Explore Tuscany by bike

Bike tours in Tuscany

4 tours see all tours

In brief

Historic beauty and delicious surprises

Tuscany is one of the most sought-after destinations for cyclists, with iconic routes leading through white gravel roads, cypress-lined avenues, medieval villages, vineyards and art cities. The more you pedal, the more you immerse yourself in a landscape that feels almost painted — from the rolling Chianti hills to the Renaissance skyline of Florence. Regain your strength with a well-deserved gourmet break: Chianti Classico, bistecca fiorentina and fresh pecorino are never far away.

TO KNOW

Florence, Siena, Chianti, and everything in between

Florence and its Renaissance treasures, the Leaning Tower of Pisa, and Siena — home to the famous biannual Palio — are the unmissable anchors of any Tuscany cycling itinerary. But the real magic often happens in between: the Chianti hills and their world-famous wine, the walled town of Monteriggioni, the medieval towers of San Gimignano. In Tuscany, even the detours are worth it.

Organized bike tours in Tuscany

Start your Tuscan adventure worry-free and let us handle the logistics. We’ll book comfortable hotels and guesthouses along the route, transport your luggage stage to stage, and have your rental bike — or e-bike, if the Chianti hills call for a little extra help — ready and waiting at the start. Our operating base is right in Pisa, with over 150 bikes and a dedicated on-site colleague who delivers the bikes, transfers the luggage, and is your point of contact throughout the trip. We also provide an app with maps, a roadbook, points of interest, GPS tracks, and a seven-day-a-week support service.

Tours

Round tour from Pisa to Florence

Discovering Pisa, Florence and everything in between has never been easier: our round tour offers cycling stages within everyone’s reach, along quiet secondary roads and short stretches of scenic white gravel. You’ll soak up the romantic atmosphere of the Tuscan countryside before arriving in the magnificence of Florence. And don’t rush past Lucca and Pistoia — lesser-known but equally beautiful, they often turn out to be the highlights of the trip.

Siena and the Chianti hills

For cyclists with stronger legs and a taste for a challenge, this is Tuscany at its most rewarding. The route winds through the Chianti hills with numerous climbs and descents, connecting Pisa and Florence via Siena and some of the region’s most enchanting medieval villages — Gaiole in Chianti, San Gimignano, Monteriggioni. The landscapes are spectacular, the wine is world-famous, and the cuisine is every bit as good as the scenery.

FAQ

Our promise to those who travel with us is this: cycle easy, travel light. These words capture the essence of what we do. Choose your favourite cycling holiday and leave the rest to us: itinerary, handpicked accommodation, luggage transfer between stops and multilingual dedicated assistance.

Our Tuscany cycling holidays have been carefully refined over many years — these are well-tested itineraries that we know inside out, from the best back roads to the most rewarding stops along the way. We also have a dedicated operating base in Pisa, with over 150 bikes and an on-site colleague who handles bike delivery, luggage transfers and on-tour support from late March to early October.

Tuscany is a great cycling destination from March through to October. Spring is the finest time to ride: mild temperatures, the countryside in full bloom, and far fewer crowds than in summer. September and October are equally rewarding. July and August are perfectly manageable, though the heat can be demanding on the hillier sections, making an e-bike a very sensible choice.

Our routes take you through some of the most iconic landscapes and cities, like Florence, Pisa, Siena, Lucca, the Chianti hills, the medieval towers of San Gimignano, the walled town of Monteriggioni. But the real pleasure of cycling here is everything in between: the quiet white gravel roads, the hilltop villages, the vineyards, the unexpected views around every bend. For a deeper look at what Tuscany has to offer, read our complete travel guide on the blog.

On our self-guided bike tours in Tuscany, we provide everything you need to find your way: detailed maps and route descriptions, and access to the Ride with GPS app, with GPS tracks and route content, available offline too.

You can rent the bike that suits you best — it will be ready and waiting at your starting point. You can choose between an e-bike and a standard bike and, if you’re travelling with family, there are plenty of accessories for children of all ages, from child seats to bike trailers. On some trips you can also bring your own bicycle. Check the trip page for full details on available bikes.

Wearing a helmet while cycling in Tuscany is not required by law. For your safety, we always recommend wearing one, so make sure to bring yours.

Every morning you leave your luggage at the reception desk and we take care of transporting it to your next accommodation. We will provide you with luggage labels and drop-off times. During the day, you can carry your essentials in the side bag provided with your rental bike. The service is always included in the price. Cycling light makes all the difference.

Accommodation varies depending on the trip. It can range from hotels and guesthouses to B&Bs. We handpick every property with care, favouring those conveniently located along the route. Breakfast is always included. For full details, check the “Comfort” section on the trip page.

Every bike tour includes: handpicked accommodation with breakfast, luggage transfer, route materials and multilingual assistance. Depending on the trip, you can add extra services to your quote, such as bike rental, meals, extra nights and transfers.

Yes, and that’s one of the best things about self-guided tours. You pick the date that suits you, within the tour’s season. A few tours have fixed start days for logistical reasons — this is always flagged on the tour page.

From the moment you book until you’re back home, we’ve got you covered. On self-guided trips, it is good to be prepared for the small mechanical hiccups that come with cycling — that’s why we provide a full repair kit with everything you need to handle a flat tire on your own. For anything else, our support line is available 7 days a week, from 8 AM to 8 PM.

We strongly recommend it. A good policy should cover medical expenses, trip cancellation and cycling-specific incidents. Travel insurance is not included in the tour price and must be arranged independently before your trip.

It is simple: choose your trip, get your quote, and book directly online by filling in the required details and paying a deposit by credit card or bank transfer. Within 3 working days we will send you a confirmation email or an update. If you have any questions or doubts, get in touch. We are available by phone or email.

Assistance

Luggage transportation
Traveling light makes all the difference! All travel itineraries come with our signature luggage transport service: simply leave your bags at the front desk each morning and we’ll drop them off at your next lodging.

 

Tour information
We’ll send you all the tour information before you set off on your adventure. It contains practical information, instructions on how to reach the starting point, a list of hotels, and answers to frequently asked questions. For our self-guided tours, we’ll also hand over detailed maps and roadbooks, in either physical or digital format, so you can follow the route on your own.
No need to worry about figuring out which turn to take if you opted for one of our group trips; in this case, your chaperone will gladly tell you where to go next!

 

Need help?
We plan your trip carefully to prevent any mishaps, but in case you need assistance, we’re available for support 7 days a week, from 8 a.m. to 8 p.m.

Discover more

Girolibero Cycling holidays

Holidays on cycle paths and the best cycle tourism routes in Italy and Europe, featuring accommodation in selected facilities, luggage transport services, informational materials, bike rentals, and dedicated assistance.

Discover all bike tours

Travelers’ Tips and Stories

Famous for its Renaissance cities brimming with history and art, Tuscany also boasts charming villages nestled in lush green hills, such as San Gimignano and Volterra, and excellent cuisine that will delight every tourist’s palate

Tuscany travel guide, the best places to visit

Receive our newsletter

Loving what you have read so far? Stay in the loop and get free travel tips, ideas, and news from us!

Any doubts?

Search by topic and find answers to your questions on Girolibero holidays and services.

prices
tour-notes