Tuscany is a paradise for enthusiasts of cyclotourism as it boasts a good network of roads and paths and has little traffic, inviting cyclists to venture amid landscapes seemingly from yesteryear. The possibilities are endless and there are routes for all difficulty ratings. In this post we cover a route from Siena to Florence in two or three stages – depending on how fit you are – crossing a region where one of the world’s most famous red wines is produced – Chianti. With beginners in mind, we have chosen an easy itinerary stretching for 95 km. While it does include slopes, particularly in the area known as Colline del Chianti, you will find it is well worth the effort, as the route takes you through a stunning countryside, and inquiring travellers will be rewarded with amazing stories and local hosts eager to help and strike up conversation. There are exquisite culinary experiences awaiting you, too.

Jewels of Tuscany

As soon as you land at Florence’s international airport, head for the city’s historic centre. If you choose a morning flight, before going to pick up your bikes at the hire shop, you can walk around the monumental area of what is the cradle of the Renaissance.

Renaissance Tour

A quick but really spectacular walk starts at the Piazza del Duomo, which looks onto the Cathedral of Santa Maria del Fiore with its huge dome – the work of Brunelleschi – and its beautiful facade faced with Tuscan marble. Next up is the Piazza della Signoria with the stunning Palazzo Vecchio, the Neptune Fountain, a reproduction of Michelangelo’s David and a collection of statues of the Medicis, prominent among them being Perseus with the Head of the Medusa,by Cellini. The last stretch of our stroll involves crossing the emblematic Ponte Vecchio over the river Arno.

Ice-cream, Bicycles and Trains

We recommend you hire your bicycle at Florence by Bike and then head for the Firenze Santa Maria Novella railway station, less than 1 km from the bike shop.

If you fancy a genuinely artisan ice-cream, stop off at I Gelati del Bondi, at Via Nazionale 61R (on the corner of the Via Faenza), as you will pass by it on your way to the station. They sell ice-creams made by the master, Vetulio Bondi. Consider that people travel to Florence for a few hours solely to attend private classes by this artigiano gelatiere.The train ride to Siena takes 90 minutes (timetable at http://www.trenitalia.com). Only the regionali trains allow bikes on board – there’s an area set aside for them at a charge of 3.5 euros per bike.

Once in Siena, your best bet is to head straight for the hotel, park your bike and go out to enjoy the afternoon and evening in a city which is lively and picturesque throughout. Your way to the Piazza del Campo – where they hold the spectacular, hair-raising Palio di Siena horse race – is lined with many charming restaurants. When choosing a menu, remember that you’re going to be pedalling the next day.

The Essence of Chianti

You cycle out of Siena along the SR222 secondary road, also known as the Via Chiantigiana, which starts at Siena’s central train station and crosses the whole region as far as Florence. After an initial climb, you take an early detour along a more solitary road, the SP102. It leads to Corsignano, Vagliagli and Radda in Chianti, the tarred stretches interspersed with sections of typical Tuscan strada bianca, a dazzling, bright, white compacted-earth surface.

Here, you cycle between hills carpeted with vineyards and olive groves, flanked by rows of cypress trees and past various wineries, notably Terra di Seta (1 km before Vagliagli) and Capannelle (on the outskirts of Gaiole in Chianti), where you can join guided tours and tastings of local wines and virgin olive oils.

The village of Radda in Chianti is a good spot for taking a breather and refuelling. From here, you could go for an optional, 17-km detour loop to visit Castello Vertine and Gaiole in Chianti. This small, tranquil village is a centre of pilgrimage for devotees of vintage cycling. The vintage bike festival known as L’Eroica is held every first Sunday in October here, an event which draws over 7,000 cyclists on vintage bikes. If you want to shorten the ride slightly and save yourself the odd climb, from Radda in Chianti head straight for Panzano. There, connoisseurs of quality meat should stop and sit down to a meal at the Officina de la Bistecca – the former Antica Macelleria Cecchini– where you will meet Dario Cecchini, a craft butcher who imbues his creations with passion and know-how. There are several menus – including a vegetarian one – for both lunch and dinner, but the undisputed star dish is Bistecca a la Fiorentina, still cooked and served on the bone. This experience is key to understanding Dario’s pure, contagious love of his trade, meat and land – he descends from eight generations of butchers. He is so enthralled by his craft that he offers guests the chance to be “a butcher for the day”.

Florence In Style

From Panzano, the road leads down to Greve in Chianti, and then continues on to Chiocchio and Strada in Chianti. Here, you leave the SR222 and head for Ferrone and Impruneta along local roads with the aim of entering Florence via its most spectacular, panoramic access – San Miniato Hill.

From Impruneta, the SP70 takes you to Cascine del Riccio where you have to climb a very steep, narrow street up to San Michele a Monteripaldi. Once on the top, you cycle past some stately villas in the direction of Piazzale Michelangelo, at which point the town lies at your feet. This undoubtedly provides the perfect end-of-route picture.

For the finishing touch to your cycling “escapade”, we recommend booking ahead to dine at Essenziale, chef Simone Cipriani’s new restaurant, which wows guests with a minimalist yet friendly and carefree ambience. Here, the traditional Tuscan recipes della nonna have been reworked and reappraised in subtle, delicate and amusing terms. The Conoscersi tasting menu (3 dishes for 35 euros) and La persistenza de la memoria (5 dishes for 55 euros) are a feast of flavours and sensations, as well as a journey into the culinary essence and history of the region. At Essenziale, you will also be taken aback by the lack of any barriers between the kitchen and dining area, while the chef personally serves and describes his creations and reveals his secrets.

Practical Guide

- Route Navigation: you can check out the 95 km itinerary we have just described at this Google Maps link. To plan other routes, the best paper map is Firenze, Siena, Chianti by Kompass.

- Duration: everyone can split up the route at will, depending on accommodations and the number of days available. To enjoy everything the region has to offer, you should ideally devote 3 or 4 days to the trip.

- Choosing Bikes: if you fly with Vueling, you can take your own bike on the plane, but, as the bike tour is only a two-day ride, it may be more convenient to hire one at your destination. At Florence by Bike they renew their fleet every year and have all kinds of bicycles. Touring bikes are the most suitable for the route we have laid out. If you’re worried about slopes, they also have electric bicycles (90 euros for 2 days), which will allow you to negotiate climbs effortlessly.

- Accommodation: available accommodation in Siena and Florence is in overwhelming supply, but be sure to book in advance to secure rooms in the historic centre. En route, your best bet is to look for small B&Bs or go for agritourism.

Text by Sergio Fernández Tolosa & Amelia Herrero Becker

Images by Con un par de ruedas and Giovanni Rasoti

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