Classic Tuscany Self-Guided main pictures
Classic Tuscany Self-Guided main pictures

Classic Tuscany Self-Guided

Immerse yourself in the purest beauty! This memorable bicycle trip takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses, wonderful historic centers, and cheerful locals. You will ride from the Crete Senesi to the lands of the Vino Nobile di Montepulciano and Brunello di Montalcino, passing the "ideal city" of Pienza. Then the medieval atmosphere of Siena and San Gimignano will welcome you, and finally, the Chianti Classico and the romantic routes of the Eroica will close your wonderful journey.

| Cycling | Active | 8days/7nights | Self-Guided | From € 2170 € 1870* |


Brunello di Montalcino, Nobile di Montepulciano and Chianti wines

Brunello di Montalcino, Nobile di Montepulciano and Chianti wines

The amazing towns of Siena and San Gimignano

The amazing towns of Siena and San Gimignano

The Crete Senesi landscape

The Crete Senesi landscape

The Eroica routes

The Eroica routes

Day to Day

B: Breakfast; L: Lunch; D: Dinner;
1Benvenuti in Toscana!Warm Up
2San Gimignano to Gaiole in ChiantiCycling 55Km/1100mB D
3Gaiole in Chianti to AscianoCycling 50Km/630mB D
4Asciano to PienzaCycling 50Km/1100mB
5Pienza to MontalcinoCycling 40Km/890mB
6Montalcino to SienaCycling 50Km/850mB
7Siena to San GimignanoCycling 60Km/950mB

Tour Map

Day 1: Benvenuti in Toscana!

Tour briefing, bike fitting and warm up ride

We suggest you arrive at Florence airport, according to your needs we’ll shuttle you, or we’ll meet directly at our accommodation in San Gimignano city center. San Gimignano is a Unesco heritage site thanks to its many scenic towers and its long history, one of the first independent communes of Italy. After a mandatory toast with a local wine like Vernaccia di San Gimignano, ancient wine with a distinctive character, we'll 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, a perfect start for the upcoming adventure.

Overnight: San Gimignano

Day 2: San Gimignano to Gaiole in Chianti

An Epic day along the Eroica roads

We leave San Gimignano surrounded by pristine Sangiovese vineyards, admiring the distinctive skyline as we move towards the Chianti Classico region. In the past this area was the scene of fierce clashes between the cities of Florence and Siena, disputing over these lands for a long time, in this regard it is interesting the legend of the black rooster, symbol of the region, that we invite you to read. This area today it's a place of wonderful serenity and beauty.
But let's not forget we are also in the realm of the Eroica, the iconic vintage bike ride across the Chianti region, so we will have an exciting taste of the Strade Bianche experience, gravel roads with well-trodden surfaces where it will be fun and romantic to ride. The route winds through the pretty villages and countryside of Castellina in Chianti and Radda in Chianti, up to Gaiole in Chianti, where we will spend the night.

Overnight: Gaiole in Chianti
Included: Breakfast Dinner

Day 3: Gaiole in Chianti to Asciano

At the origins of Chianti Classico wine

Let's cross the Chianti area, and conquer the Brolio Castle by climbing among cypress trees. This stunning property is probably the most important symbol of the Chianti area. It belongs to the noble Ricasoli family, of which the most illustrious representative was the baron Bettino di Ricasoli, a prominent politician of the just Kingdom of Italy but, above all, a researcher and wine entrepreneur of great foresight. After years of research and experimentation, in 1872 the Baron was finally able to define a method, which became the official formula for the production of Chianti wine. We’ll pedal coasting the fortified walls of the Castle, then we’ll immerse ourselves in the vineyards in the valley. We could have an aperitif at the classy Rapolano Thermal Baths, with great views over the bare Senesi Hills. Elisa and Andrea will host us at their agritourism with pool. Before dinner, let us taste their great extra virgin olive oil.

Overnight: Asciano
Included: Breakfast Dinner

Day 4: Asciano to Pienza

Across the beautiful villages of Montepulciano and Pienza

Today we ride 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 Montepulciano where a stop is mandatory to taste one of the best Italian wines: the Vino Nobile di Montepulciano docg. We end in the amazing village of Pienza, known as the “ideal city” and considered to be the incarnation of a Renaissance utopia, UNESCO World Heritage Site as well. Here we'll taste some great Pecorino cheeses made by local shepherds settled here a few generations ago from the island of Sardinia.

Overnight: Pienza
Included: Breakfast

Day 5: Pienza to Montalcino

In the land of the Brunello di Montalcino wine

We leave the romantic Renaissance atmosphere of Pienza, heading towards the kingdom of Brunello di Montalcino, one of the most renowned and precious wines in the world. The itinerary winds its way through barren fields, woods, olive groves and vineyards, of course, wonderful vineyards planted with Sangiovese grapes, called "Brunello" in this area. After crossing the river Orcia, we meet the majestic Sant’Antimo Romanic abbey, marvelously immersed in the countryside. If you are lucky you could listen to the monks’ Gregorian chant, a really unique experience. The last climb of the day leads us to the village of Montalcino, which in addition to the pride of a great wine can also flaunt a beautiful medieval village.

Overnight: Montalcino
Included: Breakfast

Day 6: Montalcino to Siena

From the vineyards of Montalcino to the rolling hills of Siena

From the top of the Montalcino hill, we descend along an exciting descent taking us under the medieval walls of the ancient city of Buonconvento. Then we go up through the typical landscapes of the "Crete Senesi", made up of rolling hills, gullies, lonely farmhouses, and small parish churches. Riding along the landscapes you have admired many times in postcards and photos of Tuscany will provide unique emotions.
The day ends right in Siena, a lively but still authentic city. Siena is the most medieval town of Tuscany, divided in "Contrade" (districts), and famous for its Palio, a medieval horse race taking place twice a year in the Piazza del Campo square. Today we'll taste the energetic Panforte, the typical Siena spice cake, made out of nuts and candy fruit, a perfect snack for bike riding!

Overnight: Siena
Included: Breakfast

Day 7: Siena to San Gimignano

Across the Val d'Elsa up to the Manhattan of Medieval times

Shortly after leaving Siena we meet the ancient walled village of Monteriggioni. Its medieval walls are almost intact, covering a length of 570 meters and interspersed with 14 towers and two gates, the Porta Franca (towards Siena) and Porta S.Giovanni (towards Florence). The village was built by Siena on a hill dominated and monitored by the Via Cassia / Francigena. Its ideal position made it possible to control the valleys in the direction of Florence, a historic rival of Siena, which at that time was visibly expanding its territory.
The ride will lead us to San Gimignano, an Unesco heritage site thanks to its many scenic towers and its long history, one of the first independent communes of Italy. Make sure to have time to have an aperitif with a proper Vernaccia di San Gimignano, ancient wine with a distinctive character.

Overnight: San Gimignano
Included: Breakfast

Day 8: 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!

Included: Breakfast

The accomodations

Bel Soggiorno Hotel - San Gimignano
Bel Soggiorno Hotel - San Gimignano
San Gimignano

Cozy accommodation in a typical 14th-century building, with a perfect location in the heart of the ancient town, to discover the magic and charm of San Gimignano on foot.

Badia a Coltibuono
Badia a Coltibuono
Gaiole in Chianti

A villa that was previously a monastery, situated in an expansive landscape, rich in symbolism and at the same time, quiet and intimate.

Il Molinello Agriturismo - Asciano
Il Molinello Agriturismo - Asciano

Il Molinello is a cozy accommodation in the rolling hills east of Siena, better known as the Crete Senesi. Alessandro and Elisa produce high-quality extra virgin olive oil. If you want a super local experience, this is definitely the place!

Hotel Corsignano - Pienza
Hotel Corsignano - Pienza

Beautiful, functional and, above all, ecological. This is our comfortable 4-star hotel, set in the frame of Tuscany’s most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley, passing along the colorful roads you have always dreamed of.

Dei Capitani Hotel - Montalcino
Dei Capitani Hotel - Montalcino

In this ancient building, you can breathe the typical atmosphere of an ancient Tuscan village. The property offers a large garden with a swimming pool overlooking the valley of the vineyards where the fine Brunello is produced.

Italia Hotel - Siena
Italia Hotel - Siena

Few steps away from the north gate of the old town, completely renovated, “comfort inclusive” rooms, super breakfast. Italia hotel is your house in Siena.

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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. You can book your bike on the Booking / Information form.

Price and Supplements

Tour Price: € 1870 per person
Deposit: 30%, Balance: 45 days before departure

This price includes:
 7 nights in nice hotels 4*
 7 breakfast and 2 dinners
 Welcome meeting and tour briefing
 Maps, route notes or GPS tracks
 Luggage transportation inn2inn
 Telephone assistance
 Peace of mind being with our experienced team

This price not includes:
 Local Taxes (approx. 10 €)
 Drinks at Dinner

Road Bike Carbon + Ultegra: € 220

E-Road Bike Carbon + Ultegra: € 400

Road Bike - Flat Bar Carbon + 105/Sora: € 200

Touring Bike: € 110

High season supplement: € 250 (Jun 26 - Sep 04)

Single room supplement: € 250

Solo Traveller: € 450

Flex Rate

more than 60 days - 100% refund of deposit
60 days to 30 days - 70% refund of the trip price will be made
29 days to 15 days - 50% refund of the trip price will be made
14 days to 0 days - 100% cancellation fee

Self Guided Tour

This means you will pedal free at your pace following maps and tracks received during our pre tour briefing at your arrival. We will advise you where to have lunch and dinner, about sightseeings along the road and where to find technical assistance. You can start on any day of the year.

With just 4 people, this tour can be ride as a Guided Tour

In our Guided tours you have:

  • A cycling guide riding with you showing his region
  • Van support with water, electrolytes and snacks, available if you want to skip the hardest climbs
  • A daily picnic lunch featuring local and fresh products
  • Dinners at hotel or restaurants featuring traditional food
  • Shuttles from arrival airport and to departure airport
Ask for a quote and Go Guided

This tour is ready to book

Book now or ask for more information

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.
This tour is ready to book