- 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!
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.
- Meals: Breakfast
- Ascent: 1,050 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!
- Meals: Breakfast, lunch
- Ascent: 1,500 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.
- Meals: Breakfast, lunch
- Ascent: 1,700 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.
- Meals: Breakfast
- Ascent: 900 Metres Approx.
Being a short day, there is time to explore Pienza, a rare example of Renaissance town design. Often described as a ‘utopian city‘, it represents 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. Pienza’s location in the centre of the Val d‘Orcia, a wonderful and untouched valley, helps the town to embody the fundamental principal that humanistic architecture attempted to incorporate – the balanced relationship between Man and Nature.
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 final climb of the day will take us to the quintessentially Tuscan hilltop town of Montalcino.
- Meals: Breakfast, lunch
- Ascent: 1,200 Metres Approx.
We are getting to the end of our tour of Tuscany and the riding is smooth along the rolling hills of the region around Montalcino. Leaving the hill town, a long and gradual descent will take us back down into Val d‘Orcia. Today’s riding will be a gentle rollercoaster of superb riding through more countryside and farmland. Our destination for today is Casole d‘Elsa, a cobbled medieval town set on top of a hill, barely visited by tourists. Rewarded by the views and yet another gelato stop, we move on to our accommodation. After a dip in the pool we head back up to Casole for dinner at a traditional ‘osteria‘.
- Meals: Breakfast, lunch
- Ascent: 1,050 Metres Approx.
Our final day’s ride will take us back towards Pisa and Casciana Terme. Taking a network of minor roads, we meander over rolling hills, eventually ascending into Volterra, one of Tuscany’s most evocative hill towns. From the Etruscan gates to the remains of the Roman forum, we’ll capture the real Italian experience here. Arriving early afternoon in Casciana Terme, will not only give us time to pack up our bikes 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.
- Meals: Breakfast
Time to say our farewells as after breakfast we will take you back to Pisa airport (PSA) for your onward flights.
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 25c. 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.
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
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.
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) Support vehicle and luggage transfers
F) Airport transfer on scheduled arrival day from Pisa airport (PSA)
G) Airport transfer on scheduled departure day to Pisa airport (PSA)
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
News, Reviews & Stories
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...
Meet the guides: Gualtiero Rossano
In our quest to share our incredible guides with the world, check out our Q&A with Wally...
Customer Story: Tuscany
A journey at your own pace that explores one of the Italy's iconic landscapes...
Jane, Kent UKOustanding accommodation...
As expected I found the quality of accommodation truly outstanding.
I really didn’t know what to expect this time round and thought that current health conditions would really tarnish the trip. However, apart from the mask wearing and a few extra precautions I think Naomi and Antonio did a fantastic job to ensure the trip went ahead as seamlessly as possible. Well done!
Kevin, Oxfordshire, UKGreat guides on an excellent holiday!
The accommodation was very comfortable – some of the best I have ever experienced compared to other cycling holidays (both Saddle Skedaddle and other companies). The standard of cooking was generally very high (as it usually is in Italy)! The riding in day 3 from San Gimignano to Radda in Chianti was our favourite day and I also really enjoyed the visit to the vineyards near Montalcino.
The service provided by the tour leaders was excellent. Wally was amazing, very knowledgeable about the routes we were taking every day, taking care to indicate exactly where the steep climbs and descents were. He was also very friendly & relaxed. He set a very reasonable pace – not too fast or not too slow. He also took some great photos of the group as we rode along. And he was a very interesting companion at dinner – lots of good stories to share with the group. Antonio was great too. He did all the driving & most of the lunch preparation. He was very patient with everyone. He was also exceptionally helpful and obliging – nothing seemed to be too much trouble. I thought he did an excellent job sorting out all the little problems that people encountered with their bikes. And like Wally he was also a very entertaining dinner companion.
John, UKCharming tour leaders - we will miss them!
There was a real good mix of days and so I have no real favourite – I liked them all! The tour leaders Wally and Antonio were absolutely charming and were always looking to help and makes sure everyone was having a good time. They worked very well together and were both extremely professional and certainly added to the enjoyment of the trip and we will all certainly miss them.
Tom, New York, USAEvery day is enjoyable!
I enjoyed all the days, great scenery, friendly people and challenging rides. I enjoyed staying in the old estate and the tour of the winery. I liked that the riding got easier as the week progressed.
Our Tour Leader, Wally, is the best – very friendly and accommodating and goes out of his way to make sure everyone is treated well. He rides back and forth if someone falls behind and takes great pictures during the ride. He’s equally friendly and helpful from the first day to the last. Antonio was excellent as well – willing to help whatever the problem and an excellent bike mechanic. He’s very personable and such a hard worker.
Paul, LondonA great success...
The relaxed and competent leadership provided by Lieven was a key feature in making the holiday a great success. Information provided each day was clear and comprehensive. Favourite day? They were all good! But personally the extended section of Strada Bianchi on day 5 was very enjoyable.
We’ve been on a tour with Leiven before—excellent leader! The 3 guides were very professional, making sure that all cyclists were supported throughout. Bike great and good technical support from the guides. We’ve now been on 3 Skedaddle trips and have enjoyed each one immensely.
Martin, BristolReally enjoyed the holiday...
Would highly recommend Saddle Skedaddle and this trip in particular. Very knowledgeable and friendly guides (Lieven & Nicola), who both worked hard to ensure that things went smoothly and we had an enjoyable time.
Varied and interesting lunches from Lieven & Nicola, who always seemed to find a great location. Always plenty of food, juice and water available. Liked the idea of set meals at dinner, as we could benefit from local produce, and made ordering much easier.
Had a great holiday with a lovely bunch of people – thoroughly enjoyed it & would definitely recommend it to others.
Great mix of climbs, flat sections & really enjoyed the section of Strada Bianca too. Beautiful scenery & great company. Also loved the 2nd Agriturismo – stunning place to stay with lovely relaxing atmosphere, excellent host & wonderful food& wine.
Robert, ReadingI cannot imagine anyone having a bad experience with Skedaddle....
Superb – cycling is by far the best way to see a country and experience what most tourists miss as they speed past in metal boxes between one busy attraction and their hotel. We get to experience what life is like off the beaten track due to the fantastic routes chosen by Skedaddle and to see, smell and soak in the fantastic place that Tuscany is. Quite simply, there are not enough superlatives to describe how beautiful the Tuscan countryside and the accommodation chosen were – and they got better day after day. The guides are without doubt what make the experience fun, stress free, challenging and rewarding – I have tried a couple of other companies recently and come back to Skedaddle because nobody does this as well as you.
Massimo, Nicola and Gianfranco were all excellent – they went out of their way to provide the best service they could. It didn’t feel like it was just a job to them, it was almost like they were part of the group – enjoying the trip themselves and making sure we enjoyed it at the same time. So many other parts of the service were excellent, but it is the guide that truly make Skedaddle stand out above other companies.
Gina, SurreyAnother wonderful trip superbly organised by Skedaddle...
Massimo & Nicola were superb at keeping us all together en route and always utterly cheerful! Excellent riding companions and majority were Skedaddle regulars which goes to show that you just keep doing what you‘re doing. It’s very good and we’ll keep coming back.
The secret is your wonderful cheerful guides that make each one of us feel comfortable and important to them. Always willing to go to extraordinary lengths to help us with unforeseen mechanical problems – very grateful and very happy!