My Personal Experience

Just the thought of cycling among the rolling Tuscan hills is enough to increase a biker’s pulse… and the region’s rich culinary diversity the perfect thing to slow it down.

So as I prepare to tackle L’Eroica and Tuscany’s „Strade Bianche“, the legendary white gravel roads, the motto is „Ride Fast, Drink Slow“. OK, maybe just fast enough, I haven’t been known for breaking land speed records.

Chrome bling & steel frames as far as the eye can see. Bottom tube gear shifters. Pedal cages and straps instead of clipless and wool jerseys instead of spandex. These are some of the rules of the L’Eroica ride, which offers a unique and unforgettable atmosphere. There are five fantastic routes to choose from, each with its own individual character. From Siena to Florence and Montalcino, the heart of Chianti Classico, one of the most famous wine regions in the world.

L’Eroica has become quite a large  international event series in recent years: it now takes place in eight countries. Founded by Giancarlo Brocci in 1997, what started as a vintage ride in Gaiole (Chianti region of Tuscany) with approximately 25 people showing up on that first, cold and rainy Sunday morning, has grown to attract over 7.000 participants and approximately 30.000 spectators. The population of Gaiole is 2.758! So one can just imagine how that translates in a town this size, when 13X the number of its population congregate there throughout the day.

When it comes to prep tips, in this case I’m referring to L’Eroica Gaiole which takes place in early October, registration opens in February and usually closes within a couple of days because the limited number of spots are coveted (Note: you will need a medical certificate in order to take part.). And when it comes to booking an accommodation, if you want to be close to the action (eg. in the town of Gaiole), book early because the town doesn’t have anywhere near the number of rooms needed for an event this size.

The region of Chianti Classico, home of the Sangiovese grape, offers so much in regards to cycling and scenery that it’s almost impossible to take it all in. It’s truly breathtaking. And regardless of the route you choose, each has a multitude of wineries worth visiting.

Cycling the ‘Strade Bianche’ at the foot of Castello di Brolio, home of Barone Ricasoli, Italy’s oldest winery.

The Chianti Classico region is sandwiched between Florence, Siena and Monte San Savino and though it is in the heart of the Chianti region, they are two separate appellations. Ask winemakers in these regions what the differences are and you’ll receive many different answers, some more complex than others, but in order to keep it simple: think of Chianti Classico like Manhattan with Chianti being New York’s boroughs (thank you Barone Francesco Ricasoli for that analogy).

The star of the show in both regions is the Sangiovese grape with Chianti Classico allowing for a minimum of 80% and 20% blended with other red grape varieties and Chianti actually allowing the use of 10% of white grape varieties in the finished blend. Chianti Classico is easily recognised by the “Gallo Nero”, the black rooster, which adorns each bottle of the member wineries which follow the strict quality standards set by the consortium. You will find white wines in both regions but reds are definitely prevalent.

Though the ride itself is on Sunday, the festivities begin on Friday. There are various events which take place and a large open market with stands selling anything and everything the vintage cycling fan could ever want or need. The positive community feeling is electric. The cycling community in general tends to be friendly and tight-knit but vintage steel & chrome, the sea of colourful wool jerseys, the culture, the history… it just has that certain something which is tough to convey in an online article alone.

I woke up at 4:30 a.m. on ride day and decided to take in the early morning atmosphere in Gaiole. The ‘calm before the storm’ if you will. The first group of riders, who ride the longest routes, leave between 5:00 and 7:00 am. Dead quiet only broken by the clicking sound of vintage wheel hubs or a group of riders talking in a whisper as they rode by me, towards the centre of the town and starting line.

First things first, coffee. I obviously wasn’t the only one with that idea. Absorbing the anticipation in the air, the friendly, positive atmosphere, the joking, the smiles… it all put me at ease. I couldn’t wait to get home, have breakfast, put on my vintage gear, hop on the saddle and take off at 8:30 a.m., when our group was set to begin the 90K route.

When the starting pistol popped, the head of the snake started to inch forward and we began to roll towards Brolio. I will never forget the experience of riding the very slight downhill, in a peloton with countless other riders; feeling their close proximity, nobody talking, just hearing the whirring of wheels on the asphalt and the sound of gears changing when the road hit a positive incline. I just took it all in, smiled and knew this was going to be an epic day.

Make sure you have a spare tire or two as ‘le strade bianche’ can be very unforgiving. And make sure that your bike and especially your brakes are in perfect working order: there was a downhill section after Panzano, which was absolutely insane. The type of steep and long which will melt your brake pads if you don’t rotate your braking, switching from back to front in short spurts. And considering I’m not a featherweight, my front rim got so hot that my tire popped. A quick fix but the craziest thing happened while I was behind the road barrier fixing my tire: a rider was speeding down the hill perched on her top tube with her feet on the ground, trying to stop ‘Flintstone style’ in her hi-top converse ‘Chucks’.

Her partner, quite a few metres behind, was yelling “Steer towards the grass, towards the side of the road… the graaaaaaasssss…”, and that’s what got my attention. When I realised she was headed straight for the barrier, I threw my wheel down and jumped out to hold her back as best I could. Quite a jolt to us both but the worst was avoided. And just two corners ahead of us, a rider slammed into a tree and had to be transported by ambulance to the nearest hospital. I don’t know all the details but it was very serious from what I’d heard afterwards.

I don’t want to sound negative or like a grade-school teacher but I can’t emphasise enough the need for safety on a ride like this, especially considering a good part of it is on gravel. I just feel that events like L’Eroica, which not only attract cycling fans but also retro/vintage fans alike, some think the ride is easy-going. Heck, even the 45K ‘Leisure Ride’ had insane sections to it, which I never would have anticipated given the name of the route.

 L’Eroica, and the atmosphere it offers, is truly unique but the rides are not flat 20K ‘Tweed Rides” through major cities. And the more popular these events become, the more people wish to take part. But some will underestimate what the rides truly entail just for the sake of saying “I rode L’Eroica”.

I definitely gained a ton of respect for my vintage Chesini after the abuse it took in such riding conditions. I also gained a ton of respect for the vintage cycling community and the great people I had the opportunity of meeting while in Tuscany.

The riding is a ton of fun but the check-points are a true highlight, not just because of the food and wine, but it’s where you get the chance to shoot the breeze with complete strangers, admire more bikes and bling than you could ever absorb… and if needed, get something fixed if need be.

Unfortunately I will be skipping L’Eroica Gaiole in 2019 as I’ll be on the go but that’s even more of an excuse to visit one of the other L’Eroica events… L’Eroica Britannia seems awesome with its retro family festival character, there’s also a L’Eroica Germania as of this year, I’ve always wanted to do some riding in Spain, and I have good friends in California…  hhhhmmmm, decisions, decisions.

If you ever feel like riding L’Eroica but can’t make it out when the event is taking place, there is always the ‘Permanent Route’ (approx. 200 km), which you can ride all year round. The route is well documented and signposted.

Ride safe, ride ON, ride far and drink slow.

Winery Tips:

During my week long stay in Gaiole I had the pleasure of meeting a variety of fantastic winemakers and personalities:

From Rory de Pentheny O’Kelly, the 24 year old winemaker at LA CASA DI BRICCIANO who’s family runs a small but fine organic farm, and DIEVOLE, a large winery in Vagliagli which was purchased by the Bulgheroni Group a few years back and has proven it’s possible to be big but still produce class rather than mass, to renowned Sean O’Callaghan of the newly founded IL GUERCIO.

Each with their own unique story and philosophy, each proving that Chianti Classico is doing very well and offering many interesting things to come.



Borgo di Gaiole – apartment complex near the center of Gaiole. Book via booking.com, airbnb.de or fewo-direkt.de

DIEVOLE winery in  Vagliagli, 12 kilometers north of Siena. A wine resort with luxurious rooms and cottages, ca. 200 EUR/room/night. Località Dievole 6, 53019 Castelnuovo Berardenga, Siena


Le Cose Buone Gaiole – a small and inviting trattoria in the center of Gaiole offering traditional Tuscan fare and fish dishes. Mid-priced. Via Bettino Ricasoli, 71, 53013 Gaiole In Chianti, +39 0577 749085

DIEVOLE Winery, Bar & Restaurant. High-End Tuscan cuisine. Mid to high price range. Località Dievole 6, 53019 Castelnuovo Berardenga, Siena
T. +39 0577 322613, info@dievole.it

Anonima X Castelnuvo Beradenga. Fine Tuscan cuisine in a relaxed atmosphere. Mid to high price range. Piazza Marconi, 9, 53019 Castelnuovo Berardenga, +39 347 048 5649


Tuscany Bicycle Gaiole: Bike rental (also E-Bikes), tours, repairs and apparel
Via Bettino Ricasoli, 96, 53013 Gaiole, tuscanybicycle.com

Chianti Bicycles Castelnuovo Beradenga: Bike rental and tours. Via del Chianti 40,
53019Castelnuovo Berardenga, info@chiantibicycles.it

Cycling routes related to L’Eroica:

45 KM tour

75 KM tour

135 KM tour

209 KM tour

Permanent Route, ca. 200 KM (signposted): eroicagaiole.com/permanent-route