Arrive in the glorious town of Monopoli overlooking the Adriatic Sea. Get lost in the labyrinth of streets amidst whitewashed houses. Visit the main church, known as Basilica concattedrale Maria Santissima della Madia patrona, and the stunning unique squares. In the afternoon enjoy the sea breeze while sipping a fresh local white wine tasting and the famous “taralli”. Marvel at the Marchesale Arch, an original entrance to the old town

Today’s ride is a gradual climb from the Adriatic sea to the gently undulating valley of Itria. Through the typical Murgia landscape with olive groves and fields surrounded by low stone walls. Stop at Castellana Grotte for a rest and to visit an immense underground cave system, one of the largest in Europe. Continue on to Alberobello, the Trulli capital of the world and a UNESCO Heritega town. Alberobello is unique for having over 1000 trulli, or white washed stone houses with
conical roofs.

Challenge: 46,5 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.