The very best of Tuscany reveals itself when you move beyond the guidebook.
Discover Tuscany by bike, riding through rolling hills, vineyards and iconic towns such as Florence, Siena, Pienza and San Gimignano. Each day brings a new blend of history, scenery and authentic Italian charm.
Follow beautiful country roads lined with cypress trees, olive groves and vineyards, with thoughtfully designed routes for different riding levels. It’s the perfect way to experience the landscapes that make cycling in Tuscany so unforgettable.
Ride through Chianti wine country, visit welcoming local wineries and enjoy traditional Tuscan food, celebrated wines and long, relaxed moments around the table.
Discover the legendary Strade Bianche and Tuscany’s famous white gravel roads. A journey where cycling, culture, food and wine come together in true Italian style.
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.
Ride through Chianti vineyards to charming Greve.
Climb to Castellina and its hilltop history.
Conquer the legendary White Roads!
Pedal through Tuscan hills to two of the most iconic towns.
Cycle through striking, moonlike landscapes and rolling clay hills.
Go truffle hunting in the Tuscan woods.
Sip Chianti wines with amazing vineyard views.
Stroll through Siena’s medieval streets and legendary "contrade".
Take in the timeless beauty of Val d’Orcia’s rolling hills, cypress paths, and quiet villages.
Enjoy open-air dining under the stars in iconic Tuscan hilltop towns.
Slow down, breathe it in and enjoy the rhythm of the landscape, the food and the ride. This is Tuscany at its purest — warm, scenic and unforgettable.
Your Tuscan adventure begins! Upon arrival, you'll meet your friendly guide and head straight to your hotel where, once settled, we'll ensure you're perfectly set up with a professional bike fit.
We will then do our first ride into the heart of Chianti, surrounded by history, beauty and the unmistakable spirit of Tuscany. A perfect first taste of the landscapes, flavours and cycling culture that make this region unforgettable.
Hotel Villa Le Barone | Panzano in Chianti
Prepare to climb deep into the heart of the Chianti Classico region. Our route takes on the area's iconic, rolling Chianti Hills, which are crowned with majestic medieval towns, still enclosed by their original seven-century-old stone walls.
Our destination and well-earned reward is the stunning hilltop fortress of Castellina in Chianti. Take a moment here to soak in the serene beauty, a peaceful contrast to the historic conflicts between Siena and Florence that defined this land.
But the real highlight awaits: a perfect, well-deserved Italian gelato to celebrate the climb before we return to the hotel!
Hotel Villa Le Barone | Panzano in Chianti
Our journey continues as we descend from the fortified hilltop village of Radda in Chianti toward the picturesque town of Gaiole in Chianti.
Gaiole is the gateway to some of Tuscany’s most legendary cycling. It is the birthplace of the famous Strade Bianche race, which follows the rustic, white gravel farm routes that dramatically crisscross the Tuscan panorama. Near here also stands the stunning Brolio Castle, a symbol of the region’s enduring history.
As the spires of Siena come into view, prepare to be completely overwhelmed by its medieval sublime. The grand finale of this leg is one of Italy's most beautiful, historic cities.
Hotel La Torre alle Tolfe | Siena
After a good breakfast, today's ride first brings us to the storybook castle of Monteriggioni. This entire fortified town, famously featured in the movie Gladiator, is completely encircled by a crown of imposing walls - a breathtaking sight that truly transports you back in time.
Next, we head to San Gimignano, a magnificent UNESCO World Heritage Site. Known as the "Medieval Manhattan," San Gimignano's noble families once competed to build the tallest towers, with 72 rising above the town in the 13th century. Today, fourteen of these magnificent towers still dominate the sky.
Hotel La Torre alle Tolfe | Siena
Prepare for a truly unique cycling experience across the Crete Senesi, the "clays of Siena." You will ride over what was, for two million years, an ancient ocean seabed. Today, this land of grey-blue clay, chalk, and rock salt creates an otherworldly landscape, often compared to the surface of the moon.
Our cultural ride visits historic villages: Asciano, a 13th-century Sienese stronghold, and Buonconvento, showcasing Sienese landscape painters.
The day concludes in Montalcino with a planned dinner where you will enjoy traditional Tuscan dishes paired with the region’s iconic, world-renowned wine, Brunello di Montalcino.
Chiostro di Pienza | Val d'Orcia
We start the morning early, setting off toward Montepulciano, one of Tuscany’s most famous and charming hilltop towns. Enjoy a leisurely ride through rolling landscapes, culminating in a stop for a well-deserved coffee in the heart of this iconic village.
After soaking in the sweeping views and unforgettable atmosphere, we return to the hotel for check-out. It’s time to say arrivederci to Tuscany after an truly unforgettable cycling experience.
Wake up to quiet countryside, vineyards and cypress-lined hills.
Cycle through rolling hills, vineyards and timeless hilltop villages.
Stop in a village square for a proper Italian coffee break.
Enjoy a well-earned lunch filled with authentic local flavours.
Raise a glass as the afternoon light turns the Tuscan hills golden.
Choose the departure that suits you best and reserve your place on the tour.
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 Luxury Tuscany and Vineyards tour.
Please plan to meet us at Florence Train Station (Santa Maria Novella) at 2pm. Your guides will contact you via WhatsApp 24 hours in advance to confirm the name of the staff member meeting you.
Following the conclusion of the tour, we will assist you with planning and booking of onward travel. We will run one transfer to Florence Train Station (Santa Maria Novella) 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 Florence to the first hotel is approximately 1 hour. Transfer back to Florence train station on the last day takes around 2 hours.
The general road conditions in Tuscany are good, and most roads are quiet with light traffic. The majority of the roads are tarmac, but we will also be riding on some gravel roads - these are well maintained and enjoyable whether you’re on a road, gravel, or E-bike.
The food in Tuscany is exceptional, with a variety of local specialties to enjoy. Restaurants now cater for both vegan and vegetarian diets. Homemade local red wines like Brunello and Chianti are a must-try!
The hotels on this tour have pools, so we recommend bringing swimming costumes. Hotels also provide good Wi-Fi, bar service, and air conditioning. Some facilities may incur an extra charge.
We welcome the opportunity to discuss a private tour with you should you be in a group of six or more. A private tour allows you to choose dates and personalize the itinerary according to your requirements.
The weather in Tuscany is excellent during the spring and autumn months. It can be hot in July and August, so those who prefer cooler riding conditions should consider joining us in April, May, September, or October. Ride times may be adjusted to account for extreme weather events.
Are you thinking about joining us? You probably have some questions! The best way to reach us is via email — we’ll reply within 24 hours. Please check your spam/junk folder if you haven’t heard back. 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.
Carefully selected hotels in Tuscany’s most beautiful locations — from the rolling hills of Chianti to the spectacular Val d'Orcia.
More unforgettable journeys across Italy — from the majestic Northern Lakes to the iconic trulli of Puglia.
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.
info@italybiketours.com →
