The Chianti Classico main pictures
The Chianti Classico main pictures

The Chianti Classico

Cycling through the history of the red wine. History, enogastronomy, art, nature and joy of life, all together in a wonderful bike trip from Siena to Florence. Between these two pearls of world heritage, here stretches the the Chianti Classico territory: the quintessential Tuscany, an area blessed by a peaceful countryside and charming villages, producing one of the best wine worldwide by 2500 years. We’ll feel we are cycling inside a renaissance painting!


Nobile di Montepulciano e Chianti wines

Nobile di Montepulciano e Chianti wines

The strong and alive traditions in Siena

The strong and alive traditions in Siena

The Crete Senesi landscape

The Crete Senesi landscape

Elisa's delicious kitchen at Il Molinello

Elisa's delicious kitchen at Il Molinello

Day to Day

B: Breakfast; L: Lunch; D: Dinner;
1Benvenuti in Toscana!Warm up rideD
2Montepulciano loop tourCycling 70Km/1200mB D
3From Asciano to SienaCycling 40Km/750mB
4From Siena to San Casciano Val di PesaCycling 50Km/800mB D
5San Gimignano loop tourCycling 60Km/600mB D
6From San Casciano Val di Pesa to FlorenceDepartureB

Tour Map

Day 1: Benvenuti in Toscana!

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. After a mandatory toast with a local wine we properly introduce the whole tour and we make a careful bike fitting, then you’ll be ready for your warm up ride to the pretty medieval town of Serre di Rapolano, a perfect start for the upcoming adventure. Elisa and Andrea will host us for the first two nights, let us tasting their great extra virgin olive oil.

Overnight: Asciano
Included: Dinner

Day 2: Montepulciano loop tour

Your first ride is a beautiful loop through the Val d’Orcia, a quintessential tuscan landscape, made out of rolling hills dotted with cypress trees, its landscape is listed as a UNESCO World Heritage Site. 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. We’ll pass through the stunning village of Montepulciano where a stop is mandatory to taste one of the best Italian wines: the Vino Nobile di Montepulciano docg.

Overnight: Asciano
Included: Breakfast Dinner

Day 3: From Asciano to Siena

Today you leave the peaceful olive grove of Elisa and Andrea in the direction of Siena. The ride will cross the splendid Crete Senesi, the typical Tuscan countryside, among rural village, rolling hills covered with olive groves and cypress hedges, plowed fields and small churches. You’ll have even the chance to enjoy some Strade Bianche (gravel roads), home of the popular cycling event Eroica, the legendary race that every October brings thousands of enthusiasts to pedal through the lands of this wonderful region. The day ends within the ancient walls of the wonderful city of Siena, a jewel of late medieval architecture.

Overnight: Siena
Included: Breakfast

Day 4: From Siena to San Casciano Val di Pesa

We leave Siena worldwide famous for the fascinating "Contrade" (districts) and for its Palio, a medieval horse race taking place twice a year in the Piazza del Campo square. We suggest to take some energetic Panforte with you, the typical Siena spice cake, made out of nuts and candy fruit, perfect for bike riding!

The ride is across the heart of Chianti Classico, you can stop for rest in the pretty Castellina in Chianti, part of the original “Lega del Chianti” with Gaiole and Radda. 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. Then we’ll enter the Val di Pesa, considered the Florence wine area, a place internationally famous thanks to its wine, there we’ll stay in a wine resort, having a great wine tasting.

Overnight: San Casciano Val di Pesa
Included: Breakfast Dinner

Day 5: San Gimignano loop tour

You are riding along the old pilgrimage route called the Via Francigena, where pilgrims and noblemen once traveled north to south through Europe to get in Rome. A quick overview of the history and village plan of San Gimignano (the town of the towers) followed by some free time to visit the amazing churches, ancient walls, boutiques and art galleries, before to take the way back to our countryside hotel.

Let’s discover the typical landscapes of the Chianti Classico area, sinuosus roads going across huge vineyards and pretty villages. We are riding along the old pilgrimage route called the Via Francigena, where pilgrims and noblemen once traveled north to south through Europe to get in Rome. A quick overview of the history and village plan of San Gimignano (the town of the towers) followed by some free time to visit the amazing churches, ancient walls, boutiques and art galleries, before to take the way back to our countryside hotel.

Overnight: San Casciano Val di Pesa
Included: Breakfast Dinner

Day 6: From San Casciano Val di Pesa to Florence

Prepare for entering one of the most shining world heritage jewels by bike, such a great experience!

We start among vineyards and olive grows, along the route we’ll see the landscape gradually change into the peaceful the landscape changes gradually, from vineyards and olive groves to a lovely detached houses on the hills that dominate the city.

In the late afternoon we’ll go downtown for a nice walk before of a fantastic dinner in the Renaissance capital, celebrating the Chianti Classico wine, of course!

Overnight: Firenze
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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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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