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 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 agriturismos’ to fabulous villas and hotels 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.
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 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 - 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 visit Tuscany.
This tour can start any day of the week in Lucca to Siena or reverse from Siena to Lucca.
Tuscany North
Click below to reveal the itinerary, distance each day and elevation of this wonderful cycling holiday around the North of Tuscany…
Arrive in Lucca and stay inside this beautiful medieval walled town. It’s the home of the famous composer “Puccini” and every night there is concert and recital 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, cafes and bars to enjoy the evening stroll. You can walk or cycle around 4km of the walled town. This is a beautiful town really is a hidden gem!
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 its a very flat route.
Cycle to Montecatini Terme – with a stop over in the small village of Montecarlo for lunch, arrive in Montecatini Terme which is a small baroque town famous for its Spa facilities . In the evening I always send all guests lovely small hilltop village of Montecatini Alto access via an 1899 wooden Funicolar – stay in a centrally located hotel. This is a relaxing stay not hurried with nice alfresco bars and restaurants to choose from. 38km 322m Elevation or longer and more interesting route would be 51km 750m elevation.
Cycle to Vinci – the route becomes more rural as you head east through many vineyards and olive groves to the birthplace of Leonardo di Vinci; visit his house and the beautiful museum nearby. Stay overnight in a family-run Agriturismo offering a typical Tuscany menu. The family produce their own wine and olive oil. The route is 28km and 330m elevation.
on day 5 You have a choice, as you may feel 63km, especially in the high summer temperatures, would be too much to cycle to San Gimignano ; that being the case, we can break the day into two stages. The day before is a short ride from Montecatini Terme to Vinci. itinerary is to cycle from Vinci to the hilltop historical town of San Miniato (26km 303m Elevation). The other option is to cycle from Vinci to San Gimignano beautiful hilltop walled town (Unesco world heritage site) famous for its many towers; this day would be accommodation would be in the very centre of this historical town . Distance is 63km 1.035m Elevation.
Cycle to San Gimignano, a beautiful hilltop walled town (Unesco world heritage site) famous for its many towers, accommodation is in the centre of the town. This is a unique medieval town whilst it’s busy during the day once all the day trippers have left the town it becomes earily quiet as if your back in the 15th C as the only people are the few guests staying in just 3 hotels visiting the local restaurants in the town. Enjoy award winning Gelato, in front of the hotel is the world champion Gelato (ice cream) winner 3 times! Distance is 42km 739m Elevation.
Cycle to the stunning medieval town of Siena (Unesco world heritage site) and stay overnight in the north of the town to make it easier to arrive at the hotel – visit and enjoy alfresco drinks or meals in the famous Piazza del Campo, famous for the Palio di Siena horse race in July and August. Routes are beautiful 61km 1,011m Elevation or more direct route 42km 589 Elevation.
Check out of the hotel and take the train to Florence for your onward destination or airport. Or if you have decided to save 1 night by not staying in San Miniato or perhaps you have visited Pisa before therefore stay just 1 night in Lucca you can therefore stay 2 nights in Siena which allows you to cycle to Chianti and return back to Siena hotel. 67km 1,00om elevation . Shorter route available but would involve gravel route.
I always try and stay off as many 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 30 – 63km elevation depending on the day. Remember you can shorten the tour as you may not have enough time to do the full 7 night tour , you can also change the itinerary and chop and change the overnight stops i.e. skip Pisa because you have been there before and stay longer (say stay 2 nights) in Siena which then gives you the opportunity to cycle to Chianti and return to a Siena hotel.
Holiday Highlights
- Visit the Leaning Tower of Pisa
- Stay overnight in Lucca’s beautifully preserved 15th-century medieval town – Tuscany’s hidden gem!
- Stay overnight in Montecatini Terme lovely small Baroque spa town, and also visit Montecatini Alto with its stunning views and medieval setting.
- Enjoy many local amazing cuisines and local wine from the many overnight stays.
- Visit Vinci the birthplace of Leonardo di Vinci * Stay in quality accommodation, with fantastically warm hospitality all hand-picked by me.
- The Itinerary can change, you can decide to skip Vinci or San Miniato it all depends on the distance you wish to cycle per day
- Visit and stay overnight in San Gimignano and Siena, both stunning medieval towns.
- Using secondary roads, you immerse yourself at a much slower pace to enjoy the delights of the countryside, its villages, towns and its people.
- I will provide you each day with a list of places to enjoy a coffee break and lunch or wine tasting so you can maximise your Tuscan experience.
- Chill out on your final night in Siena in the famous Piazza del Campo and enjoy a well-earned glass of Chainti Classico!
Prices included for Tuscany North
- Choose any day of the year to start your holiday you have complete flexibility
- 7 nights accommodation on a bed and buffet breakfast basis, accommodation is personally chosen and known to me
- Vinci agriturismo offer wine and olive oil tasting as they produce their own wine and olive oil.
- Deliver 2 Hybrid Bikes to Lucca
- Rental of 2 Hybrid Bikes helmets and water bottle & puncture kit provided
- Collect 2 Hybrid Bikes in Siena
- Luggage service included x 5 or 6 times depending on overnight stops
- You can decide to skip Vinci or San Miniato, it all depends on the distance you wish to cycle x day or if you wish to stay extra night in Siena .
- Specially created GPS routes for each day, which can be downloaded to your iPhone or Garmin with locations indicated for coffee and lunch stops and places of interest along the way
- My knowledge and insight of the area to give you the best experience of a Tuscany bike holiday
- Daily Contact with me to see your progress.
There is flexibility in the programme, If you wish, you can stay two nights in Siena, we can remove San Miniato overnight or remove 1 night off in Lucca in case you have been to see the Leaning Tower of Pisa . However, you would need to decide if you can manage the cycle ride to San Gimignano, which is 63km.
In finishing the tour in Siena you have the opportunity the next morning to take the train to Pisa or Florence airport for your return journey.
Price from £1,399 per person based on two people sharing.
Extra Services
- Upgrade to Carbon or Electric hybrid or road Bikes .
- Pisa or Florence Airport transfer to Lucca.
- Siena transfer to Pisa or Florence Airport.
- Additional days pre or post tour can be arranged
Tuscany South
Click below to reveal the itinerary, distance each day and elevation of this wonderful cycling holiday around the South of Tuscany…
Holiday Highlights
Surrounded by olive groves and the vineyards of Chianti, Siena is one of the most beautiful cities of Tuscany and probably the best-preserved medieval city. Set on three hills, the city is drawn together by winding alleyways and steep steps, whilst the Piazza del Campo stands at its heart and the Duomo and St Maria della Scala serve as additional cultural landmarks. Famed for the “Palio”, held in one of the most well-known medieval squares in the world, the “Campo” is where the annual historic horse race takes place on 2 July and 16 August.
Cycle to Chianti, one of Italy’s Most Famous Wine areas. Chianti wine is one of the most appreciated wines around the world. Once you leave Siena after 4km you will not experience any more major traffic for the rest of the tour. Along the route you will cycle past wine estate’s and visit Castellina in Chianti . Stay inside the medieval hilltop town of Radda in Chianti in the heart of Chianti and stay inside a fabulous 4-star hotel. Distance 44km 650m Elevation.
Today is a day of visiting a number of wine estates in the Chianti area – visit three 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. Distance 38km 658m Elevation.
Heading south to the region of Crete Sinesi you will see very much a change in the geography and landscape.The Crete Senesi is characterised by rolling hills and a variety of landscapes that change with the seasons. In the summer, you can see sunflower fields, while in the spring, wheat fields and red poppies are in bloom. The panoramic views are stunning as you cycle south towards Asciano. Accommodation staying in either a hotel in Asciano , historical house in Serre di Rapolano area or agriturismo nearby or something a bit more special like a stunning castle. Distance very panoramic 68km 993m Elevation, or short route is 49km 708m elevation.
Cycle to Pienza, an exquisite Renaissance medieval small town with stunning views of the countryside. The route today will take you through many little villages along the way, ideas to stop for coffee or lunch options will be highlighted . 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. Enjoy various sampling Pecorino cheese in a number of shops in the town . One of the cafe bars I highlight is a great way to enjoy a welcome Prosecco sitting down to stunning views of Monte Amiata . Distance 38km 831m Elevation or can be extended to include gravel sections if you like.
Cycle to the imposing medieval hilltop town of Montepulciano, Italy. Enjoy coffee break in the main 14th C Palazzo Communale the town is Surrounded by vineyards, it’s known for its Vino Nobile di Montepulciano red wine. wine estate will be recommended to enjoy wine tasting and lunch with stunning scenery . Various routes are offered starting from 39km 758m Elevation or longer .
Cycle to Montalcino and discover this 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. Distance 30km 607m Elevation or longer route if required 43km 922m Elevation or longer.
Check out of the hotel, private transfers can be arranged for you to Buonconvento train station 20minutes away or to Siena train station 1 hour away for your onward destination or airport.
- Visiting the famous medieval towns hilltop towns of Radda In Chianti, Pienza , Montepulciano and Montalcino.
- Riding through stunning landscapes, wide-open fields, cypress-lined hills, and many famous vineyards of the region.
- Fabulous local insight into traditional Tuscan life: the food, the wine, the culture.
- Cycling through the historic wine regions of Tuscany, sampling the best wines of Chianti, Montepulciano, and Montalcino.
- Experiencing Italian culture at its finest. Staying in quality accommodation, with fantastic warm hospitality all handpicked by me.
- Visit the wine and the renowned cheese establishments of Pecorino in Montepulciano and Pienza.
- Cycle along the rolling hills of Chianti & Crete Sinesi, plus cycling through the stunning UNESCO heritage region of Val d’Orcia.
- I will provide each day a list of places to enjoy a coffee break and lunch so you can maximise your experience.
- Finishing off on your last night in Montalcino with a glass of a 5-year-old reserve Brunello of Montalcino world-renowned wine.
Prices included For Tuscany South
- Choose any day of the year to start your holiday you have complete flexibility.
- 7 nights accommodation in good mix of quality accommodation on a bed and buffet breakfast basis, accommodation is personally chosen and known to me.
- Deliver 2 Hybrid Bikes to Siena accommodation
- Rental of 2 Hybrid Bikes, helmets and water bottle & puncture kit provided.
- Collect 2 Hybrid Bikes from Montalcino.
- Luggage service included x 4 times.
- Especially created GPS routes for each day, which can be downloaded to your iPhone or Garmin with locations indicated for coffee and lunch stops and places of interest along the way.
- My knowledge and insight of the area to give you the best experience of a Tuscany bike holiday.
- Daily Contact with me to see your progress.
Price from £1,399 per person based on two people sharing.
Extra Services
- Upgrade to Carbon or Electric hybrid or carbon racing or gravel bikes.
- Pisa or Florence Airport transfer to Siena .
- On the last day of checking out, a private transfer can be arranged to take you to Buonconvento train station for your onward train journey.
- Montalcino transfer to Pisa or Florence Airport or transfer to Buonconvento or Siena train station .
- Additional days pre or post-tour can be arranged.
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 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 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, 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. 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 local knowledge.
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.
