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Trip Highlights
  • Typical Chianti countryside of olive groves and cypress trees
  • Medieval cobbled squares in which to enjoy a morning cappuccino
  • Sprawling Chianti vineyards where you can enjoy famous wines
  • UNESCO World Heritage Sites such as San Giminano and Siena
5 nights from£845.00
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Cycling Through Chianti

We can tailor make this trip for you

What we love About Cycling Through Chianti

We love...The Views
There is nothing quite as dramatic as the views across Chianti. Olive groves and vineyards stretch out in front of you and the hills roll for miles and miles. Cypress trees line quiet roads and you can cycle on the famous Strada Bianchi, the famous Tuscan white roads,
We love...Chianti Wine
This emblematic wine is made across Tuscany, but the historic heart lies in between Florence and Siena, where you will be cycling. Stop in local vineyards to taste wines dating back to Roman times, or visit the major producers to taste prestigious labels and great vintages.
We love...Cobbled Squares and Stunning Architecture
From the cobbled squares of Greve in Chianti and Radda in Chianti to medieval hilltop villages, Tuscany's architecture is something to behold. Visit San Giminano and discover the ancient skyscrapers and ride to the huge piazza in Siena.

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Day by Day

Day 1Arrival

Arrive into Pisa or Florence and we will pick you up from the airport.

Day 2Cycle into Chianti
Total distance50kmTotal climb890m

Today you will ride out into the lush Chianti countryside. Your ride will take you to the beautiful town of Strada in Chianti and as you head further south, you will notice the air changing, the smell of grapes drifting through the breeze and be greeted with miles and miles of vineyards. Stop in Greve in Chianti to discover the local town square, or should we say triangle, and enjoy a coffee. To blend in, remember cappuccino is a morning drink in Italy and not to be drunk after lunch!

From Greve you will head towards Panzano, a medieval town that has been fought over by Siena and Florence for hundreds of years. If you are riding this route on a Sunday, the town has a morning outdoor market selling cheeses, meats, flowers and other Chianti favourites. From Panzano you will ride back to the hotel.

Day 3Explore San Giminano
Total distance58kmTotal climb1000m

Leave your bags for collection in the morning and ride out today on our favourite Tuscan route. The morning will take you up some hills for about 10km before a long downhill through San Benedetto. Then it’s a climb to San Giminano, a sight for any seasoned traveller, and a UNESCO World Heritage Sight. Encircled by its medieval walls and with its hilltop views, 12th century skyscrapers loom over the Piazza della Cisterna. We recommend a plate of Pappardelle, a favourite in Tuscany, in one of the numerous restaurants and cafes in the town.

From there, the route heads back out into the countryside finishing with a bit of climbing up to your hotel for the evening.

Day 4Exploring the South of Chianti
Total distance60kmTotal climb1500m

You can leave your bags at the hotel as you will be returning there at the end of the day. Today’s route is a beautiful loop taking in some climbing and some downhills through this undulating and hilly countryside.

You will pass through Radda in Chianti, a beautiful medieval town, perched on a hill with stunning views. From there, it’s on to Gaiole in Chianti, famous for it’s green gold olive oil. Deep tasting, spicy and peppery olive oil, is a feature of Chianti and you will notice colour and texture changes as you ride through the region.

The route takes you past Castello di Brolio where Baron Bettino Ricasoli invented the Chianti formula in 1872 so feel free to stop and explore the castle. From there, it’s back through the Cypress tree lined roads to the hotel.

Day 5Cycle to Siena
Total distance40kmTotal climb700m

You can leave your bags in the hotel as we will be returning later in the evening. Today’s ride takes us on a loop and into Siena, a UNESCO World Heritage Site. The Piazza del Campo is the highlight with it’s open square featuring the Mangia Tower.

The city will be flying the flags of the local contrade, or city ward and the right to fly the flag is won and lost in an epic biannual horse race known as the Palio di Siena. The horse race has been run since the 14th century and the Piazza del Campo is turned from a square with people milling about, to a horse track featuring bareback riders being thrown from their mounts in ever tightening turns. If you happen to be in Siena on 2 July and 16 August, this is one of the most thrilling Tuscan experiences.

Leave a bit in the legs as the ride back to the hotel is mainly uphill.

Day 6Departure

Enjoy a leisurely breakfast at the hotel and you will be transferred back to the airport for your return flight home.

Key Stats

6day holiday
Or tailor your trip
60km avg
Expect to ride about 60km per day

How's the Weather? in Chianti

The SpringMarch to May
Tuscany generally has a mild climate so Spring is a very pleasant time to ride, especially as you move through April into May. Temperatures are not sweltering and the summer crowds have not descended.
The SummerJune to August
The summer is hot and you're likely to experience good weather with warm temperatures. July & August are exceptionally warm and you are likely to want to ride early and stay out of the midday sun.
The AutumnSeptember to November
September is a great time to visit Tuscany as temperatures drop from the stifling summer heat. Cycling will be hugely enjoyable in the early Autumn. November has the most rainfall so plan your trip to be home before then.
The WinterDecember to February
The winter is best avoided for cycling in Tuscany as you're likely to experience cold weather and rain.

Area InformationFor Chianti

If there is a better cycling experience than riding through Tuscany then we haven’t found it yet. Explore the medieval fortified towns of San Giminano and Montepulciano, sip cappuccino in a Chianti town square and roll through the endless olive groves and vineyards.

Cypress trees will line your routes and under the warm Tuscan sunshine life’s daily stresses just melt away.

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