Gusto Cycling has been providing tours for over 15 years , offering a wide range of Tuscany cycling options to suit all tastes. Tuscany has it all, History, Art, Culture, amazing gastronomy and great wine! plus the added bonus of an enjoyable cycle through its varied countryside and medieval places, which have hardly changed for over 600 years!
It’s no surprise that Tuscany is so popular and draws people from walkers and cyclists. Its undulating countryside, and hilltop medieval towns with rewarding and far-reaching views is a satisfying end to great days cycling at your own leisurely pace.
It’s a relaxing holiday where you stop for a cappuccino when you like, have a relaxing lunch whenever you want, enjoy a wide variety of accommodation from agriturismo’s to good quality hotels to a 15C Monastery or Castello to suit your budget. After a day of discovery, enjoy delicious local home-cooked cuisine and a glass of wine from one of the many vineyards dotted all over the countryside.
Tuscany South Cycle Holidays
The emphasis is to discover, enjoy, and admire Tuscany and all its cultural treasures as you cycle along quiet country roads; some are undulating, of course. A new feature is the introduction of electric hybrid bike which have proven more and more popular for those who want to enjoy a cycling experience with their partner or friends and still keep fit!
Tuscany North or Tuscany South - Self Guided Your Choice!
There are two distinct self guided cycling holidays which will be give you a great insight into Tuscany up close which via a bike experience gives you the opportunity to visit many little villages and small towns which only by bike allows. The options are Tuscany North and the other Tuscany South; see below each detailed tour proposal and then decide which one is for you or if you wish to make any changes.
Remember, the tour can start any day of the week and in any month, you have complete flexibility to decide when to start the tour in order to take advantage of good flight times.
This tour can start any day of the week in Lucca to finish in Siena or reverse the tour to from Siena to finish in Lucca.
If you would like to explore more of Tuscany, there are two wonderful ways to combine the highlights of our Tuscany North and Tuscany South tours.
Several guests have enjoyed joining both tours together, adding a couple of extra nights for rest days to create a 17-day holiday. This offers time to discover Tuscany at a relaxed pace, enjoy its historic towns and villages, and savour the local food and wine.
For keen cyclists who prefer longer days in the saddle, riding around 100 km a day, I can also design a shorter, more challenging itinerary combining northern and southern Tuscany.
As a starting point, the following circular itinerary brings together some of the region’s most memorable towns, with overnight stays that are as much a part of the experience as the cycling itself:
Day 1 – Arrive at Pisa or Florence Airport → Montecatini Terme
Settle in and prepare for your cycling adventure.Day 2 – Montecatini Terme → Siena
Ride towards one of Tuscany’s most magnificent medieval cities.Day 3 – Siena → Radda in Chianti
Explore the heart of Chianti, with its vineyards, hilltop villages and beautiful countryside.Day 4 – Radda in Chianti → Pienza
Head south to the Renaissance town of Pienza and the celebrated landscapes of the Val d’Orcia.Day 5 – Pienza → Montalcino
Enjoy another memorable day in the Val d’Orcia before staying in the hilltop town renowned for Brunello wine.Day 6 – Montalcino → Volterra
Continue towards the atmospheric Etruscan town of Volterra.Day 7 – Depart Volterra → Pisa or Florence Airport
This is an initial seven-day outline, with arrival and departure arrangements, daily distances and routes to be refined around your preferences.
With 16 years of experience specialising exclusively in Tuscany, I can tailor the holiday to your preferred pace, interests and available time—whether that means longer rides, shorter stages, extra nights or time to enjoy a wine estate visit.
Let me know how many days you have in mind and the distances you enjoy riding, and I will put together a proposal especially for you.
Tuscany Cycling Holidays
Both North and South Tuscany Tours offer a varied mix terrain of rolling hills, medieval towns, small villages with tree-lined cypress trees, vineyards, and olive trees; Tuscany south has more climbing; its certainly not all flat in Tuscany… choosing an electric bike would make the journey much easier and less stressful and would be recommended for either Tuscany North or South. If you feel you are not quite fit enough or capable of completing the distance you will be very surprised that the use of electric hybrid bike will invigorate you with basic fitness will be fine to complete the tour .
In July and August, I would always recommend an electric bike in all cases just because of the heat and humidity will zap your energy . These bikes will allow you to enjoy the daily ride and arrive without too much stress.
Each tour will give you get the chance to see amazing hilltop medieval towns/villages, stunning views of the countryside, wine estates, historic towns, great food, and wine in a relaxed and enjoyable cycle day going at your own pace.
I hope the tours above give you a better idea of routes and key places of interest each day. Remember, Tuscany offers cycling enthusiasts an ideal scenario for all levels to anyone just wishing to pedal calmly while enjoying the beauty of TUSCANY.
Contact today about planning your Cycling Holiday In Tuscany.
What are the most popular cycling routes in Tuscany?
The most popular week-long tour includes stays and routes to include in Lucca, Pisa, Montecatini Terme, Vinci, San Gimignano, Radda in Chianti, Asciano , Montisi, Pienza, Montepulciano, Montichielo, Montalcino, San Quirico, and Buonconvento all offering small off the beaten track routes offering secondary quiet roads, medieval settings, and stunning countryside. Above all else great locations to stop for coffee breaks , stunning lunch stops or the many wine estates as you cycle on each of the tours .
The route includes some sections of “Strade Bianche” white gravel roads, which is a major feature in this part of Tuscany and is the reason why a famous vintage cycle event takes place every year (since 1992) in October in Gaiole in Chianti; its called L’eroica.
Here at GustoCycling, we have everything to make your cycling holiday in Tuscany a memorable one. Fantastic tours, excellent accommodation, perfect cycle routes, a wide range of bikes for you to use and my local knowledge to provide a memorable tour. Do please view Tripadvisor to give you the confidence that my attention to detail will provide a wonderful and adventurous tour.
Please contact us by filling in the form below, or call me personally at +44 (0)7515-941879 or email marco@gustocycling.com.
Please take the opportunity to read the many, many positive reviews of Gusto Cycling Tours on Tripadvisor or Google reviews.
I am very passionate about my tours, which are all bespoke, my attention to detail will ensure the holiday experience of a lifetime.
