L’Eroica & Tuscany Gravel Tour
L’Eroica and Tuscany Gravel 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) for 4 days, we’ll be perfectly positioned in the centre of Gaiole to enjoy Italy’s best cycling festival, L’Eroica, before then departing Chianti to explore the region further.
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 Chianti hills as we prepare the legs during the first few days and enjoy all that the different areas of Chianti have to offer, while also soaking up the atmosphere of the L’Eroica Festival, featuring the best ‘antique/vintage’ cycling market you’ll ever see and a carnival atmosphere, with cyclists from all over the world.
Following our daily rides through Chianti and its unforgettable Tuscan countryside, culminating in the ride of a lifetime – L’Eroica, we’ll then depart Chianti for more superb rides through the Colli Senesi and the Val d’Orcia, the rolling hills around Siena, and of course our pinnacle ride into medieval San Gimignano. 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 Bianche and L’Eroica.
Welcome to ChiantiFollowing 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: 39.2km
Elevation: 715m
The Black RoosterWe 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: 62.4km
Elevation: 1154m
Exploring the Medici HeartlandToday 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: 1733m
L'Eroica - Long CoursesYour 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 212km
Elevation: 2380m or 3819m 
South of SienaToday we’ll transfer from our Chianti base, heading south of Siena for three nights, where we’ll stay close to the beautiful and iconic Pienza. We’ll roll out and up to the climb of Castello di Brolio, which has an incredible story of ten centuries of nobility of the Ricasoli family, who are still in residence today. As we track further south we’ll ride through the Crete Senesi: a hilly area almost bare of vegetation, which creates a truly magnificent moonscape, on your way to the Val d”orcia and one of the most beautiful towns in Italy, to our delightful hilltop villa.
Highlight: Riding through the ever changing ever landscape.
Distance: 82.6km
Elevation: 1662m
Into Brunello CountrySetting off in the direction of Umbria and traversing through a picture-postcard landscape through tiny villages, before reaching one of Tuscany’s prettiest towns, Montepulciano.
Highlight: The quiet and open landscape around Montepulciano
Distance: 68.1km
Elevation: 1286m
Our Tuscany bike tour takes you to the town of 14 towersThis 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 from the Val d’Orcia to what many consider is the most beautiful part of Tuscany,
Highlight: The final kilometres with vista of San Gimignano and its 16 towers in the distance.
Distance: 105.3km
Elevation: 1631m
Pricing & Dates
Show Price As
7995
per person twin share / Maximum 14 guests
2026
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
- Our L'Eroica & Tuscany cycling tours include 7 nights accommodation, twin share with private bathroom.
- Single occupancy available. Talk to us when booking
- All breakfasts
- Lunches on the road
- All dinners at a range of our favourite restaurants and osteria’s, including local wines at each dinner*
- *wine provided at dinner is to accompany meals / beverages ordered by guests will incur additional charges
Ride Support
- Professional bilingual ride guides with extensive cycling experience, local knowledge and first aid experience, ensuring your riding experiences are truly local and take in many of the undiscovered back roads and rolling hills of this spectacular and diverse region.
- Unique GPS routes, provided on tour as part of our bike tours in Tuscany.
- Support van on daily rides, with mechanical support and your safety as our priority.
- Nutritious snacks and water are provided
Transfers & Activities
- All transfers / transportation from pick up to drop off, including baggage and bike transportation.
- Entrance fees to sites and tours / activities included in non riding partner program
Ride Kit
- 2 piece, Italian made A’QTO Cycling Kit including jersey and bib shorts.
- Laundry for your cycling clothing.
Not Included
- Airfare.
- Bike hire.
- Travel & International Medical Insurance
- Guide Gratuities
- Specific gels and energy bars
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.
Accommodation
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 first 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.
Testimonials
L’EROICA WAS THE HIGHLIGHT
It’s easy to make it all about the riding and what comes with it, but there was just so much that was arranged for our group in the way of eating, drinking and sight-seeing that it all just blurred into this wonderful trip. For us, it was everything we had hoped for, the place, the people, the culture, the food and wine and, of course, the riding.
