Touring by bicycle is an ideal way to explore Chianti country. Gregor Brown of Cycling Weekly recommends an itinerary - and the best places to stop off for authentic food and wine

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Cypress trees lining rolling hills, fresh pasta served with ragu di cinghiale (wild boar stew) and deep red wines flowing – what’s not to love about a cycling tour through Tuscany? Italy, and more precisely Tuscany, is like a trip to Mecca for the cycling, food and wine faithful. Nowhere else can you find such a mix of history, food and – what everyone needs on a holiday – a take-it-easy attitude.

A bicycle tour provides the best way to connect the dots because those two wheels changed the country.

They helped locals to build a nation in the Industrial era. Once known only locally Sangiovese wines spread throughout Italy with the help of the bicycle, then on to Europe and eventually the world.

On the bike, you can stop and put your foot down to smell the warm Tyrrhenian breeze blowing over rows of vines or spot a local to ask: ‘Dov’eun buon trattoria qua vicino?’ (‘Where is there a good restaurant nearby?’)

Getting started

Florence, known as the cradle of the Renaissance, offers a good base with its endless museums and monuments to visit Florence by Bike (www. florencebybike.it) rents bicycles for those who need them and if you want a guide, contact Riding with Cosimo (www.ridingwithcosimo.com).

The truly cycle-minded must visit Filofficina (www.facebook.com/ biciepocafirenze) and its Eroica vintage bikes on the south side of town. Stay there for the day, finding a local bar to tuck into Brunello and porchetta cold cuts.

One popular restaurant in this artisan Oltrarno zone is II Santo Bevitore (www.ilsantobevitore.com) where, judging by the ‘holy drinker’ name, wine-lovers are served well.

Book one or two days ahead to ensure you have a spot. If ribollita – a Tuscan vegetable and bread soup – is not your thing then consider any dish with a lampredotto (tripe) sauce, for those who like adventure, or the famous bistecca Fiorentina (a healthy loin steak, served rare to medium-rare).

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From Florence

The rolling hills south of Florence towards Siena flow like a sea of green and golden waves. A challenging hill rewards you with a breathtaking view and descent to another wine valley.

Ride south through lmpruneta. Depending on your abilities, you could either go up through La Panca to Passo de Sugame then down to Greve or through Chiocchio to Greve. In Panzano, you’ll be rewarded with a couple of great restaurants.

If you haven’t indulged in a Fiorentina steak yet, now is your chance at the Officina Della Bistecca (www.dariocecchini.com). To start, share a carpaccio di culo and a bottle of II Molino di Grace Chianti Classico.

Back-track down the road to Lamole and turn up to Vignamaggio (www.vignamaggio.com) to stay for the night or if the steak gave you extra strength, push on to Radda. From Radda, you can decide to make it a two- or three-day tour.

Given the extra day, you can ride a loop around the Radda countryside. Cycle out towards Badia a Coltibuono (www.coltibuono. com), turning first to descend then climb to Castello di Brolio (ricasoli.com). A tour of the castle’s gardens is a must with its wine tasting included.

Around Radda

Ride on to Carlino d’Oro (+39 0577 747 136), a simple and honest Tuscan trattoria with views of the rolling countryside. Pair a plate of tagliatelle and ragu with Brolio wine.

Dessert? The spectacular road down through San Regalo towards Pianella. At the main road, turn right and climb back through Gaiole to reach Radda.

Villa Campomaggio Resort & Spa (www.hotelvillacampomaggio.it) in Radda offers a perfect base for your trip. Its bar serves the best wines from the Val d’Arbia and Val di Pesa to accompany a light dinner.

Travel north on the third day via Castellina and the hilltop town of San Donato in Poggio. Just before San Donato, you can stop at one of the many wineries that offer tastings and have restaurants.

Try Casa Emma (www.casaemma.com), which is surrounded by Sangiovese and Merlot vines. Then continue through to San – Casciano to reach Florence. Once there take a seat outside a bar and reflect on the day.

Perhaps ask the owner for a dinner recommendation; chances are there is an authentic trattoria nearby.

Gregor Brown is based in Florence, writes for Cycling Weekly and covers major cycling races including the Giro d’ltalia and Tour de France