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 is the perfect thing to slow it down.

As we prepare to tackle L’Eroica and Tuscany’s „Strade Bianche“, the legendary white gravel roads, we amend the VELOVIN motto to „Ride Fast, Ride Far, Drink Slow“. OK, maybe just fast enough to finish within the alotted time, I haven’t been known for breaking any land speed records.

L’Eroica is an annual vintage bike ride which usually takes place at the beginning of October. It’s not a race as no time is kept and only vintage bicycles are allowed to partake (1987 is the latest year). In the past years L’Eroica has expanded internationally and annual races can now be found in California, South Africa, Japan and Great Britain just to name a few. 7.000 cyclists have converged in Gaiole for the 2017 and 21st edition of L’Eroica, the largest vintage ride on the planet. In total over 25.000 spectators will take over Gaiole, a small town with a population of 2.700, in order to view the spectacle.

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 lycra. 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.

Montalcino, home of the famous Brunello wines. Some of Italy’s and the world’s finest.

The routes span from the 45 Km. “Leisure Route” to the epic 209 Km. loop. Even if you can’t make it to Tuscany in late September/early October it’s possible to ride these routes at any other time during the year (.gpx tracks of the various routes are below) and tackle the gravel roads with the ride of your choice if vintage steel isn’t your thing. For those who prefer to ride strictly on asphalt, there are many route alternatives and the signposting is great in the entire region if you feel like winging it without navigation.

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.

View of Castello di Brolio towering over its vineyards. The castle is home of Barone Ricasoli, Italy’s oldest winery.

The first serious climb of every L’Eroica route is up to Castello di Brolio.

The most famous and historical of all, Barone Ricasoli, located in the medieval Castello di Brolio is the oldest winery in Italy. Located approximately 10 kilometers from Gaiole, it is one of the main highlights of L’Eroica as it’s tied to the first serious climb of the ride with an incredibly rewarding view once you reach the top and free flowing descent which follows.

The Chianti wine we know today, is thanks to Barone Bettino Ricasoli, as he communicated his “formula” in 1872. When discussing Chianti and Chianti Classico it’s important to differentiate between the two:

The fantastic views in Tuscany’s Chianti region are endless.

View of the Siena Cathedral.

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).

Wine must and grape skins macerating.

Grape skins (pomace) macerating in the wine must (freshly crushed fruit juice).

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.

During our one week stay in Gaiole we had the pleasure of meeting a variety of fantastic winemakers and personalities:

1. 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,
2. 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,
3. Sean O’Callaghan and his newly founded project: IL GUERCIO,
4. Francesco Ricasoli, the torchbearer of Italy’s oldest winery,
5. to, last but not least, the dynamic duo of Andrea & Stefano at LE COSE BUONE in Gaiole.

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

Endless stretches of ‘strade bianche’ to explore with my 1979 Chesini – completely original, every screw, except for the saddle and grip tape. I purchased the bike from an 81 year young gentleman in Southern Bavaria who obviously took very good care of it.

We hope you enjoy our Tuscan series and feel free to offer feedback. We look forward to hearing from you.

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


Arrival by car:
Via the Brenner highway and Verona or Basel and Milan on the A1/E35 towards Bologna and Florence.


Località Dievole 6,
53019 Castelnuovo Berardenga, SI
+39 0577 322613

Winery in Vagliagli, 12 kilometers north of Siena. A wine resort with luxurious rooms and cottages, ca. 200 EUR/room/night.

Borgo di Gaiole – apartment complex near the center of Gaiole. Book via or


Le Cose Buone Gaiole
Via Bettino Ricasoli, 71
53013 Gaiole In Chianti, SI
+39 0577 749085

A small and inviting trattoria in the center of Gaiole offering traditional Tuscan fare and fish dishes. Mid-priced.

Località Dievole, 6
53019 Castelnuovo Berardenga, SI
+39 0577 322613

Winery, hotel & bungalows, bar & fine dining. High-End Tuscan cuisine. Mid to high price range.

Anonima X
Piazza Marconi, 9
53019 Castelnuovo Berardenga, SI
+39 347 048 5649

Fine Tuscan cuisine in a relaxed atmosphere. Mid to high price range.


Società Agricola DIEVOLE
Località Dievole 6 (fraz. Vagliagli)
53019 Castelnuovo Berardenga, SI
Tel. +39 0577 322 613

Sean O’Callaghan
Via G. Rossa, 10
53017 Radda in Chianti, SI
Tel. +39 335 429 613

Barone Ricasoli
Loc. Madonna a Brolio
53013 Gaiole di Chianti, SI
Tel. +39 0577 7301

Località Bricciano, 39
53013 Gaiole in Chianti, SI
Tel. +39.0577.749 297

Fattoria Fèlsina
Via del Chianti, 101
53019 Castelnuovo Berardenga, SI
+39 0577 152 3789


Tuscany Bicycle Gaiole:
Via Bettino Ricasoli, 96
53013 Gaiole in Chianti, SI

Bike shop in the heart of Gaiole. Rental (also E-Bikes), tours, repairs and apparel.

Chianti Bicycles
Via del Chianti, 40
53019 Castelnuovo Berardenga, SI

Bike rental and tours.

Cycling routes related to L’Eroica:

The next L’Eroica Gaiole will take place on October 7, 2018 with (registration closed in February but you can still ride along, you just won’t get the welcoming kit, start number, finishing medal or food at the pit-stops – but there are bars and restaurants all along the routes). There are five routes to choose from, price for participation is EUR 70,00 per person and a medical certificate is required.

For more information, please visit

45 KM:

75 KM:

135 KM:

209 KM:

Permanent Route, ca. 200 KM (signposted):

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