L’Eroica & Tuscany Cycling Tour

Enjoy the beauty of Tuscany and heritage of L’Eroica cycling at its best.
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Mountain Illustration displaying a cycling tour difficulty rating of eight out of ten

L’Eroica and Tuscany Cycling Tours Overview

This tour combines all the best that cycling, L’Eroica and Tuscany have to offer.  Immersing ourselves in Gaiole in Chianti (the heart of L’Eroica), we’ll then explore the region and be perfectly positioned in the centre of Gaiole to enjoy Italy’s best cycling festival, L’Eroica.

Expect amazing days on the bike with picturesque landscapes and leisurely dinners where true artisans share with you their passion for the simplicity and seasonality of Tuscan cuisine.

L’Eroica is not just about vintage steel frame bikes with downtube shifters and toe-clips, woollen jerseys, leather shoes and white gravel roads. It’s that and a whole lot more.

With unique climbs on the Strade Bianche that seem to never end, and which test both body and mind, to the mystical feel of candle lit paths, traditional bowls of ribollita soup and Chianti wine at rest stops, L’Eroica is a ride like no other. It is a truly unique and special event celebrating the golden years of cycling and has become renowned worldwide for its festive spirit and captivating emotion.

Rediscover a taste for adventure with us on our L’Eroica and Tuscany Tour and lose yourself in the beauty that is Tuscany. 

A refreshment stop during L'Eroica
Riding l'eroica on steel bikes through the Tuscan countryside
A man in a woolen jersey at L'eroica cycling through a little Tuscan Hamlet
Riders on the strade Bianche during L'eroica

The L’Eroica and Tuscany Tour Itinerary

Welcome to L’Eroica & Tuscany

You’ll have plenty of time to acclimatise and enjoy diverse rides across the Tuscan hills as we prepare the legs during the first few days and enjoy all that the different areas of Chianti have to offer before we get ready to soak up the atmosphere as we roll into Gaiole on Thursday, the same day that the L’Eroica Festival starts, featuring the best ‘antique/vintage’ cycling market you’ll ever see and a carnival atmosphere, with cyclists arriving from all over the world.

You’ll enjoy daily rides through the superb Colli Senesi and the Val d’Orcia, the rolling hills around Siena, and of course Chianti and its unforgettable Tuscan countryside, culminating in the ride of a lifetime – L’Eroica. We’ll do a different ride each day, exploring some of the most spectacular areas of Tuscany and have you fully prepared to take on the  famous Strade Blanche and L’Eroica.

Following our welcome lunch, today’s ride to a hilltop hamlet is the perfect introduction to Chianti with the idyllic rolling hills striped with vineyards and backed by dense wooded forests and the little villages that dot the landscape.

Highlight: The picturesque hilltop hamlet
Distance: 50km
Elevation: 890m

A ride profile a beautiful ride around Gaiole in Chianti

This is a truly typical Tuscan day on the bike where you will encounter undulating quiet country roads amidst the rolling hills, woods, olive groves and vineyards as you wind your way towards the Val d’Orcia, to what many consider is the most beautiful part of Tuscany,

Highlight: Entering into the Val d’Orcia and its spectacular landscape
Distance: 94km
Elevation: 1530m

Today you explore the beauty and challenge of the Chianti hills, with the ride including more sustained climbing with 5 distinct climbs as we traverse through some of the most iconic vlilages between Siena and Florence.

Highlight: The beautiful and free flowing descents
Distance: 75km
Elevation: 1282m

We set off in the direction of Siena before we we join part of the Strade Bianche course, enjoying one of it’s gravel climbs before making our way towards Castellina in Chianti and Radda in Chianti.

Highlight: The postcard perfection of the landscape at every  turn.
Distance: 70km
Elevation: 1010m

Today is a bit of a rest day on the bike in preparation for the grand event – L’Eroica. You head out after a leisurely start on a traditional coffee shop ride. Expect one climb and a landscape with olive groves and vineyards vying for dominance, as you wind your way past incredible views. There will be plenty of time for on-the-bike conversation as you make your way to our stop for caffe e torta (coffee and cake) and then making our way back to the villa.

You can take the opportunity to spend more time in the village and market, ensuring you are prepared for tomorrow or simply enjoy soaking up the atmosphere of the now bustling town.

Highlight: Enjoying the atmosphere in the village as the festival grows.
Distance: 28km
Elevation: 395m

Your ride entry to L’Eroica is guaranteed. With entries limited and every year the event selling out in no time, to have your entry secured as part of our group is priceless. Whatever your distance, this is the pinnacle of the week and the most amazing and special ride you will ever do.

Steel frame bikes with downtube shifters and toe-clips, woollen jerseys and leather shoes, you are ready. You roll down into the piazza in darkness, stop by the bar to ensure that you have enough espresso to get through the day and head over to the start line. Whether you’re up for the biggest challenge set with the 209km ride or joining in the festive spirit at the end of the 135km ride, it’s your choice.

Highlight: The view of rolling along the gravel roads, with Siena bathed in a golden hue at dawn.
Distance: 135 or 209km
Elevation: 2380m or 3887m

Today, you will take in part of the L’Eroica route and climb up to Castello di Brolio, set amidst olive groves and vineyards, before the challenge of one good long climb on the Strade Bianche, joing the other “heroic” cyclists.

Highlight: The Strade Bianche
Distance: 46, 81 or 106km
Elevation: 755m, 1612m or 1793m

Pricing & Dates

per person twin share / Maximum 14 guests

Show Price As


30th September – 7th October 2024
1995 (deposit)
A map of Chianti and Tuscany

Start Location & Details

City: Florence, Italy
Drop Off Location: Santa Maria Novella Train Station
Drop Off Time: 11:00am

Finish Location & Details

City: Florence, Italy
Drop Off Location: Santa Maria Novella Train Station
Drop Off Time: 11:30am

Inclusions & Details

A plate of Tuscan salami, cheese and bread

Accommodation & Meals

A rider getting their hire bike adjusted on a Italian cycling holiday

Ride Support

Bottles of Chianti Classico

Transfers & Activities

Two piece italian made cycling kit

Ride Kit

Not Included

Have More Questions About Our Tuscany and L'Eroica Cycling Tour?

See our FAQs page for answers to common questions.

Bike Hire & Gear

Full Carbon Road Bikes

You can choose to hire a Pinarello or Bianchi with a compact crankset.

Colnago vintage steel bicycle for L'eroica

Vintage Steel Bikes

Need a beautifil pre-87 steel machine with downtube shifters? We partner with Roberto, a Tuscan local with a large supply of cycling history. These bikes are not your old “clunkers”……think Pinarello, Guerciotti and Cinelli with full campy. You’ll want to take it home with you.


Enjoy our hand-picked selection of boutique hotels and family-run villas across Tuscany which reflect the true character of Tuscany and its beautiful, warm and open people with whom we’ll share our experience.

Included is our beautiful hilltop villa within walking distance to Gaiole’s piazza and L’Eroica’s world famous vintage bike market. Perched on a hill overlooking Gaiole and with stunning views across the rolling hills, there is no better place to be than at our family run B&B which we have selected for your final 4 nights. You’ll be right amongst the action of the L’Eroica Festival, while also feeling relaxed and away from it all as the Villa grounds, infinity pool and views take in the spectacular Tuscan countryside.

accommodation in Tuscany
The gardens of our Tuscan accommodation
Tuscan accommodation
A pool in the tuscan countryside
A room with a view in Tuscany
Our dinner table with views of the Tuscan Landscape

Food & Wine

Enjoy with us the very best food and wine experience of Tuscany. For centuries, the wholesome elements of the earth and sun have determined the flavours of the region. World famous wines from a terroir that is among the most important in the world, to olive oils made with ancient rural wisdom and paired with dishes created from simple, fresh produce of the land.

We will enjoy a richly diverse food and wine journey which includes home cooked meals with our hosts where beautiful Autumn produce combines with traditional cooking methods and hospitality that is second to none and beautifully prepared meals in our favourite local osterias and restaurants that capture the very essence of Tuscany’s open and warm character.

Insalata caprese
A tuscan grill with charcoal
A group of riders and non riding partners enjoying a long Tuscan lun
A simple and sensational pizza
A panna cotta with fruit
First course of salami, cheese, tomatoes and basil


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