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L’Eroica & Chianti Tour

  • Tour Type

    Granfondo

  • Riding Level

    Active

  • Location

    Radda in Chianti, Tuscany

  • Duration

    6 days | 5 nights

  • Length

    74 - 104km daily

  • Climb

    600 - 1,530m daily

1 Oct, 2025 - 6 Oct, 2025

We promise this tour will show you a side of riding that you have never experienced before! It will re-ignite your senses and leave you with a feeling of admiration for the incredible cycling heroes in history who won races on wonderful vintage bikes with their downtube shifters, long brake cables and toe-clips. As Giancarlo Brocci, creator of L'Eroica, has said “We want people to rediscover the beauty of fatigue and the thrill of conquest”.

L’Eroica, a non-competitive and globally renowned cycling event. With 5 different course lengths, it’s accessible to everyone (46km, 81km, 106km, 132.6km and 212.5km).

Prior to the L’Eroica Ride on Sunday, the 1st of October, we will enjoy three days of cycling on modern road bikes (Full carbon – superb road bikes with disc brakes and electronic shifters). We’ll explore the Tuscan countryside and the beautiful city of Siena, while sampling the delicious local cuisine, savouring the local wines and indulging in the Italian culture.

We will then swap our bikes for a weekend of riding on a pre-1987 Vintage classic. A morning coffee ride will allow you the chance to get used to your new bike, before an afternoon of rest in preparation for the epic L’Eroica Ride!

What makes this tour one of our guests’ favourites? You don’t have to worry about anything – we will provide two bikes (one new and one vintage), and supply you with your very own vintage kit… which means if you are as fashion-conscious as our Italian friends then you will look just the part dressed in the classic celeste Bianchi Kit or rosso vino Eroica! And of course, start numbers are guaranteed.

Book now and guarantee your place in this iconic event as this tour will sell out quickly. Read the story by Michiel about their latest adventure at L´Eroica here.

We have partnered with Eroica as an Official Tour Operator, to deliver you a number of unique experiences on this tour. Immerse yourself into the history of cycling one of the most unique and spectacular events of the season, L´Eroica in Gaiole!

Price: From €3,980 Selling out - last spots available!

Tour Highlights

  • Guaranteed start number for L'Eroica Gaiole
  • Ride on the stunning Tuscan roads and in a UNESCO World Heritage List region
  • Includes 3 days of riding a superb road disc bike, and 2 days riding on a vintage pre-1987 bike
  • Vintage cycling kit (woolen jersey, bib-shorts, cap, gloves) is included
  • L'Eroica & GTP goodie bag
  • Castello di Broglio private vintage collection visit
  • Luxury accommodation at CDH Radda in Chinati **** & Hotel Le Fontanelle***** hotel

Itinerary

Day 1 - Wednesday

Benvenuto & welcome ride - 45km / 1000m

We will meet you at Florence airport in the morning and transport you to our hotel, CDH Hotel Radda **** which overlooks the beautiful medieval town of Radda in Chianti. We’ll help you get fitted to your bike, we’ll hand out the team kit, and make final preparations before this afternoon’s ride. A 45km ride will take us through the beautiful vine-covered Tuscan countryside, where we will pass through the small hamlets of Panzano and Dudda. Upon returning to our hotel and after discussing the week’s program, we’ll enjoy a hearty Italian dinner.

Day 2 - Thursday

Chianti Classico - 74km / 1,530m

Chianti Classico is one of Italy’s most famous wines and today we will enjoy riding in the region. It will be a spectacular ride as we ride through vine-covered hills and along roads lined with cypress trees. We will tests our skills on parts of Strade Bianche (the white gravel roads) using our Road bikes (like in the modern professional peloton) and stop for a well-deserved coffee in Castello di Brolio … or even better a glass of Chianti Classico! After all, it was Barone Ricasoli who was responsible for the creation of the wine. A special visit to their private vintage collection that the Castello di Brolio has underground has been arranged, followed by a super wine tasting. Today, Castello di Brolio is recognised as the oldest winery in Italy and still remains in the Ricasoli family!

Day 3 - Friday

San Gimignano & Siena - 107km / 1,460m

Today’s ride takes us east from Radda in Chianti down a swooping descent towards San Gimignano, a small walled medieval hilltop town. Defined by its tower houses, San Gimignano is also referred to as “The Town of Fine Towers”. We will enjoy a photo stop in the town before riding south towards the beautiful city of Siena. After a delicious lunch, we will depart the UNESCO World Heritage Site and head north passing through the beautiful town of Castellina in Chianti before arriving back at our hotel. In the late afternoon, we will attend a special dinner in the heart of Chianti with a special wine tasting degustation.

Day 4 - Saturday

Coffee Ride, Vintage Bike test & markets - 38km / 600m

It is time to prepare for L’Eroica. After yesterday’s ride, our team will have swapped your modern-day bike for a pre-1987 Bianchi bike! Yes, you’ve got it … think of toe clips, brake cables, downtube shifters and a woollen cycle kit! In the morning we will collect our vintage bikes and before heading into our test ride, you will have the chance to experience the pre-L’Eroica atmosphere and markets in Gaiolle. We will then ride from Gaiolle in Chianti to our new superb hotel, the 5-star Hotel Le Fontanelle, testing the bikes and ensuring they’re as comfortable as possible ahead of L’Eroica. An extended afternoon coffee ride will see us test the bikes on the rolling hills of Chianti and on the Strade Bianche.

Day 5 - Sunday

L'Eroica Gaiole - Course length : 212.5km / 132.6km / 106km / 81km / 46km

After an early breakfast, we will arrive to the start area in the centre of Gaiole. It will feel like you have been catapulted back in time as you are surrounded by thousands of riders, on vintage bikes clad in vintage kit. The excitement will be growing and at 5.00am, the first riders cross the line for the longer courses 209km/103km. If you want to indulge in spirit of the ride then it will be an 8am start for 78km/46km and 9am start for the 32km course. Your best day ever on the bike is about to start. Whichever course you have chosen enjoy the L’Eroica experience. And don’t forget to stop at the feeding stations and taste the local specialties … you will need them to make it to the finish and share your best moments with us.

Day 6 - Monday

Departure

All good things must come to an end. After a last cornetto and espresso (or cappuccino, or macchiato), the shuttle will take you back to the airport. Time to go home and share your L’Eroica stories (and photos) with your envious cycling friends!

Aditional information

What's Included?

The full L'Eroica experience, stunning landscapes, Strade Bianche, delicious food, new friends and beautiful Tuscan landscapes.

  • Guaranteed registration for L’Eroica Gaiole in Chianti and L’Eroica goody bag
  • 3 nights at CDH Hotel Radda in Chianti**** & 2 nights at Hotel Le Fontanelle*****
  • Meals: breakfast & dinner (Superb dinners by the way)
  • Picnic lunch during rides
  • Energy nutrition
  • Bianchi bike rental (Infinito CV 2023, carbon frame, Disc, Ultegra Di2 12 SP)
  • Vintage rental bike for L’Eroica weekend
  • Wine tasting and extra activities withing our program
  • Knowledgeable and experienced guide(s)
  • Fully supported tour with vehicle and mechanic
  • Cleaning kit and tool kit available for use
  • Full vintage cycling kit (jersey, shorts, cap & socks)
  • Laundry service
  • Road book including all the details you need to know on your trip
  • Gpx files – for Garmin device upload
  • Transfers from and to a designated airport, within a predefined time window

What’s Not included?

  • Flights/transportation to the defined pick-up/drop-off locations
  • Travel Insurance
  • Alcoholic & non-alcoholic drinks

Views from the road

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