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Time stands still in Tuscany. You’ll find that out for yourself once you get here and pedal through this Italian slice of heaven. This week-long, self-guided bike journey will have you cruising down cypress-lined gravel roads, medieval hilltop hamlets, and endless vineyards. Everything will be arranged for you, all you’ve got to do is show up and soak in bella Italia at your own pace—making enough time for espressos, delicious gelatos, and world-class wines. As the day gently fades into evening hues, you’ll retreat to luxe hotels and villas, all incredibly unique and charming in their own way.

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  • Sections of the iconic L’Eroica

    You’ll cycle along parts of the legendary L’Eroica, Tuscany’s world-famous vintage bike rice

  • Superb Tuscan wines & food

    Pair local pasta dishes with Vino Nobile di Montepulciano and Brunello di Montalcino

  • Truly get to know Tuscany

    Explore some of the most beautiful roads and hamlets of Chianti and Siena province


The gravel roads of Tuscany and its pristine bucolic landscapes are the perfect setting for a serene self-guided bike journey. Spend a week cycling along beautiful roads and hamlets of Chianti and Siena provinces, and soak in everything Italian along the way. The beloved Italian cuisine is always a good idea, but make sure to also taste espresso, gelatos, and delicious red wines. You’ll ride on both gravel and asphalt roads, your luggage will be transferred between accommodations, and you’ll stay at fantastic villas and hotels.

  • Make your way to Pienza, a wonderful renaissance town in Tuscany. Pienza is a remarkable example of renaissance architecture and it’s truly a treat to just stroll around its cobblestone streets. After a bike fitting, go for a short bike ride to Bagno Vignoni, a thermal spa town dating back to Roman times, and Madonna di Vita Leta chapel.

    Accommodation: Hotel Relais Il Chiostro di Pienza
    Distance: 25 km / 15 miles
    Elevation: +558 m / +1,830 ft | -565 m / -1,854 ft
    Terrain: 12 km (7.5 miles) asphalt, 13 km (8 miles) gravel

    Pienza in Tuscany
  • Today’s tour starts with a circular ride from Pienza. Red poppies blossom and overflow the verdant wheat fields of Tuscany in spring, and nowhere is it more brilliant than the hills of Val d’Orcia, a UNESCO World Heritage Site.

    Pedaling through corridors of cypress trees, follow the gravel tracks off the beaten path through a timeless slice of Tuscany and enjoy an espresso at La Foce, overlooking the roads you just conquered. By lunchtime, arrive to Montepulciano, the jewel of southern Tuscany, full of renaissance palaces. After relaxing a while, return to Pienza with a stop in Monticchiello, the quintessential Tuscan hill town.

    Accommodation: Hotel Relais Il Chiostro di Pienza
    Distance: 51 km / 31.5 miles
    Elevation: +872 m / +2,860 ft | -875 m / -2,870 ft
    Terrain: 17 km (10.5 miles) asphalt, 34 km (21 miles) gravel

    Cycling quiet roads of Tuscany
  • To get to Montalcino, you’ll pedal along sections of the Eroica route called Lucignano d’asso and Pieve a Salti. After 6 km on a paved road, take the white road toward Cosona and reach the hamlet of Lucignano—perfect for an espresso stop. After a brief paved road section, start the Pieve a Salti section on a gravel road. Enjoy 9 km up and down through the bucolic scenery!

    Arrive in Buonconvento by lunch time. The last push of the day is reaching the famed town of Montalcino—this will be a 10-kilometer climb on both paved roads and gravel though vineyards. Once there, it’s warmly recommended that you visit the fortress and admire the valley you’ve just biked through. Make sure to treat yourself to a glass of Brunello at dinner!

    Accommodation: Hotel Il Giglio or Vecchia Oliveira in Montalcino
    Distance: 41 km / 25 miles
    Elevation: +855 m / +2,805 ft | -807 m / -2,647 ft
    Terrain: 17 km (10.5 miles) asphalt, 24 km (15 miles) gravel

    Montalcino town in Tuscany
  • Today you’ll get to pedal along one of the most beautiful gravel sections of L’Eroica—a route and a yearly event that celebrates the golden age of cycling with thousands of cyclists. From the heart of Brunello di Montalcino, Tuscany’s most beloved wine region, you’ll ride to the top of Passo del Lume, starting the Castiglion del Bosco section (the biggest Brunello winery & farm).

    Once in Bibbiano, cycle through another section called La Piana and reach Murlo after 30 km. Rest, have a cup of coffee, and tour the village. Get back on the road and get ready for another legendary Eroica section to Radi, with some steep but short ups and downs. Reach Ville di Corson and have a well deserved lunch. From there, you have 12 km left on a paved road to Siena.

    Accommodation: Villa STR in Siena
    Distance: 58.5 km / 36 miles
    Elevation: +1,015 m / +3,330 ft | -1,229 m / -4,032 ft
    Terrain: 32 km (20 miles) asphalt, 24 km (15 miles) gravel

    Murlo in Tuscany
  • After a gourmet breakfast, head out into the magical Chianti. Exit from Siena via the Eroica gravel section of Pieve a Bozzone, Vico d’Arbia, making your way through wheat fields before reaching vineyards.

    After 15 km, reach Pianella—take a long glorious section to Canonica A Cerreto, Vagliagli, through Chianti classico vineyards. You’ll pass by castles and old hilltop hamlets! Reach Radda in Chianti for lunch time after a 38-kilometer ride mostly on gravel roads. After getting some rest, hop back on your bike and finish the last 8 km to Gaiole following the Eroica route.

    Accommodation: Hotel Castello Spaltenna
    Distance: 48.5 km / 30 miles
    Elevation: +923 m / +3,028 ft | -874 m / -2,867 ft
    Terrain: 12 km (7.5 miles) asphalt, 34 km (21 miles) gravel

    Gaiole, Chianti in Tuscany
  • Today is reserved for exploring all the villages around Chianti and the hamlet of Chianti Senese. Departing from Gaiole, reach Castello di Brolio after 10 km and stop at the Agribar cafe—it’s a must where everyone seems to meet! Continue riding along the gravel section of Eroica and then along secondary roads to Castelnuovo Berardenga.

    Have some lunch and get back on the saddle to explore other small villages—San Gusmé and Villa a Sesta, then back to Brolio. There are two options for returning to Gaiole, one downhill and flat (somewhat easier) or a challenging uphill to Castagnoli and downhill to Castello di Meleto.

    Accommodation: Hotel Castello Spaltenna
    Distance: 55 km / 34 miles
    Elevation: +1,013 m / +3,324 ft | -1,013 m / -3,324 ft
    Terrain: 44 km (27 miles) asphalt, 10 km (6 miles) gravel

    Brolio castle, Italy
  • To end your trip, you have an optional short ride to Badia a Coltibuono—a 21-km loop on paved road. Come back to Gaiole where you’ll leave your bikes if you rented them. This marks the end of your self-guided journey through Tuscany!

    Distance: 21 km / 13 miles (optional)
    Elevation: +395 m / +1,295 ft | -420 m / -1,378 ft

    Badia a Coltibuono
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Meet your guide

Cicloposse is a bike tour operator based in Tuscany, dedicated to delivering unforgettable cycling experiences and active vacations throughout Italy. With their passion for biking and love for travel, they are committed to providing excellent services while being socially responsible and creating low-impact trips that respect the environment. They pride themselves in working with local people and small businesses, enabling their guests not only to experience the authentic essence of Italy, but also to positively impact communities they visit. Cicloposse offers seamless organization, meticulous attention to detail, and fostering genuine connection with their guests.


5.00 (3 reviews)
Kathy and Rick P. (source: Guide’s website)

Rick and I just arrived back in the USA and wanted to take a moment to let you know that we had a wonderful Gravel Bike Trip. We thank you for the extraordinary job organizing, responding and planning the tour. The hotels were lovely and everyone was so helpful. Your Bike Trip Handbook was very helpful and will be a treasured souvenir from our trips. We will definitely look into taking another bike tour with your company and have already passed the word on to many of our friends and relatives. Maybe Sardinia! We do not have Instagram but will share our five star rating on sites listed. It was great working with you and I wish you the best with your tours this Summer. Thanks Again.

Jan and Tom D. (source: Guide’s website)

We had such a wonderful week biking through Tuscany and were so pleased with you and your Cicloposse family. It was very enjoyable working with you and your company’s expertise allowed us to have a stress free week. We will certainly recommend you to everyone who inquires.

Caroline P. (source: Guide’s website)

Thank you for arranging a very fun and successful trip for all of us. We loved every day of biking and it was really just what we needed. The accommodations were also excellent and so was the gear. we had no problems at all, … thank you again for all your coordination. We will definitely let others know about Cicloposse and will be in touch again if we want to travel elsewhere through Italy, or to have you connect us with a “partner” company in a different country who does similar tour organizing.

Things to know

  • What you get on this adventure:

      • 7-day self guided gravel bike tour in Tuscany
      • Accommodation for six nights in excellent hotels
      • Six breakfasts (special dietary requirements can be accommodated)
      • All baggage transfers
      • Route notes, maps, elevation gain and city map
      • RidewithGPS App – navigation offline
      • Sightseeing, restaurant and shopping suggestions
      • Pick-up of bikes and gear in Gaiole
      • Keepsake Cicloposse water bottle
      • Sales taxes

    What’s not included:

      • Transportation to Italy
      • Lunches and dinners (though you’ll get the best
      • local recommendations)
      • Bikes — available to rent, price per person for the entire tour
        • Gravel or e-bike $275
        • Hybrid bike — $195
      • Travel and medical insurance — optional
  • This self-guided gravel bike tour in Tuscany is rated to be moderate to challenging. Exact daily distances and elevation gains are listed in the itinerary, but in general, prepare for your trip with regular conditioning at least two months in advance.

    While this is a self-guided tour and you can pedal at your own pace, you’ll make the most of this adventure if you’re fit enough to cover daily itineraries without struggling too much. You’ll cycle on gently rolling terrain, there will be some hills and climbs, both on asphalt and gravel. You can make it easier for yourself by renting an e-bike with your guides.

    Keep in mind that you’ll cover between 25 and 58 km (15.5-36 miles) daily and that you’ll have to reach your booked accommodations for the night.

  • This is a list of clothing & footwear we recommend you bring:

      • Cycling shorts (padded shorts recommended, try them out before the tour)
      • Riding jerseys
      • T-shirts and/or casual shirts (quick-dry)
      • Bathing suit
      • Bike socks and/or sports socks (quick-dry)
      • Dress or casual socks
      • Windbreaker or cool-weather jacket (rainproof and breathable)
      • Light rain jacket or poncho (cheap version is fine—insurance on sunny days!)
      • Bike shoes
      • Riding gloves
      • Underwear (quick-dry)
      • Sweater or fleece
      • Slacks or light jeans (quick-dry, wrinkle resistant)
      • Belt
      • Comfortable walking shoes
      • Sandals


      • Passport, wallet and ID
      • Waterproof, zip-lock type plastic bag for your valuables
      • Health insurance card
      • Travel insurance card
      • Cash, credit cards and/or travel cheques
      • Electronic chargers (for camera, MP3 player, e-reader, cell phone)
      • Adaptors or convertors

    First aid kit

      • Insect repellent
      • Antiseptic cream or antibiotic ointment
      • Antihistamine tablets for hay fever
      • Sunscreen and total bloc
      • Throat lozenges or hard sweets
      • Painkillers
      • Band-aids and ‘Second Skin’ for blisters
      • Rehydration salts
      • Multi-vitamins
  • Yes! If you’d like to skip the hassle of bringing a bike with you to Tuscany, your guides offer bike rental. Prices are per person and for the entire week if cycling:

      • Hybrid bike — $195
      • Gravel or e-bike — $275
  • A self-guided tour is an independent exploration without a formal guide leading the way. Instead of being part of a group with a tour leader, you will navigate the tour yourself, using resources provided by the operator, such as maps, guidebooks, audio guides, or digital apps.

    For this gravel bike tour in Tuscany, your guide will arrange terrific accommodation for you with six breakfasts. All your baggage will be transferred from one accommodation to the next. You’ll get detailed route notes, maps, daily elevation gains and distances, and a city map. For navigation offline, you’ll use the RidewithGPS app.

    Another great thing about going on a self-guided journey is that your local guide will provide you with all the sightseeing, restaurant, and shopping suggestions you could imagine! This way you can be sure you’re truly getting the authentic Tuscan experience.

  • Group sizes and pricing

      • It takes a minimum of 2 people for this self-guided gravel bike tour in Tuscany to operate.
      • The maximum group size is set at 16 people.

    Gravel bike tours in Tuscany can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors older than 16 may be permitted to join the gravel bike tour in Tuscany on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

  • To get to your gravel bike tour in Tuscany, the nearest airports are Rome Fiumicino (FCO) and Florence Airport (FLR). It’s up to you whether you’d like to rent a car to reach Pienza, the starting point of your tour, or you’d like to use public transport. Driving with a car takes between 1.5-2.5 hours to Pienza, depending on where you land.

    For the public transport option, after landing you have to reach Chiusi. The easiest option would probably be to take the train. Once in Chiusi, you can take a bus or a taxi to Pienza, the starting point of your gravel bike tour in Tuscany.

  • We highly recommend that you cover all your bases with both emergency medical and travel insurance.

    With medical insurance, if you have an accident or medical emergency on or off the mountain, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more. Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans.

    We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to. If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!

  • A 30% deposit to secure your place is due upon booking. The remaining amount is paid 3 months (90 days) prior to departure. Once the trip is confirmed by the guide, the cancellation policy stated below applies.

      • If Client cancels the Booking anytime prior to thirty (30) calendar days in advance of the trip, Client is entitled to a refund in the amount of fifty percent (50%) of the total amount paid when Booking.
      • After that deadline, Client is not entitled to any refund.
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