EROICA MONTALCINO

Eroica Montalcino Experience 2026

by

ITB Italy Bike Tours

A Lake Iseo-based tour operator specializing in bespoke cycling holidays in Italy. An official partner of Terra Eroica, the Giro d’Italia, Strade Bianche, and Maratona dles Dolomites, offering experiences that blend cycling, culture, and gastronomy, catering to riders of all levels.

Trip duration

5 days, 4 nights, 4 days on bike

Accommodation level

RURAL GLAM

Formula

Self guided

Trip style

Gravel, Eroica pure vintage style, Roadbike

Diffculty level

★ ★ ★

Total distance & elevation

338 km / 5630 m D+

Price from

1.699,00

Montalcino & Val d'Orcia full time experince

The timeless thrill of vintage cycling through Tuscany’s legendary roads. This isn’t just a ride - it’s a journey through time, beauty, and passion.

Discover the soul of Tuscany on the legendary roads of Eroica Montalcino in this thrilling self-guided tour. Feel the crunch of the Strade Bianche beneath your wheels as you explore the Val d’Orcia, one of Italy’s most breathtaking landscapes. Every turn reveals a postcard view: rolling vineyards, silvery olive groves, and hilltop villages where time seems to stand still.

Whether you’re here to soak in Tuscany’s stunning scenery or to chase your love of cycling, Eroica Montalcino lets you live the true spirit of the sport’s golden age. It’s a celebration of courage, endurance, and the simple joy of the open road - an unforgettable tribute to one of Tuscany’s most exhilarating cycling experiences.

And when the ride ends, there’s no better way to toast the day than with a glass of Brunello di Montalcino, savoring the local flavors that make this land so irresistible. Tuscany is waiting - ready to capture your heart and your senses.

Included

Package includes:

  • 4 nights 3* or 4* accommodation
  • All breakfasts
  • 2 dinners
  • Airport transfers
  • Entry L’Eroica Montalcino
  • Wine tasting and wineyard tour
  • IBT vintage jersey
  • City taxes

OPZIONI

Not included

  • Travel Insurance (must be purchased before the tour)
  • Flights
  • Vintage bike hire
  • Vintage Helmet
  • Lunches
  • All beverages at meal times Beverages at mealtimes (water and coffee are complimentary during meals that are included in the package)
  • Tips and gratuities

Daily program

  • Day 1 - Arrival & Welcome Loop (35 km | 600 m) - Hotel Salivolpi | Castellina in Chianti
    After picking you up at Florence Airport, you will settle into your charming Tuscan base. Stretch your legs on a gentle 35 km loop in the afternoon, breathing in the rolling hills and golden light of your first Tuscan afternoon.
  • Day 2 - Monteriggioni & Chianti (50 km | 800 m) - Hotel Salivolpi | Castellina in Chianti
    Today, you’ll pedal through rolling vineyards, sun-dappled olive groves, and storybook villages, pausing to soak in the medieval charm of Monteriggioni—it’s like stepping back in time, with every corner revealing a new piece of Tuscany’s timeless beauty.
  • Day 3 - Ride to San Quirico (65 km | 700 m) - Hotel Wellness Center Casanova in San Quirico d’Orcia
    Cycle through the heart of Tuscany’s countryside toward San Quirico, where every hilltop reveals a postcard-perfect view. Pause in charming villages, savor local treats, and let the rolling hills and cypress-lined roads surround you.
  • Day 4 - Eroica Day (153 km | 2930 m) - Hotel Wellness Center Casanova in San Quirico d’Orcia
    The big day is here! Tackle the legendary Eroica route. Gravel roads, historic villages, and sweeping vistas make this a ride you’ll remember forever.
  • Giorno 5: Arrivederci!
    After breakfast, take a moment to reflect on your Tuscan adventure before we send you on your onward journey — with memories, photos, and a full heart.

Accommodation level

RURAL GLAM: 3-night stay in a 4-star hotel or traditional Tuscan accommodation, providing authentic hospitality and comfort.

Formula

GUIDED: You will have an expert cycling guide at your disposal: They will accompany you throughout the route, providing you with detailed information about the area and the history of Eroica's roads. You can enjoy the journey in complete peace of mind, without worrying about planning the itinerary or facing the most challenging climbs alone.  

Rider level

LIVELLO 3 / Eroica Challenger: For cyclists who love challenges and want to relive the original Eroica experience on a vintage or muscle bike. You will cover a maximum of 40-50 km per day with an elevation gain of 1000-2000m (depending on the days and itinerary). Get ready to pedal on challenging roads and experience the thrill like the cyclists of the past.

Dates and prices

28th May - 01st June 2026
Group guided Self guided Single supplement €249 / Room upgrade available: Yes
from € 1699
Listed periods don't fit? Ask for your own custom tour

What people say about us

Chianti landscape along Eroica route
Gravel, Eroica pure vintage style

INTIMATE EROICA, CYCLING SOLO IN THE MOST BEAUTIFUL PLACE IN THE WORLD!

I was alone, and cycling solo in those places is beautiful: you never get bored, just look up from the handlebars to realize that you are blessed and lucky to be there.

Read the story

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Share your intimate Eroica

With effort, enthusiasm, excitement, amazement, curse words, smiles, tears, and infinite joy; no matter how you did it, how many days it took, or when you crossed the finish line. Your Eroica journey is like no other.
Don't keep it to yourself, tell us your story and inspire others!

OK, I SHARE IT! EROICA STORIES

Thank you

THANK YOU "EROICO"

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Terra Eroica staff

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