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Strade Bianche Explorer

Self-Guided Gravel Riding Holiday




8 days

Prices from

£1,595 P.P.
Explore this spectacular region of Italy, as you ride some of the best and well-known gravel routes in Tuscany. You'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 fantastic hidden gems.
This is quintessential Tuscan gravel riding, bringing together great riding with typical Italian style and plenty of local delicacies to keep you fuelled.
Along the way you'll experience a mix of classic gravel roads with some smoother tarmac road sections allowing you 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 you'll test your skills on some short sections of more challenging terrain. 
Your week's riding will take you 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 you 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, you'll touch some of the most important towns of Tuscany most of which are listed as UNESCO World Heritage Sites: Radda in Chianti, San QuiricoPienza, Siena, and Montalcino as well as lesser-known villages, such as CastelnuovoAsciano, and Murlo
As you loop round towards the northwest and ending in the Colline Pisane, you'll pass the incredible hilltop towns of Monteriggioni and San Gimignano. Combining magical views with fabulous sections of white limestone Strada Bianca roads, you'll experience iconic Tuscany - but, from your week of riding, you'll have also encountered the quiet backroads, forest trails and special local cafes that make Tuscany so special. 
Talking of Tuscany, you can’t miss out the wine! Every region has its own unique speciality and you'll 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

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

Following arrival at Italy’s Pisa airport (PSA), you’ll make the 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
  • Ascent: 900 Metres Approx.

Your Tuscany Gravel journey starts 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 you begin with a gentle descent and within only a few kilometres of leaving Radda, you’ll join a section of the Strade Bianche of the Eroica which leads you on the start of your 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 you begin to get accustomed to the rolling countryside that will characterise your week’s riding. The rest of the day’s ride sees smooth gravel routes taking you through dense forests and past Chianti vineyards, and views of old Tuscan castles scattered on the hill tops.

On leaving Castelnuovo Berardenga this afternoon you’ll enter the Colline Sienesi region, with a very panoramic Strada Bianca route which takes you 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.

You’ll start the day with a sweeping descent to the Arbia valley, firstly on tarmac then combining smooth Strade Bianche and small country roads as you 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 you back onto the hilltops.

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

Day 4
Val D’Orcia loop
40 Miles / 65 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,300 Metres Approx.

This morning you can skip packing your bags and instead take your time to enjoy a relaxing breakfast as today’s loop ride will bring you back to San Quirico where you 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 you’ll be able to set a bit of time aside to explore the roman remains and take pictures by the steaming pools.

Moving on, you’ll pick up a network of gravel roads that take you on a rolling ride through vineyards and cyprus trees. After crossing the Orcia river you can continue along the planned route to Pienza which takes you 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 you’ll continue your journey through the UNESCO protected landscape of Val d‘Orcia. Your return to San Quirico starts on some rougher gravel tracks before you 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! Your first coffee stop is in Montalcino, where you’ll have a little time to stroll around, visit the castle and perhaps buy a bottle or two of Montalcino Brunello to stash for later?

Leaving this stunning hill-top town, you’ll 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, you’ll 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. Your 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
  • Ascent: 1,000 Metres Approx.

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

Leaving via the backroads, you’ll 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 you come out of a forested track, the imposing walled town of Monteriggioni will stand ahead of you on a hilltop. Following the winding road you’ll ride right up to the entrance gates where there is a choice of delicious gelato places to pick up your reward!

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

Day 7
Colle Val D’Elsa to San Gimignano and Pancole
19 Miles / 30 Kms Approx.
  • Meals: Breakfast
  • Ascent: 620 Metres Approx.

Your final day in the saddle sees you riding through the hills of Val D’Elsa towards the picture perfect San Gimignano. As the view opens up revealing the ‘Town of Towers‘, you’ll no doubt be stopped in your tracks as you take in one of the prettiest and best preserved medieval settlements in Italy.

We’ve kept the millage today forgiving to give you plenty of time here to take a break from the bikes and walk around San Gimignano. Enjoy a coffee, climb one of the towers and end your trip in style with a scoop of the ice cream which often wins 1st prize at the world ice cream championships!

Leaving San Gimignano it’s just a few more kilometres to Pancole and your accommodation for the night.

Day 8
Departure: Pancole near San Gimignano / Pisa
Non Riding Day
  • Meals: Breakfast

Time to say your farewells to Italy as after breakfast you’ll be taken back to Pisa airport (PSA) for your onward flights.

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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.

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Dates & Prices

Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

2024 25 Mar – 30 Oct

Season 1 – £1595 03 Apr – 17 Jun and 04 Sep – 30 Oct

Season 2 – £1795 25 Mar – 02 Apr and 18 Jun – 03 Sep

2025 24 Mar – 29 Oct

Season 1 – £1675 24 Mar – 16 Jun and 03 Sep – 29 Oct

Season 2 – £1885 17 Jun – 02 Sep

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) Local representative (with welcome meeting)

D) Access to the an app for holiday information and navigation

E) Luggage transfers

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

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

H) Financial Protection through ABTOT

What's not Included Cross

A) Bike hire (available if required)

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

C) Single room (available if required)

D) Travel insurance

E) Meals not stated in the itinerary

F) Personal clothing and equipment

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

H) Entrance fees to museums and other attractions en route

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

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The Essentials

Travel Options

Your tour starts in Radda and finishes in Pancole, near San Gimignano.

Airport transfers are included in the cost of your tour. We ask that you fly into and back from Pisa airport (PSA). Please aim to arrive between 09:00 and 15:00 and depart between 11:00 and 19:00.

Please check with Skedaddle before making any travel arrangements.

Please note – If you make travel arrangements that fall outside of the above time windows there may be an additional charge for your 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 Carbon Gravel bikes, great bikes with good quality components. These bikes are 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 on our hire bikes. This holiday is self-guided and there will be luggage transfers to carry your main baggage however if you would like to bring handlebar or seatpost bags to carry some small items during the day then these can be fitted to the bikes or you could use a small back-pack for any essentials.

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News, Reviews & Stories

Gravel Riding Tips & What To Expect

If you're a roadie or mountain biker then here's what to expect when you hit the gravel trails.

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.


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