+44 (0)191 265 1110   info@skedaddle.com

Tuscany - Strade Bianche Explorer

Guided Gravel Riding Holiday




8 days

Prices from

£1,995 P.P.
Join us as we ride some of the best and well-known gravel routes in Tuscany. We'll explore some of the classic Strade Bianche routes of the Eroica and sections of the historic Via Francigena pilgrimage route, linking everything together with ancient trading routes, mule tracks and our own favourite hidden gems.
This is quintessential Tuscan gravel riding, bringing together great riding with typical Italian style and plenty of local delicacies to keep us fuelled.
Along the way we mix up the classic gravel roads with some smoother tarmac road sections allowing us to move through the different regions and avoid some of the steeper climbs! Some narrow woodland trails add a bit of extra to the riding as we test our skills on some short sections of more challenging terrain. 
Our week's riding takes us on a loop south through the Chianti region and to the iconic views of the Colline Sienesi lined with cypress trees. A two-night stay affords us time to explore the UNESCO World Heritage sites of Val D’Orcia and Pienza and to see the hotsprings of Bagno Vignoni. Along the route, we touch some of the most important towns of Tuscany most of which are listed as UNESCO World Heritage Sites: Radda in Chianti, San Quirico, Pienza, Siena, and Montalcino as well as lesser-known villages, such as Castelnuovo, Asciano, and Murlo
As we loop round towards the northwest and ending in the Colline Pisane we pass the incredible hilltop towns of Monteriggioni and San Gimignano. Combining magical views with fabulous sections of white limestone Strada Bianca roads we'll experience iconic Tuscany but from our week of riding we'll have also shared the quiet backroads, forest trails and special local cafes that make Tuscany so special to us. 
Talking of Tuscany, we can’t miss out the wine! Every region has it's own unique speciality and you will have the opportunity to taste the classic reds of Chianti, Brunello di Montalcino and Nobile di Moltepulciano, or a refreshing cool glass of Venraccia of San Gimignano as well as sampling the lesser known, but just as delicious, wines of the Colline Pisane 

Holiday Highlights

  • Riding some of the classic “Strade Bianche” of Tuscany as well as lesser-known gravel routes
  • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
  • Exploring the region on a mix of terrains
  • Riding the stunning UNESCO heritage region of Val d’Orcia
  • Relaxing in small villages for a coffee with the locals
  • Easing along the rolling hills of the ‘Colli Sienesi’
  • Chilling out with a post-ride Chianti or Brunello

Back to Top


Day 1
Arrival: Pisa / Radda in Chianti
Non Riding Day

Following arrival at Italy’s Pisa airport (PSA), we make the short transfer to the charming town of Radda in Chianti.

Depending on flight arrival times, there should also be time to have a quick leg stretch on your bikes before your evening meal in one of the town’s great restaurants.

Day 2
Radda in Chanti to Asciano
37 Miles / 60 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 900 Metres Approx.

We have chosen to start our Tuscany Gravel journey right in the heart of the Chianti region, and more precisely right on the classic Eroica route.

Radda in Chianti’s hilltop position affords a forgiving start to the day as we begin with a gentle descent and within only a few kilometres of leaving Radda we join a section of the Strade Bianche of the Eroica which leads us on the start of our journey towards the picturesque Colline Sienesi region.

It’s not long before the undulating hills of the wine-growing region start to kick in and we begin to get accustomed to the rolling countryside that will characterise our week’s riding. The rest of the day’s ride sees smooth gravel routes taking us through dense forests and past Chianti vineyards, and views of old Tuscan castles scattered on the hill tops.

On leaving Castelnuovo Berardenga this afternoon we enter the Colline Sienesi region, with a very panoramic Strada Bianca route which takes us along the ridgeline of the chalky hills before descending to Asciano, a typical Tuscany town set inside old, fortified walls.

Day 3
Asciano to San Quirico d’Orcia
40 Miles / 65 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,180 Metres Approx.

We start the day with a sweeping descent to the Arbia valley, firstly on tarmac then combining smooth Strade Bianche and small country roads as we follow the Arbia river to Buonconvento. The Piazza Centrale, close to the walled monastery is the perfect place for a morning coffee stop ahead of the next section of climbing to take us back onto the hilltops.

Our climb out of Buonconvento is rewarded with some fantastic riding along remote tracks in the chalky hills. Back on the Eroica route, we pedal surrounded by 360 degrees of stunning Tuscan landscape of hills lined with cypress trees before finally reaching our destination in San Quirico d’Orcia where will stay for the next two nights.

Day 4
Val D’Orcia loop
35 Miles / 57 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,300 Metres Approx.

This morning we can skip packing our bags and instead take our time to enjoy a relaxing breakfast as today’s loop ride will bring us back to San Quirico where we will stay another night. The riding options from this well-positioned town are numerous but all will start with a ride to the well-known hot springs of Bagno Vignoni where we set a bit of time aside to explore the roman remains and take pictures by the steaming pools.

Moving on, we pick up a network of gravel roads that take us on a rolling ride through vineyards and cyprus trees. After crossing the Orcia river we can continue along the planned route to Pienza which takes us along some classic white gravel roads, or those who would prefer a few more miles can opt for some smoother tarmac and take the longer, hillier route via Monticchiello.

From the stunning Pienza, and suitably refuelled from the obligatory coffee stop we continue our journey through the UNESCO protected landscape of Val d‘Orcia. Our return to San Quirico starts on some rougher gravel tracks before we rejoin another stretch of carefully managed Strada Bianca.

Day 5
San Quirico to Vescovado
31 Miles / 50 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,000 Metres Approx.

Another day of riding and a few more adventurous trails this afternoon! Our first coffee stop is in Montalcino, where we’ll have a little time to stroll around, visit the castle and perhaps buy a bottle or two of Montalcino Brunello to stash in the support van for later?

Leaving this stunning hill-top town, we ride on another classic section of Strada Bianca through woodland towards Castiglion del Bosco and on to Bibbiano. Adding a bit of adventure on a narrower track, we follow an old mining trail leading us to Murlo, a very small village where another stop is required at the only café which is run by two old ladies and is the epitome of Italian hospitality. Our hotel is a short tarmac section away and a perfect ending to another great ride!

Day 6
Vescovado to Colle Val D’elsa
40 Miles / 65 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,000 Metres Approx.

A smooth but rolling Strada Bianca will lead us today to the outskirts of Siena, where we will switch onto a final stretch of tarmac to ride into this lively and bustling city. Stopping in Piazza del Campo for a coffee, we set some time aside to stroll to the imposing Duomo and take in the atmosphere of the stunning provincial capital.

Leaving via the backroads, we head towards the “Montagnola” a forested hill to the northwest of Siena. The riding is more adventurous on more uneven terrain, mixing some forest tracks with gravel country roads. As we come out of a forested track, the imposing walled town of Monteriggioni will stand ahead of us on a hilltop. Following the winding road we ride right up to the entrance gates where there is a choice of delicious gelato places to pick up our reward!

From Monteriggioni we link onto the historic pilgrimage route of the via Francigena where a smooth gravel country road leads us to Val d’elsa and our accommodation.

Day 7
Colle Val D’Elsa to Volterra via San Gimignano
32 Miles / 52 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,300 Metres Approx.

Our final day in the saddle sees us taking on the longest ride of the week, but it’ll be so worth it. For the first section of the day we’ll begin following country roads through the hills of Val D’Elsa towards San Gimignano. As the view opens up revealing the ‘Town of Towers‘, we’ll no doubt be stopped in our tracks as we take in one of the prettiest and best preserved medieval settlements in Italy.

We should have plenty of time here to take a break from the bikes to walk around San Gimignano, climb one of the towers and taste the ice cream which won 1st prize at the world ice cream championships!

Leaving San Gimignano we’ll head on towards our home for the evening in Volterra.

Day 8
Departure: Volterra / Pisa
Non Riding Day
  • Meals: Breakfast

Time to say our farewells as after breakfast we will take you back to Pisa airport (PSA) for your onward flights.

Back to Top

The Cycling


Although each day’s riding is designed to vary to take in the best of the area and routes, we will be averaging around 60% off-road, mixing in tarmac sections to link up the best gravel tracks and take the pinch out of some of the hills. The Strade Bianche tend to be wide, good compact gravel, though there could be some small bumps and occasional potholes and looser gravel at the edges. Even the country roads will have a mixed surface, from farm roads with potholes and if rainy, mud, to sections with loose small stones. Forest tracks (approximately 5% of the overall offroad sections) are a mix of smooth trails and uneven surface and may feature some uphill sections that require carrying the bike for very short portions.

Our 3-4 grade for this holiday reflects the distances ridden on the often hilly nature of the Tuscan landscape with daily ascents and descents of between 900m and 1300m. You can expect short and sharp climbs alongside longer, steadier ascents. The descents will be just as frequent with sections of loose gravel to tackle, particularly on the corners. You can find more information on riding on gravel surfaces here in our Guide to Gravel Trails

This tour is designed to be ridden most comfortably on a gravel bike. If you are bringing your own bike then we recommend tyres to be set up tubeless with a minimum width of 35mm and with some steep uphill sections, we suggest a wide range of gears.


Gravel Riding Grade

Grade 3-4 : Moderate/Active

Moderate/Active – Aspects of both our grade 3 and 4 holidays. Distances generally between 40-75 miles / 65-120 kms per day.

For gravel and off-road cyclists with stamina and a good level of fitness.

This is gravel riding for experienced riders.

The gravel trails will be predominantly loose in nature and can include sections of much larger pebbles/small rocks. You will definitely need to pick your line carefully.

Traction may be difficult on climbs and descents can be loose and a little sketchy at times.

There might be sections of smooth/non-technical singletrack and the surface width will vary from one section to the next.

If you’re bringing your own bike, we would recommend a minimum tyre width of 38mm.

Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!

For more information about our grading system click here.

Is this suitable for you?

Holidays that are graded as a 3-4, will have aspects of both our grade 3 and 4 holidays. You’re an experienced off-road rider and enjoy riding on a variety of surfaces and gradients. You can happily pick the smoothest line on a trail and don’t mind some trail obstacles to navigate over and around. You have a good level of fitness and are happy with spending 6 hours and more on the bike each day. You will be an enthusiastic and fit road cyclist or mountain biker and either already own a gravel bike or are seriously considering buying one.

For more information about the grading of this holiday in particular, please check out the terrain section which will give you some specifics of what to expect on this tour.

Back to Top

Dates & Prices

Secure Your Holiday With A Deposit

Book now with a £200 deposit and nothing more to pay until 60 days before departure. Choose a date to start your booking and see all prices, including bike hire and single room supplements.

Select a date to view prices and book
Start Date
End Date
Price p.p.
Start Date
Return Date
8 days

Whats Included Tick

A) Accommodation (shared twin / double en-suite rooms)

B) Meals as per the itinerary (B-Breakfast, L=Lunch, D=Dinner)

C) Full tour service, including Skedaddle guides

D) Unless stated, at least one leader qualified in First Aid

E) GPX files available on request

F) Support vehicle and luggage transfers

G) Airport transfer on scheduled arrival day from Pisa airport (PSA)

H) Airport transfer on scheduled departure day to Pisa airport (PSA)

I) Financial Protection through ABTOT

What's not Included Cross

A) Bike rental (available if required)

B) Flights and charges for travelling with your bike (if applicable)

C) Meals not stated in the itinerary

D) Travel insurance

E) Single room (available if required)

F) Personal clothing and equipment

G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)

H) Entrance fees to museums and other attractions en-route

I) Airport transfers on days other than the scheduled arrival / departure days

Back to Top

Private Departures

Private Departures

Are you keen to only travel with your family or friends? Struggling to find the right date? Well, we can organise a private departure for this tour and tailor aspects to suit your group's specific needs. Contact our friendly team and we'll help you turn your dream into reality.

The Essentials

Travel Options

Your tour starts in Radda and finishes in Volterra.

Group airport transfers are included in the cost of your holiday and both the arrival and return transfers from Pisa (PSA) will be co-ordinated with the group flight schedule.

We will provide you with details of suitable flight/arrival/departure schedules as flight timetables become available.

Please check with us before making any travel arrangements to ensure we have reached the minimum number required to guarantee your holiday and to ensure your arrangements fit with our scheduled transfers.

Please note If you make travel arrangements that fall outside of the scheduled transfer windows, there may be an additional charge for individual transfers.


Each night we’ll be staying in a carefully selected mixture of 3* hotels and guesthouses.

We always, where possible, try to use locally owned accommodation, allowing our guests to fully experience some real Tuscan hospitality. Chosen for their location, comfort and charm we‘re positive you’ll be well looked after and well rested, ready for your ride the next day.

Accommodation (shared twin or double rooms) will be en-suite.

Bike Hire

If you don’t own a suitable bike or would prefer to avoid bringing your own we have gravel bikes available to rent.

These bikes are typically Specialized Diverge or Giant Revolt Carbon Gravel bikes, great bikes with good quality components. These bikes are generally set up tubeless with 700×38c tyres. They provide a comfortable riding position and wide range of gears, running a 2×11 drivetrain with 32/48 chainrings and 11×34 cassette. They are fitted with hydraulic disc brakes.

If you do decide to rent we can include a helmet and all necessary spares for the trip. Please request helmets at the time of booking.

Please also let us know if you plan on bringing your own clip-in pedals, or if you will use the flat pedals which our rental bikes come fitted with.

Given the variety of shapes and sizes of on bike luggage and the fact the mechanisms for fitting them varies so much, we aren’t able to safely accommodate customers own frame bags and on bike luggage on our hire bikes. This holiday has vehicle support and the riding group will meet the support vehicle at regular intervals, so you should be able to get away with using jersey pockets to carry any ride essentials. You are welcome to use a small back-pack on sections where you think it’s necessary.

Back to Top

News, Reviews & Stories

NEW! Gravel Riding Holidays

Gravel riding epitomises the very best of what we love about cycling. We'll give you an insider's view of what it's all about here...

Your Guide To Gravel Riding Skills

We cover essential skills for cyclists who want to conquer any gravel terrain! Read this for expert tips and advice.

Gravel Riding Holiday FAQs

Everything you need to know! We put all your questions and more to our gravelly-gurus and this is what they came back with.


No reviews available yet!

You May Also Like...

Back to Top