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 £1645.00 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 Ponte Vecchio.

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. Marco Ottaviano Il Gelato on Via Matteo Palmieri is a favourite as they use seasonal fruits and not too much sugar.

Spend some time visiting Michelangelo's David, wonder in the magnificence of the Duomo and watch life go by in this extraordinary city.

Your bike will be delivered today.

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 couple of larger hills stand in your way of some lovely gentle downhill through Certalo. Stop in along the route in quiet Tuscan countryside to enjoy a coffee and relax in your surroundings. To blend in, remember cappuccino is a morning drink in Italy and not to be drunk after lunch!

The rest of your journey to the hotel is uphill but it is worth the effort as you arrive at your hotel. The grounds are stunning, the pool beautiful and the vista is endless.

Today's ride is approximately 60km with about 1200m of climbing.

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 downhill sections for about 20km. Then it's a climb to San Giminano, a sight for any seasoned traveler, 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 back up to the hotel.

Today's cycling is approximately 56km with 9500m of climbing.

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 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 Castellina in Chianti and some spectacular roads leading to this hidden Chianti landmark. Castellina's history goes back to the Bronze Age and like Gaiole, it's  neighbour, it's well known for its deep tasting, spicy and peppery olive oil. You will notice the colour and texture changes in the olive oils you taste as you ride through the region.

Today's cycling is approximately 60km with 1000m of climbing.

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 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, that has been run since the 14th century. Run on 2 July and 16 August, 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 traveling at this time, this is one of the ultimate Tuscan experiences.
Your hotel tonight is the stunning Castello di Casole. This is a hotel quite unlike any other. Offering stunning views over the countryside from the pool and sat within opulent grounds, this is our favourite luxury hotel in Tuscany.

Today's cycling is approximately 70km with a 1200m climbing.

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.

Map of cycling route in Tuscany from Florence


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.