Bicycle Tour Tuscany

What are the most popular cycling routes in Tuscany?

The most popular week long tour includes stays and routes to include in San Gimignano , Radda in Chianti, Trequanda, Montisi, Pienza, Montepulciano, Montichiello, Montalcino, San Quirico and Buonconvento all offering small off the beaten track routes offering secondary quiet roads, medieval settings and stunning countryside and above all else great locations to stop for coffee breaks, stunning lunch stops. The route includes some section 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.

This event is world renowned with over 7,500 cyclists from all over the world converging on this small town to participate in the discovery of  Southern Tuscany by cycling on old steel vintage bike with various sections of gravel roads as a way to recall the hey day of Italian Cycling when all there was were gravel roads in the 40’s and 50’s (which was the golden era of Italian cycling ) and a chance to remind one self of the ride conditions and experiences but the added bonus of eating and drinking along the route which makes this event extra special.

Gusto Cycling Offer 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 enjoyable cycling through its varied countryside and medieval places which have hardly changed for over 600 years!

Its no surprise that Tuscany is so popular and draws people from walkers and cyclists. Its undulating countryside, hilltop medieval towns with rewarding and far reaching views is a satisfying end to great days cycling as your own leisurely pace.

Its a relaxing holiday where you stop for a cappuccino when like, have a relaxing lunch when ever you want, enjoy a wide variety of accommodation from agriturismos’ to fabulous villas and hotels to suit your budget. At night after a day of discovery enjoy a delicious pasta and a glass of wine from one of the many vineyards dotted all over the countryside.

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 in 2014 is the introduction of electric bikes which has proved more and more popular for those who want to enjoy a cycle experience with their partner or friends and still keep fit!

Why Gusto Cycling?

I’ve been a avid cyclist all of my life, I started my cycle business in 2010, my style and attention to detail has seen my business grow year on year , what is particular nice apart from the very positive feedback is that i am now beginning to see repeat customers returning for different itineraries or via recommendations or who are using my services again for of Tuscan Bike Rental.

In the summer I’m based with my family in Montecatini Terme  a small but beautifully relaxing spa town (located between Lucca and Florence)  its a great base for customers to consider a holiday experience and to co-ordinate and support the many customers enjoying their cycling holiday in Tuscany. I like to give a very personal service with attention to detail which is my hallmark and as is shown in the many positive feedback

Marco Mori
Marco Mori – Gusto Cycling 

What is the best time of year to visit Tuscany?

May/June/September/October – due to the perfect cycling temperature and less traffic and better accommodation being available

Cycling Holidays in Tuscany

Before creating a tour , we need to ascertain where would you like to cycle and what would you like to experience.

Tuscany has some of the most amazing scenery , history and iconic medieval Towns , I would like to give you some information to gauge your interest as to what type of cycling you would like to do and for how long you would like to cycle each day.  Do you want to stay in one place,  enjoy a two centre stay or full cycle tour staying in different accommodations and towns each night or every 2 nights.

I make a point of showing the lesser known area’s of Tuscany to cycle and visit off the beaten track so to speak. This way you enjoy a more relaxed tour rather then visiting some of the more iconic big city with the challenges of major traffic to contend with .

One option is Tuscany North: This tour can start in Lucca heading to Siena or start from Siena heading to Lucca 

Day 1 – Arrive in Pisa/Florence airport – transfer to Lucca and stay inside the medieval walled town, a real cycle friendly  medieval town, in the summer they have open air concerts, and many festivities. it’s the home of Puccini and every night there is concerts and recitals a small event paying homage to Puccini & Verdi by having a short opera in the beautiful church of San Giovanni located inside the medieval walled town.

Day 2 –  Cycle along the River Serchio towards to the famous Leaning Tower of Pisa then cycle back towards the medieval town of Lucca to your accommodation.

Day 3 – Cycle to Montecatini Terme – lovely small spa town with hilltop town of Montecatini Alto access via Funicolar – stay in a 3 or 4 centrally located hotel, this is a relaxing stay not hurried with nice alfresco bars and restaurants to choose from as well as taking the funicular to Montecatini Alto for the stunning views and the beautiful medieval square for lunch or dinner.

Day 4 – Cycle to Montecarlo small medieval village with lovely views of the countryside  and then visit local wine estate for wine tasting and lunch return to Montecatini Terme.

Day 5 – Cycle to Vinci – home of Leornardo di Vinci , visit his house and the beautiful museum nearby – stay in a lovely family agriturismo just outside Vinci.

Day 6 – Cycle to San Gimignano beautiful hilltop walled town (Unesco world heritage site) famous for the towers and stay 5km outside in a nearby family owned agriturismo,

Day 7 – Cycle to the stunning medieval town of Siena (Unesco world heritage site) stay overnight in a 3 or 4 star hotel – visit and enjoy alfresco drinks or meal in the famous Piazza del campo famous for the Palio di Siena horse race in July and August

Day 8 – Check out of the hotel in Siena and take the train to Florence or Pisa Airport and your onward destination.

I have produced similar tours for families, distance are short from 35 – 70km depending on the day.


To really find quiet roads then you have to look at starting in Tuscany South.

Day 1 – San Gimignano beautiful hilltop walled town (Unesco world heritage site) famous for the towers and stay 5km outside in a nearby family owned agriturismo,

Day 2 – Cycle to Chianti area,  One of Italy’s Most Famous Wines. Chianti wine is one of the most appreciated wines around the world.  stay inside the medieval town of Radda in Chianti in the heart of Chianti and stay inside a fabulous 4 star hotel.

Day 3 – Cycle around the Chianti area – visiting 3 different wine estates and Gaiole in Chianti, its not a long cycle day but a nice and fun day out to relax amongst the vineyards and enjoy lunch & wine tasting.

Day 4 – Heading south to the region of Crete Sinesi and Val d’Orcia UNESCO World Heritage Area staying in the Serre di Rapolano area  either staying in an Agriturismo or something a bit more special in a stunning castle 

Day 5 – Cycle to Buonconvento and stay in nearby Agriturismo or the hill top medieval town of San Quirico 

Day 6 – Cycle to Pienza, exquisite Renaissance medieval small town with stunning views of the countryside. Pienza is home to the world famous pecorino cheese. Pienza is located in the heart of Val d’Orcia a region desiganted Unesco world heritage.

Day 7 – Cycle to the imposing medieval hilltop town of Montepulciano, Italy. Surrounded by vineyards, it’s known for its Vino Nobile di Montepulciano red wine.  For lunch and return to Pienza.

Day 8 – Cycle to Montalcino and discover the beautiful medieval town, one of the most evocative towns in the Val d’Orcia with stunning views of the countryside – Montalcino is home to the world famous Brunello di Montalcino Wine that defines this tiny Tuscan outpost. Both offer a mix terrain of hills but Tuscany south has more climbing its certainly not all flat Tuscany….you get the chance to see amazing hilltop medieval towns, wine estates , historic towns and great food. I hope this gives you a better idea of routes and how what you want to experience

Average rides are in the region of 40 – 70km depending on each days route I plan.

Both Tours offer a mix terrain of hills but Tuscany south has more climbing its certainly not all flat Tuscany….you get the chance to see amazing hilltop medieval towns, wine estates , historic towns and great food. I hope this gives you a better idea of routes and how what you want to experience

Contact us today about booking your Cycling Holiday In Tuscany.

Gusto Services

* I will be able to hand pick the accommodation which I personally know, providing a nice mix of good quality hotels and agriturismo’s to give you a balanced flavour of TUSCANY

* Arrange to deliver the bikes to the start of the tour – you can choose Hybrid, E-bike or Carbon bikes all with helmets

* Arrange the luggage to be delivered to your next location – no need to worry this is being taken care of care of each day.

* Specially create routes with locations for coffee and lunch and wine visit where appropriate via GPS cycling application which you can download to your Garmin or Iphone. it’s very easy i’ve used in throughout 2018 and it worked very well with my clients. All you need is an iphone cycling mount to place on the handlebars.

* if you wish you can arrange airport transfers to the start of your holiday when you first arrive or

* Arrange on the last day when you check out of your hotel a transfer to the nearest train station in order to take the train to your onward journey

* Inside Knowledge of the area you are cycling, in order to give you the very best experience for coffee stops, lunch and wine tasting or places of interest

If you wish to decide on your own itinerary

Just give me an idea where you want to go and when, and I’ll put together a custom itinerary that suits your interests, your schedule and your budget including all the logistics. Important consideration is cost: you can decide at what level of accommodation you would like to have finest hotels, villas, farmhouses or agriturismo. If you need more information just contact me at marco@gustocycling.comor call on+44 (0)7515 941879

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