The Ultimate Guide to Cycling Tuscany

Thinking about cycling Tuscany? You’re in for one of the best riding experiences in Europe. Few places mix smooth roads, rolling hills, historic towns, and legendary food the way Tuscany does — and that’s before you even touch the famous Strade Bianche gravel.

This guide keeps things practical, fun, and easy to use — perfect whether you’re planning your first trip or coming back for more.

What you’ll find in this guide

• A clear overview of Tuscany 

• When to go 

• The best base towns

• Top must-see places in Tuscany

• The most iconic cycling routes and areas

• Best cycling tours

• How to get to and around Tuscany

• And much, much more

Why Cycle Tuscany

Tuscany is one of Italy’s most rewarding regions for cyclists, offering a rare combination of beautiful terrain, rich culture, and strong cycling infrastructure.

Here are the key reasons riders from all over the world choose Tuscany for their cycling holidays:

1. Varied terrain for all levels

Tuscany offers everything from gentle vineyard hills and scenic valleys to challenging climbs in the Apennines and fast, flat rides near Lucca and the coast. You can easily mix different riding styles in one trip.
Not sure how to combine all these in one trip? Ask our experts!

2. Iconic white gravel roads (Strade Bianche)

Tuscany is home to the famous “strade bianche” — white gravel roads made legendary by the Strade Bianche professional race. These quiet rural roads provide some of the most atmospheric gravel riding in Europe.

3. A rich cultural and historical backdrop

Cycling here means riding through medieval towns, UNESCO landscapes, fortified villages, monasteries, and postcard-perfect hilltops. Every route comes with built-in sightseeing.

4. Food, wine, and local flavour along the way

Tuscany blends cycling with gourmet culture: Chianti Classico tastings, pecorino from Pienza, handmade pasta, olive oil mills, and farm-to-table trattorias. Refuelling becomes part of the experience.

If you’d like to combine the culinary experience with cycling, check out our Wine & Bike Tour.

5. Strong cycling infrastructure

The region has thousands of kilometres of cycling routes, quiet secondary roads, rental shops, and accommodations used to hosting cyclists. Everything you need is easy to find.

6. Compact, accessible region with huge variety

Tuscany is large enough to offer:

• diverse terrains but

• compact enough to explore efficiently.

You can ride from vineyard hills to coastal flats or from medieval towns to mountain climbs without long transfers.

7. A long and favourable cycling season

Thanks to its Mediterranean climate and varied elevations, Tuscany offers excellent riding conditions from early spring to late autumn. Lower-altitude and coastal zones remain rideable even in winter.

Quick Overview of Tuscany as a Cycling Destination

Tuscany is one of Europe’s most complete cycling regions — a place where varied landscapes, reliable cycling infrastructure, and genuinely bike-friendly services all come together.

Below is a quick breakdown of what defines Tuscany as a cycling destination.

Location

Tuscany is located in central Italy, stretching from the Tyrrhenian Sea on the west coast to the foothills of the Apennine Mountains in the east. The region covers roughly 23,000 km², making it:

• large enough to offer diverse riding conditions but

• compact enough that coastal flats, rolling inland hills, and mountain climbs are all within easy reach.

It includes well-known provinces such as Florence, Siena, Pisa, Lucca, Arezzo, and Grosseto. Tuscany’s central position also makes it easy to combine a cycling holiday here with other regions like Umbria, Emilia-Romagna, or Lazio.

Landscapes

Few places offer as much landscape variety as Tuscany. Here’s what you should know at a glance:

• Central Tuscany features the iconic rolling hills of Chianti, Val d’Orcia, and Crete Senesi — a mix of vineyards, olive groves, cypress-lined ridges, and medieval hill towns.

• Northern Tuscany around Lucca and the Versilia coast is flatter and ideal for faster, easier rides. To the east, the terrain rises into the Apennines, where longer and cooler climbs appeal to riders seeking more elevation.

• The Maremma coastline adds something different again: pine forests, coastal plains, gentle seaside roads, and wide-open views. Because the landscapes change quickly across short distances, it’s easy to build a mixed itinerary with different riding styles day to day.

Cycling Infrastructure

Tuscany has developed one of Italy’s best cycling networks, supported by thousands of kilometres of quiet rural roads and mapped cycling itineraries.

The region is famous for its “strade bianche” — white gravel roads that run through farmland, vineyards, and ridges, and feature in major professional races.

Traffic drops noticeably once you leave major cities, and the dense network of secondary roads makes it possible to design loop rides without backtracking. Whether you’re self-guided or on a tour, the infrastructure makes route-planning simple and riding smooth.

Bike-Friendly Services

Cycling tourism is well supported across Tuscany, including essential services, such as:

• rental shops for road, gravel, and e-bikes;

• repair workshops;

• luggage-transfer services;

• and hotels equipped with bike storage and washing facilities.

Many cafés and restaurants in cycling areas are accustomed to riders stopping mid-route, and most towns offer easy access to water fountains, small grocery stores, and shaded rest points.

Towns like Lucca, Siena, Pienza, and Greve in Chianti in particular have built strong reputations as cycling hubs. Combined, these services make Tuscany not only beautiful to ride, but also easy and comfortable to navigate.

When to Go

Tuscany has one of the most enjoyable and cyclist-friendly climates in Italy. With mild springs, warm but manageable summers, long golden autumns, and rideable low-altitude winters, the region offers excellent cycling conditions for most of the year.

• March–June: Prime cycling season with perfect temperatures

• July–August: Hotter inland — best for early starts or coastal routes

• September–October: Ideal late-season weather with quieter roads

• November–February: Mild but variable conditions, best near the coast and lower elevations

Below is an overview of what to expect in each season so you can plan your Tuscany cycling trip with confidence.

Spring (March–May)

Spring is one of the very best times to cycle Tuscany. The landscapes turn lush green, vineyards start to come alive, and the air is crisp and clear — perfect for long days in the saddle. Temperatures rise steadily without the intensity of summer, and the classic rolling hills are at their most scenic. Traffic is still moderate outside major holiday weekends.

Temperatures: 15–24°C

Best for: All cyclists — ideal balance of warmth, daylight, and comfort

Why ride in spring:

• Pleasant temperatures for both long climbs and relaxed rides

• Longer daylight hours

• Vibrant green hills and excellent visibility

• Perfect for road, gravel, and e-bike routes across all regions

Summer (June–August)

Summer in Tuscany is beautiful but warm, especially inland around Siena, Chianti, and Val d’Orcia. If you plan to cycle in these months, timing matters: early-morning starts are essential. The coastal areas and northern zones near Lucca stay cooler thanks to sea breezes. Expect more visitors in tourist hotspots and busier roads around beaches.

Temperatures: 28–35°C (hotter inland in July–August)

Best for: Early starters, coastal riders, and shorter scenic loops

Good to know:

• Start early to avoid midday heat

• Coastal routes offer cooler temperatures

• Expect more tourists, especially near Pisa, Lucca, and the beaches

• Gravel routes and open ridgelines get very hot mid-day

If your heart is set on cycling in summer but prefer cooler climbs and quieter roads, consider riding in the Alps. The Dolomites or Slovenia just across the border are wonderful this time of the year.

Autumn (September–November)

Autumn is often considered the best season for cycling Tuscany. The heat drops quickly, the light turns golden, and the region enters the harvest period — a fantastic time for wine lovers. September is warm and lively, while October and early November are quieter, ideal for long scenic rides through Chianti, Val d’Orcia, and the Maremma.

Temperatures: 18–28°C in early autumn, cooling to 12–20°C by November

Best for: Warm but comfortable weather, quieter roads, and cultural exploration

Why ride in autumn:

• Stable, comfortable temperatures

• Clear skies and perfect visibility for ridge rides

• Fewer crowds after mid-September

Harvest season: wine tastings, olive oil mills, and local festivals

Winter (December–February)

Winter is not ideal for cycling, but Tuscany’s lower elevations and coastal areas remain mild enough for enjoyable riding.

If you are set on cycling during this months, we’ recommend exploring our epic bike tours in Spain and Portugal.

Top Cycling Routes in Tuscany

Tuscany is packed with world-class cycling terrain, but a few regions consistently stand out for their scenery, road quality, and overall riding experience.

From iconic white-gravel sectors to panoramic vineyard loops and breezy coastal roads, these are the areas riders return to again and again.

In a nutshell: the top cycling regions:

1. Chianti Classico

2. Strade Bianche & Siena

3. Val d’Orcia & Crete Senesi

4. Lucca & the Northern Hills

5. Maremma & the Tuscan Coast

6. The Apennines & Casentino

These regions form the backbone of a great cycling trip in Tuscany. Below, we take a closer look at each one — what makes it special, why cyclists love it, and who it’s best suited for.

1. Chianti Classico

(Greve – Panzano – Radda – Gaiole – Castellina)

Best all-around region for classic Tuscan hills, vineyards, and ridge-top views

Chianti Classico is Tuscany’s signature cycling landscape. The area is filled with winding roads through vineyards, olive groves, and medieval wine towns, with steady climbs and long panoramic ridges. Traffic is moderate, and the scenery changes constantly, making it perfect for riders who want the quintessential Tuscany experience without extreme gradients.

Why cyclists love it:

• Iconic Tuscan scenery in every direction

• Steady, manageable climbs and rewarding descents

• Roads connect beautifully → endless loop options

• Wine villages perfectly spaced for food and coffee stops

• Smooth tarmac + quiet secondary roads

Good for: intermediate riders, road cyclists, e-bikes, scenic explorers

2. Strade Bianche & Siena

(Siena – Asciano – Radi – Castelnuovo Berardenga)

The best region for white gravel and the legendary Strade Bianche sectors

This area forms the core of Tuscany’s famous “strade bianche” network — white gravel lanes used in the Strade Bianche pro race. The mix of rolling hills, ridge passes, and remote farm roads creates some of Europe’s most iconic gravel cycling. Expect beautiful views and a nostalgic, old-world atmosphere.

Why cyclists love it:

• Rideable sections of the real Strade Bianche race

• Smooth, well-maintained gravel with predictable gradients

• Big-sky landscapes and panoramic ridgelines

• Perfect balance of challenge and enjoyment

• Siena makes an unbeatable start/finish town

Good for: gravel riders, road cyclists comfortable on gravel, strong e-bikers

3. Val d’Orcia & Crete Senesi

(Pienza – Montalcino – Montepulciano – San Quirico d’Orcia)

Best region for postcard landscapes and rolling, cinematic roads

Val d’Orcia is one of Italy’s most photographed regions — and even better on a bike. Long, rolling hills, cypress-lined avenues, and wide-open scenery create a rhythmic ride that feels like cycling through a Renaissance painting. Expect sustained rolling terrain rather than sharp climbs.

Why cyclists love it:

• Tuscany’s most iconic viewpoints

• Long, scenic ridges perfect for photography

• Ideal terrain for steady effort rides

• Excellent wine towns for mid-ride stops (Brunello, Vino Nobile)

• Both road and gravel routes work beautifully here

Good for: intermediate riders, photographers, gravel fans, scenic road riders

4. Lucca & the Northern Hills

(Lucca – Monte Serra – Garfagnana – Versilia Coast)

Best region for flatter miles, smooth climbs, and summer-friendly riding

Lucca is Tuscany’s most cyclist-friendly base for those who want variety with lower difficulty. The plains around Lucca are flat and fast — a rarity in Tuscany — while the nearby hills offer longer, cooler climbs like Monte Serra. The Versilia coast adds laid-back seaside cycling.

Why cyclists love it:

• Plenty of flat or undulating routes

• Monte Serra = one of Tuscany’s best long climbs

• Cooler temperatures in summer

• Strong cycling culture + many rental shops

• Easy access to the coast

Good for: beginners, endurance riders, summer travellers, mixed-ability groups

5. Maremma & the Tuscan Coast

(Castagneto Carducci – Bolgheri – Populonia – Marina di Alberese)

Best region for summer cycling and quiet, scenic coastal roads

The Maremma coastline is perfect for cyclists wanting sea breezes, pine forests, gentle gradients, and quieter roads than the inland hotspots. The area around Bolgheri offers rolling wine-country terrain, while the southern Maremma opens up into wild coastal landscapes and national parks.

Why cyclists love it:

• Cooler temperatures in summer

• Flat to rolling coastal roads

• Pine forests and seaside promenades

• Fewer crowds than inland Tuscany

• Excellent food and wine (Bolgheri Superiore region)

Good for: summer riders, casual cyclists, e-bikes, relaxed touring

(PHOTO)

6. The Apennines & Casentino

(Arezzo – Camaldoli – Passo della Calla – Pratomagno)

Best region for challenging climbs and cooler mountain air

For strong riders, the Apennine foothills and Casentino forests offer long climbs, shady roads, and crisp temperatures — a welcome change from Tuscany’s hot valleys. Expect big elevation gains, forested routes, and rugged landscapes.

Why cyclists love it:

• Long, steady mountain climbs

• Cooler temperatures in warm months

• Low-traffic roads in natural parks

• Perfect for big training days

• Spectacular descents into Casentino and Arno Valley

Good for: advanced cyclists, climbers, gravel adventurers

Best Base Towns in Tuscany

Choosing the right base can make or break your cycling experience. Tuscany has many beautiful towns, but some work far better for cyclists thanks to terrain variety, road access, bike services, and overall convenience.

Here are the best places to use as your home base — depending on the kind of rides you want.

Lucca

Lucca is one of Tuscany’s top cycling hubs. The terrain around the town is surprisingly flat for Tuscany, making it perfect for warm-up days, recovery rides, and long, fast loops. You also have quick access to hillier terrain north toward the Apennines. The town itself is lively, walkable, and full of cafés — ideal for post-ride evenings.

Why base here:

• Excellent mix of flat and hilly rides

• Strong bike culture + many rental and repair shops

• Close to Pisa Airport

• Beautiful walled old town for rest days

Best for: Riders who want variety, easier routes, and convenience.

Siena

Siena sits at the heart of classic Tuscan cycling. The famous Strade Bianche gravel roads extend right from town, and you’re surrounded by rolling hills in every direction. It’s a stunning, medieval city with great food, but expect more climbing than in northern Tuscany.

Why base here:

• Perfect access to Strade Bianche

• Endless rolling hills and vineyard loops

• Close to Chianti + Val d’Orcia

• Iconic historic centre

Best for: Gravel lovers, road cyclists who enjoy climbing, and anyone wanting the “classic Tuscany” experience.

Greve in Chianti

Greve sits in the centre of Chianti Classico wine country — a dream setting for scenic, quieter rides. Roads wind through vineyards, olive groves, and panoramic ridges, with climbs that are challenging but steady. Smaller and calmer than Siena, perfect for a countryside-based trip.

Why base here:

• Chianti’s best climbing and ridge views

• Quieter countryside roads

• Easy loops to Panzano, Radda, Gaiole, Castellina

• Wine-focused region with great food

Best for: Riders wanting peaceful, scenic routes and a village atmosphere.

Pienza

Pienza is the perfect base for exploring Val d’Orcia — one of the most photographed landscapes in Italy. Expect rolling terrain, cypress-lined hills, and iconic Tuscan views around every corner. It’s gravel heaven and one of the best places for intermediate and advanced riders.

Why base here:

• Direct access to Val d’Orcia’s classic roads

• Beautiful loops to Montalcino, Montepulciano, San Quirico

• Great for both road and gravel

• UNESCO landscapes

Best for: Scenic riders, photographers, and anyone wanting the pure “Tuscany countryside” feel.

Montalcino

A paradise for experienced cyclists. Montalcino sits high on a hill, so every ride starts or ends with a climb. The surrounding area mixes smooth tarmac with top-tier gravel routes — including stretches of the Eroica and Strade Bianche corridors. After your ride: Brunello wine.

Why base here:

• Challenging climbing routes

• Excellent gravel and mixed-terrain options

• Authentic medieval atmosphere

• Brunello wine culture

Best for: Strong riders and gravel enthusiasts.

Volterra

Volterra is a great base if you want quieter, less-discovered cycling. The town sits on a steep hilltop, offering instant views and spectacular descents. The rides here are remote, scenic, and perfect for cyclists wanting something beyond the Chianti-Val d’Orcia triangle.

Why base here:

• Remote, peaceful cycling

• Long ridge roads and valley loops

• Dramatic landscapes with fewer tourists

• Authentic Tuscan town with Etruscan history

Best for: Riders seeking quieter routes and cinematic landscapes.

The Best Way to Experience Tuscany? Cycle from Village to Village

These towns make fantastic bases — each with its own charm, scenery, and cycling routes. But the truth is, the absolute best way to experience Tuscany is by riding from village to village.

Moving through the landscape day by day lets you soak in everything that makes Tuscany magical and see new places every day.

Many cyclists worry this kind of trip is complicated — “What about the luggage?” “What if we get lost?” “Is it too much to plan?”

Good news: it’s not complicated at all.
With our cycling tours in Tuscany, you'll have everything sorted out, including luggage transfers, detailed gps routes, bike-friendly acommodation etc. No logistics for you, just pure joy on the bike. We are here for you, just say the word.

Must-See Places in Tuscany

Tuscany packs an incredible amount of history and scenery into a small area: medieval cities, UNESCO-listed landscapes, fortified hill towns, hot springs, and world-famous wine regions — all connected by quiet cycling roads.

These are the places that define the region’s character and are easy to visit on or off the bike.

How to Get To/From Tuscany

Tuscany is easy to reach from abroad thanks to several international airports both inside and just outside the region. These airports provide the most convenient access for cyclists traveling from the UK, Europe, the US, Canada, Australia, and beyond.

Florence Airport (FLR) – Amerigo Vespucci

Tuscany’s main international airport, located just outside Florence. Small, efficient, and ideal if your cycling trip starts in Florence, Chianti, Siena, or central Tuscany.

• Direct flights mainly from major European cities

• Quick tram or taxi ride to Florence centre

• Easiest gateway to Chianti and the interior hills

Pisa Airport (PSA) – Galileo Galilei

The largest international airport in Tuscany with the best overseas and low-cost connections.

• Direct flights from many European cities

• On-site train station with fast links to Pisa, Lucca, Florence, and the coast

• Best airport for Lucca, Northern Tuscany, and the Tuscan Coast

Bologna Airport (BLQ) – Guglielmo Marconi

Just north of Tuscany, but a major international gateway with many long-haul options.

• High-speed trains connect Bologna → Florence in ~35 minutes

• Often cheaper and more frequent flights

• Great for riders who need global connections or flexible schedules

How to Get Around Tuscany

Tuscany has a reliable public transport network that makes it easy to move between major towns, sightseeing areas, and cycling bases. Below is the cyclist-friendly overview, now including the official transport providers you’ll encounter during your trip.

Trains – Trenitalia (Official Rail Operator)

All regional trains in Tuscany are operated by Trenitalia, Italy’s national rail company.

What cyclists need to know:

• Regional trains (R and RV) allow bikes onboard for a small fee.

• You must enter the marked bike carriages.

• High-speed trains (Frecciarossa, Frecciargento, Italo) do not accept fully assembled bikes unless bagged.

• Trenitalia connects all major towns: Florence, Siena, Pisa, Lucca, Arezzo, Grosseto, and coastal areas.

Buses – Autolinee Toscane (Official Regional Bus Network)

All public buses across Tuscany are operated by Autolinee Toscane, which unified the entire region’s bus services. This is the company you’ll use for any inter-town bus journey within Tuscany.

Good to know:

• Buses reach areas not served by trains, especially rural zones like Chianti, Val d’Orcia, and village-to-village routes.

• Bike transport is not guaranteed — policies vary by vehicle type and driver discretion.

• Buses are best used for passengers only, not for moving bikes.

Ideal for: transfers between small towns, getting to accommodation, and moving around when your luggage is being transported separately.

City Transport – ATAF (Florence Urban Transport)

In Florence and its surrounding area, urban buses and city connections are managed by ATAF.

Notes for cyclists:

• Good for passenger transfers within Florence

• Not suitable for carrying bikes

• Useful for getting from hotels to train stations or city landmarks

Driver’s windshield view, Tuscany hills, cypress alleys, steering wheel in foreground, shallow DOF, photorealistic, 4K.

Taxis & Private Transfers

A popular choice for cyclists arriving with bike bags or moving between rural accommodations.

Why use them:

• Door-to-door service

• Flexible timing

• Helpful for reaching smaller villages not served by trains or buses

• Common around: Florence, Pisa, Siena, Lucca, and major tourist hubs.

Car Rentals

Useful for arrival and departure days, especially if you’re transporting bike cases.

Pros:

• Easy access to rural hotels

• Flexible for multi-base trips

• Good for groups with luggage

Cons:

• Not practical during cycling days

• Limited parking in historic towns

Bike-Friendly Tips

• Always choose Trenitalia regional trains for bike travel.

• Avoid high-speed trains unless your bike is fully packed into a bag.

• Check for the bike symbol on train carriages before boarding.

• Rural train stations may have limited facilities — bring water.

• E-bikes are heavy: ground-level platforms make boarding easier.

Need more practical info on travelling to Italy? Check our ultimate guide on cycling holidays in Italy.

Top Cycling Tours in Tuscany

Tuscany is packed with world-class riding, but these cycling tours hit the sweet spot.

Iconic gravel, rolling wine hills, medieval ridge roads, and big-view climbs — each itinerary showcases a different flavour of cycling Tuscany.

Whether you want fast tarmac, legendary Strade Bianche, or a full “taste it all” adventure, these are the rides that deliver the goods.

Plan Your Tuscany Cycling Adventure

Planning a cycling trip in Tuscany is doable on your own — but with so many routes, hill towns, and rural roads, the logistics can get overwhelming fast. Picking the right bases, finding bike-friendly stays, and organizing transport all take time and local know-how.

That’s where we come in.

We handle:

• Bike-friendly accommodation

• Digital guidebook + daily route notes

• GPS tracks for every stage

• Luggage transfers

• Local tips, highlights, and hidden gems

• Full support before and during your trip

Send us an inquiry and we’ll help you create the perfect cycling holiday in Tuscany.