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.


Tuscany North Self Guided Tour
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 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.

