A Journey Through Tradition and Beauty
Step into the heart of Tuscany on a truly exclusive cycling adventure, where history, culture and authentic experiences come together in perfect harmony. Your journey begins in Siena, where you will witness the legendary Palio horse race in the iconic Piazza del Campo — a centuries-old celebration of community, passion and skill.
Pedal through the rolling Chianti hills, where vineyards, olive groves and picturesque villages such as Radda and Castellina reveal the timeless beauty of the Tuscan countryside. Ride the famous Strade Bianche white gravel roads, surrounded by sweeping views of medieval towns and sun-drenched landscapes.
Explore the medieval towers of San Gimignano, wander its charming streets and immerse yourself in the region’s history. Delight in hands-on experiences such as truffle hunting with local experts, then savour authentic Tuscan cuisine and fine regional wines in intimate, welcoming settings.
Each evening, relax in carefully selected hotels tucked into stunning landscapes, sharing stories and laughter with fellow cyclists and your dedicated IBT guides. This is Tuscany like no other — immersive, authentic and unforgettable, with every moment crafted to inspire and delight.
Thanks to Italy bike Tours! It was not just a cycling tour — but we created timeless memories with them, friendships and quite moments through out our tour which we’ll cherish for a lifetime.
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!!
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.
Discover what makes this cycling holiday unforgettable, both in the saddle and beyond the ride.
Experience Tuscany’s legendary white gravel roads.
Pedal through the historic climbs surrounding the Town of Fine Towers.
Cycle through vineyards, olive groves and timeless Tuscan villages.
Enjoy beautiful rides through Chianti’s rolling countryside.
Take on varied terrain, from smooth roads to flowing gravel paths.
Experience one of the world’s most thrilling and historic horse races.
Visit a local Contrada’s ceremonial space and museum.
Join a traditional Contrada dinner on the evening before the race.
Wander through the medieval streets of the famous Town of Fine Towers.
Search the Chianti forests with a local expert and their trained dog.
Experience Tuscany at its most iconic — from Chianti and the Strade Bianche to San Gimignano, truffle hunting and the unforgettable Palio di Siena.
Welcome to Italy and the start of an amazing adventure on and off the bike! The IBT team will be there to greet you and whisk you away to your charming hotel, tucked into the stunning Chianti hills.
Take a moment to relax while we get your bike ready for the week ahead. Then, join us for a gentle ride to shake off the travel and soak in your first taste of Italy, finishing with a lively aperitivo.
Enjoy dinner and local wines, meet fellow guests, and glimpse the week ahead in Tuscany.
Hotel Belvedere di Sanleonino | Castellina in Chianti
Today’s ride takes you to the stunning hilltop city of San Gimignano, a UNESCO World Heritage site. As a well-deserved reward for your climb, we’ll pause for a gelato in the “Town of Fine Towers,” soaking up the charm and history of this medieval gem.
Back at the hotel, unwind with a shower and some relaxation before enjoying a delicious regional dinner with the team, recharging for tomorrow’s scenic loop.
Hotel Belvedere di Sanleonino | Castellina in Chianti
Today we ride to Siena, a city of quiet beauty and timeless charm. You’ll experience one of cycling’s most iconic roads - the Strade Bianche, Tuscany’s famous white gravel routes.
Roll through the stunning hills lined with cypress trees, soaking in the sweeping, majestic landscape as you ride.
In the evening, enjoy dinner in Siena with a local Contrada (community team), immersing yourself in the excitement and tradition of tomorrow’s Palio horse race - a once-in-a-lifetime adventure all in one trip.
Hotel Belvedere di Sanleonino | Castellina in Chianti
Today offers a truly unforgettable experience as the contradas, tradition, and individual courage come together in Siena’s extraordinary medieval ritual - the Palio horse race.
This is no ordinary race; it’s a dramatic test of skill, strength, and community spirit, where both horse and rider face an astonishingly challenging course.
After the race, you’ll visit one contrada’s ceremonial space and museum, gaining an up-close look at the vibrant history and living traditions of the Palio.
Hotel Belvedere di Sanleonino | Castellina in Chianti
Your day begins with a scenic Chianti loop by bike, winding through rolling hills, vineyards, and iconic cypress-lined roads. As you pedal through charming villages like Radda and Castellina in Chianti, you’ll soak in the stunning landscapes and the true essence of Tuscany.
In the afternoon, trade your bike for an unforgettable truffle-hunting adventure, guided by an expert and their trained dog. Stroll through fragrant oak forests, discover the secrets of this prized delicacy, and finish the day with a tasting of freshly foraged truffles paired with exquisite local wines.
Hotel Belvedere di Sanleonino | Castellina in Chianti
All good things must come to an end, and after an incredible few days of cycling, discovery, and unforgettable experiences, it’s time to bid farewell to Tuscany. Our team will be on hand to ensure a smooth departure, helping you with transfers and onward travel so you can leave with ease and comfort.
Wake up in Chianti with coffee, quiet hills and Palio anticipation.
Ride Tuscany’s iconic white roads through vineyards and cypress-lined hills.
Step inside Siena’s traditions and discover the spirit of a local Contrada.
Feel Piazza del Campo erupt as Siena’s legendary horse race comes alive.
End the day with local wine, Tuscan food and stories from an unforgettable race.
Reserve your place and experience Tuscany at its most iconic, from the Chianti hills to Siena and the unforgettable Palio.
Choose the bike that best suits your riding style. All three options are included for the full duration of your tour.
Explore epic landscapes! Lightweight, responsive, and adventure-ready. Perfect for gravel, touring, and thrill seekers.
Cruise in comfort with flat handlebars, smooth ride, and stylish design. Ideal for relaxed, scenic holiday cycling.
Glide through your holiday with ease; upright comfort, smooth handling, and stylish design making every ride relaxing, scenic, and unforgettable.
Looking for a different bike model? Contact us at alberto@italybiketours.com
Everything you need to know before joining us — from what’s included to transfers, riding in Tuscany, local cuisine, hotels and practical information for your Palio di Siena experience.
Please arrange to meet us at Florence Train Station (Santa Maria Novella) at 2 pm 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 of onward travel following the conclusion of your tour. We will run a morning transfer to Florence Train Station, leaving the hotel at 10.30 am.
For alternative destinations or departure times, please contact us at alberto@italybiketours.com .
Please consider eating lunch before we collect you from Florence. The transfer time from the train station to the hotel is around 45 minutes.
The general road conditions in Tuscany are very good. With a mix of smooth asphalt and rugged Strade Bianche, plus terrain ranging from gentle slopes to challenging hills, the region offers stunning views and rewarding rides at every turn.
Tuscany’s cuisine is a celebration of simple, fresh ingredients and traditional flavours. Known for its rustic dishes, local produce such as olive oil, truffles and Pecorino cheese plays a key role, along with Tuscany’s famous Chianti wines.
The hotel on this tour has a pool, and we recommend bringing your swimming costume. The hotel also offers laundry service, good Wi-Fi and bar service. Some facilities may be subject to an additional charge.
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.
We welcome the opportunity to create this experience as a private tour for your group. A private departure gives you greater flexibility when choosing your dates and allows us to personalise selected elements of the itinerary according to your requirements.
Whether you are travelling with friends, family or a cycling group, our team can help tailor the experience while keeping the highlights of Tuscany, the Strade Bianche and the Palio di Siena at the heart of the tour.
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.
If you’d like help arranging any hotels or activities before or after your tour, please contact lynn@italybiketours.com .
Stay in the heart of Tuscany at a carefully selected 4-star hotel, surrounded by the vineyards, rolling hills and timeless landscapes of Chianti.
More unforgettable ways to experience Italy — from the legendary roads of the 1000 Miglia to the iconic route from Milan to Sanremo.
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.
You can also chat to us online using the button at the bottom right of the page, or send us an email directly.
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