L’Eroica & Tuscany Cycling Tour

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

L’Eroica and Tuscany Cycling Tours Overview

Join us for a unique Tuscan cycling adventure as we bring together the very best of our Tour of Tuscany with 4 amazing days in Gaiole in Chianti for L’Eroica.

This tour combines all the best that cycling, L’Eroica and Tuscany have to offer.  Starting in San Gimignano, we’ll then explore the Val d’Orcia and finally be perfectly positioned in the heart 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. 

Join us for our full 9 day/8 night adventure and be ready to take on L’Eroica with amazing rides in the Tuscan hills and plenty of training in your legs.
Or choose your own adventure by joining us for the first 4 nights of the tour on our Tuscany leg or the last 4 nights of the tour to experience the very best of L’Eroica. Limited places available so please enquire via email.

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 arrive to San Gimignano 6 days before L’Eroica rolls out of Gaiole in Chianti.

We’ll prepare the legs during the first few days and enjoy all that the different areas of Tuscany 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 is the perfect introduction to cycling in Tuscany. A very beautiful loop through the Colli Senesi, to a quintessential hilltop hamlet, before returning to San Gimignano and its majestic 14 towers. This is an easy roll that allows you to make any micro-adjustments to your hire bike as you need.

Highlight: The stunning vista of San Gimignano’s towers
Distance: 41km
Elevation: 732m

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: 104km
Elevation: 1816m

A superb day in the Val d’Orcia as we meander through some of its ancient cobblestoned hamlets, roll along its beautiful open roads and enjoy the free flowing descents. Pure magic.

Highlight: The four beautiful and free flowing descents
Distance: 67km
Elevation: 1282m

Expect rolling hills and an undulating picture-postcard landscape that is speckled with small groves of olive trees, vineyards and through tiny villages, before reaching one of Tuscany’s prettiest towns, Montepulciano.

Highlight: The quiet and open landscape around Montepulciano
Distance: 77km
Elevation: 1628m

As we leave the majestic Val d’Orcia, today’s ride will take in three distinct climbs with the landscape changing as we pass into the Crete Senesi and then again as we enter into Chianti, with its idyllic rolling hills striped with vineyards and backed by dense wooded forests and little villages that dot the landscape. We’ll roll past the the iconic Castello di Brolio and into the home of L’Eroica, Gaiole in Chianti

Highlight: Riding into the home of L’Eroica to a festival atmosphere
Distance: 84km
Elevation: 1648m

It’s time for you to explore on your vintage bicycle the sensational cypress lined backroads of Chianti, made famous by its wine, and the iconic Strade Bianche with their beautiful winding descents and climbs with incredible panoramic views. Today we ensure that we and our bikes are ready for tomorrow’s L’Eroica.

Highlight: The absolute beauty of Chianti
Distance: 49km
Elevation: 876m

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

AUD$3995 pp twin share Tuscany (4 nights) / AUD$4495 pp twin share L'Eroica (4 nights)

Show Price As


28th September – 6th October 2025
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 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.

Non-Riding Partners

As part of our L’Eroica cycling tour of Tuscany, non-riding partners enjoy an active and dedicated travel program, designed to deliver a diverse range of activities and the best experiences Tuscany has to offer. Whether its guided walks around the hills of Chianti, visits to beautiful castles and hilltop towns, guided sightseeing tours, meet the producer experiences and cooking classes or enjoying the festivities of L’Eroica along with our riding group, non riders experience the diverse beauty, scenery and culture of Tuscany. With an itinerary curated by Nancy and delivered together with a range of partners and guides whom she personally selects, It’s sure to be a holiday in Tuscany you’ll never forget.

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 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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