A Vintage Cycling Journey Through the Heart of Tuscany
Embark on a nostalgic pilgrimage to the birthplace of vintage cycling with an immersive L’Eroica holiday in Gaiole in Chianti, where the golden age of the sport comes alive among Tuscany’s rolling hills and cypress-lined roads.
This is far more than a bike tour. Ride the legendary Strade Bianche in authentic classic wool jerseys and experience the event on pre-1987 steel-frame bikes, reliving cycling history in its purest form.
Choose from accessible shorter routes or take on the epic 205 km challenge through the Val d’Orcia, surrounded by some of Tuscany’s most iconic landscapes.
Along the route, L’Eroica’s famous ristori turn every stop into part of the experience, replacing energy gels with handmade pici pasta, local olive oil and bold Chianti Classico wine.
With a curated L’Eroica 2026 tour package, you’ll benefit from guaranteed event entry, professional mechanical support for your vintage bike and carefully organised logistics throughout the journey.
It is an unforgettable blend of cycling heritage, determination, Tuscan culture and timeless Italian elegance — a celebration of why cycling can be so much more than sport.
An epic, and for me super challenging week cycling non elec bikes over the rolling Tuscan hills! Matteo is an excellent and patient guide aided by Andrea on water van duty. Great company, super food and left feeling super satisfied on this our second tour. Looking forward to next year!
The guys are super pros, I felt really safe at all times during the trip. John and Ivan made us feel comfortable 100% of the time, always knew the way, alternative routes, where to take us and where to stop, how difficult it would be day by day, so it was amazing. They also let us pretty relaxed to take our time and enjoy the ride. I definitely want to come back!!
I had an unforgettable experience with Italy Bike Tours team - Unexpected Tuscany on a multi-day cycling tour through some of the most beautiful towns in the region: San Miniato, San Gimignano, Siena, Montalcino, and Montepulciano. Each ride was about 50 - 60 km, taking us through stunning Tuscan landscapes filled with vineyards, rolling hills, and quiet countryside roads.This wasn’t just a tour; it was a deeply memorable way to experience the heart of Tuscany. Beautiful routes, great company, delicious food and wine, and top-notch guidance. Highly recommended!
10 out of 10. There is nothing to fault. Great to eat local food and drink local wine, the accommodation was always good, the scenery was picture postcard beautiful and our guides, Fausto, Giovanni and Carlo were amazing. Always cheerful and nothing was too much trouble Thank you for a wonderful experience. I highly recommend this tour.
I successfully completed this IBT tour, which more than exceeded its name. I loved it! I was very apprehensive on my first day, but hey!, it turned out I was a natural. The route was amazing, the scenery dreamlike, the organization seamless. But the biggest accolade goes to Fausto, Giovanni, and Carlo - the BEST guides ever! Ciao Marianne
This e-bike tour was an adventure of a lifetime. Our tour director and all our hosts and guides were wonderful and well organized. Almost 400km of Tuscan hills that were challenging at times, but every stop and town were wonderful to visit. We would not have seen Italy in the same way, if it weren’t for the bikes. What a fun group to travel with! I’ll cherish these memories for a long time.
From Gaiole in Chianti and Tuscany’s legendary Strade Bianche to vineyard-lined roads, medieval villages and the unique atmosphere of L’Eroica, discover a journey that celebrates vintage cycling, Tuscan culture and timeless Italian style — on and off the bike.
Ride the legendary white gravel roads and experience the unmistakable spirit of the original L’Eroica route.
Cycle through stunning vineyards, olive groves, medieval castles and the rolling hills of Chianti.
Discover the unique feel of expertly fitted classic steel-frame bikes and ride in true vintage style.
Enjoy a relaxed recovery ride through sun-drenched Tuscan landscapes after the main event.
Glide through sweeping descents and take on the beautiful climbs that make Tuscany so unforgettable.
Unwind in the 16th-century elegance of Villa Curina Resort in the heart of Chianti.
Savour a curated vineyard lunch paired with bold local Chianti Classico wines.
Take in rolling hills, olive groves, cypress-lined roads and postcard-perfect views.
Refuel at authentic trattorias with pici, fresh bread, pecorino and other local favourites.
Discover the secrets of Tuscany’s “liquid gold” during a guided local olive oil tasting.
Experience L’Eroica in the heart of Chianti — from a relaxed welcome loop and vineyard-lined rides to the legendary event itself, followed by a gentle coffee ride and authentic Tuscan food, wine and olive oil experiences.
The first day of our L'Eroica cycling holiday begins with a smooth transfer from the airport to Gaiole in Chianti, where the rolling hills of Tuscany await.
After settling in, our mechanic will help you with a professional bike fitting to ensure every rider is perfectly set up for the days ahead.
Once the bikes are adjusted, we embark on a short, scenic ride through the Chianti countryside, offering the perfect opportunity to test the bikes and enjoy the stunning landscapes before the adventure truly begins. It’s a relaxed start, setting the tone for the exciting days to come.
Villa Curina Resort | Castelnuovo Berardenga
Today’s ride takes us through the picturesque hills of Chianti on vintage bikes, embracing the spirit of L’Eroica. We cycle through winding roads surrounded by vineyards and olive groves until we reach the charming town of Castellina in Chianti.
Here, we pause for a well-deserved coffee in the town square, soaking in the medieval atmosphere. After a leisurely break, we continue our ride to a stunning vineyard, where we enjoy a delicious lunch paired with local wines.
Refreshed and recharged, we then pedal back through the Tuscan landscape, with the afternoon sun casting a golden glow over the rolling hills.
Villa Curina Resort | Castelnuovo Berardenga
On L'Eroica day, we rise early to the sound of the countryside awakening, ready for an unforgettable adventure. The gravel roads beckon, and we set off on a unique route winding through the hills of Chianti, each turn revealing a new breathtaking vista.
Along the way, we make a stop at a traditional food station, where local delicacies like crusty bread, cured meats and pecorino cheese give us the energy to power through.
The charm of L'Eroica lies not only in the challenge of the ride but in the unforgettable experience of cycling through a living, timeless landscape, where every kilometre feels like a step back in history.
Villa Curina Resort | Castelnuovo Berardenga
The day after L'Eroica, we enjoy a relaxed morning with a leisurely coffee ride through the scenic Tuscan countryside. The cool morning air and quiet roads set the perfect tone for a gentle spin, soaking in the beauty of rolling hills and vineyards.
In the afternoon, we visit a local agriturismo, where we experience the authentic flavours of Tuscany. The highlight is a guided olive oil tasting, where we sample some of the region’s finest oils and learn about the harvest and production process. It’s a tranquil, indulgent day and the perfect way to unwind after the event.
Villa Curina Resort | Castelnuovo Berardenga
All good things must come to an end. After a relaxing breakfast and time to chat through the experiences of the weekend and the completion of L’Eroica, our staff will get you where you need to be for onward travel.
Start with fresh bread, pastries, coffee and local produce before preparing your vintage bike.
Set out on a classic steel-frame bike and follow the legendary white roads of Chianti.
Pause at an authentic L’Eroica rest stop for bread, pecorino, cured meats and local flavours.
Recharge with homemade pici pasta, Tuscan specialties and a glass of Chianti Classico.
Finish the day among vineyards and medieval villages with an aperitivo and stories from the ride.
Join us in Tuscany for an unforgettable L’Eroica experience — vintage bikes, legendary Strade Bianche, Chianti landscapes and guaranteed entry to one of cycling’s most iconic events.
Choose how you want to experience Tuscany — on a modern gravel bike or in true L’Eroica style on a classic vintage machine built for the legendary Strade Bianche.
Lightweight, responsive and adventure-ready. A modern gravel bike made for Tuscany’s rolling hills, white roads and long scenic rides.
A beautifully crafted classic bike made to embrace Tuscany’s white gravel roads and ride in the timeless spirit of L’Eroica.
Have a question about bike sizing or availability? Contact us at alberto@italybiketours.com
Everything you need to know before joining our L’Eroica cycling experience in Tuscany — from what’s included and transfers to the Strade Bianche, local cuisine, hotel facilities and practical information for the event.
Please arrange to meet us at Florence Train Station (Santa Maria Novella) at 1pm on Day 1. We will contact you via WhatsApp in the days leading up to the start of your tour to confirm your transfer and the name of the staff member collecting you.
We can assist you with planning and booking onward travel following the conclusion of your tour. We will run one transfer to Florence Train Station, leaving the hotel at 10.30am. For alternative destinations or departure times, please contact us at alberto@italybiketours.com.
The transfer time from Florence to the hotel is approximately 1h30. The same transfer will take place on the last day, bringing you back to Florence Train Station.
The roads in Tuscany are generally in good condition, especially on main roads. You will ride on the iconic Strade Bianche (gravel white roads). Drivers are used to sharing the road with cyclists and are typically respectful.
Tuscany is one of Italy’s most rewarding regions to explore by bike, with quiet country roads, rolling hills, vineyard-lined lanes and the legendary Strade Bianche. Some sections can be steep or loose under the wheels, so good bike handling and a steady pace are important. Local drivers are generally accustomed to cyclists and are typically respectful when sharing the road.
Expect authentic Tuscan cuisine, from pappardelle al ragù and panzanella to exceptional local red wines.
The hotel on this tour has a pool, good WiFi and bar service. Some facilities may incur extra fees.
October in Italy typically brings fresh days, with average temperatures ranging from 20–28°C (68–82°F).
Are you thinking about joining us? You probably have some questions! There are a number of ways to contact us. Email is best — we will reply within 24 hours. Please check your SPAM/JUNK folder should you not have received an email in this time. You can also find a contact form at the bottom of this page!
Four nights in the heart of the Chianti countryside at Villa Curina Resort — a refined historic retreat surrounded by vineyards, olive groves and the rolling hills of Tuscany.
More unforgettable experiences in Tuscany — from the spectacle and tradition of the Palio di Siena to another iconic celebration of vintage cycling in Montalcino.
Discover more cycling experiences, destinations and ideas for your next Italian adventure in our latest brochure.
View Our 2026 & 2027 Brochure →If you would prefer to give us a call and talk cycling and Italy, please WhatsApp us on the number below and we will arrange a call back.
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