- 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
A fantastic holiday discovering beautiful hilltop villages, meeting some great local people and enjoying wonderful food and wine. Can’t thank the team enough!
Following arrival at Pisa airport (PSA), we will transfer you to the charming town of Casciana Terme, a spa town retreat. You will receive your road book and we will provide you with all the information you will need for the duration of your trip, before we leave you to start your self-guided tour of Tuscany. Depending on your arrival time, 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: 1,300 Metres Approx.
Your first day’s ride will take you from Casciana Terme to the gem of Tuscany, San Gimignano. Leaving the hills around Pisa, the riding is gentle as you roller coaster along the roads of the ‘Colli Pisane‘, taking a network of minor roads past woodland, vineyards and small towns.
Just before you stop for your lunch you gradually climb through lush green woods, before the final descent towards San Gimignano. You will stop in your tracks as the view opens up, ahead of you the ‘Town of Towers’ and one of the prettiest and best preserved medieval settlements in Italy.
You should have plenty of time to walk around San Gimignano, climb one of the towers and taste the ice cream which won 1st prize at the world ice cream championships. A short ride will take you to your 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 your first day riding in Tuscany!
- Meals: Breakfast
- Ascent: 1,500 Metres Approx.
Leaving the charming town of San Gimignano, today’s ride is a rollercoaster through a picturesque landscape, with many little medieval fortified villages perched on top of the hills, such as Castellina in Chianti and Radda in Chianti.
You will have time to ride up and through many of these small towns, absorbing the whole Tuscan experience. With incredible views, intimate piazzas and some wonderful boutiques and art galleries, these towns make a perfect itinerary for your bike ride. Your destination for today is Radda in Chianti.
Staying at the accommodation in the centre of Radda in Chianti, you have time to enjoy the atmosphere of this hill top town and indulge in some fine wine tasting and dining at some of the best restaurants of the region.
- Meals: Breakfast
- Ascent: 1,700 Metres Approx.
Today you leave Radda in Chianti and ride through Gaiole and on to Castelnuovo Berardenga, on your way to Pienza. Today’s ride takes you 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.
You will then ride past Meleto, San Donato in Perano and Brolio Castle. You can rest your legs in Asciano, yet another little medieval town set on a hillside, above the Ombrone Valley.
After a final roller coaster climb through the ‘Colli Sienesi‘, you will reach Pienza, your destination for today’s ride, the quintessential renaissance town in Tuscany.
- Meals: Breakfast
- Ascent: 900 Metres Approx.
Pienza is 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, you 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 the Italian landscape. You then 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. On to Castiglione d’Orcia with its picturesque stone paved streets and Romanesque church, the final climb of the day will take you to the quintessentially Tuscan hill town of Montalcino.
Narrow streets lined with boutiques, art shops and wine shops allows for a relaxing time. For wine lovers, Montalcino Brunello wines can be tasted in one of the many wine bars, savouring some of the best reds that the area has to offer.
- Meals: Breakfast
- Ascent: 1,200 Metres Approx.
You are getting to the end of your cycling in 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 you back down into Val d‘Orcia. Today’s riding will be a gentle roller coaster of superb riding through more countryside and farmland. Your 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, you move in to your accommodation. After a dip in the pool you can then head back up to Casole for dinner at a traditional ‘osteria‘.
- Meals: Breakfast
- Ascent: 1,150 Metres Approx.
Your final day’s ride will take you back towards the rolling Pisan hills and Casciana Terme. Taking a network of minor roads, eventually ascending to Volterra, one of Tuscany’s most evocative hill towns. From the Etruscan gates to the remains of the Roman forum, you’ll capture the real Italian experience here. Arriving early afternoon in Casciana Terme, not only will it give you time to sort out your bikes but also to make the most of the hot springs and more fine dining and wine. A great way to end Italy’s ultimate riding experience.
You 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 some climbs with short steep sections 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 offer alternative routes to riders who prefer not to ride these short un-surfaced 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 loved the variety of scenery, awesome views and beautiful towns! The representatives were very helpful and ensured we had all we needed for our self-guided trip.
Dates & Prices
Daily departures available. The season prices below are applicable for all start dates between and inclusive of the stated dates.
2021 26 Mar – 30 Oct.
Season 1 – £1290 pp – 08 Apr to 21 Apr, 03 May to 26 Jun, and 02 Sep to 30 Oct
Season 2 – £1545 pp – 26 Mar to 07 Apr, 22 Apr to 02 May, and 27 Jun to 01 Sep.
2022 26 Mar – 30 Oct.
Season 1 – £1290 pp – 26 Mar to 14 Apr, 02 May to 24 Jun, and 04 Sep to 30 Oct
Season 2 – £1545 pp – 15 Apr to 01 May, and 25 Jun to 03 Sep
Hotel upgrade option applies to 4 out of 7 nights – San Gimignano, Radda in Chianti, Pienza & Montalcino.
A) Accommodation (shared twin / double en-suite rooms)
B) Meals as per the itinerary (B=Breakfast, L=Lunch, D=Dinner)
C) Local representative (with welcome meeting)
D) Detailed route notes and maps
E) 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) City tax to be paid at each accommodation (amount varies)
J) Airport transfers on days other than the scheduled arrival / departure days
Our travel guide to 2021
Travel with the seasons! We highlight some of the incredible experiences we can’t wait to share with you...
Meet the guides: Gualtiero Rossano
In our quest to share our incredible guides with the world, check out our Q&A with Wally...
Why we love Italy!
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Jerry, HampshireA fantastic cycling holiday...
A fantastic cycling holiday through the Tuscan countryside, discovering beautiful hilltop villages, meeting some great local people and enjoying wonderful food and wine (and of course gelato). When we completed our ride we wanted to start all over again. The organisation of the holiday was really good. There were no problems or issues. It was quite clear that Saddle Skedaddle had spent time building positive linkages and relationships with taxi companies, hotels. BnB’s etc. All of the accommodation was really good with a couple of absolute stand out fantastic places. We did not meet the Skedaddle representative directly but everyone who we met from hotel managers/staff to the people picking up our luggage or delivering our bikes were absolutely clear about their roles and any questions or issues we had. It was quite obvious that you have a really strong network and system. The luggage transfers and airport transfers were also absolutely excellent. Can’t thank the team enough.
Cycling to Radda in Chianti was fabulous, where we had a lovely days cycling and then arrived in Radda to stay in a BnB that was also the local Wine Bar. The ride from Radda to Pienza was absolutely beautiful, cycling through woods and then cycling along a ridge for 10 – 15 km looking across to Siena over to one side before the climb up to Pienza.
This is not a ‘cheap’ holiday (neither is it too expensive), however the accommodation, routes, support and bikes meant that it was really fabulous and money well spent. It was especially good that we could do this holiday to our own timetable. We just gave you the dates and you ‘built’ the holiday for us. We have used other companies but Saddle Skedaddle have a very well developed product range, and we would love to do do the same holiday again, as well as look to explore other similar types of holiday around Europe!
Angela, HampshireHospitality was exceptional...
Difficult to say which was my favourite! San Gimignano to Radda in Chianti (Day 3) and Radda in Chianti to Pienze (Day 4) were the very best of all. I especially liked the small hotels and bed and breakfast accommodation. Best of all was in Chianti where the welcome and hospitality we received was exceptional. I loved the variety of scenery, awesome views and beautiful towns and villages, and I appreciated the fact that the routes were very largely along quiet roads, with main road sections kept to a minimum. The representatives were very helpful and ensured we had all we needed for our self-guided road cycling holiday. As this was a self-guided holiday it was extremely useful to have such clear route notes and maps, as well as the Garmin routes.
Victoria, LondonA great trip...
The accommodation locations were perfect. It was so hot but it was blissful to cool down in the pool at the agriturismo. The food was superb! Christina the host is an amazing chef and host. the food was delicious, she even packed us off every day with lunches as we had so much food left over from breakfast!
The cycling was all very good. Blimey – some of those hills – a 10km one in 35 degrees nearly polished us off! Views were worth it at the top though!