Your cycling holiday starts in one of the oldest settlements in Italy, Matera. After arrival you are free to relax or explore. Since paleolithic times man has lived here in dwellings dug into the honey-coloured soft stone of the surrounding hillside. Over centuries more houses were added above and below each other, connected by a maze-like network of stairways and exterior corridors. Looking across the valley, the town looks like a huge human rabbit warren. It’s extremely picturesque and is protected as a world heritage site but not so long ago its inhabitants were amongst the poorest in Italy, living without running water or electricity. You’ll spend the night in this atmospheric town before starting your cycling adventure in the morning.

Leave Matera and set off on your bike across a rural plain. The land is quite arid here, Basilicata is one of the driest regions in Italy and seas of wheatfields are punctuated with just a few olive groves. After a while you pass from Basilicata, the instep of Italy, into Puglia, the heel, and immediately the landscape becomes greener. Your route is lined with lush meadows and ancient olive groves contained by picturesque dry stone walls. Eventually you arrive in Alberobello, a pretty town famous for the preponderance of ‘Trulli’ houses within its confines. These charming, circular stone dwellings were designed to keep the occupants cool during the long hot summers.

Today’s ride leads you through the Valle d’Itria dotted with small hamlets and pretty vineyards. We recommend stopping to taste the wine produced in this region, as it really is very good. Take a break in the pretty, hilltop town of Locorotondo before pressing on eastwards. In the early afternoon you arrive in Ostuni, the ‘white town’, so named because of its whitewashed buildings standing out against the sky. From the top of the town you can enjoy superb views out over the Adriatic coastline 6 kms away to the east. The narrow streets of this quaint little place are a pleasure to explore on foot.

The day starts with a train journey of about 70km, with your bike, to the town of Lecce. You’ll spend more time here in three days time but for now you mount up and ride south along quiet, winding lanes lined with gnarled old olive groves and ancient stone walls. This peaceful and enjoyable ride ends at the fortified port town of Gallipoli. The town occupies a strategic position and has a long history of repelling attackers as well as being overrun. A visit to the impressive fortress will provide you with more details on its violent past. The narrow, winding streets of the old town have a Moorish feel to them and are a delight to explore in the evening.

Continue south along the Ionian coastline, the route passes numerous idyllic beaches so it’s a good idea to have your swim stuff packed in your pannier today. After this lovely coastal ride you arrive in the small town of Santa Maria di Leuca. The town marks the point where the Ionian and Adriatic seas meet and has that lovely end-of-the-earth, remoteness about it. This is probably why it has attracted quite an eccentric population many of whom live in the numerous, quirky but luxurious villas that abound here. Spend the night in this pleasant little town.

Bid the Ionian Sea farewell and say hello to the Adriatic as you head northwards along its rocky coastline. Today is all about superb sea-views, pretty coastal villages and quaint ports. The swim spots are not as frequent as on yesterday’s ride but they do exist so be sure to pack the swim stuff again. You could also stop off at the Zinzulusa Cave, a stunning Grotto with clear turquoise waters and/or the spa town of Santa Cesarea, known for its sulphurous mineral springs and mud therapy treatments. Otranto itself is an enchanting old town and the waterfront promenade is the perfect place to enjoy a delicious meal after the day’s activities.

Your last day of cycling takes you further along the coast to Torre dell’Orso – a great place for a swim by the way – and then inland to the Baroque city of Lecce. The city has been dubbed the Florence of the South and makes a lovely finale to the cycling holiday. Narrow little streets suddenly open up to reveal baroque treasures seething with detail, like the incredible Basilica di Santa Croce. Historically, Lecce was always the powerhouse of Puglia and this is evident in its opulent and ornate architecture. Perhaps celebrate your achievement with a nice meal in one of the town’s many restaurants.

After breakfast it is time to head for home or your next adventure.