Travel to Puglia where glorious Polignano a Mare gazes out across the Adriatic Sea. Settle in at your hotel, then go out and get lost in the town’s bright-white maze of lanes. Meander past Chiesa Madre church or linger on the piazza at San Benedetto and Dell’Orologio. Snap a photo of the ancient gateway into the old quarter, the striking Marchesale Arch, a grand send-off for tomorrow’s first route.

Venture inland and get to know Puglia on the inside as you cycle to the dream-like caves of Grotte di Castellana. Capture the quiet coolness underground then trek to the magical land of Trulli in Alberobello, where amusing white-washed huts sport pointed roofs and beckon you to stay. Which is perfect since we’ve booked the night for you here! A once-in-a-lifetime chance to live in a fantasy world, if just for a moment.

Challenge: 36 km, 500 m ascent, 100 m descent

Historic Murgia is built upon a karst plateau of olive groves, south-facing vineyards and classic ‘masserie’ farmhouses. Pause to taste a tiny bit of DOC wine in medieval Cisternino, then cycle out to spell-binding Ostuni on the Adriatic Coast. Hidden behind massive walls, the heart of the city guards a Gothic treasure: the 15th-century cathedral of Santa Maria Assunta.

Challenge: 40 km, 300 m ascent, 500 m descent

Roll down to Ostuni Station and catch the train to Lecce, where your cycling route begins. Ride into peaceful countryside on quiet roads through olive groves. Linger in small historic towns like Copertino and Nardò, walk down shady lanes in the old centre or relax with a perfect cappuccino. Cycling to Gallipoli you’ll come upon loads of splendid spots for a refreshing swim in the Ionian Sea.

Challenge: 52 km, 240 m ascent, 330 m descent

Snaking along the coast to the southernmost tip of Puglia, you run out of land at the dramatic divide between the Ionian and Adriatic Seas. Paddle in a paradise of turquoise waters and fine white sand on Torre del Pizzo beach. Recently refreshed, ride onward to magnificent Santa Maria di Leuca with its ideal beaches and wacky, wild, colourful mansions.

Challenge: 51 km, 200 m ascent, 170 m descent

Soak up the salty sea breeze on a high coastal route, winding gently along clifftops with phenomenally distracting views. Ready to make your own National Geographic special cycling feature, you stop to sign some autographs. Wait, back to reality: you stop for a glimpse of Grotta Zinzulusa then glide out to Otranto, a Greek-come-Roman port frequented by merchants and thrill-seekers.

Challenge: 53 km, 520 m ascent, 530 m descent

Parallel the seaside and Alimini Lakes, cruising along between fresh- and saltwater. Get into Greek Salento, where traces of former colonies still influence local language, traditional cuisine and bright architectural styles. You’ll wish you were more of an artist, as you imagine painting these brilliant whites against a cobalt blue sea. Take your time on the way to Lecce then get lost in its palatial passions (with nearly one hundred palaces!), steeped in history and brimming with Roman treasures.

Challenge: 52 km, 120 m ascent, 90 m descent

Your cycling trip comes to an end this morning after breakfast. Add on an optional airport transfer or extend your stay with extra nights in Lecce.