Arrive in Alberobello, a UNESCO World Heritage Site famed for its whitewashed trulli — fairytale-like stone houses with conical roofs. Stroll through its picturesque lanes and get a taste of traditional Apulian life.

Pedal into the rolling countryside of the Murgia region, through vineyards, olive groves, and whitewashed villages. Stop in Locorotondo, with its unique circular layout, and climb to Cisternino, a charming maze of stone houses and narrow streets. Sample local taralli, friselle, or handmade orecchiette along the way. The day ends in Ostuni, the gleaming “White City,” perched high above the sea.

Shorten the ride: Train available from Alberobello to Martina Franca or Locorotondo

Say goodbye to the hills and descend into the flatlands of Salento, where silvery olive trees blanket the red soil. Stop in Oria, a town rich in history with a castle built by Emperor Frederick II. End the ride in Manduria, home of Primitivo wine, where vineyards stretch as far as the eye can see.

Cycle along the Ionian coast, where ancient watchtowers guard stretches of golden sand. Stop in Porto Cesareo for a seafood lunch by the sea. Continue to Gallipoli, a historic fishing town with a charming old quarter on an island. Don’t miss the underground olive oil mills and sunset on the waterfront.

A relaxed coastal ride with fragrant pines, myrtles, and hidden coves. Detour to Punta della Suina or Lido Pizzo for a swim. End at Santa Maria di Leuca, where the Ionian and Adriatic seas meet at Italy’s southernmost point. Watch the sun set from the lighthouse square – an unforgettable moment.

Today’s ride is along one of Italy’s most scenic coastal roads. Pass cliffside villages, hidden grottoes, and the famous Zinzulusa Cave. Pause at Santa Cesarea Terme and Porto Badisco, the mythical landing place of Aeneas. Arrive in Otranto, Italy’s easternmost town, known for its medieval cathedral and Aragonese castle.

Follow the Adriatic coast northward through sandy bays and pine woods. Swim at Sant’Andrea or Torre dell’Orso, then head inland past the wetlands of Le Cesine nature reserve, a birdwatching paradise. Visit Acaya, a rare example of a Renaissance fortified village, before reaching Lecce, the stunning capital of Salento and home to some of Italy’s most ornate Baroque architecture.