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