Dream tour Tuscany380 kilometres of cycling through Italy's jewel box

Daniel Simon

 · 22.11.2023

Dream cycle path - in front of the old upper town of Colle di Val d'Elsa.
Photo: Daniel Simon
Pure pleasure! A journey through Tuscany appeals to all the senses. You should take your time, because there is so much to discover.
Tuscany has always exerted a magical attraction on travellers from all over the world. And rightly so, as author and photographer Daniel Simon discovered on his two-week cycle tour.

It's always fun to read the poorly translated marketing phrases in tourism brochures. "The cyclist is an ancient and discreet pioneer who lets himself be lulled by the curves of a land ...". Well, the cycle traveller in Tuscany is no longer a pioneer. And we don't feel at all antique on our bikes. On the contrary - especially here in Chianti with its forests and vineyards or in the unspoilt Crete with its gentle hills, there is certainly no more contemporary way of travelling to get to know the country, culture and people.


If you want to experience Tuscany with all your senses, you should take your time, as there are many culinary and cultural delights to discover on the almost 400-kilometre-long dream cycle tour. Daniel Simon, travel writer and photographer

At the end of our round trip, we want to enjoy the unique flair of the art metropolis of Florence. That's why we take advantage of advance ticket sales before we set off so that we can admire the famous paintings in the Uffizi Gallery and Michelangelo's David in the Galleria dell'Accademia without having to queue for hours. We quickly leave the Renaissance city on the Arno behind us and are soon captivated by the landscape of the beginning Chianti. After a long ascent, we arrive hungry in the pretty little town of Greve. Our first stop is the "Antica Macelleria Fallorni". In the large traditional butcher's shop, the ceilings are full of wild boar ham and salami. Hundreds of wheels of cheese are stored in a vaulted cellar, exuding a flavoursome aroma. We order a platter of various delicacies and a prepaid wine card so that we can elegantly sample a wide variety of Tuscan wines.

Most read articles

1

2

3

No cycling holidaymaker should leave Tuscany without extensive wine and cheese tastingPhoto: Daniel SimonNo cycling holidaymaker should leave Tuscany without extensive wine and cheese tasting

The next day on the journey to Radda, we encounter more and more racing cyclists, some on very old bikes. Was the statement about the ancient pioneers true after all? Once we arrive in the town, the situation is clarified. The next day, the historic L'Eroica cycle race takes place. We will experience this fascinating spectacle up close, as parts of our route lie on the race route. We feel a little ashamed as the participants struggle up the gravel ramps of the "strade bianche" on their lovingly restored bikes, while we casually crank past on our thirty gears, completely out of place. At least we are able to help a rider with a flat tyre. The poor chap had forgotten his puncture repair kit from the excitement of the early morning start.

How do you like this article?

Historic cycle race L'Eroica

Every year in October, the historic cycle race takes place in Gaiole in Chianti. Most of the participants start on racing bikes. The rules are strict. For example, bikes must be built before 1987, have frame gears, exposed brake cables or hook pedals. Four route lengths (38, 75, 135 and 205 kilometres) demand everything from the riders, especially because large parts of the route lead over gravel roads, the "strade bianche".

If you have the opportunity, don't miss the historic L'Eroica cycling racePhoto: Daniel SimonIf you have the opportunity, don't miss the historic L'Eroica cycling race

However, the L'Eroica is not a race in the true sense of the word. It is more about the event itself, marvelling at lovingly restored bikes from many decades of cycling, talking shop with like-minded people and rummaging for historical material at the flea market. On the days of the event, there is an exuberant festival atmosphere in the small town. www.eroicafan.it


Travelling through Chianti is like a beauty contest. One winery is even more imposing and noble than the next. One place even more lovingly restored than the last. As we roll southwards past Siena, the picture changes. The vineyards give way to undulating, seemingly endless farmland that shimmers in all earthy colours. There is an old farmstead on almost every hill. Many of these farms are adorned by the characteristic curved cypress driveway. The villages are more original, simpler, but no less beautiful. The Crete south of Siena are not so heavily frequented by tourists. A pleasant side effect: a piece of delicious pecorino often costs only half of what we paid in Chianti. In Pienza, we are so impressed by the abundance of culinary delights that we lose track of time while sampling the many delicatessens.

Cyclists may well encounter wild boar in the oak forests of TuscanyPhoto: Daniel SimonCyclists may well encounter wild boar in the oak forests of Tuscany

In the late afternoon, a visit to the tranquil village of Bagno di Vignoni is on the programme. Even the Romans used the healing springs. Instead of a piazza, a large medieval thermal pool adorns the town centre. It is already dark at night and we are still en route to our stage destination of Montalcino. There is a suspicious crackling and crackling in the dense oak forest. We share the last few kilometres on the main road with lorries speeding past. Our worries were not entirely unjustified. The very next day, a horde of wild boar suddenly bursts out of the bushes in front of us. There are still plenty of wild animals in Tuscany and it is not uncommon to see foxes, deer, lynx and even porcupines in addition to wild boar.

After the many landscape experiences, we treat ourselves to a two-day break from cycling in Siena. The magnificent Gothic buildings bear witness to a rich history. Every stroll through the winding streets of the city inevitably ends at the imposing, shell-shaped Piazza del Campo. Before continuing our journey, we pack a Torta Senesi with figs and nuts from the famous Pasticceria Nannini into our bike bag.

Tourist magnet: the town of San Gimignano with its medieval town centrePhoto: Daniel SimonTourist magnet: the town of San Gimignano with its medieval town centre

A visit to San Gimignano is a must, but unfortunately the town with its famous towers has degenerated into a large souvenir shop over the last twenty years. Whole busloads are channelled through the historic alleyways every minute. We therefore plan our overnight stop in Colle di Val d'Elsa. Tuscan life pulsates without too much tourism in this town known for its crystal glass production. The lift ride through a mountain tunnel that connects the new lower town with the historic upper town is a real experience. Here we enjoy a quiet evening with a succulent bistecca fiorentina and plan the rest of our journey, which will take us through some wonderful landscapes before we roll back into bustling Florence.

Magnificent building: the "Cattedrale di Santa Maria Assunta" in Siena. Once a year (usually in autumn), the famous mosaic floor can be viewed in its entirety.Photo: Daniel SimonMagnificent building: the "Cattedrale di Santa Maria Assunta" in Siena. Once a year (usually in autumn), the famous mosaic floor can be viewed in its entirety.

Dream tour Tuscany

I combined my passion for cycling with my love for my old adopted home. My aim was to plan an "ideal tour" that connects the most attractive places via the most scenic routes. There are still many "strade bianche" in Chianti and in the Crete south of Siena. These public roads are unpaved and covered with fine gravel. They are rarely used and are therefore perfect for cycling. The terrain is hilly throughout, but the climbs are mostly moderate. Picture-book views over the classic cultural landscape are guaranteed.

Daniel Simon, travel author, photographer and Tuscany expertPhoto: Daniel SimonDaniel Simon, travel author, photographer and Tuscany expert

Don't miss this on a cycle tour through Tuscany:

  1. Wine tasting at the Caparzo winery near Montalcino (Brunello) and at Castello di Brolio (Chianti). Put a bottle in your pannier and have the boxes sent to you.
  2. Wild boar sausage and ham from the Antica Macelleria Falorni in Greve in Chianti
  3. The small town of Pienza is located in one of the most picturesque landscapes in Tuscany, is beautiful in its own right and has fantastic delicatessens with the best pecorino.

Tour itinerary

Florence - Greve in Chianti - Radda in Chianti - Gaiole in Chianti - Castelnuovo Berardegna - Pienza - Bagno Vignoni - San Quirico d'Orcia - Montalcino - Siena - Colle di Val d'Elsa - San Gimignano - Certaldo - Tavernelle Val di Pesa - San Casciano - Florence

GPX data

You can download the GPX track for the cycle tour through Tuscany download here for free or find it in the MYBIKE Collection on komoot

Best time to travel

Early April to mid-July and September to mid-November. August is too hot for cycling and Tuscany, one of the world's most popular holiday destinations, is very crowded in the high season.

Accommodation

If you are staying in one place for longer, you can rent a holiday flat or a room in one of the many beautifully situated country houses or wineries. Sylvia Stich and her team offer an exquisite selection. www.terra-antiqua.com

If you change towns every day on your route, you will find hotels and guesthouses to suit all requirements. Tuscany is so busy, even in the low season, that you should plan and book your accommodation in advance. The most popular booking portals offer the largest selection.

Travelling by train

Daily with the CityNightLine from Munich to Florence. Bicycle transport must be reserved. An international bike card must be booked in addition.

Attention when travelling to Munich: Bicycles cannot be taken on the ICE.

Maps

  • Kompass hiking and cycling maps, Tuscany 1:50,000, (set of 4 maps) WK 2440
  • Marco Polo Leisure Map Tuscany, 1:125,000

Travel guide

  • Tuscany Travel Guide, Michael Müller Verlag
  • DuMont Art Travel Guide Tuscany
  • Cycling tours in Southern Tuscany, Fresh Air Edition
  • Cycling experience: Tuscany, Bruckmann Verlag
  • bikeline Radtourenbuch: Cycling Atlas Tuscany, Verlag Esterbauer

More info

ENIT - Italian National Tourist Board, https://www.enit.it/en

Most read in category Tours