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Tuscany and L’Eroica

The Best of Southern Tuscany culminating with the Eroica Ride and Festival

Download a Detailed Itinerary

Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:

  • A thorough daily itinerary
  • Details for exact accommodations
  • What to expect
  • Travel planning tips

Please provide your contact information so that we can say “benvenuto”. After submitting the form, you will be able to download the itinerary immediately.


Three nights in a southern Tuscan Farmhouse combined with L'Eroica, the world's greatest cycling event
Destination
Italy, Tuscany
Activity
Biking, Gravel Rides
Level
Intermediate, Advanced
Level

Perfect for the cycling newbies who already enjoy being active, or anyone who just wants to take it easy.

Pedal at a meandering pace, stopping to take pictures, savor a leisurely lunch and explore the surroundings. Enjoy quiet roads along flat and rolling terrain zigzagging through vineyards, olive groves and farmland.

  • Average daily distance: 35-45 miles
  • Terrain: flat and rolling

Our Athletic Beginner tours are perfect for those who aren’t avid cyclists, but are fit and love to exercise regularly.

On these trips, you’ll enjoy a flowing pace with plenty of time throughout the day to indulge in the local specialties, take in the local culture and enjoy the magnificent views. There will be an occasional hill, more rolling terrain and higher mileage than an Easy tour.

  • Average daily distance: 35-45 miles
  • Terrain: flat and rolling
  • Our guides will offer cycling clinics and one-on-one coaching in cadence, positioning and the art of shifting efficiently on rolling hills.

You love being active and cycling is your preferred way. You are in good physical condition and ride whenever you can.

Intermediate tours maintain a steady pace with opportunities to push yourself by tackling challenging climbs with great descents over stunning terrain. You’ll still have time to explore and enjoy the landscape and towns you’ll visit.

  • Average daily distance: 40-50 miles
  • Terrain: rolling with some hills

You are an avid cyclist who trains regularly, participates in bicycling events and is eager to plan their next bicycling vacation. You enjoy a vigorous ride, challenging climbs and thrilling descents.

These “Epic” and “follow the race” tours are spectacular and have plenty of classic climbs and are perfect for cyclists who covet long mileage with lots of hills and varying terrain.

  • Average daily distance: 45+ miles
  • Terrain: hilly with long climbs
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Duration
7 days / 6 nights
If diving into a Tuscan landscape by bicycle is your idea of heaven on earth and riding back in time on the world's most legendary vintage ride seems like a pure pedaling nirvana, this one's for you!
From $5,700 PP 7 days / 6 nights
From $5,700 PP 7 days / 6 nights
Book Now
Schedule A Call
Download Itinerary
If diving into a Tuscan landscape by bicycle is your idea of heaven on earth and riding back in time on the world's most legendary vintage ride seems like a pure pedaling nirvana, this one's for you!

Experience the beauty of Tuscany on a seven-day journey filled with picturesque roads, unforgettable meals, and exceptional wines. Our adventure begins in the peaceful countryside of Serre di Rapolano and winds through the Val d’Orcia toward the Chianti region, where twisting streets and warm, stone-brick villages create an atmosphere straight out of a storybook. Each day, we pedal past olive groves and vineyards, soaking in the romance and nostalgia of classic cycling. The journey culminates in Gaiole at the legendary L’Eroica vintage cycling festival, where riders from around the world gather to take on Tuscany’s iconic white gravel roads in a celebration of sport, camaraderie, and pure joy.

Tour Essence

  • Participate in L’Eroica, the world’s greatest cycling event
  • Experience the Eroica Festival with delicious local specialities, music, local cycling celebrities, vintage cycling stands and so much more!
  • Stay in an family run agriturismo and a luxury hotel near the Eroica
  • Cycle through the UNESCO World Heritage site of Val d’Orcia
  • Learn about the production of olive oil
  • Indulge in traditional Tuscan cuisine
  • A special Eroica Gift box
  • Vintage Eroica Jersey
  • View our Top Photos from Tuscany and L'Eroica

What to Expect

Terrain
Rolling and hilly with breathtaking views
Start Location
Serre di Rapolano
End Location
Radda in Chianti
Mileage
Average Daily: 30/45 miles Total: 180/280 miles
Elevation
Average Daily: 2,400/3,700 ft Total: 14,700/22,500 ft
Woman biking through Tuscany
Closeup of an old bike seat
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What's Included

Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.

What’s Included
  • Van support
  • Expert, bilingual guides
  • 1 wine tasting
  • 1 Tuscan cooking lesson
  • 1 olive oil lesson
  • Guaranteed entrance to L’Eroica
  • A special Eroica Gift box
  • Vintage Eroica Jersey
  • Shuttle at the beginning and the end of the tour

What’s Included

  • Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
  • Vintage bike rental for the Eroica
  • Garmin Edge Explore GPS loaded with the GPX tracks of your rides
  • Two water bottles
  • Saddle bag with repair kit
  • Optional: Map holder on handlebar 

Pedal Options

  • Flat pedals
  • Half-toe pedals (without straps)

What’s Not Included

  • Helmet
  • Optional: clipless/SPD pedals with shoes
  • Optional: your own saddle
Ciclismo Classico high-performance road bike for Italy bike tours, designed for cycling enthusiasts exploring scenic Italian landscapes and iconic routes.

La Classica Ribelle

Carbon Road Bike Included
Bianchi C-Sport bike

Bianchi C-Sport 2.5

Hybrid Bike Included
E-bike bicycle with electric motor and gears, ideal for Italy bike tours and scenic rides.

E-Road Bikes

Electric Bike Call for Pricing.
High-performance black electric mountain bike for Italy cycling tours and scenic bike trips across Italy's best cycling routes.

E-Hybrid Bikes

Electric Bike Call for Pricing.
Co-Motion Periscope Torpedo bike

Co-Motion Periscope Torpedo Tandem

Tandem Call for Pricing.
  • All accommodations
  • All breakfasts
  • 3 lunches
  • 6 dinners
  • Cooking class by a local chef
  • 1 wine tasting
  • Multiple Eroica and Vintage bikes lectures and tutorials

Dates

2026

Sep 29-Oct 5
Available
From $5,700 PP 7 days / 6 nights
From $5,700 PP 7 days / 6 nights
$1,140 Optional Single Supplement
Book Now
Schedule A Call
Download Itinerary
Any of our tours can be made private. Contact us to learn more.
Go Private
Guaranteed

Confirmed tours are dates that have been selected by us that have a very high probability of reaching the minimum group size for us to run the tour and for you to receive the best Ciclismo Classico experience. These tours are confirmed as much as a year in advance, compared to our regularly scheduled tours which are confirmed around 90 days prior to departure.  When you place your deposit for a confirmed tour, you have the green light to make your pre and post travel plans and even book your flight with our personal guarantee that your tour will run!

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Optional Single Supplement

If you are traveling alone, this optional single supplement will guarantee you a room to yourself at each hotel. The cost of a single room is often more than half the price of a shared room, so this additional supplement reflects that increased cost for each night over the course of the trip.

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