0207 157 1519
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: Take plenty of sun cream and don’t let the breeze disguise the heat! – Check out our advice on cycling in the heat. 

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 £1649.00 per person


Choose your departure date:


Come and explore the stunning Chianti countryside. You will visit 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 airport and Love Velo will pick you up and take you to your hotel in Florence. Spend the afternoon exploring the capital of Tuscany and take an evening stroll on the ...Show More

DAY 2Explore Florence

Today is a chance to immerse yourself in Florence before you start your ride into the heart of Tuscany. In our opinion, the most important thing to do is find gelato and we know just the place. M...Show More

DAY 3Cycle into Chianti

Leave your bags at hotel for collection and it's time to ride out of Florence and into the lush Chianti countryside. You will gently climb out of Florence towards San Casciano before another coup...Show More

DAY 4Explore San Giminano

There's no need to pack your bags today as you will be returning to the same hotel this evening. Today is one of our favourite Tuscan routes. The morning will see you spend most of your time on d...Show More

DAY 5Exploring 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 60km loop taking in some climbing and some downhills through this undulatin...Show More

DAY 6Cycle to Siena

Pack up your bags today and they will be collected from the hotel. Today's ride takes us down through the countryside and into Siena, a UNESCO World Heritage Site. The Piazza del Campo is the hig...Show More

DAY 7Rest Day

Today is a day to rest your legs after a few days on the bike. You are in one of the finest hotels that Tuscany can offer so relax and unwind.

DAY 8Departure

Today 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.


Your accommodation will be in the best hotels in Tuscany. From a cool boutique art hotel in Florence to a luxury Tuscan retreat set within sprawling Chianti vineyards, we have put together the ultimate luxury cycling trip in Tuscany  
You will be met and collected at Pisa or Florence airport before being whisked away to the hotel in Florence. On you 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 very well and have put together some recommended routes in GPX format 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 title 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.
The bike we will provide you with is a fabulous Pinarello hybrid bicycle, perfect for exploring the Tuscan countryside. If you want to upgrade to a road bike, we can offer you a fabulous Pinarello bike………  
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.