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Holiday Highlights
- Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
- Staying in quality accommodation, with fantastically warm hospitality
- Easing along the rolling hills of the Colli Sienesi
- Riding the stunning UNESCO heritage region of Val d’Orcia
- Stopping off at the lovely San Gimignano and Montalcino
- Chilling out with a post-ride Chianti
We got to experience what life is like off the beaten track and soak in the fantastic place that Tuscany is. There are not enough superlatives to describe how beautiful the accommodation was!
Itinerary
Following arrival at Italy’s Pisa airport (PSA), we make the short transfer to the charming spa town of Casciana Terme, a quiet retreat where you can spend the rest of the day relaxing and enjoying the facilities.
Depending on flight arrivals, 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 Casciana Terme to San Gimignano
- Meals: Breakfast
- Ascent: 1,130 Metres Approx.
Our first day’s ride will take us from Casciana Terme to the gem of Tuscany, San Gimignano. Leaving the hills around Pisa, the riding is gentle as we roller-coaster along the roads of the ‘Colli Pisane‘, taking a network of minor roads past woodland, vineyards and small towns. Just before we stop for lunch we gradually climb through lush green woods, before reaching the small walled medieval hill-top town of San Gimignano.
This fascinating ‘town of towers’ is one of the prettiest and best preserved medieval settlements in Italy and we should have some time to walk around the square and taste the World Ice-Cream Championships 1st prize winning ice cream! The town is also known for its white wine Vernaccia di San Gimignano but we might save that for later!
A short ride later will take us to our delightful hotel, surrounded by vineyards and rolling hills. Depending on the time of year, a dip in the pool and relaxing with a drink, makes a great finish on our first day riding in Tuscany!
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Day 3 San Gimignano to Radda in Chianti
- Meals: Breakfast, lunch
- Ascent: 1,100 Metres Approx.
Leaving the charming town of San Gimignano, today’s ride is a roller-coaster through a picturesque landscape of little medieval fortified villages perched on top of hillsides, such as Castellina in Chianti and Radda in Chianti.
We have time to ride up and through many of these small towns, absorbing the whole Tuscan experience along the way. With incredible views, intimate piazzas and some wonderful boutiques and art galleries, these towns make a perfect passage for our journey. Our destination for today is Radda in Chianti.
The village, famous for its wine, is located between the valleys of the rivers Pesa and Arbia on a forested hillside in the Chianti Classico region. After settling into our accommodation, we set off to a renowned ‘Enoteca’ where we have the opportunity to try some of the best of the Chianti wines produced in the region.
Show ProfileDay 4 Radda in Chianti to Pienza
- Meals: Breakfast, lunch
- Ascent: 1,550 Metres Approx.
Today we leave Radda and ride to Gaiole in Chianti and on to Castelnuovo Berardenga, on our way to Pienza. Today’s ride takes us further south past hills blanketed with vineyards and thick forests. This whole region is dotted with castles, once defensive systems but now privately owned by wine producers.
We ride past Meleto, San Donato in Perano and Brolio Castle. We will rest our legs in Asciano, yet another little medieval town set on a hillside, above the Ombrone Valley. After a final rollercoaster climb through the ‘Colli Sienesi‘, we reach the outskirts of Pienza, our destination for today’s ride, the quintessential renaissance town of Tuscany.
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- Meals: Breakfast
- Ascent: 1,270 Metres Approx.
In the morning we spend a little more time enjoying Pienza, located in the centre of the Val d‘Orcia. Pienza is often described as a ‘utopian city‘, representing one of the best-planned Renaissance towns, where a model of ideal living and government was attempted, based on the concept of a town able to satisfy the needs of a peaceful and hardworking populace.
Leaving Pienza, we continue with a fantastic descent and a superb ride into the heart of Val d’Orcia, a UNESCO heritage region with conical hills lined by cypress trees, the ultimate aesthetic of Italian landscape.
We ride on to San Quirico d’Orcia and Bagno Vignoni where legend has it that St Catherine and Pope Pius II both bathed in the thermal waters here. On to Castiglione d’Orcia with its picturesque stone-paved streets and Romanesque church.
The next climb of the day will take us to the quintessentially Tuscan hilltop town of Montalcino, best known for its Brunello red wines. Here we stop for lunch, taking our time for a walk through the old town with its many osterie and wineshops.
In the afternoon, leaving the hill town, a long and gradual descent will take us back down towards Buonconvento and onto a gentle rollercoaster of superb riding through more countryside and farmland. The aim for today is the village of Vescovado near the hilltop hamlet of Murlo, where after settling in at our hotel we may well have a dip in the pool before sitting down for dinner.
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Day 6 Vescovado to Volterra
- Meals: Breakfast, lunch
- Ascent: 1,765 Metres Approx.
From Vescovado today we head for the ancient Etruscan town of Volterra. Our route takes us north in direction of Siena to then veer west through the lesser known, but no less beautiful scenery of the Montagnola Senese hills. Here we cycle on small secondary roads between pastures, fields and old farm houses to Pievescola, Mensano and the enchanting medieval village of Casole d’Elsa, little known and well worth some time off the bike.
Eventually we will reach busy Volterra, one of Tuscany’s most evocative hill towns steeped in Etruscan, Roman and medieval history. After checking into our hotel and freshening up we can go out for a walk to explore the ancient remains, including the Etruscan gates and necropolis or the remains of the Roman forum and theatre. History and archaeology buffs may well pay a visit to the Museo Etrusco, one of Italy’s finest.
Show ProfileDay 7 Volterra to Casciana Terme
- Meals: Breakfast, lunch
- Ascent: 400 Metres Approx.
Our final day’s ride will take us back towards Casciana Terme. Taking a network of minor roads, we meander over rolling hills, stopping off in Lajatico, the home town of the famous Italian tenor Andrea Bocelli.
Arriving early in the afternoon in Casciana Terme will not only give us time to pack up our bikes without rushing, but also to make the most of the hot springs, indulging in thermal baths and more fine dining and wine. A great way to end Italy’s ultimate riding experience.
Show Profile- Meals: Breakfast
Time to say our farewells as after breakfast we will take you back to Pisa airport (PSA) for your onward flights.


Understanding Profiles
Use these profiles to see:
- Distance in Km (horizontal axis)
- Ascent / Descent in metres (vertical axis)
Click 'see gradient' to see:
- Distance in Km (horizontal axis)
- % Gradient (vertical axis)
Please check the scales on both graphs, and both axes as they both may differ from day to day.
White vertical lines indicate unpaved sections or slightly rougher terrain. Using both graphs, alongside the grading and terrain information provided, will give you a full picture of how flat, bumpy or steep the climbing on your particular tour is going to be. Please keep in mind this is an indicative guide and GPS units and software produce different statistical information.
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Gallery
The Cycling
Terrain
We will be riding mostly on well-surfaced tarmac roads, through countryside linking up some of the most important hilltop centres in this stunning region. Tuscany is predominantly hilly, so you can expect climbs every day, some short steep sections, some longer ones, followed by meandering descents.
Tuscany is also famous for its ‘Strade Bianche’ (unsealed white roads) which host their own annual road cycling race; L‘Eroica. You will have an opportunity to ride some short stages of the L‘Eroica route so we recommend that riders avoid super lightweight racing tyres and opt for a slightly more robust tyre, such as a puncture resistant 28c. These will also be useful when on the approach to some of our rural accommodations which are often dirt road or gravel driveways.
Strade Bianche roads are entirely rideable on road bikes however we can provide vehicle transfers or offer alternative routes to riders who prefer not to ride these short unsurfaced stages.

Road Cycling Grade
45-60 miles / 70-95 kms per day
For riders with experience, good fitness & a decent level of skill
Some features that may be experienced more frequently in a higher grade tour
Most days include a couple of significant climbs
Some long days & some steep to very steep sections
Not for beginners
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?
You’re definitely not a novice rider, you’re fit, you ride regularly at weekends, sometimes staying on the bike for much of the day, you love your bike! You also enjoy a challenge and if you haven’t already done so you’re keen to attempt a semi-serious to serious mountain pass or two. You’re as comfortable with the prospect of descending from the top of a col as you are with the idea of climbing it and you’re confident that you have the skills to do so safely. You’re not necessarily a “racer” but you can crank up the pace a little when it’s necessary and you don’t mind forgoing a coffee stop if the schedule demands it occasionally. You probably own and use clipless pedals. You have good control of your bike and can take a drink from a water bottle without having to unclip and put your feet on the ground. Whilst you find a full day in the saddle fulfilling you’re not obsessed and as much as you are looking forward to the riding on your holiday, you’re also looking forward to a little local culture and cuisine. Grade 3 would be a good option 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.
I really appreciated the efforts and the personal touch put into the spread provided for us. Dinner – absolutely fantastic, I’ll be reminiscing and dreaming about each meal for years to come.
Dates & Prices

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Whats Included 
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) Group airport transfer on scheduled arrival day from Pisa airport (PSA)
H) Group 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
J) Tips for guides, drivers, support staff

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
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