Tour Type
Granfondo
Riding Level
Active
Location
Siena, Tuscany
Duration
6 days | 5 nights
Length
40 - 104km daily
Climb
600 - 1,530 m daily
We promise this fun and celebratory tour will show you a side of riding that you have never experienced before! It will re-ignite your senses, create memories and leave you in awes for the incredible cycling heroes in history who won races these bikes with their downtube shifters, long brake cables and toe-clips. As Giancarlo Brocci, creator of L'Eroica, has said “We want people to rediscover the beauty of fatigue and the thrill of conquest”.
Get ready for the ultimate Tuscan cycling party! On Sunday, 4 October 2026, you’ll be lining up for L’Eroica Gaiole – the world’s most famous, non-competitive vintage cycling festival. With five spectacular routes ranging from a fun 46 km cruise to an epic 212.5 km challenge, there is a perfect slice of gravel for everyone.
Before the retro madness begins, we’ll spend three days exploring the postcard-perfect Tuscan countryside and the historic streets of Siena on top-tier modern road bikes (think full carbon, disc brakes, and crisp electronic shifting). It’s the perfect excuse to spin the legs, sample incredible local cuisine, savor world-class wines, and fully dive into the Italian lifestyle.
Then, the real magic happens. We swap our modern machines for a weekend aboard a pre-1987 vintage classic. A relaxed morning coffee ride gives you the perfect chance to get used to your new steel steed, leaving the afternoon free to rest up and soak in the electric festival atmosphere.
Why is this a guest (and guide) favourite? Because we handle absolutely everything! We provide both of your bikes, guarantee your entry ticket, and even supply your very own vintage kit. Whether you choose the classic celeste Bianchi look or the deep rosso vino Eroica jersey, you’ll look just as fashion-forward as our Italian hosts.
As an Official Tour Operator partnered with Eroica, we have unlocked exclusive experiences just for our crew. Don’t wait – entries to this iconic event sell out incredibly fast.
Read Michiel’s story about our latest Eroica adventure here, lock in your spot, and get ready to make cycling history in Gaiole!
Tour Highlights
Welcome to Tuscany! Our team will meet you at Florence Airport in the morning to whisk you away to our beautiful hotel near Siena. Once we arrive, we’ll get you perfectly fitted to your bike, hand over your exclusive team kit, and make the final preparations for the week ahead.
This afternoon, it’s time to spin the legs on our official welcome ride! We’ll head out on a scenic 45 km loop through the rolling, vine-covered Tuscan countryside, passing through charming historic hamlets along the way. After returning to the hotel, we’ll get together to chat through the exciting program for the week before raising a glass and diving into a fantastic, hearty Italian welcome dinner.
Chianti Classico is one of Italy’s most famous wines and today we will enjoy riding in the region. It will be a spectacular ride as we ride through vine-covered hills and along roads lined with cypress trees. We will tests our skills on parts of Strade Bianche (the white gravel roads) using our Road bikes (like in the modern professional peloton) and stop for a well-deserved coffee in Castello di Brolio … or even better a glass of Chianti Classico! After all, it was Barone Ricasoli who was responsible for the creation of the wine. A special visit to their private vintage collection that the Castello di Brolio has underground has been arranged, followed by a super wine tasting. Today, Castello di Brolio is recognised as the oldest winery in Italy and still remains in the Ricasoli family!
Today’s ride takes us east from Radda in Chianti down a swooping descent towards San Gimignano, a small walled medieval hilltop town. Defined by its tower houses, San Gimignano is also referred to as “The Town of Fine Towers”. We will enjoy a photo stop in the town before riding south towards the beautiful city of Siena. After a delicious lunch, we will depart the UNESCO World Heritage Site and head north passing through the beautiful town of Castellina in Chianti before arriving back at our hotel. In the late afternoon, we will attend a special dinner in the heart of Chianti with a special wine tasting degustation.
It is time to step back in time and get ready for L’Eroica! While you were resting after yesterday’s ride, our team was busy swapping your modern machine for a classic, pre-1987 vintage Bianchi. Get ready to embrace the pure, retro magic of leather toe-clips, exposed brake cables, downtube shifters, and a classic wool cycling kit.
We will push off straight from the hotel on our vintage steeds for a dedicated test ride through the rolling hills of Chianti. This gives you the perfect opportunity to dial in your setup, get comfortable with the retro handling, and kick up a little white dust on the legendary Strade Bianche. Our route brings us directly into Gaiole in Chianti just in time for lunch, where we will dive straight into the electric pre-L’Eroica atmosphere. You’ll have the whole afternoon to explore the vibrant festival markets, soak up the buzz, and maybe hunt for some extra vintage treasure. Afterward, we’ll head back to the hotel to relax before enjoying a fantastic dinner nearby.
After an early breakfast, we head to the start area in the absolute heart of Gaiole in Chianti. You will feel like you’ve been instantly catapulted back in time, surrounded by thousands of riders on vintage steel, proudly clad in retro wool kits. The energy and excitement in the air is palpable.
The early birds taking on the epic 209 km and 132 km routes will start crossing the start line at 4:30 AM under the stars. For those looking to fully indulge in the relaxed, festival spirit of the ride, the 81 km and 46 km courses set off at 8:00 AM.
Whichever distance you choose, your best day ever on a bike is about to begin. Soak in every single mile of the L’Eroica experience, and whatever you do, do not skip the legendary feeding stations! Swap your energy gels for local Tuscan specialties, cured meats, and a splash of Chianti wine – the ultimate fuel to carry you to the finish line, where the GTP team will be waiting to toast your heroic achievement.
All good things must come to an end, but what a ride it’s been! After one last perfectly pulled espresso and a flaky cornetto, it’s time to load up the shuttle and head back to Florence Airport.
You’re heading home with a bit of Tuscan dust on your shoes, a vintage jersey packed in your bag, and some serious bragging rights. Get ready to flood the group chat with photos and share your legendary L’Eroica stories with your incredibly envious cycling friends. Safe travels, heroes!
What’s not included?
