Best of Tuscany Self-Guided main pictures
Best of Tuscany Self-Guided main pictures

Best of Tuscany Self-Guided

A bike ride through purest beauty! This memorable bike tour takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses, wonderful historic centers, and cheerful locals. Really exciting moments on the bike await you. From the sinuous ups and downs through rolling hills to the exciting passages under the ancient walls of medieval towns. From the vineyards of Brunello d Montalcino and Nobile di Montepulciano to the farmhouses surrounded by olive groves. From the museum cities of Florence and Siena to the legendary places of the Eroica. Prepare your legs and your heart for an unforgettable journey!

| Cycling | Avid | 7days/6nights | Self-Guided | From € 1820 € 1370* |


Brunello di Montalcino, Nobile di Montepulciano and Chianti wines

Brunello di Montalcino, Nobile di Montepulciano and Chianti wines

The amazing towns of Siena, Florence and San Gimignano

The amazing towns of Siena, Florence 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 FlorenceCycling 70Km/1250mB
3Florence to Gaiole in ChiantiCycling 82Km/1740mB
4Gaiole in Chianti to AscianoCycling 70Km/1200mB D
5Asciano to MontalcinoCycling 90Km/1800mB
6Montalcino to San GimignanoCycling 100Km/1500mB

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.

Array Overnight: San Gimignano

Day 2: San Gimignano to Florence

In the lands of Chianti Classico

We leave behind the towers of San Gimignano, and head towards the beautiful countryside north of the town. At the end of the long descent that slopes down the Elsa river, you can stop for a coffee in the pretty village of Certaldo, famous for being the birthplace of the poet and novelist Giovanni Boccaccio. Here you can visit his house or relive the amusing scenes told in his Decameron, such as the famous one of Friar Cipolla (onion) which is set right between the alleys and the church of the village. The itinerary continues through the Sangiovese vineyards of Val di Pesa in the heart of the Chianti Classico area, and then leads us to the hills overlooking Florence, from which you will enjoy one of the most beautiful urban views in the world!

Array Overnight: Firenze
Included: Breakfast

Day 3: Florence to Gaiole in Chianti

Through the Chianti Classico wine-growing area

Today you will cross the legendary territories of Chianti Classico those that, according to the legend of the black rooster, were crossed at dawn at a gallop by the knight of Florence, in the challenge with the city of Siena launched to put an end to the disputes and establish a definitive border between the two rival cities. Today Chianti Classico is the trademark of a wine production specification, undoubtedly one of the most famous in the world, in whose logo the legendary black rooster always stands out. A history spanning over 300 years, which began in 1716, when Cosimo III, the Grand Duke of Tuscany, set the boundaries of the Chianti wine production area. This means that we will go through vineyard and wineries, but in fact not only because there will also be woods and fascinating villages. We are also entering the territories that host the legendary Eroica cycling race, which takes you back to the romantic dusty atmospheres of cycling of the past, made up of little technology, effort and a lot of passion.

Array Overnight: Gaiole in Chianti
Included: Breakfast

Day 4: Gaiole in Chianti to Asciano

On the legendary roads of the Eroica

We are 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 other highlight of the day is undoubtedly the city of Siena, that you will meet about halfway through. Siena is a lively but still authentic city, it's considered 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. Here you'll have the chance to taste the energetic Panforte, the typical Siena spice cake, made out of nuts and candy fruit, a perfect snack for bike riding! Then you go through the typical landscapes of the "Crete Senesi", made up of rolling hills, gullies, lonely farmhouses, and small parish churches, up to your cozy Agriturismo in Asciano countryside. A long day that will have tired your legs but filled your heart with precious experiences

Array Overnight: Asciano
Included: Breakfast Dinner

Day 5: Asciano to Montalcino

In the land of Nobile di Montepulciano and Brunello di Montalcino wines

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. Then we get to 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. 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.

Array Overnight: Montalcino
Included: Breakfast

Day 6: Montalcino to San Gimignano

Towards the towers of medieval Manhattan

Your tour continues along a beautiful landscapes which seems drawing by a Renaissance painter. Ten kilometres of descent take you down from the Brunello's land to Val d'Arbia we’ll cross the capital of Val D’Arbia region. After the neat village of Buonconvento, surrounded by fortified walls dating back to XIV century, the route climbs to the village of Murlo, with a quite strong agricultural heritage and inhabited since Etruscan times. Then a very relaxing long stretch between fields awaits us. The small town of Casole Val d'Elsa is the ideal place to stop for a break and have a quick but tasty meal. Finally, the arrival among the towers of San Gimignano, one of the best examples of urban architecture, created by the rich Tuscan merchants of the late Middle Ages. Once in town, relax in the wonderful Piazza della Cisterna in front of a glass of the noble Vernaccia di San Gimignano wine, or an ice cream from the historic Dondoli Gelateria, the perfect end of a memorable day.

Array Overnight: San Gimignano
Included: Breakfast

Day 7: Departure

Arrivederci Amici!

It’s time to say goodbye, but we know that Tuscany touched your heart and you want to be back in the Med with us!

Included: Breakfast

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.