Settle in at your accommodation then step outside and breathe in the incredibly fresh, crisp Mediterranean air. Wander Otranto’s dreamy town centre in the evening light, then select a spot for dinner. An introduction to the delights of Puglia, a moment to fill all five senses and a chance to prepare for the phenomenal walking adventure ahead.

Start out with an ideal warm-up hike into Idro Valley, which gives Otranto (‘Hidruntum’) its evocative name. The source of the Idro River lies hidden just 5km from Otranto, at a place called Monte S. Angelo. Walk into earthy aromas on fertile land filled with orchards, olive trees, orange groves and vegetable patches. Begin by hiking the left bank upstream, cut past gnarly olive trees and stop for a quick pic at the sturdy stone chapel of S. Angelo. The walk the right bank back into Otranto, affectionately known for its beauty as Italy’s ‘Pearl of the Orient’.

Challenge: 2 hours, 7.5 km, 95 m ascent, 95 m descent

Negotiate an intriguing maze of lanes as you trek through the old town toward the new port. Then pick up a flat, gravel coast path passing idyllic coves and ominous reminders at WWII bunkers. Opt for a short detour inland to a colourful ‘bauxite lake’ then hurry on to choose your favourite of many enticing beach stops bathed by crystal-clear waters. Heading for the unmistakeable lighthouse at Punta Palascia, you squeeze confidently through knee-high Mediterranean bushes knowing you are on the right track! Clear days afford views to the Albanian mountains as you gaze out over the Adriatic Sea from the easternmost point of Italy just 71 km away from the coast of Albania.

Challenge: 5 hours, 12.5 km, 270 m ascent, 240 m descent

The first stop on today's walk coincides with the beautiful inlet at Porto Badisco, just opposite the local bar/newsagent/supermarket where they make great coffee and sandwiches to go. Stepping out along a shepherds’ trail, you hug the coast and pass typical stone ‘pagliari’, round, flat-topped shepherds’ huts. Six kilometres into the walk, your route moves inland and climbs up toward a plateau where you traipse through high fields on footpaths. Plan to pause for a picnic at a pretty pine grove for some welcome shade on sunny days. A surfaced road leads downhill, as you hike the last section into the exotic spa town of Santa Cesarea Terme with yet a few more fab swimming spots.

Challenge: 4 hours, 13 km, 200 m ascent, 170 m descent

Hiking up a surfaced road out of Santa Cesarea, you connect to an ancient grassy gravel track lined with dry-stone walls. Narrow paths keep inland, traversing fields to reach the ancient Messapian settlement of Castro with its imposing high walls. Spend time inspecting the old town and perhaps pause for lunch, then stroll down to the port for a paddle. Trundling along the coast on an uneven, rocky trail, you come upon stunning Acquaviva Cove, a hidden inlet and fantastic swimming spot, where a fresh water spring bursts out of the rock at sea level. Refreshed and renewed by rejuvenating seawater, you charge off in ascent through a densely forested valley up to Marittima.

Challenge: 4.5 hours, 11.5 km, 310 m ascent, 245 m descent

Purchase a scrumptious sandwich before you take off on a surfaced road winding among immense olive orchards. Pick up the first of many traditional ‘tratturi’, part of an ancient network of paths used by locals to hike down to the sea or connect to nearby villages and orchards. Every stone seems to have a story and the landscape tells centuries-old tales of tough peasant life. With huge sea views as a backdrop, you walk down to Tricase Porto and stop for a perfect ‘caffè in ghiaccio’ (iced coffee) … and perhaps a swim? The last bit on tarmac ends at Marina Serra, a tiny coastal hamlet with its own ideal swimming spots.

Challenge: 4.5 hours, 13.5 km, 310 m ascent, 370 m descent

On your last day of walking, you start off on a short uphill trail with a slightly scary name, the ‘enemy's path’: Sentiero del Nemico, where centuries ago unexpected visitors could lie in ambush. A brief stretch on the paved coast road takes you inland again, back to the ancient ‘tratturi’ to reach the rocky cove at Novaglie, another splendid beach stop. Heart-stopping views on ‘Cipolliane path’ lead to framed fantasy vistas from the cave, cliffs and bridge. Last chance for a swim at tiny Ciolo Cove! Then you hike up Ciolo Valley you get the train in Gagliano del Capo and travel back to Lecce for one last night in this beautiful Baroque town.

Challenge: 5 hours, 12.5 km, 530 m ascent, 380 m descent

Your self-guided walking holiday comes to an end this morning after breakfast. Departure from Lecce is by public transport or a pre-arranged private transfer.