Glorious Gravel

Off:Roader Toscana

3.5 Stages | 325km


16th - 20th Oct




325 kms

Ride Overview

A three stage off-road epic in the home of gravel cycling: the white roads & rolling hills of Tuscany.

Averaging 90km per day on a mix of traditional white roads, singletrack and back country lanes, we ride from San Gimignano to Siena and over to the Chianti hills taking in sections of l’Eroica & the classic Strade Bianche.

With a max group size of 24 riders, lovely locally owned hotels, delicious Tuscan food & wine and some of the best gravel riding on the planet, this is the perfect mix of epic riding & fun post ride socials in beautiful places.

“3 and a bit (prologue) of the best days on a bike I’ve ever had” – Karl, 2022 rider.


Deposit £299 | Private Single £1,599 | Shared Twin / Double £1,399


  • The home of gravel cycling! With a massive network of gravel roads and an amazing history in this bike mad region, Tuscany truly is the home of off roading.
  • Food, Wine & Culture: Each evening we enjoy local food & wine as we alternate between small hotels in the rolling hills and a night in stunning Siena.
  • Iconic white roads: Ride sections used in the legendary Strade Bianche & L’Eroica as well as some stunning local secret spots our local crew are lucky enough to spend the year exploring.

Included in Ride Package


4 nights in charming 3 & 4* locally run hotels.. Choose private single, shared twin (2 beds) or shared double (1 bed) rooms.

Airport Transfers

Fly into Pisa (PSA) and our friendly team will be there to collect you on arrival day and drop you back when you leave.

3 Epic Stages

And a prologue! We break the group into small groups with guides & support vehicles so you can just focus on the epic riding.


Bring some money for drinks in the evening but our package includes 4 dinners, 3 lunches & 4 breakfasts.


Real food and mechanical support are waiting for you every 35km with a mix of sports bars, fruit and local specialties.


We move your overnight bags from hotel to hotel each day and provide a day bag to collect at lunch with spare kit etc.


We start the ride with a short but hilly 26km prologue to make sure the legs & bike are in good condition for bigger rides to come.

This stage should take between 1.5 and 2hrs with 3 climbs (2km on tarmac , 1.5km on gravel & 3km on tarmac) before getting home for a beer and the briefing for the weekend.


Distance: 26km
Elevation: 750m
Ride Difficulty: 3/5
% Off Road: 55%

The first big day! Today takes us from the rolling hills around San Gimignano to the beautiful city of Siena.

The route starts on tarmac with a warm up climb after 4km (3km at 5.5%) before we hit our first gravel.

The main challenge of the day is a gravel climb coming a third into the ride (4km at 7%) but after this the route is mostly rolling with some stunning views in the hills to the South West of Siena. 


Distance: 96km
Elevation: 1900m
Ride Difficulty: 4/5
% Off Road: 50%

The Queen Stage of the tour. Starting out in Siena, we head south and ride the classic 8km San Martino in Grania section as featured in Strade Bianche. This is a long false flat with some punchier parts and you can see the gravel road stretching out for miles in front of you.


After this we head north into the Chianti hills for some gravel and tarmac roads on glorious rolling terrain and finish in the stunning town of Radda in Chianti.


Distance: 111km
Elevation: 2500m
Ride Difficulty: 4.5/5
% Off Road: 50%

The final stage takes us back over the hills and through the heart of the Chianti region. The toughest of the climbing is in the morning on fresh legs as we head west back into Siena province where the terrain is lumpy but few long climbs.


After our main feed stop the final part of the ride is on great rolling roads (a mix of gravel & tarmac) before a finish on the outskirts of San Gimignano.


Distance: 89km
Elevation: 2000m
Ride Difficulty: 4/5
% Off Road: 55%

Event Overview

Our Off:Roader series are non-competitive, designed to take you off the beaten track with a group of friendly, supportive riders. The whole event is social starting on arrival day with a gentle prologue and a cold beer all together at the finish line.


Each evening we eat together and have a ride briefing where our UK event manager goes through the next stage & our Tuscan hosts talk us through the region we will be riding through.


This is a small group ride with maximum 24 people. We have 4 guides to ride with you in small groups of people going at your pace. 


We have regular feed stops at local cafes and a lunch stop each day. Our support van is always on call if you need anything. We take delight in our reputation of providing multi stage rides of a lifetime and nothing is too much trouble to ensure you have a great time.

Accommodation & Meals

We stay on Wed & Sat night in San Gimignano at a charming 3* superior hotel with great local food. 

After this we head into Siena for Thurs night with dinner in the town centre and time to explore this amazing place.

On Friday we stay in the lovely village of Radda in Chianti at a pretty 4* hotel with a pool, spa and excellent chef.

In the evenings we all eat together in the hotel or a local restaurant. We will send across a menu of what we will be eating before departure and there will be options for vegans & all dietary requirements.

Equipment & Packaging

We will send a full packing list but early October in Tuscany is similar to May in Mallorca – we should get warm sunny days but mornings & evenings can be fresh so knee & arm warmers will be useful as well as normal layers (gilet, wind-proof jacket etc). Last year we rode in 20 to 24 degree sunshine after cooler early mornings. We don’t go high in the mountains so we are unlikely to get extreme conditions.


Evenings are casual but bring a jacket and don’t forget to pack swimmers. You will need to bring one small sided item of luggage which we will take from hotel to hotel and you will get a small day bag on arrival where you can pack extra clothing etc to collect at the second checkpoint.


The ride takes in a mix of gravel roads, tarmac and some off road sections on dirt / grass. It is ideal for gravel bikes with all rounder tyres (35mm plus).

Event Program

16th Oct (all day): Arrive into Pisa airport, see below for transfer times.


16th Oct (3pm): Prologue (26km) starts.


16th Oct (7.30pm): Pre Ride briefing & dinner.


17th Oct: 9am stage start. 7.30pm briefing & dinner


18th Oct: 8.30 stage start. 7.30pm briefing & dinner


19th Oct: 8am stage start. 7.30pm briefing & dinner


20th Oct: Departure day, see below for transfer times.


Arrange flights into and out of Pisa (PSA). 

On 16th Oct, arrive before 11.30am for a 12pm transfer (arrive at hotel just after 1pm).

On 20th Oct, the first transfer leaves the hotel at 7am for flights departing Pisa after 10.30am. The later transfer leaves the hotel at 12pm for flights leaving Pisa after 3.30pm.

The transfer takes approx 1hr15mins. 

Yes, we have Sonder Camino gravel bikes to rent for £199 in all sizes from S to XL. You can find these in the checkout once you have selected your room option.

Yes, in the checkout there is a box to put whoever you want to share a room with. If you are booking a double room (2 people, 1 bed) please select 2 people in the checkout.

You can secure your place with a deposit of £299. This is non-refundable so we strongly suggest you get travel insurance before booking (you can also purchase cancellation insurance in the checkout).

Full payment is due 3 months before departure (July 16th), we will send you a reminder when this is due.