Embark on a nostalgic pilgrimage to the birthplace of vintage cycling with an immersive L’Eroica holiday in Gaiole in Chianti, where the golden era of the sport comes alive amidst the rolling, cypress-lined ridges of the Tuscan countryside. This isn't merely a bike tour; it is a soul-stirring journey across the legendary Strade Bianche (white gravel roads), where riders clad in authentic classic wool jerseys conquer historic routes on pre-1987 steel-frame bikes.
Whether you tackle the accessible short loops or the epic 205 km challenge through the Val d’Orcia, the experience transcends sport to become a sensory masterpiece, featuring world-famous ristori (rest stops) that trade energy gels for handmade pici pasta, local olive oil, and bold Chianti Classico wine.
By securing a curated L’Eroica 2026 tour package, you gain guaranteed entry to this oversubscribed event, professional mechanical support for your vintage machine, and the chance to relive cycling history in its purest, most heroic form - blending breathtaking landscapes, gritty determination, and the timeless elegance of Italian heritage.
Official L'Eroica Tour Operator
Wine Tasting
Superb Hotels
Eroica Montalcino Route
Non-Riders Welcome
Transfers
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.
19 km | 310 m
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 for a professional 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 a 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
66 km | 1060 m
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
209 km | 2650 m (Long course)
132 km | 2200 m (Medium course)
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
34 km | 480 m
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, learning about the harvest and production process. It’s a tranquil, indulgent day, a perfect way to prepare for the adventure that lies ahead.
Villa Curina Resort | Castelnuovo Berardenga
All good things must come to an end, and after a relaxing breakfast chatting through the experiences of the weekend and the completion of the L’Eroica our staff will get you where you need to be for onward travel.
Want to stay a little longer? To add extra days before or after your tour, just contact lynn@italybiketours.com and we’ll help you extend your trip.
| Dates | Price | Availability | |
|---|---|---|---|
| Thu 1 Oct - Mon 05 Oct | From €1899 | Available | Book Now |
*Bike hire starting from 40€ per day
Ridley ASTR GRX600 – Explore epic landscapes! Lightweight, responsive, and adventure-ready. Perfect for gravel, touring, and thrill seekers.
Vintage Bike – A beautifully crafted vintage bike, made to embrace the white roads of Tuscany and ride in the timeless spirit of Eroica Montalcino.
| Where to Meet |
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. |
|---|---|
| Drop off Location |
We can assist you with planning and booking of 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. |
| Transfer Time |
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. |
| Road conditions |
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. |
| Cuisine |
Expect authentic Tuscan cuisine, from Pappardelle al Ragù and Panzanella and exceptional local red wines. |
| Hotel Facilities |
The hotel on this tour has a pool, good wifi and bar service. Some facilities may occur in extra fees. |
| Weather |
October in Italy typically brings fresh days, with average temperatures ranging from 20-28°C (68-82°F). |
| What Happens Next? |
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! |
VILLA CURINA RESORT ★★★★
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!
ITA: +39 320 638 4713
Or you can chat to us online by clicking the button at bottom right of page.
Drop us a direct email to: info@italybiketours.com
