valley´ in the heart of Tuscany. The participants of this grand event pull on vintage clothing and jump on a steel bike in spectacular fashion over the white gravel roads. The locals cheer for you like the heroic days of Binda, Gagliardoni and Bartali as quaint towns with names like Greve, Panzano and Radda in Chianti roll-on by.
The party back in Gaiole in Chianti is one of pure fun and friendship. There is no talk of times or distance ridden as this united cycling family simply shares stories of a unique day of cycling! During the evening we will yet again celebrate our cycling achievements and new friendships formed with a glass of quality red!
Distance: 75km / Meals: Breakfast & Dinner Included / Sleep: Chianti
Day 5 – Medieval Siena
After breakfast we say goodbye to Chianti and cycle for Siena. The cycling follows rolling terrain with several ‘white gravel’ road detours. The arrival to Piazza del Campo in Siena is a truly special moment. The medieval piazza is one of Europe’s greatest squares! The twice-a-year horse-race, Palio di Siena, is held around the edges of the piazza.
During the late afternoon there will be plenty of time to explore the medieval old town. The streets resemble an open-air museum and finishing for a group dinner in this magical city will be something to remember for years to come.
Distance: 75km / Meals: Breakfast & Dinner Included / Sleep: Siena
Day 6 – Piensa & Montalcino
Today´s route heads towards Asciano and the famous ´Senesi Crete´. The clay fields during earlier days were overworked and abandoned and erosive forces have created a lunar landscape. As the kilometres roll-by the beautiful rural landscapes of the Val d´Orcia are uncovered (UNESCO World Heritage Site). Follow roads lined with the regions characteristic and emblematic cypress trees. The jewel of the Val d´Orcia region is the small renaissance towns and there will be time to soak up the medieval history of Pienza and Montalcino.
Distance: 100km / Meals: Breakfast & Dinner Included / Sleep: Siena
Day 7 – San Gimignano Towers
This morning there will be a 45min van transfer to San Gimignano. This small walled medieval town is a must-see when visiting Tuscany. Its 13 medieval towers reach for the heavens and were built as symbol of family status. After a chance to explore over lunch we will now be ready for the afternoon ride.
The area surrounding San Gimignano is highly regarded for its historical, cultural and natural treasures. The undulating roads will keep you interested throughout as the ride moves north towards Lucca our home for the next two nights. There are many 1-3km climbs and descents on twisting roads that pass quiet towns.
Distance: 85km / Meals: Breakfast Included / Sleep: Siena
Day 8 – Siena to Florence
Just for good measure and our final ride will dissect the famous Chianti wine region. Cycling from Siena you will wave goodbye to the imposing Renaissance wall which surrounds the entire city. The ride will head north to Florence and take in a total of 80km and 1100m of elevation gain. It will be an excellent challenge to round out what has been a fantastic week riding through Tuscany!
Tonight it will also be time to enjoy a farewell dinner with the tour guides in one of Florence’s preserved plazas. Tales of wonderful cycling experiences will flow like the local wine!
Distance: 80km / Meals: Breakfast & Dinner Included / Sleep: Florence
Day 9 – Arrivederci
Following breakfast our guides will be available to transfer you to Florence Airport. We look forward to cycling with you again soon!
Meals: Breakfast included
Cycling Tour Grading
Dates & Prices
| Dates | 30 Sept – 8 Oct 2027 |
| Duration | 8 nights / 9 days |
| Price (per person) | 3850 € (twin share) |
| Bike Hire | Carbon Road Bike (Di2): 350 € E-Road Bike: 500 € |
| Single Room Supplement | 750 € |
5% Discount for Groups of 4 or more!
Go Private: Round-up some Friends & Ask Us for a Customised Package!
Client Reviews (l’Eroica & Tuscany)
Peter (Griffith, NSW, Australia)
When you have crazy cyclist´s from Australia who want to cycle Europe, Who do you call? Paul from Sierra Sports. Great Tuscany schedule, fun times at the l’Eroica vintage gran fondo ride, amazing cycling captured memories which will never be forgotten, incredibly well balanced with fantastic wine, food and companionship. An experience that has us returning for more!
Leigh (Melbourne, VIC, Australia)
Cycling through tuscany was a highlight far more than I expected. The group was a lot of fun, the tour was a great experience. The riding, the tour guides, Italy i can’t wait to come back.