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This trip is Self Guided allowing you to discover the area and explore on your own but we can arrange guiding if you prefer.
This trip is ideal for Cycling Breaks with Friends and Seasoned Cyclists.
British Cycling say: Don’t let the breeze disguise the heat. Check out our advice on cycling in the heat. 
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Tailor-Made Experiences

We can tailor this trip to meet your requirements. If you are looking for a different duration, itinerary or other services please enquire today and get a truly unique experience.

from £745.00 per person

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TRIP HIGHLIGHT WHAT WE LOVE

Come and explore the stunning Chianti countryside. You will cycle through all the main Chianti towns, explore endless olive groves and vineyards, and see incredible medieval cities such  as San Giminano and Siena, UNESCO World Heritage Sites.
DAY 1Arrival

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

DAY 2Cycle into Chianti

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

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 it's 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

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

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.

Map of a cycling holiday in Tuscany
6 DAYS
60 KM/DAY AVERAGE
TUSCANY
WHAT’S THE WEATHER

AREA
INFORMATION

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. 

Weather
INFORMATION

Tuscany can be visited from early March or April all the way through to November. The weather can be cooler in the Spring and Autumn which can make for great cycling conditions. The height of summer is particularly hot but is great for lazy days on the bike soaking up everything Tuscany has to offer.

PACKAGE DETAILS MORE INFORMATION

Your accommodation will be in quiet villas and agriturismos, expertly picked for their tranquility and surroundings. 
You will be met and collected at Pisa or Florence airport before being whisked away to the heart of Chianti. On your final day, you will be taken back to the airport.  
Your trip will be bed and breakfast but we can upgrade you to half board if you prefer. Please just let our cycling experience team know when you enquire.  
The holiday is a self guided holiday allowing you to explore Tuscany at your own pace. We know the area incredibly well and have put together some recommended routes in GPX format (of varying distances) which allows you to download these to most GPS enabled devices, and with certain software, to your smartphone. These will be sent to you once you have booked your holiday with Love Velo and each file will be titled with a short description of the ride and the distance. If you would like to see the profile of each route, we recommend that you download the files before your holiday and open them with a GPS viewer. If you would like guiding instead, please just ask our cycle experience team.  
If you choose not to have a guide, you will want to know that your bike is in great condition and that you won’t have any mechanical problems during your ride. Our bikes are extremely well serviced and maintained but in the very unlikely event there is a mechanical issue with the bike (not including basic maintenance such as slipped chains or punctures), we will provide you with an emergency number for someone to come out and repair or replace your bike.  
You can choose between a flat bar hybrid bike, e-bike, carbon framed road bike or even carbon road bike with DI2 electronic gearing.  
Your bike will come equipped with essential tools for you to repair a puncture, replace an inner tube or fix a slipped chain.  
Your bags will be collected each morning and taken from your accommodation to the next night’s accommodation. We suggest you keep a day bag with you for all your essentials. 
Travel to Pisa or Florence is not included but please ask our cycling experience team if you would like us to book flights for you.   
We consider travel insurance to be essential. Accordingly, it is a condition of making a booking through us that you have suitable insurance cover for the booking you have made and any activities which you expect to take part in. This insurance as a minimum should cover cancellation, baggage loss, accidents and health issues while you are away. We also recommend that you take your policy details with you when you travel. Please ask our cycling experience team if you would like us to arrange travel insurance for you.