Eroica Heritage Montalcino & Pienza

Trip duration

6 days, 5 nights, 3 days on bike

Accommodation level



Self guided

Trip style

E-bike (eMTB), Gravel / Mountain Bike

Diffculty level

★ / ★ ★

Total distance & elevation

160 km / 2800 m D+

Price from


Embark on an epic adventure and experience the perfect blend of cycling, culture, art. An immersion in the historical and gastronomic heritage of the lands of Eroica: Siena, Pienza, and Montalcino.

This package is an unmissable exclusive proposal by Terra Eroica, designed for those who wish to immerse themselves in the authentic essence of Tuscany. It's a journey that goes beyond cycling on the roads and permanent routes of Eroica, allowing you to discover, visit, delve into and savor the historical, cultural, and artistic treasures:

  • Explore breathtaking landscapes on the Tuscan hills, pedaling on your favorite bicycle;
  • Visit museums, castles, churches, and artisan workshops, immersing yourself in the rich historical and artistic heritage of Siena, Val d'Orcia, and Montalcino;
  • Indulge your palate with the authentic culinary and wine experience of Brunello, Val d'Orcia, and Crete Senesi.

The Eroica Heritage tour offers various options and a unique hospitality experience, combining the Rural/Glam atmosphere for a complete immersion in the charming villages along the way. Choose from our additional services, such as luggage transportation, on-route assistance, guided tours, and bike rentals. Explore all the available options below.


The package includes:

  • Terra Eroica Travel Book
  • The Gold of Montalcino and the Temple of Brunello: ticket for entry and visit with audio guide to the Temple of Brunello, Archaeological Museum, and Diocesan Civic Museum
  • Pienza City of Light "All inclusive Pass": a unique ticket to visit Palazzo Piccolomini and its Garden, Palazzo Borgia with the Diocesan Museum, the Crypt with its Labyrinth, and the Cathedral. The Pass also includes an audio guide for immersing yourself in history and art.
  • Luggage transportation between accommodations and basic technical assistance
  • GPS tracks / Komoot App
  • 5 nights with breakfast in double rooms (2 in Montalcino + 2 in Pienza + 1 in Buonconvento)
  • 1 wine tasting in Montalcino
  • Medical/baggage insurance


  • Terra Eroica box with original Eroica kit: musette, cap, water bottle, and G. Brocci's book "L'Eroica, Storie, Imprese e Sogni sulle Strade Bianche" (+ € 60,00)
  • Bike & equipment rental (MTB, Gravel, E-bikes, road bike, Eroiche/vintage)
  • Bike guide to lead the group
  • Van for support, technical assistance, and safety along the route
  • Extra nights on the first and/or last day
  • Half board in hotel
  • Experience/activities in the stage locations (tastings, cooking classes, wellness)
  • Cancellation insurance
  • Transfer from/to airports or other locations

Not included

  • Dinners, lunches
  • Drinks and additional services
  • Tips and other extras
  • Tourist tax

Daily program

The complete program, 6 days, 5 nights, and 3 days of cycling.

  • Day 1: Arrival in Montalcino
    Free time to visit this enchanting medieval village, renowned worldwide for its extraordinary production of precious Brunello di Montalcino wine. Don't miss the frescoes of the Church of Sant'Agostino, the collections of the Archaeological Museum and the Diocesan Civic Museum. We will also visit the Temple of Brunello, an immersive and emotional journey through multimedia stations, videos, interviews, and artistic masterpieces. At the end of the visit, at Enoteca Bistrot 'Tempio del Brunello,' enjoy a wine tasting of 3 wines: 1 Brunello Vendemmia, 1 Brunello Vigna, and 1 Brunello Riserva. Dinner on your own and overnight stay.
  • Day 2: Cycling - Montalcino to Pienza (40 km / 750 m D+)
    Cycle through the roads of Eroica and Eroica Montalcino in the Val d'Orcia Park, a perfect blend of art and nature. There are three sections of dirt roads, totaling 14 km. The only notable detail is the steep descent from Vignoni Alto to Bagno Vignoni, which is, however, cemented. Pienza has been a UNESCO World Heritage Site since 1996. Considered the ideal city of the Renaissance, it was commissioned by the humanist Enea Silvio Piccolomini, Pope Pius II, and it stands unchanged in the midst of the bright landscape of the Val d'Orcia. We will delve into its history and art, visiting the magnificent historic center with the "All inclusive Pass," a unique ticket valid for 2 days, which allows you to explore independently with an audio guide: Palazzo Piccolomini and its Garden, Palazzo Borgia with the Diocesan Museum, the Crypt with its Labyrinth, and the Cathedral. Dinner on your own and overnight stay.
  • Day 3: Pienza - Sightseeing
    A day dedicated to further exploring the sites included in the "All inclusive Pass" in Pienza. Dinner on your own and overnight stay.
  • Day 4: Cycling - Pienza to Buonconvento (km / m D+)
    The arrival is scheduled in time to allow for individual visits to the fourteenth-century Tuscan village, one of the most beautiful villages in Italy. Buonconvento will welcome you with its red brick houses and narrow streets, inviting you to wander and discover its wonderful Palaces, including Palazzo Podestarile, Palazzo Comunale, and the eighteenth-century Palazzo Taja. Overnight stay in a hotel.
  • Day 5: Cycling - Buonconvento to Montalcino (62 km / m D+)
    Upon arrival in Montalcino, there will be time to recharge and prepare for the final dinner with a tasting of local specialties at a selected venue.
  • Day 6: Departure
    After breakfast, you will have free time before concluding the services.

Accommodation level

RURAL GLAM: A mix of rustic charm of farm stays and the elegance of residences in small towns. Savor local cuisine and fine wines in exclusive settings and immerse yourself in the beauty of the Tuscan countryside. Whether you stay in an ancient farmhouse or a refined residence in a small town, comfort and elegance are always guaranteed. RURAL GLAM is the ideal choice for an authentic and luxurious experience. Siena Hotel Athena / Il Battistero**** - Montalcino: Hotel dei Capitani*** – Pienza: Hotel Relais Il Chiostro di Pienza****

Tour category

RING TOUR: The ring tour faithfully follows the permanent Eroica routes, with possible variations to reach the stopping points. It starts and ends in the same location, with daily stages and changes of accommodation at each stage. The organization takes care of luggage transport. The ring tour is a complete and adventurous cycling experience, with each stage planned to ensure a balance between distance and time available to enjoy places and experiences.


SELF-GUIDED This formula involves traveling the itinerary in complete autonomy: , by yourself. We will provide you with all the documentation and the Komoot app to guide you. We will give you all the necessary tools to plan your trip and guide you along the route, so that you can fully enjoy the experience.

Rider level

LEVEL 1 - E-bike Explorer: This level is perfect for cyclists who want to explore the white roads of Eroica comfortably. You will cover between 25 and 40 km per day with a elevation gain of 800-1500m (depending on the days and itinerary) using an e-bike. The assistance of the e-bike will allow you to enjoy the views without the need for excessive effort during climbs.

LEVEL 2 - Chianti Cruiser: This level is suitable for cyclists who want to explore the white roads of Eroica without facing long distances or challenging climbs, even with muscle bikes (gravel, mountain bike, road bike). You will cover a maximum of 30-40 km per day with an elevation gain of 800-1200m (depending on the days and itinerary) using a conventional bicycle. Take your time to enjoy the views, taste the Tuscan cuisine, and discover the hidden gems of this paradise place.

Dates and prices

on request
RURAL GLAM Montalcino E-bike (eMTB) Gravel / Mountain Bike
from € 750,00
Listed periods don't fit? Ask for your own custom tour

What people say about us

Chianti landscape along Eroica route
Gravel / Mountain Bike, Eroica pure vintage style


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.

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Servizi per cicloturisti

Bike room videosorvegliata in struttura
Orari posti flessibili
Servizio transfer
Lavanderia gratuita
Guida cicloturistica
Noleggio bici
Officina per riparaz

Servizi hotel

Self check-in
Reception 24h
Wi-fi gratuito
Piscina outdoor
Centro benessere
Sala fitness
Ricarica auto elettriche

Servizi spa e wellness

Massaggi e trattameni
Wi-fi e bagno turco
Sauna finlandese

Servizi family

Piscina riservata ai bambini
Spa aperta ai bambini
Mini club/area giochi
Servizio baby-sitter
Disponibilità di biciclette
Baby menu



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