Eroica Heritage Siena & Pienza

Trip duration

7 days, 6 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
  • Opa Si Pass Ticket - Duomo Siena for visiting: Duomo, Baptistery of San Giovanni, the Crypt, the Opera Museum, and the panoramic terrace of Facciatone
  • 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
  • 6 nights with breakfast in double rooms (3 in Siena + 1 in Montalcino + 2 in Pienza)
  • 1 tasting menu dinner at a selected restaurant in Siena
  • 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, 7 days, 6 nights, and 3 days of cycling.

  • Day 1: Arrival in Siena
    Arrive in Siena, check-in at the hotel, and settle into your reserved rooms. Free time for an orientation walk in the historic center of Siena. In the evening, enjoy your first gastronomic experience in this rich land of traditions with dinner at a selected restaurant just a few steps from the Baptistery. You will be welcomed at the intimate restaurant "In Carrozza" located in the picturesque Vicolo delle Carrozze, once a notorious place and later a carriage remise. Here, you will savor refined flavors of a seafood-based Tasting Menu while experiencing the ambiance of bygone eras.
  • Day 2: Siena - Sightseeing
    A full day dedicated to individual sightseeing in Siena with the OPA SI PASS, a pass that allows you to freely visit, within 3 consecutive days, the Cathedral, one of the most beautiful Christian cathedrals, the Baptistery of San Giovanni, the Crypt with its underground premises, the Opera Museum, and the panoramic terrace of Facciatone, offering an unforgettable view of Siena and the Tuscan countryside. Dinner on your own and overnight stay.
  • Day 3: Cycling - Siena to Montalcino (53 km - 32.9 mi / 1170 m - 3839 ft D+)
    Of the 53 km (32.9 mi) to be covered with an elevation gain of almost 1170 meters (3839 ft), 30 km (18.6 mi) will be on dirt roads distributed in three different sections. While the first two sections will feature gentle undulations, the last section, the famous Castiglion del Bosco, which has seen the passage of the Giro d'Italia on multiple occasions in addition to Eroica, includes a 7 km (4.3 mi) uphill stretch with gradients exceeding 10%. Starting from Siena, the route enters the Val di Merse, and you will experience the strong contrast between its forests and the scenic landscapes of the sinuous clay hills of the Crete Senesi. After the small village of Bibbiano, you will enter the territory of Brunello and Val d'Orcia, an area included in the UNESCO World Heritage List. Montalcino will be your reward after the last intense effort, offering breathtaking landscapes. You will have enough time to visit this enchanting medieval village, renowned worldwide for its extraordinary production of precious Brunello di Montalcino wine. In the afternoon, visit the Temple of Brunello, where you can immerse yourself in an immersive and emotional journey through multimedia stations, videos, interviews, and artistic masterpieces, followed by a tasting of Rosso di Montalcino. Don't miss the frescoes of the Church of Sant'Agostino and the collections of the Archaeological Museum and the Diocesan Civic Museum. Dinner on your own and overnight stay.
  • Day 4: Cycling - Montalcino to Pienza (40 km - 24.9 mi / 750 m - 2461 ft 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 (8.7 mi). 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. You 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 5: 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 6: Cycling - Pienza to Siena (63 km - 39.1 mi / 880 m - 2887 ft D+)
    From Pienza, after 5 km (3.1 mi), you will enter the permanent route of Eroica, and there will be a total of 5 sections of gravel roads, covering approximately 38 km (23.6 mi) without any particular technical difficulties. The passage from the Val d'Orcia to the Crete Senesi will be scenically captivating and will accompany you until the gates of Siena. Dinner on your own and overnight stay.
  • Day 7: 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

su richiesta
RURAL GLAM Roundtrip, starting point Siena E-bike (eMTB) Gravel / Mountain Bike
from € 970,00
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.

Read the story

Sign up for our newsletter

Keeping up to date with Terra Eroica is as easy as riding a bike. Shall we get started?

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!


Thank you


Your request has been successfully submitted, we will reply to you as soon as possible. A copy of your message has been sent from to your email address.

Terra Eroica & C-Way staff


Sign up for our Newsletter


Concept, Design, Web



Thank you

Your message has been sent successfully






Request information


- Request a quote

Tour selected:

Your data

Stay from to *

Room allocation 1


Nome struttura ricettiva

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



Morbi at diam ipsum. Nullam lobortis velit ut interdum commodo. Sed saggitis purus ultrices, maximus eros quis, bibendum erat. Vestibulum gravida semper leo, nec consectetur eros tincidunt sed.


Richiedi offerta


Select period and filter the site based on your holiday dates