Tuscany's Legendary Gravel Routes

6 nights
27 miles/day
Self guided from EUR € 1690
Bike tour in Italy
Rider Level: Enthusiast Electric bike tours Primarily bike paths

Tuscany's Legendary Gravel Routes


Rider Level: Enthusiast Electric bike tours Primarily bike paths

6 nights
27 miles/day

Self guided from EUR € 1690
Bike tour in Italy

Tap above to jump to different sections of this tour

  • Discover Authentic Italian life, Renaissance Heritage and Historic Vineyards

    With its timeless landscapes, ancient towns, and vineyards, Tuscany offers unparalleled views of authentic Italian life. The region's simplicity, art, and cuisine make it an unforgettable destination in the heart of Italy.

    Gravel biking in Tuscany offers a deeper connection with the region's scenic beauty, leading cyclists along off-the-beaten-path trails and allowing for the exploration of all the elements that embody the essence of Tuscany. Riders can interact with local communities and discover hidden gems nestled in the center of the Italian countryside.

    The Strade Bianche route, with its iconic white gravel roads, and the nostalgic route of the L’Eroica combine challenging sections with picturesque landscapes in culturally rich locations like Siena, Montepulciano, and Montalcino.

    Don't miss this immersive exploration of Tuscany that combines sport, heritage, and the beauty of the region!

    Learn more about bike tours in Italy and Tuscany

    • Siena in Tuscany, Italy. Patrick Schneider@Unsplash
    • Wine-tasting in Montepulciano, Tuscany, Italy. PictureSeeker@Unsplash
    • Siena in Tuscany, Italy. CC:Raymond Lafourchette
    • Italian delicacies! Christian Mackie@Unsplash
    • Piazza del Campo in Siena, Tuscany, Italy. CC:Guido Haeger
    • Duomo di Siena in Siena, Tuscany, Italy. Agatha Depine@Unsplash
    • Montepulciano, Tuscany, Italy. Lukas Zczechowicz@Unsplash
    • Fresh pasta dishes in Italy! Sorin Popa@Unsplash

    View more photos


    • Pienza and Siena- UNESCO sites with Renaissance charm
    • Strade Bianche- Iconic white gravel routes.
    • Tuscan Countryside- Historic vineyards and undulating hills.
    • Montepulciano and Montaclino- renowned wine region and home to Brunello di Montalcino wine.
    • L'Eroica- Internationally recognized vintage bike route
    • Tuscan Cuisine- Authentic pasta fresca and superb wine.

  • Discover Authentic Italian life, Renaissance Heritage and Historic Vineyards

     Tour Description Daily Program 

  • Daily program

    Day 1: Pienza - Bagno Vignoni - Pienza (15 mi / 25 km)
    This cycle adventure begins in Pienza, a UNESCO World Heritage site in Tuscany's Val d'Orcia. Often dubbed the "perfect town," it’s celebrated for its Renaissance architecture and cobblestone streets.

    Following a brief welcome meeting and bike fitting, set off on the first ride to Bagna Vignoni, a historic thermal spa town with therapeutic hot springs. The town features a large rectangular pool in Piazza delle Sorgenti dating back to Roman times, surrounded by medieval buildings and the Madonna di Vita Leta chapel.

    Elevation gain: +558m
    Surface: 8 mi. gravel / 7 mi. asphalt

    Day 2: Pienza - Montepulciano - Monticchiello - Pienza (32 mi / 51 km)
    Embark on a cycling adventure from Pienza today. Pedal through cypress tree-lined paths, recalling scenes from films like Gladiator and The English Patient. Explore off-the-beaten-path gravel tracks and take a moment to enjoy an espresso at La Foce, overlooking the conquered routes. Continue your journey to Montepulciano, celebrated for its Renaissance architecture and renowned as a prominent wine-producing region, especially known for the Vino Nobile red wine. On your way back to Pienza, make a stop in the village of Monticchiello, a quintessential Tuscan hill town.

    Elevation gain: +872m
    Surface: 21 mi. gravel / 11 mi. asphalt

    Day 3: Pienza - Montalcino (25 mi / 41 km)
    The best route to travel from Pienza to Montalcino includes Eroica sections Lucignano d'asso and Pieve A Salti. Depart from Pienza, covering 3 mi. on a paved road before turning onto a white road towards Cosona and arriving at the hamlet of Lucignano – a stop at the local emporio for an espresso is a must. After a short ride on the paved road, transition to the Eroica gravel section Pieve a Salti, offering a picturesque rural landscape with 6 mi. of undulating terrain. Reach Buonconvento by lunchtime, and prepare for the ascent to Montalcino, part paved and part gravel, passing through vineyards and wineries. Upon reaching Montalcino, a visit to the fortress is highly recommended to enjoy the breathtaking view of the traversed valley.

    Spend the evening in Montalcino with its medieval charm, ancient architecture, and world-famous Brunello di Montalcino wine.

    Elevation gain: +855m
    Surface: 15 mi. gravel / 10 mi. asphalt

    Day 4: Montalcino - Siena (37 mi / 59 km)
    L'Eroica, meaning "The Heroic," is an annual celebration of cycling's golden age. Held every October, thousands of dedicated cyclists transport themselves back in time to tackle gravel roads using vintage bikes of the past. Today, you’ll experience your own journey into cycling's heroic origins by riding one of L'Eroica's stunning gravel sections in the heart of Brunello di Montalcino, Tuscany's renowned wine region. Starting at Castiglion del Bosco, the largest Brunello winery and farm owned by the famous Italian fashion designer Ferragamo, you'll navigate through Passo del Lume Spento, Bibbiano, La Piana, and Murlo, encountering legendary Eroica sections with steep yet brief ups and downs. Ville di Corsano provides a perfect spot for a light lunch before the final 7 mi. along a secondary paved road to Siena.

    Explore Siena with its historic UNESCO World Heritage Site center, offering a blend of art, history, and distinctive Tuscan charm.

    Elevation: +1015m
    Surface: 16 mi. gravel / 21 mi. asphalt

    Day 5: Siena - Gaiole (or Gaiole in Chianti) (29 mi / 47 km)
    Today's destination is the town where the Eroica cycling event begins. Following breakfast, venture into the enchanting Chianti region, leaving Siena through an Eroica gravel section at Pieve a Bozzone and Vico d'Arbia. Traverse wheat fields before entering the celebrated vineyards of Chianti Classico. Covering approximately 9 mi., reach Pianella and embark on a scenic journey through Canonica A Cerreto and Vagliagli, exploring the charming Chianti Classico vineyards with castles and hilltop hamlets. Arrive in Radda in Chianti for lunch after a 23 mi. ride, mostly on gravel roads.

    Conclude the day in Gaiole. Explore the town center, indulging in authentic Tuscan cuisine, strolling through picturesque streets, and sampling regional wines in a local wine bar.

    Elevation: +923m
    Surface: 21 mi. gravel / 8 mi. asphalt

    Day 6: Gaiole - Castello di Brolio - Gaiole (34 mi / 54 km)
    Today is dedicated to exploring all the villages and hamlets of Chianti Senese. Begin your journey from "Castle di Spaltenna" in Gaiole and reach Castello di Brolio where a coffee awaits at Agribar in front of the winery, a popular spot for cyclists and locals alike. Proceed through a short gravel section of Eroica before navigating very secondary roads to Castelnuovo Berardenga, providing numerous lunch options. Back on your bike, visit other small villages like San Gusmé and Villa a Sesta before returning to Brolio. To reach Gaiole, opt for the easier downhill road or the challenging uphill route to Castagnoli, followed by a descent to Castello di Meleto.

    Elevation: +1013m
    Surface: 7 mi. gravel / 27 mi. asphalt

    Day 7: Gaiole - Badia a Coltibuono - Gaiole (13 mi / 21 km)
    The tour ends today. If time allows and you’d like one last adventure, consider cycling the short loop to Badia a Coltibuono, a historic abbey surrounded by vineyards and olive groves.

    Surface and terrain

    Travel 30 - 35 miles per day along the Strade Bianche and l'Eroica routes which present diverse terrains featuring challenging gravel roads, hills, and scenic countryside.


    These are sample hotels and may vary based on availability.

    Pienza: Relais il Chiostro

    Montalcino: Hotel Giglio or Vecchia Oliviera

    Siena: La Villa STR

    Gaiole: Castello di Spaltenna

    How to get there

    Tour start:
    To reach Pienza, fly into Rome or Florence, then take a train to Chiusi-Chianciano Terme (1.5-2 hrs) and a bus or taxi to Pienza (45 mins).

    Tour end:
    Returning from Gaiole, take a bus or taxi to Siena (1 hr). From Siena, connect to Florence Airport by train and taxi/shuttle (1.5-2 hrs) or to Rome Fiumicino Airport by train via Rome Termini (3 hrs).

    Discover Authentic Italian life, Renaissance Heritage and Historic Vineyards

     Tour Photos Dates & Prices 

  • Dates

    Daily departures, Mar 15 - Oct 31, 2024


    Tour Package

    Per person, double occupancy €1690
    Single-use room (1 person / 1 room) €2250

    Bike Rental

    Gravel bike €250
    Touring bike €180
    Electrically-assisted bike €250

    Included services

    • 6-nights accommodation in a standard hotel
    • 6 breakfasts
    • Route notes, maps, elevation gain, & city map
    • 'Ride with GPS' App with navigation offline
    • Luggage transfers

    Bike rentals

    Bike options available on this tour:

    Gravel bike: Scott Addict Gravel 20

    • Frame:  Addict Gravel Disc Hmf / Imp Carbon Technology/Gravel Race Geometry
    • Rear Derailleur: Shimano Ultegra Rd-R8000-Gs  22 Speed
    • Brakes: Shimano Br-R8070 Hyd Disc 160/F And 160/Rmm Sm-Rt800 Cl Rotor
    • Saddle: Syncros Tofino Regular 2.0 Cutout
    • Tires: Schwalbe G-ONE Bite Performance 700x45C

    Electrically-assisted bike: Scott E-Sub Cross 10

    • Frame E-Sub 6061 Alloy
    • Fork: Suntour Nex-E25 Lo Ds 15mm Ta Tapered
    • E-Drive System : Bosch Performance 250w System W/ 500wh Power Tube Battery /
    • Rear Derailleur: Sram Nx 11 Speed
    • Brakes: Shimano Br-M365 Disc
    • Size: S,M,L / Man & Woman Model

    Bike Protection:
    Bike protection can be purchased at the time of booking. You can read more about that HERE.

    Tour Company

    Discover Authentic Italian life, Renaissance Heritage and Historic Vineyards

     Daily program Tour Reviews 

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    Discover Authentic Italian life, Renaissance Heritage and Historic Vineyards

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