We offer two wonderful tour options in either the North or South of 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 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 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 cycling experience with their partner or friends and still keep fit!
There are two distinct Cycling Holidays to consider one is 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 in Lucca to Siena or reverse from Siena to Lucca.
Click below to reveal the itinerary of this wonderful cycling holiday around the North of Tuscany…
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. You can walk or cycle around 4km of the walled town.
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.
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.
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. 28km and 330m elevation.
You have a choice, as you may feel 63km, especially in the high summer temperatures, would be too much to cycle; that being the case, we can break the day into two stages. The day before is a short ride from Montecatini Terme to Vinci. The second day (today) itinerary is to cycle from Vinci to the medieval town of San Miniato (26km 303m Elevation) and stay overnight. 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 63km 1.035m Elevation is a choice to stay inside the centre of the town or stay 5km outside in a nearby family-owned agriturismo which would be 68km 1,169m Elevation.
Cycle to San Gimignano, a beautiful hilltop walled town (Unesco world heritage site) famous for its many towers, a choice to stay inside the centre of the town 42km 739m Elevation. Or stay 5km outside in a nearby family-owned agriturismo. 47km 1000m 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. 54km 827m Elevation or more direct route 45km 658 Elevation.
Check out of the hotel and take the train to Florence and your onward destination or airport.
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 35 – 70km elevation depending on the day.
- 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 cuisines and wine from Agriturismo’s overnight stays.
- Visit Vinci the birthplace of Leonardo di Vinci * Stay in quality accommodation, with fantastically warm hospitality all hand-picked by me.
- 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 each day with a list of places to enjoy a coffee break and lunch 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.
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
- Dinner included in Vinci agriturismo
- 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 4 times
- 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 myself 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 however, you need to decide if you can manage the cycle ride to San Gimignano, which is 63km
Price from £1,359 per person based on two people sharing.
- Upgrade to Carbon or Electric Bikes .
- Pisa or Florence Airport transfer to Lucca.
- Siena transfer to Pisa or Florence Airport.
- Additional days pre or post tour can be arranged
Click below to reveal the itinerary of this wonderful cycling holiday around the South of Tuscany…
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 races that take place on 2 July and 16 August.
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 hilltop town of Radda in Chianti in the heart of Chianti and stay inside a fabulous 4-star hotel. 44km 650m Elevation.
Cycle around the Chianti area – visiting 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. 38km 658m Elevation.
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.
Cycle to Pienza, an 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.
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.
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.
Check out of the hotel, private transfers arranged for you to Buonconvento train station for your onward destination or airport.
- Visiting the famous medieval towns of San Gimignano , 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 fantastically warm hospitality all handpicked by me.
- Visit the wine and the renowned cheese of Pecorino in Montepulciano and Pienza.
- Cycling 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 to compete flexibility.
- 7 nights accommodation in 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.
- On the last day of checking out, private transfer arranged to take you to Buonconvento train station for your onward train journey.
- My knowledge and insight of the area to give you the best experience of a Tuscany bike holiday.
- Daily Contact with myself to see your progress.
We can change the itinerary and include Cortona, if you wish; it’s a small charming town. The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 meters. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. While it has recently enjoyed tourism fame thanks to Francis Mayes’ book, Under The Tuscan Sun, it has been a tourist draw for hundreds of years; it had already garnered a mention in a guidebook in 1639. It hasn’t lost any of its appeal since then and is well worth a visit.
Price from £1,359 per person based on two people sharing.
- Upgrade to Carbon or Electric Bikes.
- Pisa or Florence Airport transfer to San Gimignano .
- Montalcino 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 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 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 us today about booking 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 and above all else great locations to stop for coffee breaks, stunning lunch stops.
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 the local knowledge. Please contact us by filling in the form below, or call us at +44 (0)7515-941879 or email firstname.lastname@example.org.