Italy - Tuscany - Giro della Toscana - Guided Road Cycling Holiday
- 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
View Holiday Schedule
|1||Arrival: Pisa Airport||Non Riding Day|
|2||Casciana Terme to San Gimignano||45 Miles / 70 Kms Approx.||1,300 Metres Approx.||B L|
|3||San Gimignano to Radda in Chianti||40 Miles / 65 Kms Approx.||1,500 Metres Approx.||B L|
|4||Radda in Chianti to Pienza||55 Miles / 90 Kms Approx.||1,700 Metres Approx.||B L|
|5||Pienza to Montalcino||28 Miles / 45 Kms Approx.||900 Metres Approx.||B L|
|6||Montalcino to Casole d’Elsa||50 Miles / 80 Kms Approx.||1,100 Metres Approx.||B L|
|7||Casole d’Elsa to Casciana Terme||45 Miles / 70 Kms Approx.||1,150 Metres Approx.||B L|
|8||Departure: Pisa Airport||Non Riding Day||B|
Meals: B = Breakfast L = Lunch D = Dinner | Please keep in mind the distances and ascent information provided are intended to be indicative and may vary from the actuals due to accommodation changes or when compared on different GPS devices and software
For more information download our trip notes
For more information download our trip notes
Great 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.
Kevin, Oxfordshire, UK
Charming 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.
Every 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.
Tom, New York, USA
A 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.
Really 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.
I 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.
Another 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!
The guides make all the difference...
Massimo is the best there is! I keep coming back because of him. Great cyclist, great person, great work ethic!
Menachem, New York
A wonderful experience!
I think all the food was excellent (evidenced by the fact I didn’t lose any weight during the week, despite the kilometres cycled every day). 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. Refreshments – the ice cold, sweet juice and the fruit and nuts were my saviours, they absolutely hit the spot. And the gelati stops were absolute gold!
Naomi was superb – very professional, accommodating and friendly. She showed genuine care, concern and interest in every single person on the trip, and made sure everyone was comfortable and happy. It was wonderful not to feel judged, pressured or rushed; to still be able to enjoy the trip.
Yes – I think the dynamic of our particular group played a big part in how much I enjoyed the trip, and how likely I would be to participate in another Skedaddle trip. I feel we were lucky to have such a great group of people who got along so well – hopefully every Skedaddle tour attracts the same quality of clientele. I was very happy with the tour – thank you very much for the wonderful experience!
Overall, a very enjoyable trip...
The office staff and staff on the trip were excellent from start to finish! Naomi was a fantastic guide and took everybody’s opinions / wishes into consideration. We saw some fantastic countryside and did some wonderful cycling.
We stopped in some lovely towns so it wasn’t all hard work! We stayed in some wonderful ‘rustic’ / authentic Italian accommodations – they were classy and not your average accommodations. Very well researched! So good value for money.
The food was excellent and at a good price, as was the wine. In fact, there was too much food on occasions but not complaining! It was our first trip with Skedaddle but I don’t feel it will be the last.
Jonathan & Claire, Bristol
He was absolutely charming and such an amusing man – very attentive. The food prepared by Massimo and Vanessa was outstanding!
Excellent – it was clear that a great deal of thought and care had been taken with the accommodation choices and I was often surprised with the quality which was far better than I expected!
Pre holiday information was very detailed and gave a good account of what to expect from the trip.
Stephen, Newcastle upon Tyne
Excellent, quality accommodation!
The quality of accommodation was really very good and so worth the extra cost. The evening meal did cost more than we had anticipated as we hadn’t realised in advance that we had no venue choice due to remote locations; the meals did represent good value but we would have preferred to know they would cost around 25 – 30 per meal (which as vegetarians is more than we had expected). However I must add that we really did enjoy the meals, and the experience of eating together in these locations was fantastic so please don’t change it!
David & Vivien, Bedfordshire
Well worth the money...
I must confess that I was initially sceptical about the holiday cost but on reflection; whilst not cheap, it was indeed a very good trip. I hope you are able to achieve this high standard accross all your holidays.
All email marketing communications from Skedaddle will come with the option to unsubscribe and you can also manage your subscription preferences by logging in to the My Account area of our website.
Give us a call on:
Drop us an email on:
- 8 days
- Prices From:
- Estimated flight price:
- Bike Hire:
- Single Room:
- Single Room:
Place to place
7 nights agriturismo/small hotel accommodation
6 days riding
Breakfasts and lunches
Guided and vehicle support
Group airport transfers
You may also like...
Riding in the unspoilt region of Spain, this journey takes you through the most stunning mountain range in western Andalucia. During the tour you'll find yourself cycling along quiet country roads and...
Come and discover this Spanish cycling gem and world-renowned wine region. La Rioja doesn't need much of an introduction… The deep red 'tinto' that has shaped the culture and land for centu...
The regions of Piemonte in Italy called Langhe and Roero have become known as one of the most important wine production areas of the country, for wines such as Barolo, Nebbiolo and Asti. Recently it h...
Skedaddle News, Views and Holiday Stories
New to Skedaddle and our latest Customer Competition winners, Angela and Jeremy Adams, recently headed on our Giro della Toscana self-guided road cycling holiday in Tuscany. It’s a journey that explores one of the country’s premier destinations with classic Italian landscapes, rolling hills…
Last Updated: 07/10/2019