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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. 

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 £1245.00 per person


Choose your departure date:


There is no better way to explore the beautiful region of Puglia than by bicycle. Our trips allow you to discover this unique unspoilt area known as the heel of Italy's 'boot' at your own pace. From historic wine towns and whitewashed hill villages to UNESCO world heritage sites and white sandy beaches, you will fall in love with the laid back lifestyle, delectable cuisine and wonderful wines.
DAY 1Arrival into Bari

Arrive into Bari airport and we will provide you with a private transfer to the beautiful UNESCO World Heritage Site of Matera. Check in, unwind and relax.

DAY 2Cycling to Alberobello

Today you will ride from Matera to Alberobello. The town of Alberobello is famous for its traditional 'trulli', small conical shaped stone buildings dating back hundreds of years. Originally trulli were constructed without the use of cement meaning they were exempt from tax as they were deemed temporary structures. The oldest trulli you will see were constructed in the 14th century so they have lasted quite well considering they were temporary!

Today's ride is approximately 75 kms. 

DAY 3Cycling to Monopoli

Today's ride sees you cycle from Alberobello to the Adriatic town of Monopoli. Enjoy the Paese Vecchio, the typically whitewashed buildings, as well as Roman alleyways leading to ancient squares where you can sip espresso with the locals.

Today's ride is approximately 50km.

DAY 4Cycling to Ostuni

Today you will ride from one whitewashed old town in Monopoli to another, in Ostuni. The old town of Ostuni, perched over the sea, goes back to Roman times. The cobbled paving from the city square banks sharply as you make your way up to the ancient cathedral and the best gelateria in the town. From there, you can head back out of town right down to the coast or even organise a day on a sailing boat from the small harbour.

Today's ride is approximately 60 kms.

DAY 5Ostuni to Lecce (By bike or train)

Today you can choose to have the day off and get the train from Ostuni to Lecce, or cycle the 85kms to Lecce. Lecce is one of the bigger towns you will visit and you will notice the countryside giving way as you get close to Lecce. Often known as the 'Florence of the South', the Piazza del Duomo is one of the best places to watch the world go by.

Today's ride is approximately 85kms although you can have the day off and use the train if you prefer.

DAY 6Cycling to Otranto

Today you will ride to Ortranto, the closest point Italy has with Albania across the water. The town is quite quiet but the beaches are buzzing with locals enjoying the crystal blue waters of the Adriatic. Take some time to hit the beach in the afternoon or visit the incredible cathedral where the macabre sight of the bones of the martyrs is displayed to commemorate the 1480 Turkish massacre as well as the medieval floor mosaic.

Today's ride is approximately 55kms.

DAY 7Cycling to Leuca

Today you will ride to the bottom tip of Italy and visit Leuca. Your ride will take you to the famous Leuca lighthouse and the Basilica which stands alongside it, built to commemorate St Peter's travels from Leuca.

Today's ride is approximately 60kms.

DAY 8Cycling to Gallipoli

Today you will ride back up to the Ionian coast and visit the old town of Gallipoli. New makes way for old as you cycle through across the bridge to the old town which stands alone in the Ionian sea. This beautiful town dates back, as legend has it, to the ancient Greek empire but centuries of conflict means you can see Roman, Greek, Turkish and even Norman influences.

Today's ride is approximately 50kms.

DAY 9Cycling to Lecce or stay in Gallipoli

Today you have the choice of staying an extra night in Gallipoli to enjoy the old town or if you prefer, you can ride back to Lecce. Please also feel free to shorten or extend you trip by asking our cycling experience team. Remember our trip can be tailored to your requirements.

DAY 10Departure

Today we will take you back to Bari airport for your return flight home.

Map of a cycling holiday from Alberobello to Lecce in Puglia


The heel of Italy's 'boot' is known for its whitewahsed hill towns, centuries-old farmland and hundreds of kilometers of Mediterranean coastline. The terrain is mainly flat and lends itself perfectly to a cycling holiday allowing you to easily explore this beautiful region of the Mediterranean.      


The Southern Italy region of Puglia boasts a wonderful Mediterranean climate. With sunshine all year round and little rainfall this is an excellent cycling destination throughout the year. Even in the warmer summer months you are never more than 30km from the sea which has a moderating effect on the weather.


Your accommodation will be in 4* hotels or tailor make your quote 
You will be met and collected at Brindisi or Bari Airport 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 Puglia 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 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.  
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 hybrid bicycle, perfect for exploring the Tuscan countryside. If you would like a road bike, please ask as we can provide these as well.  
Your bike will come equipped with essential tools for you to repair a puncture, replace an inner tube or fix a slipped chain.  
On days where you change hotel your bags will be collected in the 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 Brindisi or Bari Airport 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.