- Visiting the famous towns of Volterra, San Gimignano, Monteriggioni, Radda in Chianti and Siena
- Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
- Tasting delicious regional culinary specialities
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Experiencing Italian culture at its finest
- Having an afternoon aperitivo in Piazza del Campo in Siena
After transferring from Pisa airport you will check in at your hotel in Volterra. Located just a short distance away from the old part of town, you should have time (depending on flight times) to walk around and enjoy your first day in Tuscany. In the evening you can enjoy a nice dinner full of local specialties and meet the other members of your group. (Transfer approx. 1.5 hrs).
- Meals: Breakfast, dinner
- Ascent: 550 Metres Approx.
We’ll leave the walls of Volterra behind us and will soon embark on a breathtaking descent. Riding past isolated farmhouses surrounded by green fields, between rows of olive trees and cypresses, we’ll soon be well acquainted with just how beautiful this part of Italy really is.
We’ll follow the Val D‘Elsa on a rolling road that will take us from rural countryside to a more mountainous area of dense forest. We are now in the ‘Oasi Naturale di Castelvecchio” whose special micro climate has allowed the existence of a strong biodiversity and the survival of rare bird species such as the peregrine falcon.
Pedalling on, the view will open up and we’ll get a glimpse of the towers of San Gimignano. This fascinating “town of towers” is one of the prettiest and best-preserved medieval settlements in the whole of Italy. San Gimignano is also known for its white wine, Vernaccia di San Gimignano which is grown in the area. The old town is a UNESCO World Heritage site and we’ll take a walk through its narrow streets – a great opportunity for our first Italian gelato! (Our hotel for the night is usually just outside of San Gimignano).
- Meals: Breakfast, lunch
- Ascent: 740 Metres Approx.
Today we’ll start heading south, descending towards the plains of Colle Val d‘Elsa. We’ll ride past woodland and cultivated fields making our way towards the hill-top town of Casole d‘Elsa. The last four kilometres are challenging but the view from the top of the climb will hopefully outweigh the effort.
We should have some time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany.
We’ll leave Casole d‘Elsa on a rolling road passing small stone villages scattered throughout the countryside. Sections of the route are part of the Via Francigena, the pilgrimage route from Canterbury to Rome.
This ancient road will lead us straight to our accommodation, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. You’ve earned it!
- Meals: Breakfast, lunch
- Ascent: 650 Metres Approx.
Today we face the most difficult stage of the week, with a climb through the Chianti region. Don’t worry though, it will be rewarded with great views and a glass of Chianti wine at the end of the day!
We’ll continue our ride past vineyards and dense oak forests towards Radda in Chianti, our home for the evening. 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 can explore Radda, the perfect place to pick up some local specialties.
- Meals: Breakfast, lunch, dinner
- Ascent: 680 Metres Approx.
After breakfast we’ll set off for a stunning ride 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, where we’ll stop for a morning coffee and a chance to look around.
Back on our bikes, we’ll continue our ride on the Lauretana route, once a paved Roman road filled with travellers, artists and pilgrims. We’ll ride through the spectacularly eroded clay badlands landscape, reaching Asciano, a walled city that has its origins in the founding of Rome.
The legend goes that the sons of Remus (Aschio and Senio) fled the newly founded city of Rome that their uncle Romulus ruled. Senio camped on the banks of the river Tresa, while Aschio settled on the left bank of the river Ombrone, founding new settlements, Asciano and Siena respectively.
- Meals: Breakfast, lunch
- Ascent: 920 Metres Approx.
Today is our final day on the bikes with Siena our destination. We’ll ride a section of the “Eroica” route towards Castelnuovo Berardenga. Considered a marginal suburb of Siena, it’s actually a city full of charm, character and history.
After having a look around Castelnuovo Berardenga’s architecture and gardens, we’ll be on our way again, following a mix of tarmac and gravel roads as we get closer to Siena, with glimpses of bell towers and churches. Entering Siena from the Porta Romana will lead us straight to the heart of the city: Piazza del Campo where the famous Palio takes place. We deserve a toast with a glass of wine to celebrate the end of the tour in one of the elegant bars overlooking this vibrant square, (and since we’ve spent the week cycling through the Chianti region this may just be our tipple of choice)!
Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, dotted with hill-top hamlets. Riding is mostly on quiet tarmac roads (95% – shared with traffic, can be busier in the summer months) and some well-beaten gravel roads (5% – mostly strade bianche), with days involving riding up to hill-top towns.
You will find certain sections have some steeper more challenging climbs. Day 6 riding Colline Senesi, will prove the most challenging following a roller coaster route with some gravel sections.
We recommend hybrid bikes for this tour, but it’s possible to cycle the route on a road bike, bearing in mind that there are some short gravel sections
Leisure Cycling Grade
Distances generally between 20-45 miles / 32-72 kms per day
For the leisure cyclist with a good level of physical fitness
May include some steeper, cheeky climbs and possibly sections of varying terrain (eg. forest tracks, gravel paths etc)
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?
Although you may not cycle everyday, you do keep yourself relatively fit and maybe enjoy an afternoon out on your bike at the weekend. Your preference is perhaps for flatter terrain but you don’t mind tackling some hills, and the occasional steep climb if you can take it at your own pace. For those happy to tackle some ups and downs, and possibly some sections of varying terrain (eg. forest tracks, gravel paths etc) we’d recommend our grade 3 trips. We’d generally expect those on a Grade 3 holiday to have a decent level of physical fitness and be comfortable with some longer days in the saddle.
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) in small hotels / agriturismi / guesthouses
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) Single room (available if required, on request)
D) Travel insurance
E) Meals not stated in the itinerary
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
Travel with the seasons in 2022
Hear from our specialists! Your chance to marvel at the authentic experiences that that make these places so special...
Sarah, West YorkshireReally enjoyed every aspect of the holiday.
Great scenery, wonderful food, brilliant guides.
I cannot praise our guide highly enough. She was funny, kind, fun, spoke good English, arranged extra excursions, came out with us each evening etc. she is a very strong cyclist and make every day look easy and fun.
Jo, SheffieldThis trip was excellent
The two guides made an excellent team and did all they could to make our trip enjoyable. They constantly adjusted for poor weather etc and ensured everything ran smoothly.They are a credit to Skeddadle. Thank you!
Both tour leaders / guides were extremely knowledgeable and helpful. They were always available.
It was a bit more expensive than my skiing holidays usually are, but the standard of the accommodation was better than I have come to expect on ski holidays, which makes up for it. It was my first cycling holiday, but it won’t be my last, and Skedaddle will definitely be top of my list.
Jolene, HampshireI had a fantastic time in Tuscany
Excellent cycling, beautiful scenery and great company. There were a few cheeky climbs but the rewards were amazing views, great descents and a big sense of achievement. I also enjoyed sampling the local food and wine and with a great bunch of cyclists. The picnic lunches as always were fantastic too!
The team leader did an amazing job looking after everyone. She was always available to help with whatever we needed and always with a smile. This included extra rides for those that wanted it and lessons in speaking italian! An all round great host for our italian cycling adventure.
Marianne, HertfordshireVery good...
Our guide Cristina did a great job and made sure that everything went according to plan. Both Leif and Guiseppe were excellent guides too. Guiseppe in particular was very patient with the slower cyclists in the group and made getting up those hills a little more bearable.
Nick, WiltshireThank you....
..to our Tour Leader Cristina for making our holiday so very enjoyable. She worked hard to ensure everyone was happy, going out of her way to deliver the riding we expected. Our other guides were very good-Leif has a vast wealth of historical and local knowledge and is an excellent and polite host. Guiseppi leads at a perfect pace. Thank you both, you made it fun!
Christine, CumbriaVery good...
Every day was made very enjoyable due to the people we met. Our tour leader Cristina was fantastic. Always a smile and good sense of humour. Took us on a lovely ride on the rest day. A real people person. She has recommended the Lakes of Lombardy….we well may be tempted!