A Tuscany bike tour is one of the best ways to discover this world-famous region of Italy.
Rolling hills, cypress-lined lanes, well-kept vineyards and medieval towns create the backdrop, but what makes the experience really special is how easy it becomes when you join a supported cycling tour.
I took part in a guided bike tour of the Via Francigena through Tuscany in 2017. Since then, the team at Epic Road Rides have spoken with many local experts to understand what makes Tuscany cycling tours so worthwhile. A great operator doesn’t just handle logistics like luggage transfers, navigation and bike hire – they also add depth through local insight, curated routes and personal connections.
In this guide, we’ve chosen three very different approaches: a classic point-to-point route between two of Tuscany’s greatest cities, a small-scale operator crafting bespoke itineraries, and a luxury option offering pro-level support. Together, they showcase the range of cycling tours in Tuscany – from self-guided adventures to fully supported, high-end escapes.
Prego! (You’re welcome!)
Fran Wilson is a cyclist based in the North East of England and has a particular passion for cycle touring. Her love for cycling has seen her take on some of the UK and Europe's best-known multi-day cycle routes, including the Hebridean Way, Camino de Santiago and the Via Francigena.
Beyond exploring on two wheels, Fran is a key member of the Epic Road Rides team and is usually found writing travel guides for other cyclists who also want to explore the world by bike.
We’ve worked with all of the bike tour operators featured in this article over the years (there are links to our interviews with them in the relevant section). We have chosen to include them in this article because the Tuscany cycling experiences they offer are ones we’d suggest to a friend, or book ourselves, if we were heading to Tuscany.
1. Pisa to Florence with Girolibero
View of Florence’s impressive skyline
The riding
Cycling from Pisa to Florence is a relaxed way to see Tuscany at a gentle pace. The route links two of Italy’s most celebrated cities via quiet back roads, riverside paths, and Tuscan towns that burst with character, such as Lucca, Montecatini Terme and Vinci.
The riding is mostly flat or gently undulating, making it accessible to many fitness levels. There are also options to shorten days by train if needed. This is a slower, more immersive way to experience the landscapes between Pisa’s UNESCO-listed Leaning Tower and Florence’s Renaissance treasures than racing through in a car.
What we like
Girolibero has been running cycling holidays in Tuscany since 2009 and knows this route inside out. A dedicated team member in Pisa keeps everything running smoothly – from bike delivery and luggage transfers to on-the-ground support if issues arise.
We like the balance Girolibero strikes: well-organised logistics, flexible route variations, and carefully chosen hotels, all backed by years of refinement. Their cycling tours feel reliable and easy, without losing the charm of exploring authentic Tuscany on two wheels.
What else do they offer
Girolibero runs a wide choice of self-guided bike tours in Tuscany, including Pisa to Florence loops, tours linking Pisa, Siena and Florence, and shorter point-to-point journeys. Beyond Tuscany, they operate trips in many other areas of Italy, including Puglia, Piedmont, Umbria, South Tyrol, the Dolomites and Veneto. They also offer trips in France’s legendary Loire Valley.
More information
- Guide to Pisa to Florence bike tours offers an in-depth look at the route and what Girolibero has to offer.
- Girolibero’s website to find out more.
2. Tuscany South with GustoCycling
From Pienza overlooking Val d’Orcia UNESCO World Heritage area with Monte Amiata in the background (photo credit: GustoCycling)
The riding
Tuscany South is all about wide horizons, strade bianche (white gravel roads), and hilltop towns that look lifted from Renaissance paintings. This route links Siena with Montalcino, Pienza and Montepulciano, combining some of the region’s most historic towns with its UNESCO-listed Val d’Orcia landscapes.
Expect a mix of (largely) smooth asphalt and gravel, steady climbs and rewarding descents, plus plenty of chances to stop in wine estates and trattorias along the way. Each day feels like a journey through Tuscany’s agricultural and cultural heart.
What we like
GustoCycling is run by Marco Mori, whose family roots are in Montecatini Terme. His knowledge of Tuscany is deep, and his approach is personal – every itinerary is bespoke, with routes tailored to the group and daily check-ins to ensure everything runs smoothly.
We like the flexibility Marco offers. There are no set departure days, and if you want detours, family-friendly distances, or even a honeymoon itinerary, he’ll design it for you. It’s cycling in Tuscany with the reassurance of local expertise and the feel of travelling with a friend who knows every back road.
What else do they offer
GustoCycling focuses exclusively on Italy, with most tours in Tuscany. Options include Tuscany North (Lucca to Siena), Tuscany South (Siena to Montalcino), Chianti, and bespoke itineraries that combine multiple regions.
Marco also arranges bike hire, wine tastings and accommodation, making his trips among the best Tuscany bike tours for travellers wanting a highly personalised experience.
More information
- Guide to cycling in Tuscany provides further detail on the Tuscany cycling routes offered by GustoCycling.
- GustoCycling’s website to find out more.
3. Chianti Classico with InGamba
Dinner being prepared for guests in a cosy Italian villa (photo credit: inGamba)
The riding
InGamba’s Chianti Classico tour is their flagship Tuscany trip – born from founder João Correia’s time as a professional rider and his dream of sharing this landscape with others.
Riding here means endless ribbons of smooth asphalt, vineyard-clad hills, and climbs that test the legs before rewarding you with sweeping descents. Days are filled with panoramic views, quiet country roads, and stops to meet local winemakers and artisans. It’s the quintessential “eat, drink, ride” experience, delivered with precision and flair.
What we like
Few operators deliver cycling holidays with the polish of InGamba. Their level of service – pro-level bikes, daily massages, expert mechanics, and ride support from experienced guides – is matched by a warmth and authenticity that keeps guests coming back. More than half of their riders are repeat guests, which says it all!
We like how seamlessly they combine world-class riding with outstanding hospitality. Nothing feels left to chance, but nothing feels impersonal either. It’s an experience that’s crafted, not packaged.
What else they offer
InGamba runs luxury Tuscany cycling tours as well as luxury tours in Portugal, Spain, the Dolomites and France.
Further afield, they also operate rides along California’s coast and in the Azores. But Tuscany remains at the heart of their story, and we think the Chianti Classico trip is still the one that captures it best.
More information
- Guide to luxury bike tours delves into what InGamba has to offer in Tuscany (and beyond).
- InGamba’s website to find out more.
What’s next?
Have you been on a Tuscany bike tour before? We’d love to hear about your experience. Drop us a comment below.
Looking for more useful information to help you start planning a Tuscany cycling holiday? Don’t miss:
- The best bike hotels in Tuscany, to find your perfect base.
- The best cycling tours in Italy, for more supported trips in this classic destination.
- A guide to the best Italy cycling regions, for useful insights on other corners of the country.
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If you want someone to help you plan and book your cycling holiday, fill out this form. We aren’t a tour operator/agent but we work with lots of people who are and will do our best to put you in touch with someone that can help (within 24 hours where possible)!Fran Wilson is a cyclist based in the North East of England and has a particular passion for cycle touring. Her love for cycling has seen her take on some of the UK and Europe's best-known multi-day cycle routes, including the Hebridean Way, Camino de Santiago and the Via Francigena.
Beyond exploring on two wheels, Fran is a key member of the Epic Road Rides team and is usually found writing travel guides for other cyclists who also want to explore the world by bike.
First Published: 24 October 2025
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