L’Eroica & Tuscany Cycling Tour

Enjoy the beauty and heritage of L’Eroica cycling at its best.
Illustration displaying seven days of riding on a cycling tour
Illustration displaying a total riding distance of 505 kilometres for our L'Eroica and Tuscany cycling tour
Illustration displaying a total riding elevation of 8870 metres for our L'Eroica and tuscany cycling tour
Mountain Illustration displaying a cycling tour difficulty rating of eight out of ten

L’Eroica Cycling Tours Overview

Vintage steel frame bikes with downtube shifters and toe-clips, woollen jerseys, leather shoes and white gravel roads, this will become your favourite ride of the year.

From unforgiving climbs that 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.

Join us for a week on our L’Eroica cycling tour that combines all the best that L’Eroica, cycling and Tuscany has to offer. Expect amazing days on the bike with picturesque landscapes, long lunches and leisurely dinners where true artisans share with you their passion for the simplicity and seasonality of Tuscan cuisine.

Rediscover a taste for adventure with us at L’Eroica, Gaiole in Chianti, Italy 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 Bike Ride & Tour Itinerary

Welcome to L’Eroica & Tuscany

Arriving to Gaiole in Chianti, the home of L’Eroica, 6 days before the ride – you’ll have plenty of time to acclimatise, prepare the legs and soak up the atmosphere as the momentum builds in the days leading up to the event – you’ll be right amongst the action as the L’Eroica Festival starts to roll in to town from Thursday, featuring the best ‘antique/vintage’ cycling market you’ll ever see and a carnival atmosphere with cyclists arriving from all over the world – the lead up days are not to be missed!

You’ll enjoy daily rides through the superb Chianti hills and the 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 Chianti, and other parts of Tuscany including the rolling hills around Siena, the Crete Senesi, the famous Strade Blanche and more, all preparing you for L’Eroica.

Following our welcome lunch, today’s ride is to a quintessential hilltop hamlet, providing the perfect introduction to cycling in Gaiole in Chianti, with the idyllic rolling hills striped with vineyards and backed by dense wooded forests and the little villages that dot the landscape. It also gives you a chance to test your vintage steel machine and make any micro-adjustments to the bike as you need.

Highlight: Losing yourself in the  middle of Chianti
Distance: 50km
Elevation: 890m

Ride profile for ride into the Chianti hills

Today we will ride in the direction of Siena before veering towards the Crete Senesi: a unique, hilly and truly magnificent landscape before winding your way to back via many of the Tuscan villages, another testing climb and a beautiful descent into Gaiole and our villa.

Highlight: Rolling throught the unique landscape of the Crete Senesi.
Distance: 94km
Elevation: 1530

Ride profile into Siena and the Crete Senesi.

You will explore the beauty and challenge of the Chianti hills, with a day of more sustained climbing with 5 separate hills to conquer on our way to the country hamlet of Dudda, sitting in the wooded hills among scattered villas, country castles and stone farmhouses, before the sensational free flowing scenic descents that go on for ever.

Highlight: The five beautiful and free flowing descents
Distance: 75km
Elevation: 1788m

Ride profile to Greve in Chianti

It’s time for you to explore the cypress lined roads of Chianti made famous by its wine, on tiny back roads on our way to Castellina in Chianti for lunch and then finishing with fantastic descent down to our villa.

Distance: 70km
Elevation: 1010m


Ride Profile to Castellina in Chianti

Today is a bit of a rest day on the bike in preparation for tomorrow. You will head out after a leisurely start on a traditional coffee shop ride, to just turn the legs over. There will be plenty of time for on-the-bike conversation as you make your way to Castello di Brolio where we will stop for caffe e torta (coffee and cake).

Highlight: The sweeping bend between two ancient stone buildings with the backdrop of the ancient, open landscape, covered in vines and forest.
Distance: 28km
Elevation: 395m

Ride profile from Gaiole in Chianti to Brolio

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. It’s your choice to ride one of the five L’Eroica rides – 209km, 135km, 115km, 75km or 46km. Whether you’re up for the biggest challenge set with the 209km ride or joining in the festive spirit of the 46km ride, it’s your choice.

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

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, to get you in the spirit for Sunday.

Highlight: The Strade Bianche
Distance: 46km
Elevation: 877m

Ride Profile for iconic Tuscan ride

Pricing & Dates

per person twin share / Maximum 14 guests

Show Price As


25th September – 2nd October 2023 – Sold Out



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

While airfare, bike hire and travel insurance are not included in the Tour cost, they can be fully arranged for you. Talk to us when booking.

Have More Questions About Our Giro 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.


An easy to use GPS is provided for your use for the duration of the tour with our daily rides pre installed.

Non-Riding Partners

As part of our L’Eroica cycling tour, non-riding partners are treated with a customised travel program, designed to deliver a diverse range of activities and the best experiences Tuscany has to offer. Whether its guided walks, visits to beautiful castles and hilltop towns, guided sightseeing tours or cooking classes, Nancy personally hosts non-riding guests each day with a select range of activities to suit the group.

As our non-riding partner program is an active adventure, there is a minimum walking requirement for non-riding guests for each tour. Please enquire when booking.

Non riding partners on a walking tour of Castle Brolio
Non riding partners ona walking tour of Siena
A man painting ceramics in Tuscany
Walking through an old stone tuscan village
Non riding partners enjoying aperitivo
Non riding partners hiking in the Tuscan countryside


Enjoy 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 7 night stay. 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 Chianti. 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, to long Tuscan lunches and beautifully prepared meals in our favourite local osterias and restaurants that capture the very essence of Chianti’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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