Epic Tuscany main pictures
Epic Tuscany main pictures

Epic Tuscany

Custom tour along the epic roads of L’Eroica The Eroica is the iconic ride on vintage bikes across the whole Chianti, 200 km of pure beauty passing through many of the most beautiful tuscan cities: Siena, Montalcino, Buonconvento, plus many medieval villages surrounded by pristine San Giovese vineyards. The itinerary is along asphalted road and the “strade bianche”, typical tuscan gravel roads. The total climb is about 3500 meters, with a total length on gravel road of 110 km. During our tour we’ll visit wineries, olive oil mills, local producers and craftsman, discovering the Tuscan way of life and pleasure for healthy foods.


The Chianti countryside

The Chianti countryside

The medieval center of Siena

The medieval center of Siena

The gravel roads of Eroica

The gravel roads of Eroica

The val d’Orcia UNESCO heritage

The val d’Orcia UNESCO heritage

Day to Day

B: Breakfast; L: Lunch; D: Dinner;
1Benvenuti nel Chianti!Warm up rideD
2From Gaiole to SienaCycling 35Km/500mB
3From Siena to BuonconventoCycling 40Km/550mB
4Buonconvento loopCycling 60Km/1180mB
5From Buonconvento to CastelnuovoCycling 50Km/850mB
6From Castelnuovo to GaioleCycling 50Km/850mB D

Tour Map

Day 1: Benvenuti nel Chianti!

Tour briefing, bike fitting and warm up ride.

We suggest to arrive at Florence airport, according to your needs we’ll shuttle you or we’ll meet directly at our first hotel in Siena.

Conquered by the Medicis in 1585, Siena became a backwater, frozen in time, making it one of Europe’s finest examples of a preserved Gothic city. The high concentration of buildings from the 12th-14th centuries makes Siena unique, and the main square, “Il Campo,” is considered by many to be Italy’s most beautiful piazza. The famous bareback “Palio” horse race is held in the square twice a year. Our local guide will explain the mayhem and passion of the race, then take us to visit the cathedral and its medieval treasures.

Cycling: 10-20 km, depending on arrival time.

We’ll help you out in assembling your bikes, then we’ll be ready for our warm up ride along the peaceful countryside, a perfect start for the upcoming adventure.

Walking: 2 hours, hilly, urban hike.

While we’ll go for a ride, the Walkers will take a leisurely stroll through gorgeous Siena, one of Italy’s most enchanting cities.

Then we’ll set an aperitif to properly introduce the whole tour all together.

Overnight: Gaiole in Chianti
Included: Dinner

Day 2: From Gaiole to Siena

The origin of Chianti wine.

We start with a blast, soon after leaving Gaiole, we’ll conquer the Brolio Castle climbing among cypress trees, This stunning real estate is probably the most important symbol of the Chianti area. It belongs to the Ricasoli family, whom Bettino di Ricasoli was the creator of the Chianti wine back in the 1872. We’ll pedal coasting the fortified walls of the Castle, then we’ll immerse ourselves in the vineyards on the valley. The views become more and more fascinating when we approach Siena, majestic medieval town where we’ll stop for a visit. The old medieval center with the Duomo and its medieval buildings tells about a rich heritage, then the arrival Piazza del Campo square, made famous thanks to the Palio joust, it’s a breathtaking experience itself.

Overnight: Siena
Included: Breakfast

Day 3: From Siena to Buonconvento

Val d’Arbia, at the heart of agricultural Tuscany.

Today it’s a quite easy stage, so you can leave Siena late on the day.

The scenery it’s absolutely peaceful, with many small ancient villages, solitary farmsteads and countryside chapels. We’ll start with a rolling stretch of gravel road among the fields, riding for some km along the Via Francigena, the ancient pilgrimage route connecting Canterbury to Rome. Almost at the end of our ride we’ll arrive to the village of Murlo, with a quite strong agricultural heritage and inhabited since Etruscan times. Our final stage is the capital of Val D’Arbia region, on the neat village of Buonconvento, surrounded by fortified walls dating back to XIV century.

Overnight: Buonconvento
Included: Breakfast

Day 4: Buonconvento loop

Montalcino great wines and white truffles.

Today’s ride is the longest of the whole week, but we’ll pass through the vineyards of Montalcino, a perfect spot to chill with a glass of its well known Brunello. We are riding on the val d’Orcia, a quintessential tuscan landscape, made out of rolling hills dotted with cypress trees, site of the UNESCO heritage.

The scenery changes from dry and brown in fall and winter, to emerald green and blossoming in spring, to the amazing golden fields in summer. The longest climb of the whole week we’ll take us right in Montalcino, natural balcony over the countryside. After the mandatory aperitif, we’ll keep riding, stopping for lunch in Lucignano d’Asso. From here the road it’s quite relaxing taking us back to our hotel.

Overnight: Buonconvento
Included: Breakfast

Day 5: From Buonconvento to Castelnuovo

The Crete Senesi and Monte Sante Marie

Today we’ll start with a relaxing pace following the valley of Ombrone river, immersed in the rough and terse scenery of Crete Senesi, dotted with classy termal baths like the ones of Rapolano. Our first goal is the village of Asciano, right at the heart of the Crete area. From here we’ll climb the steep Monte Sante Marie, on of the most famous climbs on gravel of the Eroica. When on the ridge of the hill you’ll forget the challenge, thanks to the views over this unique place of Italy. Our arrival is at the luxury retreat of Villa Curina, perfectly set on a top of a hill overlooking the valley.

Overnight: Castelnuovo Berardenga
Included: Breakfast

Day 6: From Castelnuovo to Gaiole

Discovering the historical “Lega del Chianti” area

Our final stage we’ll bring us back to Chianti Senese, again along tranquil countryside roads among vineyards, stopping along the way to taste some local products directly at the farm. We’ll stop for lunch in Vagliagli, a village with a perfect view and very popular among locals, great stop to have a local dish. Then we’ll pass through Radda, part of the original “Lega del Chianti” with Gaiole and Castellina. The Lega, was a military organization created by Florence in 1384 to protect the whole area. From the original Lega del Chianti was born the Chianti wine protected area, still using the black rooster as a symbol. Few more km and we’ll be back at the starting point of our week in Gaiole.

Overnight: Gaiole in Chianti
Included: Breakfast Dinner

Day 7: Arrivederci!

Well, it’s time to say goodbye, but we are sure this part of Italy will touch your hearts and you’ll come again to visit more!

Overnight: Gaiole in Chianti
Included: Breakfast


You can bring your own bike or rent one from us, we offer great bikes from selected Italian and international brands: road bikes, leisure cycling, mountain bikes, e-bikes, all in perfect working conditions. We'll find the best solution for you during the tour customization.

This is a Sample tour

These itineraries are original tours created for real guests, so you may want something different specifically designed to suit your own wishes.
The price of every tour is available upon requests, and varies by time of year, number of guests and level of guiding.
Start dreaming looking through it, then contact us and let's talk. We'll listen to your needs, we'll suggest ideas and propose experiences, and together we'll create your perfect voyage.

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Check our GUIDED or SELF-GUIDED sections with active and cycle tours in our Mediterranean destinations.

Brendan NevinBrendan Nevin
15:07 07 Jun 23
Mediterras supported 8 of us on the cycling Gran Tour down the west coast. I would strongly recommend them - brilliant support, great local knowledge led routes and excellent bikes, We would use them again without hesitation.
Lesley KovarLesley Kovar
11:20 08 May 23
We just finished a custom tour with Mediterras, from Palermo to Marsala. What a fantastic experience! Our guide Gian Mario was so knowledgeable and attentive, his planning was meticulous. The choice of boutique hotels, as well as the restaurants he selected, were all wonderful. The rides were well planned, taking us through beautiful countryside and along spectacular coasts. Our van driver Giovanni was also awesome, he could be a professional naturalist. We are already planning our next trip with them (to Sardinia). What a treat to use a small local company that gave us such a memorable trip!
Bernie CreavenBernie Creaven
11:09 08 May 23
We loved traveling with Mediterrras!Mario and Giovanni were amazing, professional, detailed and thoughtful. They made planning this trip easy, they were super flexible when we had to change plans. They supplied us with excellent equipment (I loved my road bike), detailed maps, fun rides, history lessons, in fact we laughed our way around Sicily!We enjoyed our meals together and they booked us into beautiful hotels. Unfortunately, one member of our group had a medical emergency, they looked after him like they would a family member.I can’t wait to bike again with our new best friends!Go ahead book these local guys, you’re guaranteed a fabulous experience!Bernadette (Irish woman living and biking in Seattle).
Rich GundlachRich Gundlach
13:15 24 Sep 22
Great planning, exceptional guides. We enjoyed everything about our trip. We learned a great deal about the history and culture of Sardinia. Marcello at Mediterras made sure that everything was properly arranged and made adjustments when necessary. A great part of our enjoyment came from our interaction with our guides (Giovanni, Stefano and Danilo). They were all very knowledgeable and friendly. When it came time to part we felt like we were leaving old friends.
Doris ChapatteDoris Chapatte
11:53 12 Sep 22
We did the "big-loop" from the 20.08.2022.The big loop ist 12 days road bike around the island. We have booked the trip 1.5 weeks before (last minute) and everything has been organised perfectly. We had an extra break day every 4 days biking. And was great.Mediterras has answer to all our questions. On the day of departure, our bikes we ready, we got time to get full explanation of the tour. We got a navigation system with all the routes. Everything was very clear and very well organised. Our lugage was every evening delivered at the next hotels.The hotel has been wonderfully selected, and always at some nice location and not too far away from the center or the beach. Thank again to Mediterras team for the wonderful holidays.I would give more than a 5 Stars for this trip and the wonderful team.Doris & Jean-Luc - from Swizerland
Tadhg CookeTadhg Cooke
12:46 09 Jun 22
A fantastic introduction to cycling in Sardinia. I just rented the bike in Cagliari for a few days at the end of my holiday, with no particular routes in mind. Gian Mario kindly suggested two nice challenging routes, and sent the GPX files. I only had time for one of them - but it was an absolute gem. Starting in the city, cycling along Poetto, before turning towards the hills. After one tiny village, I didn't pass another café or shop for 40 or 50 km. Just me and the pain in my legs. Superb. The bike was a gem - a former Lotto Jumbo team bike which was ridden in the Paris Roubaix by Tom Leezer. I was a *bit* slower, but I probably enjoyed it more! Wonderful experience - lovely people - always available on whatsapp if I needed anything, which was very reassuring when I don't speak Italian or Sardu! I will definitely use them again if/when I return to Sardegna.Thanks again!
We did the Sicily Baroque tour with Mediterras. Self guided on bikes (el and manual). Gian and his team did adapt the tour for our needs and did all to make the tour enjoyable. Few problems surfaced but all were solved. The trail was interesting and added a lot to our understanding of Sicily, its landscape and life in the rural areas. Accommodations were all good, and the quality of the food in the restaurants Gian had arranged varied from good to excellent. At the end of our tour we did a walk in the hillsides of Etna arranged by Mediterras.The Etna tour was wonderful. We were lucky with weather given the circumstances. It was a bit foggy and a bit cold, but it did not rain. The guides did a good job of explaining the geology of Etna for us and the two geology-educated persons in the group! The hike was challenging, which suited the group well. The food and wine at Barbaras place was totally excellent! Six stars out of five.We were not as lucky in Taormina! It did rain cats and dogs. The drivers did adapt quite well. Did stop at several foto-ops and at the entry gate to the pedestrian street. We did wander through the Greek theatre and the pedestrian walk, did have a stop at a fancy coffe-shop/bar and then decided to skip the dinner and return early back to Syracusa.
W. B.W. B.
16:03 20 Oct 21
I found this company using google and right away Gian was very responsive. I told them what we were looking for, gave specific parameters for distance and elevation, and they put together an itinerary very quickly that completely matched what I asked for. The entire trip was seamless from the 1am pickup at airport to drop off after 10 days of cycling. The routes were on quiet wonderful roads and the hotels they chose were all great. A really good local company which does what they claim to do very well. Highly recommend.
Ilja WinkertIlja Winkert
11:14 17 Sep 21
I rented quite spontaneously a city bike for my whole stay here near Cagliari. The workshop is very well located. Grocery shopping, going to the beach and the city worked very well. Bike were in a good condition. I was properly advised. Fully recommend this place.
14:46 23 Aug 21
We are so happy that we found this rental. Very nice, helpfull and professional customer service. We recommend to everyone!
juliet clarkejuliet clarke
17:20 15 Jun 21
Mediterras arranged a self guided cycling trip through South Eastern sicily stopping in beautiful baroque towns. They arranged everything with less than a weeks notice, keeping us up to date on accommodation, bikes equipment etc.My husband and I had a wonderful time. The ride was perfect, having both been off a bike for several months, the ride was the perfect combination of hills and flats for us to really enjoy it. The accommodation was far better than what we were expecting for the price and recommendations for dinner and stops spot on. We ate incredibly well and all the hosts in the villas and hotels very welcoming and helpful.I would certainly recommend them especially arranging it all with such little notice.
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