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 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, 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!
There are 2 distinct Cycling Holidays to consider one is Tuscany North and the other Tuscany South, see below each detailed tour proposals 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…
Day 1 – Arrive into Lucca + cycle around the medieval walled town
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.
Day 2 – Lucca to Pisa visit the famous Leaning Tower
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 – Lucca to Montecatini Terme beautiful baroque spa town.
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 – Montecatini Terme to Montecarlo - Montecatini Terme
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 – Terme to Vinci - home town of Leonardo di Vinci
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 – Vinci to San Gimignano UNESCO world heritage site
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 it’s many towers, 63km 1.035m or stay 5km outside in a nearby family-owned agriturismo, 68km 1,169m Elevation.
Day 7 – San Gimignano to Siena UNESCO world heritage site
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 – Departure from Siena
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.
Click to Reveal Holiday Highlights!
• Visit Leaning Tower of Pisa
• Stay overnight in Lucca beautifully preserved 15th-century medieval town – Tuscany’s hidden gem!
• Stay overnight in Montecatini Terme lovely small Baroque spa town and visit also Montecatini Alto with its stunning views and medieval setting.
• Enjoy many local cuisines and the wine from Agriturismo’s overnight stays.
• Visit Vinci the birthplace of Leornarado di Vinci * Staying 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, it’s villages, towns and it’s people.
• I will provide each day 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 compete flexibility
• 7 nights accommodation on a bed and buffet breakfast basis, accommodation is personally chosen and known to me
• Dinner included in Vinci and San Gimignano Agriturismo’s
• 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
If you wish you can stay 1 night in Montecatini Terme and stay 2 nights in Siena instead this can easily be arranged.
Price from £1,189 per person based on 2 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…
Day 1 – Arrive in San Gimignano beautiful hilltop walled town UNESCO world heritage site
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 the heart of Chianti region to Radda In Chianti
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 return to Radda in Chianti
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 – Cycle through Crete Sinesi to an Agriturismo in Serre di Rapolano area
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, an exquisite Renaissance medieval small town
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 Return to Pienza
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
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.
Day 8 – Check out of the hotel in Montalcino
Check out of the hotel, private transfers arranged for you to Buonconvento train station for your onward destination or airport.
Click to Reveal Holiday Highlights!
• 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 on a bed and buffet breakfast basis, accommodation is personally chosen and known to me.
• Dinner included in San Gimignano & Serre du Rapolano Agriturismo’s
• Deliver 2 Hybrid Bikes to San Gimignano 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.
Price from £1,169 per person based on 2 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 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.
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 on +44 (0)7515-941879 or email firstname.lastname@example.org.