Tuscany Gravel Bike Tours | Out of the Box Florence

  • Price per person

From €350 Single-day

From €800 Multi-days

  • Age

18+

  • Guests

8

  • Tour length

Single/Multi-days

Contact us
Customize your bike trip
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Gravel Cycling Tuscany · Italy Florence & Siena

Gravel Tuscany
Ride Off-Script

Not a panoramic bus tour in disguise. Dirt roads, real hills, organic wine poured by the hands that made it, and the kind of silence you don't find on highways or in itineraries.

Strade Bianche
Legendary white roads
Eroica
Historic gravel routes
Via Francigena
Ancient pilgrimage trail
from €350
Per guide · per day · VAT included
Format
Half · Full · Multi-day
Custom routes available
Group
Private only
Exclusively for your group
Guide
Guided or self-guided
GPS route files provided
Bikes
We reserve and deliver your bike to the start
Or bring your own
Departure
Florence or Siena
Hotel pick-up for private groups
Terrain
Gravel, dirt, farm roads
Chianti · Crete Senesi · Strade Bianche
Includes
Wine & food stops
Local producers, not tourist venues
Price
€350 / guide / day
Per group · VAT included · Extras to agree

Out of the Box Florence runs private, guided and self-guided gravel bike tours across Tuscany — including the Strade Bianche and Eroica routes — with bike reservation and van transport available on every ride.

"We know roads that don't show up on Komoot, Strava, or any cycling portal. Ride with us and you'll go well beyond the tourist tracks — into the Tuscany that locals keep for themselves."
On the ride

What to Expect

Roads not on any portalTracks that don't appear on Komoot, Strava, or Google Maps — unmarked farm roads, private vineyard paths, and shortcuts locals have ridden for decades

Both iconic and non-touristic routesStrade Bianche and Eroica roads for the classics, hidden terrain for everyone else — we mix both based on what you want

Real hills, real gravelFrom smooth Chianti clay to honest farm tracks — climbs that make the espresso worth it and descents that make you grin

A pace shaped by youTerrain and conversation, not stopwatches. We adapt every ride to your fitness, your mood, and how the day feels

Extras along the way — if you want themWine tastings, cooking classes, home restaurant lunch, beer tasting, olive oil — we can combine anything you'd like to try. All agreed before the tour

The kind of silence you don't get on highwaysCountryside where tractors outnumber tourists and the only noise is gravel under your tyres

Iconic routes

The Roads We Ride

Strade Bianche
The legendary white gravel roads of the professional cycling race. Departing from Siena — the most iconic starting point in Italian gravel cycling.
Eroica Roads
The historic gravel routes around Gaiole in Chianti used by the famous L'Eroica vintage cycling event every October.
Via Francigena
The ancient pilgrimage route from Florence to Rome, crossing Chianti and the Crete Senesi on gravel and dirt tracks through Tuscan countryside.
Chianti Classico Farm Tracks
Unmarked farm roads through vineyards and olive groves between Florence and Siena. The Tuscany that maps don't show and tour buses don't reach.

Who Rides with Us

Expert riders who want routes that challenge them beyond what any app suggests

Complete beginners looking for a gentle introduction to gravel on quiet Tuscan roads

Everyone in between — we adjust the route to your level, your group, and your pace

People who want to be guided by someone who knows this terrain intimately

Independent riders who prefer self-guided with GPS files and a good briefing

Anyone curious about what Tuscany looks like when you leave the main roads behind

How it works

Tour Format & Options

Half-Day Ride

A focused route through one area — Chianti, Crete Senesi, or around Siena. Guided or self-guided. Perfect standalone or combined with another experience in the afternoon. Extras (wine, food) to be agreed.

On request / group

Full-Day Ride

The full experience. Private, exclusively for your group. Guided or self-guided with GPS files. Route adapted to your level. Any extras — wine tasting, lunch at a local producer, cooking class — agreed in advance.

€350 / guide / day · VAT included

Multi-Day Tour

We organise everything — lodging, bike rentals, daily routes, guide or self-guided, and experiences along the way. Every day different, every stop chosen for what it actually is, not what it looks like on Instagram.

On request / custom quote
Bikes, sorted

Bikes, Sorted for You

Don't want to bring your own bike or figure out how to get it to the start? We handle it end to end. Reserve a premium gravel bike through us and it will be ready and waiting at the departure point — no need to transport it yourself. You then travel with us in our own vans to the start of the ride, so there's nothing to arrange on your side. Full service, from booking to the first pedal stroke.
Multi-day itineraries

Iconic Long-Distance Gravel Routes

All multi-day tours are fully organised — we handle lodging, bike logistics, guide or GPS self-guided options, and experiences along the way. Contact us for a custom quote.

Florence → Siena
The classic. Following the Strade Bianche and Eroica roads through the Chianti Classico hills. 2–3 days. Iconic finish in Siena's Piazza del Campo.
Florence Loop: Chianti, San Gimignano & Val di Chiana
A circular ride out of Florence and back. South into the Chianti Classico hills over the historic Eroica gravel roads around Gaiole, west to the medieval towers of San Gimignano and the truffle hills of San Miniato, then east across the wide, gentle farmland of the Val di Chiana — home of the Chianina cattle — before closing the loop back in Florence. 4–6 days, fully organised, van support included.
Florence → Assisi
Along the Via di Francesco — the ancient Franciscan pilgrimage route through the Casentino, the Santuario della Verna, and the Umbrian hills to Assisi. 5–7 days.
Florence → Rome
The ultimate Italian gravel traverse. Through Chianti, Val d'Orcia, Viterbo and the Lazio countryside to Rome. Following ancient roads, stopping at local producers. 7–10 days.
Venice → Florence
From the Veneto plains across the Apennines into Tuscany. Passing through the Mugello valley and descending into Florence. A varied, rewarding traverse. 4–6 days.
Bologna → Florence
Crossing the Apennine mountains on gravel and forest roads. Short but technically interesting — big climbs, fast descents, excellent food stops both sides. 2–3 days.
Sardinia
A completely different Tuscany experience. Wild, remote, and dramatically beautiful. Gravel tracks through the Barbagia highlands, coastal roads, and shepherd paths. 5–7 days. Fully organised.
Custom Route
Have a route in mind? We'll build it. We design bespoke multi-day itineraries around your destinations, fitness level, and interests. Every ride curated, not copy-pasted.
Sustainable by Design

Not by Marketing

Tuscany is often consumed fast. We choose slow. We work exclusively with farmers, artisans, and small wine producers — people who live here, not brands that market here. Every stop on our rides supports an independent local producer. Sustainability isn't a buzzword for us. It's our business model and our neighbourhood. Ride with us and leave this region with more than photos. Leave with relationships, dust on your socks, and a story worth telling.

FAQ

Frequently Asked Questions

Our routes include the legendary Strade Bianche (the white gravel roads made famous by the pro cycling race), the historic Eroica roads around Gaiole in Chianti, stretches of the Via Francigena, and lesser-known farm tracks through the Chianti Classico wine region. Every route is handpicked by local guides who ride these roads regularly.
Strade Bianche is a professional cycling race held every March, starting and finishing in Siena, known for its white gravel roads (sterrati) through the Crete Senesi. We run guided rides over these same roads, any day of the year.
L'Eroica is a vintage cycling event held every October in Gaiole in Chianti, founded in 1997 to preserve Tuscany's white gravel roads. We offer private rides over the same historic roads outside the event dates, so you can enjoy them without the crowds.
€350 per guide per day, per group. VAT included. This is the base price — extras such as bike rental, wine tastings, cooking classes, or lunch stops are to be agreed before the tour. Multi-day and custom itineraries are quoted individually. Contact us for a tailored quote.
Both options are available. Guided tours include a local cycling guide who knows the roads, the producers, and the stories behind the terrain. Self-guided tours come with GPS route files loaded and ready, plus a detailed briefing before you set off. We recommend guided for first-time riders in the area, but experienced cyclists often prefer the freedom of self-guided.
Absolutely. You are welcome to bring your own bike. If you prefer, we can reserve a high-quality gravel bike for you and have it delivered to the starting point — just let us know when booking. We accommodate both road and gravel tyre setups.
Yes. We can reserve a premium gravel bike on your behalf and have it delivered to the starting point, so you don't need to bring or transport your own. You then travel with us in our own vans directly to the departure point — a full-service option from booking to the first pedal stroke.
Yes. Along the route we can organise wine tastings at small organic producers, a cooking class, a home restaurant lunch, olive oil tasting, beer tasting, or almost anything guests want to try. These are extras and need to be agreed before the tour so we can arrange access with the right producers. Everything is with independent, local operators — nothing tourist-facing.
Tuscany is hilly — real hills — so a reasonable level of cycling fitness is helpful. We design the route around your group's ability, not the other way around. Half-day options are more accessible; full-day and multi-day rides involve more elevation. Tell us your level and we'll build the right ride.
Yes, on full-day tours. We stop at local producers — small organic farms and family-run wineries — for wine tasting and Tuscan food. These are not staged tourist experiences: the food and wine come from the people who produce them, often poured by the winemakers themselves.
Yes — and Siena is arguably the most iconic starting point for gravel cycling in Tuscany. The Strade Bianche pro race finishes in Siena's Piazza del Campo. We offer departures from both Florence and Siena. A supplement applies for Siena departures on private tours.
We were doing gravel riding in Tuscany before it became a trend. Our guides are locals who live and ride these roads. We work exclusively with small organic farmers and independent wine producers — not tourist-facing brands. The routes go places that buses and tourist itineraries don't reach. This is Tuscany as it actually is, not as it is marketed.

You can book a tour. Or you can choose a day that feels like you stepped into
a Tuscany that doesn't need hashtags to be real.
Your call. We'll be on the gravel, waiting.

Departure

Location
Piazza della liberta/Via S. Gallo, 203, 50129 Firenze FI IN FRONT of CAFFE LIETTA

8:00

Departure Time
CHECK-IN 10 mins prior departure

17:00

Return Time
Departure Time
CHECK-IN 10 mins prior departure

8:00

Return Time

17:00

Start your ride adventure voyage experience

Tuscany gravel Tours:

Day & Multi-Day Gravel Tours in Tuscany & Beyond

Day Gravel Tuscany Bike Tour – Florence & Chianti

A full immersion in Chianti gravel culture. Vineyards, forest tracks, medieval hamlets, and a stop where wine tastes better because the soil is still on your tires.
Ideal for riders who want to meet Tuscany off the pavement and away from the expected.
Available private / customizable distance.

Day rides

One-Day Gravel Routes

All day rides are private, exclusively for your group. Guided or self-guided with GPS files. Price: €350 per guide per day, VAT included. Bikes can be reserved through us and delivered to the starting point, or you can bring your own. Extras (wine, food) to be agreed before the tour.

1 Day

Strade Bianche Ride

Ride the exact white gravel roads used by the professional Strade Bianche race, held every March and finishing on Siena's Piazza del Campo. Rolling sterrati through the Crete Senesi — some of the most photographed gravel in Italy, any day of the year.

Siena Crete Senesi Pro race roads Private
1 Day

Eroica Route – Gaiole in Chianti

The historic gravel roads around Gaiole in Chianti, used every October for L'Eroica, the vintage cycling event founded in 1997 to protect Tuscany's white roads from being paved over. Ride the same routes on a modern gravel bike, any day of the year.

Gaiole in Chianti Vintage cycling heritage Chianti Classico Private
1 Day

Val d'Orcia Gravel Ride

Cypress lines, rolling wheat hills, quiet farm roads. Pienza and Bagno Vignoni nearby. Postcard Tuscany before it became one — dust ribbons, ancient farmhouses, hand-cut cheese, and endless space.

UNESCO landscape Pienza Bagno Vignoni Private
1 Day

Volterra Gravel Ride

Wilder, wind-carved terrain. Etruscan walls, olive groves, clay ridges, medieval stone under your wheels. A route for riders who like texture, silence, and ancient history in motion.

Volterra Etruscan history Clay terrain Private
1 Day

Florence to San Gimignano

A point-to-point route linking Renaissance Florence to the medieval towers of San Gimignano through backcountry gravel and farm roads most travellers never see.

Point-to-point San Gimignano Farm roads Private
1 or 2 Days

Florence to Siena

Ride into the heart of Chianti Classico. Vineyards, stone villages, gravel climbs, and Siena waiting at the end. Two-day option includes a boutique farm stay and slow dinner under vines.

Chianti Classico Strade Bianche Farm stay optional Private
1 Day

Around Florence

Secret gravel around the Renaissance city. Olive groves, monastic roads, small villages, and the kind of views postcards envy. Perfect if you want a pure ride without leaving Florence overnight.

Florence Monastic roads Day ride Private
1 Day

Around San Gimignano

A loop through towers, truffles, Vernaccia vineyards, and dirt tracks that wind like they were drawn by hand. One of the most visually rewarding day loops in Tuscany.

Loop ride Truffle country Vernaccia vineyards Private
Multi-day journeys

Long-Distance Gravel Itineraries

We organise everything — lodging, bike rentals, guide or self-guided GPS files, and experiences along the way. All multi-day tours are fully private and custom-quoted.

3+ Days

Florence to Assisi

Two routes, two completely different journeys. The classic follows the Via di Francesco — ancient pilgrimage trails across the Casentino forests, the Santuario della Verna, and the Umbrian hills into Assisi. Our own route — the Out of the Box Way — takes you south through Siena, into the Val di Chiana past Cortona, and north through Perugia before arriving in Assisi. Slower, richer, and entirely off the tourist radar. Both options: 3–5 days, private, guided or self-guided.

3 to 5 Days

Assisi to Rome

From the hill towns of Umbria to Roman countryside trails, finishing at the Eternal City. A ride where history and dirt roads blend without trying. Ancient roads, monastery stops, and the unmistakable feeling of arriving somewhere that matters.

4 to 6 Days

Venice to Florence

From the Veneto plains across the Apennines into Tuscany. Passing through the Mugello valley and descending into Florence. A varied, rewarding traverse combining flat lagoon approaches, mountain passes, and Tuscan rolling terrain.

2 to 3 Days

Bologna to Florence

Crossing the Apennine mountains on gravel and forest roads. Short but technically demanding — big climbs, fast descents, and excellent food stops on both sides of the pass. Perfect add-on to a larger Italian itinerary.

6+ Days

Florence to Rome

The true slow-travel epic. Tuscany, Umbria, Lazio — vineyards, wheat fields, monastery roads, lakes, and the final roll into Rome. Expect variation, soul, and a sense of arriving with meaning. Every day different, every stop chosen for what it actually is.

10 Days

Venice to Rome

A bucket-list Italy gravel traverse. Water city to Eternal City. Veneto, Apennines, Tuscany, Umbria, Lazio — ten days of roads that shaped Western civilisation. This is for riders who don't want an itinerary. They want a chapter in their life.

Custom Gravel Tours &
Private Trips

We build tours that fit you, not the other way around. Every ride is curated, not copy-pasted. Tell us what matters to you and we'll design the route — whether it's a single day in the Chianti hills or a two-week traverse of Italy.

Tell us
  • How many days
  • Your riding style and gravel experience
  • Food & wine interests along the way
  • How deep you want to go into local culture
  • Guided or self-guided preference
Design Your Route

What we organise for you

  • Daily route design and GPS files
  • Local guide (or self-guided briefing)
  • Boutique agriturismo and farm stays
  • Bike reservation, delivered to the starting point
  • Van transport for you and your group to every departure point
  • Support van for multi-day tours
  • Wine tastings at small organic producers
  • Cooking classes and home restaurant lunches
  • Beer tasting, olive oil, truffle stops — anything you want to try
  • Family-run trattoria reservations
  • Transfer logistics and pick-up from Florence or Siena

This Is Not a Tour.
It's a Way to See Italy.

Gravel riding here is connection: to land, to food, to people, to history that wasn't staged for you. You don't follow crowds. You follow roads that mattered long before tourism existed.

Ride where Tuscany breathes. Ride where Italy feels real. Tell your own story — we'll guide the way.

Tell us the trip you want — or tell us who you are.
We'll craft the route that fits your spirit, not your booking number.

Possible costs

  • 55 to 75 Bike rental
  • 350 Guide per day
  • 500 Van Support per day
  • 150 to 300 Lodging
  • 200 € Min Luggage transportation per day (4 bags)
  • 55 to 75 Extra bikes for the day

Contact Us

As seen in
OutOfTheBoxFlorence
LOCAL ADVENTURES, DISCOVER NATURE AND TASTE UNIQUE DELICACIES
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Estremi identificativi SCIA:
Comune di Firenze, N° 9701/2020/SUAP
in data 29/09/2020 prot. n:250308
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Contact Info
Estremi identificativi SCIA:
Comune di Firenze, N° 9701/2020/SUAP
in data 29/09/2020 prot. n:250308
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Tuscany Gravel Bike Tours | Out of the Box Florence

Tuscany Gravel Bike Tours | Out of the Box Florence

Start from €350/800

Tuscany Gravel Bike Tours | Out of the Box Florence

  • Price per person

From €350 Single-day

From €800 Multi-days

  • Age

18+

  • Guests

8

  • Tour length

Single/Multi-days

Contact us
Customize your bike trip
Cycling along the strade bianche gravel bike tour
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Florence to Rome on two wheels - cycling tour from Florence with Out of the Box Florence
Italy gravel bike adventures self-guided tours
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Florence to Assisi cycling tour along the iconic tuscan white roads
Epic day ride on strade bianche in Tuscany - gravel tour from Florence
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Gravel Cycling Tuscany · Italy Florence & Siena

Gravel Tuscany
Ride Off-Script

Not a panoramic bus tour in disguise. Dirt roads, real hills, organic wine poured by the hands that made it, and the kind of silence you don't find on highways or in itineraries.

Strade Bianche
Legendary white roads
Eroica
Historic gravel routes
Via Francigena
Ancient pilgrimage trail
from €350
Per guide · per day · VAT included
Format
Half · Full · Multi-day
Custom routes available
Group
Private only
Exclusively for your group
Guide
Guided or self-guided
GPS route files provided
Bikes
We reserve and deliver your bike to the start
Or bring your own
Departure
Florence or Siena
Hotel pick-up for private groups
Terrain
Gravel, dirt, farm roads
Chianti · Crete Senesi · Strade Bianche
Includes
Wine & food stops
Local producers, not tourist venues
Price
€350 / guide / day
Per group · VAT included · Extras to agree

Out of the Box Florence runs private, guided and self-guided gravel bike tours across Tuscany — including the Strade Bianche and Eroica routes — with bike reservation and van transport available on every ride.

"We know roads that don't show up on Komoot, Strava, or any cycling portal. Ride with us and you'll go well beyond the tourist tracks — into the Tuscany that locals keep for themselves."
On the ride

What to Expect

Roads not on any portalTracks that don't appear on Komoot, Strava, or Google Maps — unmarked farm roads, private vineyard paths, and shortcuts locals have ridden for decades

Both iconic and non-touristic routesStrade Bianche and Eroica roads for the classics, hidden terrain for everyone else — we mix both based on what you want

Real hills, real gravelFrom smooth Chianti clay to honest farm tracks — climbs that make the espresso worth it and descents that make you grin

A pace shaped by youTerrain and conversation, not stopwatches. We adapt every ride to your fitness, your mood, and how the day feels

Extras along the way — if you want themWine tastings, cooking classes, home restaurant lunch, beer tasting, olive oil — we can combine anything you'd like to try. All agreed before the tour

The kind of silence you don't get on highwaysCountryside where tractors outnumber tourists and the only noise is gravel under your tyres

Iconic routes

The Roads We Ride

Strade Bianche
The legendary white gravel roads of the professional cycling race. Departing from Siena — the most iconic starting point in Italian gravel cycling.
Eroica Roads
The historic gravel routes around Gaiole in Chianti used by the famous L'Eroica vintage cycling event every October.
Via Francigena
The ancient pilgrimage route from Florence to Rome, crossing Chianti and the Crete Senesi on gravel and dirt tracks through Tuscan countryside.
Chianti Classico Farm Tracks
Unmarked farm roads through vineyards and olive groves between Florence and Siena. The Tuscany that maps don't show and tour buses don't reach.

Who Rides with Us

Expert riders who want routes that challenge them beyond what any app suggests

Complete beginners looking for a gentle introduction to gravel on quiet Tuscan roads

Everyone in between — we adjust the route to your level, your group, and your pace

People who want to be guided by someone who knows this terrain intimately

Independent riders who prefer self-guided with GPS files and a good briefing

Anyone curious about what Tuscany looks like when you leave the main roads behind

How it works

Tour Format & Options

Half-Day Ride

A focused route through one area — Chianti, Crete Senesi, or around Siena. Guided or self-guided. Perfect standalone or combined with another experience in the afternoon. Extras (wine, food) to be agreed.

On request / group

Full-Day Ride

The full experience. Private, exclusively for your group. Guided or self-guided with GPS files. Route adapted to your level. Any extras — wine tasting, lunch at a local producer, cooking class — agreed in advance.

€350 / guide / day · VAT included

Multi-Day Tour

We organise everything — lodging, bike rentals, daily routes, guide or self-guided, and experiences along the way. Every day different, every stop chosen for what it actually is, not what it looks like on Instagram.

On request / custom quote
Bikes, sorted

Bikes, Sorted for You

Don't want to bring your own bike or figure out how to get it to the start? We handle it end to end. Reserve a premium gravel bike through us and it will be ready and waiting at the departure point — no need to transport it yourself. You then travel with us in our own vans to the start of the ride, so there's nothing to arrange on your side. Full service, from booking to the first pedal stroke.
Multi-day itineraries

Iconic Long-Distance Gravel Routes

All multi-day tours are fully organised — we handle lodging, bike logistics, guide or GPS self-guided options, and experiences along the way. Contact us for a custom quote.

Florence → Siena
The classic. Following the Strade Bianche and Eroica roads through the Chianti Classico hills. 2–3 days. Iconic finish in Siena's Piazza del Campo.
Florence Loop: Chianti, San Gimignano & Val di Chiana
A circular ride out of Florence and back. South into the Chianti Classico hills over the historic Eroica gravel roads around Gaiole, west to the medieval towers of San Gimignano and the truffle hills of San Miniato, then east across the wide, gentle farmland of the Val di Chiana — home of the Chianina cattle — before closing the loop back in Florence. 4–6 days, fully organised, van support included.
Florence → Assisi
Along the Via di Francesco — the ancient Franciscan pilgrimage route through the Casentino, the Santuario della Verna, and the Umbrian hills to Assisi. 5–7 days.
Florence → Rome
The ultimate Italian gravel traverse. Through Chianti, Val d'Orcia, Viterbo and the Lazio countryside to Rome. Following ancient roads, stopping at local producers. 7–10 days.
Venice → Florence
From the Veneto plains across the Apennines into Tuscany. Passing through the Mugello valley and descending into Florence. A varied, rewarding traverse. 4–6 days.
Bologna → Florence
Crossing the Apennine mountains on gravel and forest roads. Short but technically interesting — big climbs, fast descents, excellent food stops both sides. 2–3 days.
Sardinia
A completely different Tuscany experience. Wild, remote, and dramatically beautiful. Gravel tracks through the Barbagia highlands, coastal roads, and shepherd paths. 5–7 days. Fully organised.
Custom Route
Have a route in mind? We'll build it. We design bespoke multi-day itineraries around your destinations, fitness level, and interests. Every ride curated, not copy-pasted.
Sustainable by Design

Not by Marketing

Tuscany is often consumed fast. We choose slow. We work exclusively with farmers, artisans, and small wine producers — people who live here, not brands that market here. Every stop on our rides supports an independent local producer. Sustainability isn't a buzzword for us. It's our business model and our neighbourhood. Ride with us and leave this region with more than photos. Leave with relationships, dust on your socks, and a story worth telling.

FAQ

Frequently Asked Questions

Our routes include the legendary Strade Bianche (the white gravel roads made famous by the pro cycling race), the historic Eroica roads around Gaiole in Chianti, stretches of the Via Francigena, and lesser-known farm tracks through the Chianti Classico wine region. Every route is handpicked by local guides who ride these roads regularly.
Strade Bianche is a professional cycling race held every March, starting and finishing in Siena, known for its white gravel roads (sterrati) through the Crete Senesi. We run guided rides over these same roads, any day of the year.
L'Eroica is a vintage cycling event held every October in Gaiole in Chianti, founded in 1997 to preserve Tuscany's white gravel roads. We offer private rides over the same historic roads outside the event dates, so you can enjoy them without the crowds.
€350 per guide per day, per group. VAT included. This is the base price — extras such as bike rental, wine tastings, cooking classes, or lunch stops are to be agreed before the tour. Multi-day and custom itineraries are quoted individually. Contact us for a tailored quote.
Both options are available. Guided tours include a local cycling guide who knows the roads, the producers, and the stories behind the terrain. Self-guided tours come with GPS route files loaded and ready, plus a detailed briefing before you set off. We recommend guided for first-time riders in the area, but experienced cyclists often prefer the freedom of self-guided.
Absolutely. You are welcome to bring your own bike. If you prefer, we can reserve a high-quality gravel bike for you and have it delivered to the starting point — just let us know when booking. We accommodate both road and gravel tyre setups.
Yes. We can reserve a premium gravel bike on your behalf and have it delivered to the starting point, so you don't need to bring or transport your own. You then travel with us in our own vans directly to the departure point — a full-service option from booking to the first pedal stroke.
Yes. Along the route we can organise wine tastings at small organic producers, a cooking class, a home restaurant lunch, olive oil tasting, beer tasting, or almost anything guests want to try. These are extras and need to be agreed before the tour so we can arrange access with the right producers. Everything is with independent, local operators — nothing tourist-facing.
Tuscany is hilly — real hills — so a reasonable level of cycling fitness is helpful. We design the route around your group's ability, not the other way around. Half-day options are more accessible; full-day and multi-day rides involve more elevation. Tell us your level and we'll build the right ride.
Yes, on full-day tours. We stop at local producers — small organic farms and family-run wineries — for wine tasting and Tuscan food. These are not staged tourist experiences: the food and wine come from the people who produce them, often poured by the winemakers themselves.
Yes — and Siena is arguably the most iconic starting point for gravel cycling in Tuscany. The Strade Bianche pro race finishes in Siena's Piazza del Campo. We offer departures from both Florence and Siena. A supplement applies for Siena departures on private tours.
We were doing gravel riding in Tuscany before it became a trend. Our guides are locals who live and ride these roads. We work exclusively with small organic farmers and independent wine producers — not tourist-facing brands. The routes go places that buses and tourist itineraries don't reach. This is Tuscany as it actually is, not as it is marketed.

You can book a tour. Or you can choose a day that feels like you stepped into
a Tuscany that doesn't need hashtags to be real.
Your call. We'll be on the gravel, waiting.

Departure

Location
Piazza della liberta/Via S. Gallo, 203, 50129 Firenze FI IN FRONT of CAFFE LIETTA

8:00

Departure Time
CHECK-IN 10 mins prior departure

17:00

Return Time
Departure Time
CHECK-IN 10 mins prior departure

8:00

Return Time

17:00

Start your ride adventure voyage experience

Tuscany gravel Tours:

Day & Multi-Day Gravel Tours in Tuscany & Beyond

Day Gravel Tuscany Bike Tour – Florence & Chianti

A full immersion in Chianti gravel culture. Vineyards, forest tracks, medieval hamlets, and a stop where wine tastes better because the soil is still on your tires.
Ideal for riders who want to meet Tuscany off the pavement and away from the expected.
Available private / customizable distance.

Day rides

One-Day Gravel Routes

All day rides are private, exclusively for your group. Guided or self-guided with GPS files. Price: €350 per guide per day, VAT included. Bikes can be reserved through us and delivered to the starting point, or you can bring your own. Extras (wine, food) to be agreed before the tour.

1 Day

Strade Bianche Ride

Ride the exact white gravel roads used by the professional Strade Bianche race, held every March and finishing on Siena's Piazza del Campo. Rolling sterrati through the Crete Senesi — some of the most photographed gravel in Italy, any day of the year.

Siena Crete Senesi Pro race roads Private
1 Day

Eroica Route – Gaiole in Chianti

The historic gravel roads around Gaiole in Chianti, used every October for L'Eroica, the vintage cycling event founded in 1997 to protect Tuscany's white roads from being paved over. Ride the same routes on a modern gravel bike, any day of the year.

Gaiole in Chianti Vintage cycling heritage Chianti Classico Private
1 Day

Val d'Orcia Gravel Ride

Cypress lines, rolling wheat hills, quiet farm roads. Pienza and Bagno Vignoni nearby. Postcard Tuscany before it became one — dust ribbons, ancient farmhouses, hand-cut cheese, and endless space.

UNESCO landscape Pienza Bagno Vignoni Private
1 Day

Volterra Gravel Ride

Wilder, wind-carved terrain. Etruscan walls, olive groves, clay ridges, medieval stone under your wheels. A route for riders who like texture, silence, and ancient history in motion.

Volterra Etruscan history Clay terrain Private
1 Day

Florence to San Gimignano

A point-to-point route linking Renaissance Florence to the medieval towers of San Gimignano through backcountry gravel and farm roads most travellers never see.

Point-to-point San Gimignano Farm roads Private
1 or 2 Days

Florence to Siena

Ride into the heart of Chianti Classico. Vineyards, stone villages, gravel climbs, and Siena waiting at the end. Two-day option includes a boutique farm stay and slow dinner under vines.

Chianti Classico Strade Bianche Farm stay optional Private
1 Day

Around Florence

Secret gravel around the Renaissance city. Olive groves, monastic roads, small villages, and the kind of views postcards envy. Perfect if you want a pure ride without leaving Florence overnight.

Florence Monastic roads Day ride Private
1 Day

Around San Gimignano

A loop through towers, truffles, Vernaccia vineyards, and dirt tracks that wind like they were drawn by hand. One of the most visually rewarding day loops in Tuscany.

Loop ride Truffle country Vernaccia vineyards Private
Multi-day journeys

Long-Distance Gravel Itineraries

We organise everything — lodging, bike rentals, guide or self-guided GPS files, and experiences along the way. All multi-day tours are fully private and custom-quoted.

3+ Days

Florence to Assisi

Two routes, two completely different journeys. The classic follows the Via di Francesco — ancient pilgrimage trails across the Casentino forests, the Santuario della Verna, and the Umbrian hills into Assisi. Our own route — the Out of the Box Way — takes you south through Siena, into the Val di Chiana past Cortona, and north through Perugia before arriving in Assisi. Slower, richer, and entirely off the tourist radar. Both options: 3–5 days, private, guided or self-guided.

3 to 5 Days

Assisi to Rome

From the hill towns of Umbria to Roman countryside trails, finishing at the Eternal City. A ride where history and dirt roads blend without trying. Ancient roads, monastery stops, and the unmistakable feeling of arriving somewhere that matters.

4 to 6 Days

Venice to Florence

From the Veneto plains across the Apennines into Tuscany. Passing through the Mugello valley and descending into Florence. A varied, rewarding traverse combining flat lagoon approaches, mountain passes, and Tuscan rolling terrain.

2 to 3 Days

Bologna to Florence

Crossing the Apennine mountains on gravel and forest roads. Short but technically demanding — big climbs, fast descents, and excellent food stops on both sides of the pass. Perfect add-on to a larger Italian itinerary.

6+ Days

Florence to Rome

The true slow-travel epic. Tuscany, Umbria, Lazio — vineyards, wheat fields, monastery roads, lakes, and the final roll into Rome. Expect variation, soul, and a sense of arriving with meaning. Every day different, every stop chosen for what it actually is.

10 Days

Venice to Rome

A bucket-list Italy gravel traverse. Water city to Eternal City. Veneto, Apennines, Tuscany, Umbria, Lazio — ten days of roads that shaped Western civilisation. This is for riders who don't want an itinerary. They want a chapter in their life.

Custom Gravel Tours &
Private Trips

We build tours that fit you, not the other way around. Every ride is curated, not copy-pasted. Tell us what matters to you and we'll design the route — whether it's a single day in the Chianti hills or a two-week traverse of Italy.

Tell us
  • How many days
  • Your riding style and gravel experience
  • Food & wine interests along the way
  • How deep you want to go into local culture
  • Guided or self-guided preference
Design Your Route

What we organise for you

  • Daily route design and GPS files
  • Local guide (or self-guided briefing)
  • Boutique agriturismo and farm stays
  • Bike reservation, delivered to the starting point
  • Van transport for you and your group to every departure point
  • Support van for multi-day tours
  • Wine tastings at small organic producers
  • Cooking classes and home restaurant lunches
  • Beer tasting, olive oil, truffle stops — anything you want to try
  • Family-run trattoria reservations
  • Transfer logistics and pick-up from Florence or Siena

This Is Not a Tour.
It's a Way to See Italy.

Gravel riding here is connection: to land, to food, to people, to history that wasn't staged for you. You don't follow crowds. You follow roads that mattered long before tourism existed.

Ride where Tuscany breathes. Ride where Italy feels real. Tell your own story — we'll guide the way.

Tell us the trip you want — or tell us who you are.
We'll craft the route that fits your spirit, not your booking number.

Possible costs

  • 55 to 75 Bike rental
  • 350 Guide per day
  • 500 Van Support per day
  • 150 to 300 Lodging
  • 200 € Min Luggage transportation per day (4 bags)
  • 55 to 75 Extra bikes for the day

Contact Us

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