Cycling Holidays in Tuscany

Gusto Cycling Offers 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!

It’s 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 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 agriturismos’ to fabulous villas and hotels to suit your budget. After a day of discovery enjoy a delicious local home-cooked cuisine 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 is the introduction of electric hybrid 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 an avid cyclist all of my life, I started in the travel business over 30 years ago working for a number of influential travel companies including Cosmos, Quo Vadis, Leger Holidays & Disneyland Resort Paris for 13 years this shaped my desire to start my cycle business in 2010, my attention to detail to make sure I create a fascinating, exciting and memorable cycling holiday has seen my business grow year on year, what is particularly nice apart from the very positive feedback on Tripadvisor 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) it’s 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 shown in the many positive feedback

Marco Mori
Marco Mori

There are 2 distinct Cycling Holidays in Tuscany North and South

Tuscany has some of the most iconic locations, I would like to give you some information to gauge your interest in what type of cycling you would like to experience.

This can start in Lucca or reverse from Siena

Day 1 – Arrive in Pisa/Florence airport – transfer to Lucca and stay inside this beautiful medieval walled town, its the home of Puccini and every night there is concerts and recitals in 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. Everyone cycles to work, there are lots of independent restaurants, cafe’s and bars to enjoy the evening stroll.

Day 2 –  Cycle along the River Serchio towards the famous Leaning Tower of Pisa then cycle back towards the medieval town of Lucca to your accommodation. 53km 255m Elevation.

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. 38km 322m Elevation.

Day 4 – Cycle to Montecarlo small medieval village and then visit local wine estate for wine tasting and lunch return to Montecatini Terme. 47km 305m Elevation.

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. 40km 486m Elevation.

Day 6 – Cycle to the medieval town of San Miniato (26km 303m Elevation) and stay outside in a family Agriturismo or 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, 68km 486m Elevation.

Day 7 – Cycle to the stunning medieval town of Siena (Unesco world heritage site) stay overnight in the north of the town to make it easier to arrive at the 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. 54km 827m Elevation or more direct route 45km 658 Elevation

Day 8 – Check out of the hotel and take the train to Florence and your onward destination or airport.

I always try and stay off as much of the main roads as possible but there will be some traffic on some sections especially entering exiting Lucca, Montecatini, and Siena. I have produced similar tours for families, distances are short from 35 – 70km elevation depending on the day.

To really find quieter 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 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. 69km 1,179m Elevation, or shorter direct route 58km 940m Elevation.

Day 3 – Cycle around the Chianti area – visiting 3 different wine estates and Gaiole in Chianti, it’s not a long cycle day but a nice and fun day out to relax amongst the vineyards and enjoy lunch. 38km 658m Elevation.

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 staying in an Agriturismo or something a bit more special in a stunning castle. 68km 993m Elevation

Day 5 – 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 designated Unesco world heritage.  38km  831m Elevation

Day 6 – Cycle to the imposing medieval hilltop town of Montepulciano, Italy. Surrounded by vineyards, it’s known for its Vino Nobile di Montepulciano red wine. 39km  758m Elevation

Day 7 – 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.  30km  607m Elevation or longer route if required 43km 922m Elevation or longer.

Tuscany Cycling Holidays

Both North and South Tuscany Tours offer a varied mix terrain of rolling hills, medieval towns, and small villages of cypress trees, vineyards, and olive trees, Tuscany south has more climbing it’s certainly not all flat in Tuscany….… choosing an electric bike would make the journey much easier and less stressful and would be recommended for Tuscany South if you feel you are not quite fit enough or capable of completing the distance.

In July and August, I would always recommend an electric bike in all cases just because the heat would tire you much quicker during the day.

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 keys places of interest each day Remember Tuscany offers for the cycling enthusiasts an ideal scenario for all levels to anyone just wishing to pedal calmly while enjoying the beauty of TUSCANY.

Contact us today about booking your Cycling Holiday In Tuscany.

Gusto Services

* I am here to design your ideal cycling holiday into an unforgettable experience if you are experienced or non-experienced cyclists drawn to Tuscany cycling is a great way to explore the region.

* You have your own unique needs and I will be able to provide a tailor-made itinerary which is my specialty and experience as I cater for a diverse range of customers wishing to experience this fascinating region.

*The bespoke itinerary is based on your requirements and interest, with this information at an early stage, I can make suggestions for places to visit or how best to spend you’re time and provide the best experience during the tour. My attention to detail of my cycling notes will make you very aware of what to look forward to well before you arrive in Tuscany so you can read up the experience to come.

*My tours are not in major cities but secondary towns and villages off the main roads in most cases where there is less traffic and to experience lesser know places of interest which will make you feel you’re getting to know the area better

*New feature is my daily contact with customers whilst on tour, I make a point of texting or emailing each day, to see how their day has been and to make any last-minute recommendations if needed.

* I will be able to handpick the accommodation, providing a nice mix of good quality hotels and agriturismo’s to give you a balanced flavour of Tuscany.

* Arrange to deliver the bikes of your choice to the start of the tour – you can choose Hybrid, E-bike, or Carbon bikes all with helmets/puncture kit/water bottle – all bikes are serviced before the bikes are delivered – they also come with a bike lock.

* I create bespoke GPS routes (ride with GPS)of your tours highlighting on each day places for coffee and lunch break recommendations and wine visit where appropriate all via GPS cycling application which you can download to your Garmin or iPhone. It’s a very easy application to use,  I always provide a text route from your home address to test the application so you can fully understand how it works. I have used this application throughout 2018 and it’s worked very well with all my clients. All you need is an iPhone cycling mount to place on the handlebars.

* Arrange airport transfers to the start of your holiday when you first arrive or when you finish the tour unless you wish to take the train to the airport.

* 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 of the region and provide places to stop for coffee, lunch and wine tasting or places of interest.

* I can create changes to the above program to suit your needs or budgets or add places that you particularly like to visit I’m very flexible and it’s my job that you will experience a great cycling holiday experience.

* I pride myself on being a very passionate advocate of cycling in Tuscany and with 10 years experience in cycling tours totally focused on Tuscany allows me to provide you provide a great cycling holiday experience.

Don’t take my word for it see the link to trip-advisor for the way I handle personally my clients travel and tour arrangements in order.

 Tripadvisor Logo

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 the finest hotels, villas, farmhouses, or agriturismo. If you need more information just contact me at

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, Monticello, 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 heyday 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 oneself of the ride conditions and experiences but the added bonus of eating and drinking along the route which makes this event extra special.

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 the local knowledge. Please contact us via form, call us on +44 (0)7515-941879 or email

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