- Staying in lovely Tuscan accommodation overlooking stunning landscapes
- Riding the Montagnola trails, the location of a well-known Sienese MTB race
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Riding down the Crete Senesi on a roller-coaster ridge ride
- Enjoying the journey across Tuscany on a variety of terrain
- Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
What an opportunity to see the Tuscan countryside in such an intimate way!
- Meals: Dinner
You will be met at Pisa airport and transferred to San Gimignano (transfer approx 90 mins), staying in an accommodation set in the outskirts of the famous town. With a plunge in the pool overlooking vineyards, the holiday is really starting. Dinner is at the estate.
- Meals: Breakfast, lunch
- Ascent: 600 Metres Approx.
Today we set off with a fun off-road section down into the lower valley before looping back towards St Gimignano. We journey south following a mix of dirt roads and trails through woods, over hills and crossing streams, through a constantly changing rolling Tuscan landscape. Most climbs will be on farm or forest gravel routes, which lead onto sections through vineyards and fields, trails and paths used mostly by local people and farmers. It can be muddy at times!
The destination for today is Strove a small hamlet not far from Abbadia Isola and Monteriggioni. After stopping in the square for a well-deserved beer we move on to our accommodation, where you can enjoy a dip in the pool before heading out for dinner.
- Meals: Breakfast, lunch
- Ascent: 750 Metres Approx.
Your first stop for today is the quaint medieval hamlet of Monteriggioni, with time to explore the castle walls and narrow streets. Leaving the fortified village, you’ll continue with a steady off-road climb through the Montagnola range which offers great options of trails and routes.
This area is a well known destination for the Gran Fondo Sienese MTB race. This area is also ideal for some fun mountain biking, as we explore the network of dirt tracks leading into the hillside forests, looping on fun rolling singletracks towards little hamlets and twisting down over rolling fields.
A final fun section of singletrack winding through forests will lead us to the outskirts of Siena. One last push on tarmac and we roll into the old walls of this quiet town. There is time to wander through Siena, visit the Palio Square and Duomo, before heading out to dinner for a mouthwatering Tuscan meal.
- Meals: Breakfast, dinner
- Ascent: 500 Metres Approx.
We leave Siena through the ancient town gates and continue our journey south on the Eroica route and into the Crete Sienesi. Arriving near the ancient Etruscan hamlet of Murlo, we enjoy a fun ride on narrow trails by the Crevole River, then up a former mining railway track to Murlo itself.
Picking up the Eroica route we head to Buonconvento were we have time to stop for a refreshing break and if inclined visit the fortified walls. With our accommodation right in the centre of town, we can enjoy some down time, joining the locals in an afternoon aperetivo!
- Meals: Breakfast, lunch
- Ascent: 1000 Metres Approx.
Our mountain bike pilgrimage continues as we head towards Pienza, right in the heart of the Unesco heritage site of Valle d‘Orcia. The route takes us along the ridge lines of the “crete” offering 360 degree views. The trails are a mix of farm tracks and dirt roads, with cheeky steep sections which will get you out of the saddle!
Today is tougher day in terms of daily ascent, and after joining a section of the Eroica, you’ll reach your accommodation in the heart of Pienza. Designated a UNESCO heritage site, Pienza is a perfect base for two nights allowing us to explore some cultural and historical sites as well as small Tuscan shops, wine bars and restaurants.
- Meals: Breakfast
- Ascent: 900 Metres Approx.
Different options are available for today’s ride. Whichever way we decide to ride the various terrains and routes will take us to San Quirico d‘Orcia. From here we descend quite steadily on a fast gravel track into the Orcia valley then loop back through fields, dense woods and past castle hamlets, until we reach the medieval hamlet of Bagno Vignoni with its healing baths and home to the legendary water nymphs.
After resting and taking time to explore the hot water springs, we head right into the centre of the Unesco heritage site of Valle D‘Orcia. From there we start a steady climb towards Pienza along some well surfaced strade bianche. Time in Pienza to absorb and visit the local sites, before indulging in another delicious Tuscan meal at one of our carefully selected local restuarants.
Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, with quaint little hamlets dotted on hilltops.
Riding is on a mix of chalky double track or “Strade Bianche” so it can be fast rolling in dry conditions, or of course, get a bit more sketchy in the wet. A mountain bike with off-road tyres is the best choice. The wider tracks will be alternated with some fun, flowing narrower trails that can be rocky and with roots in sections. On the Montagnola range near Siena, fun sections of singletrack can be a bit rocky with limestone making the trails a bit tricky in places.
There are a few steep, and a few long climbs, so fitness is more important than off-road riding skills – of course all the climbing leads to some great descents.
Mountain Biking Grade
25-50 miles / 40-80 kms per day
Aspects of both our grade 3 and 4 trips
For mountain bikers with some experience of singletrack and steeper terrain
May include rocky features and switchbacks
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?
Trips that are graded as a 3-4, will have aspects of both our grade 3 and 4 trips. If you have experience of off road riding on a variety of terrain, and would like a taste of more challenging terrain, a grade 3-4 trip could be for you. Terrain will include singletrack and steep sections (both up and down) which require more bike handling ability. Shorter technical and demanding features suchs as rocks, roots and tricky climbs will be encountered on occasion on most days. A day’s ride can see you on the trails for around 8 hours (with breaks) and covering between 25-50 miles depending on the terrain. If you’re generally fit and manage to ride frequently this could be the level for you.
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.
A truly memorable trip and has already got us planning to revisit the area. Thanks so much!
Dates & Prices
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Book now with a $250 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.
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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
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
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.
Why we love Italy!
Here are 7 things you'll only understand if you've cycled in Italy and why we're so eager for you to join us here...
Guide Profile: Naomi Lindfield
Meet Naomi, our Head Honcho of Skedaddle Italia!
Sarah, USAThank you, Skedaddle, for inventing this tour.
What an opportunity to see the Tuscan countryside in such an intimate way as cycling / mountain biking. How else could we get a guided tour – the best trails, lodging and meals all figured out for us?
When one guest lacked stamina the first day, Skedaddle got him an e-bike and for the rest of the days he did great. When another guest needed stitches a guide took her to the hospital in the van right away. These are examples of good service.
Mike, Bedfordshire, UKExcellent riding!
Excellent riding – Hard to single out one day. The mix of technical and fitness was great and I particularly enjoyed the climbing (I know, I am weird). Great planning by the guides when the original route was not suitable due to the weather – we had a great day around Montalcino.
Becky, Derbyshire, UKAll the scenery was stunning
All the scenery was stunning, so all days were enjoyable. The last day in particular as it was the only real day with any singletrack was most enjoyable in terms of MTB riding.
Susan, South ShieldsExcellent holiday
This was an amazing cycling holiday. The tour guides clearly knew the route well and were knowledgeable about the area we were cycling in. They worked hard to make sure we all had a great holiday with lots of laughs along the way.
Susan, ScotlandGreat holiday - much better than expected
All days were great in different ways – but as an experienced mountain biker the final day was probably my favourite as it included a number of downhill sections and generally some slightly more technical sections uphill too.
Peter, UKExcellent,friendly,efficient guides
Gianfranco was excellent, friendly and efficient. He really cared that each one of us had a good time. Also Juditta and Stefano were excellent. Very good at their jobs and always smiling so they brought a friendly atmosphere to the trip.
Robert, UKFantastic views!
Favourite day was the final day with best singletrack and with fantastic views of Pienza to finish the week’s riding.
Ian, London, UKGreat...
A truly memorable trip and has already got us planning to revisit the area. The crew on the ground were excellent and nothing was too much trouble. The cycling was a little harder than I imagined (as was the amount of wine we drank!!), but such great company and organisation/pace mean that it was still a holiday and not too much of a grind. The accomodation/food/routes were all stunning. Thanks so much. A dopo!