L’Eroica & Tuscany Cycling Tour
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.
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
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
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
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
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
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
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
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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
Accommodation & Meals
Transfers & Activities
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?
Bike Hire & Gear
Full Carbon Road Bikes
You can choose to hire a Pinarello or Bianchi with a compact crankset.
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.
As part of our cycling tour of Tuscany, non-riding partners enjoy 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.
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.
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.