the timeless thrill of vintage cycling through Tuscany’s legendary roads
This isn’t just a ride — it’s a journey through time, beauty and passion. Discover the soul of Tuscany on the legendary roads of Eroica Montalcino in a thrilling self-guided tour, where every kilometre captures the romance of cycling’s golden age.
Feel the crunch of the Strade Bianche beneath your wheels as you explore the Val d’Orcia, one of Italy’s most breathtaking landscapes. Rolling vineyards, silvery olive groves and hilltop villages create a constantly changing backdrop.
Ride at your own rhythm, stop when the view demands it and enjoy the freedom of discovering Tuscany on roads that have become part of cycling legend.
Whether you’re here for the scenery or for the love of cycling, Eroica Montalcino celebrates courage, endurance and the simple joy of the open road.
The experience blends beautiful riding with the timeless character of southern Tuscany — ancient villages, traditional cuisine and landscapes where the pace of life still feels wonderfully unhurried.
And when the ride ends, there’s no better way to toast the day than with a glass of Brunello di Montalcino, savouring the local flavours that make this land so irresistible.
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 the legendary Strade Bianche and the permanent L’Eroica route to the rolling vineyards, medieval villages and timeless landscapes of the Val d’Orcia, discover the authentic spirit of Tuscany — on and off the bike.
Ride the legendary white gravel roads and follow the permanent L’Eroica route through the heart of Tuscany.
Cycle through stunning vineyards, olive groves and medieval castles on unforgettable Tuscan roads.
Pedal through the distinctive lunar-like landscapes of the Crete Senesi, one of Tuscany’s most dramatic areas.
Explore some of Italy’s most photogenic roads, framed by cypress trees, rolling hills and postcard-perfect views.
Glide down sweeping descents and take on the rolling climbs that make riding in Tuscany so rewarding.
Savour one of Italy’s most celebrated wines in the place where it is made.
Explore historic towns and villages including Radda, Gaiole and Buonconvento.
Take in rolling hills, olive groves, cypress-lined roads and postcard-perfect views.
Relax in carefully selected accommodation and enjoy the warm hospitality that defines Tuscany.
Taste the best of Tuscan cuisine, from handmade pasta and local cheeses to seasonal regional specialities.
A five-day Tuscan journey through Chianti, Monteriggioni, the Val d’Orcia and San Quirico — combining scenic self-guided riding with the legendary white roads and timeless atmosphere of Eroica Montalcino.
After picking you up at Florence Airport, you will settle into your charming Tuscan base. Stretch your legs on a gentle 35 km loop in the afternoon, breathing in the rolling hills and golden light of your first Tuscan afternoon.
Hotel Salivolpi | Castellina in Chianti
Today, you’ll pedal through rolling vineyards, sun-dappled olive groves, and storybook villages, pausing to soak in the medieval charm of Monteriggioni — it’s like stepping back in time, with every corner revealing a new piece of Tuscany’s timeless beauty.
Hotel Salivolpi | Castellina in Chianti
Cycle through the heart of Tuscany’s countryside toward San Quirico, where every hilltop reveals a postcard-perfect view. Pause in charming villages, savour local treats, and let the rolling hills and cypress-lined roads surround you.
Wellness Center Casanova | San Quirico d'Orcia
The big day is here! Tackle the legendary L’Eroica route. Gravel roads, historic villages, and sweeping vistas make this a ride you’ll remember forever.
Wellness Center Casanova | San Quirico d'Orcia
After breakfast, take a moment to reflect on your Tuscan adventure before we send you on your onward journey — with memories, photos, and a full heart.
Start with fresh pastries, local produce and Italian coffee before getting ready to ride.
Follow quiet country roads and iconic white gravel through vineyards, olive groves and rolling hills.
Pause in a medieval Tuscan village for an espresso and time to enjoy the atmosphere.
Recharge with handmade pasta, local cheeses and seasonal dishes in a traditional trattoria.
Finish the day with a relaxed aperitivo and a glass of Brunello di Montalcino.
Discover the legendary white roads of Tuscany on a self-guided Eroica Montalcino experience, combining Chianti, the Val d’Orcia and the unmistakable atmosphere of cycling’s golden age.
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 Eroica Montalcino experience — from what’s included and transfers to bike hire, the Strade Bianche, Tuscan cuisine, hotel facilities and practical information for your self-guided adventure.
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 roads in Tuscany are generally in good condition, especially on main roads. You will also ride on the iconic Strade Bianche — Tuscany’s famous white gravel roads. Drivers are used to sharing the road with cyclists and are typically respectful.
Expect authentic Tuscan cuisine, from pappardelle al ragù and panzanella to local cheeses, seasonal dishes and exceptional regional red wines — including Brunello di Montalcino.
Absolutely. Non-riding partners are always very welcome on our tours. We offer dedicated non-rider experiences, allowing them to enjoy the destination in their own way while you’re out on the bike. Get in touch with our team to discover the non-rider options available for your chosen tour.
Please arrange to meet us at Florence Train Station (Santa Maria Novella) at 2pm 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.
The transfer time from Florence to the first hotel is approximately 50 minutes on Day 1. Transfer from San Quirico to Florence Train Station is around 1 hour 45 minutes on Day 5.
Tuscany rewards confident riders with rolling hills, quiet country roads, vineyard-lined lanes and unforgettable gravel sections. Some Strade Bianche can be steep, loose or uneven, so steady bike handling is important. The scenery more than repays the effort, with cypress-lined roads, medieval villages and wide-open views across the Val d’Orcia.
The hotels on this tour have wellness facilities, and we recommend bringing swimming costumes. They also offer good WiFi, bar service and, in some cases, laundry service. Some facilities may incur additional charges.
Are you thinking about joining us? You probably have some questions! Email is the best way to contact us and we aim to reply within 24 hours. Please check your SPAM/JUNK folder if you have not received a reply in that time. You can also find a contact form at the bottom of this page.
Four nights across two beautiful corners of Tuscany — beginning among the vineyards of Castellina in Chianti before continuing into the rolling landscapes of the Val d’Orcia.
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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