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 £755.00 per person


Choose your departure date:


Come and join Love Velo at the stunning 5* Castello del Nero Hotel and Spa in the heart of Tuscany. With this luxurious retreat as your home during your holiday you are ideally located to explore the surrounding Tuscan countryside with our customised GPX routes. The routes allow you to capture the true essence of Tuscany as you explore endless olive groves and vineyards and visit the mesmerising towns of the stunning Chianti countryside.

DAY 1Arrival

Arrive into Pisa or Florence airport and Love Velo will pick you up and take you to the hotel. Spend the afternoon exploring the luxurious hotel, spa and its grounds. 

DAY 2Explore San Giminano

This is one of our favourite Tuscan routes as you ride 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.

DAY 3Explore Tuscan Culture

Todays ride is a short half day taking in the beautiful Tuscan countryside as you ride a loop out to Certaldo. Stop along the route in one of the quiet villages to enjoy a coffee and relax in your surroundings taking in the true Tuscan way of life. To blend in, remember cappuccino is a morning drink in Italy and not to be drunk after lunch!

We recommend heading back the hotel after lunch to enjoy an afternoon wine tasting in the grounds or relax and indulge in the luxurious ESPA at Castello Del Nero.

DAY 4Exploring the South of Chianti

This beautiful ride takes you to Castellina in Chianti on some spectacular roads that lead to this hidden Chianti landmark. Castellina's history goes back to the Bronze Age and like Gaiole, its 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.

There is an option to continue to Radda in Chianti, a beautiful medieval town, perched on a hill with stunning views. This only adds 15km and is well worth it if you have the legs.

DAY 5Departure

Today you will be transferred back to the airport for your return flight home.

Castello del Nero cycling holiday route map


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 at the luxurious 5* Castello del Nero Hotel and Spa. Situated in the heart of the Chianti wine region, this converted 12th century castle is a sumptuous sanctuary set in its own 300 hectare estate of rolling hills, verdant vineyards and lush olive groves. Featuring Tuscany's first destination ESPA the hotel is an enchanting luxury haven in which to relax and revitalise the body and mind. 

From the moment you arrive you will find this wonderful retreat captures the true essence of the Tuscan experience whilst offering the most luxurious accommodation and highest levels of quality and service. 
You will be met and collected at Pisa or Florence airport before being whisked away to the hotel. 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.  
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.  
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.