Cycling Puglia & Matera

The town of Matera is a real jewel of southern Italy, and our hotel is just a short walk from the historic centre. There is usually time in the afternoon to wander through the narrow alleys of the town's Unesco-listed cave-dwelling district and enjoy the unique atmosphere of this enchanting city. For millennia, inhabitants of this region have carved dwellings directly into ravines and gullies made of tuff (or tufa), a characteristic honey-coloured soft stone.

These houses are called Sassi and are a Unesco World Heritage site. Matera is the only place in the world where people still live in the same houses as their ancestors did 9,000 years ago. We'll also enjoy a welcome briefing today – the perfect chance to meet the group and your expert tour leader. Stay: Hotel Belvedere, Residence Casalnuovo, or Palazzo del Sedile (or similar).

On leaving Matera, we pedal through the area that makes this town so special. Today's ride is mostly hilly with gentle ascents throughout, as we cycle on quiet rural roads among the picturesque Apulian countryside towards Alberobello. We'll pass the lovely towns of Noci and Gioia del Colle plus fairytale trulli houses that have made the historic centre of Alberobello another World Heritage site. Stay: Traditional trulli houses or Colle del Sole (or similar) (B).

Today we cycle through the lush Valle d'Itria, one of the prettiest cultural and natural landscapes in southern Italy, to the hilltop town of Ostuni. The route is rolling throughout but much shorter than yesterday's ride. This allows us to enjoy the views at a more leisurely pace with plenty of opportunities for rest stops. Along the way we pass the wine town of Locorotondo and Cisternino, both known for their historic centres filled with whitewashed houses, narrow streets, churches and elegant piazzas.

In the afternoon we reach Ostuni, known as the White City thanks to the dazzling effect of its white buildings. Stay: Relais Sant'Eligio, Masseria Valente, or Ostuni Palace (or similar) (B).

We continue pedalling through tranquil country lanes to the town of Francavilla Fontana and on to Oria. A popular destination among Apulians, Oria is famous for its 13th-century castle and delightful historic centre of cobbled streets, whitewashed walls and beautiful architecture. We continue through the countryside to a masseria, a typical Apulian converted farmhouse and our accommodation for the night. The masseria is still a working farm and most of the produce grown here, from vegetables to olives and wheat, is used daily for the preparation of local dishes. Before dinner we will have the opportunity to taste some organic olive oil produced by the family that runs the farm and accommodation. Stay: Masseria Bosco (or similar) (B).

From the masseria we cycle towards the Ionian Coast and the beautiful town of Gallipoli, known as the Ionian Pearl with its old town on a rocky island offering fantastic views both to north and south. The town itself has many churches and narrow alleys and was the largest exporter of lamp oil made from olives in the 17th and 18th centuries. There are plenty of opportunities for swimming in the Ionian sea near the popular seaside resort of Porto Cesareo (weather permitting). Stay: Hotel 33 Baroni (or similar) (B).

Leaving the Ionian Sea behind, we head across the peninsula to the Adriatic sea and the ancient Messapian town of Otranto, the easternmost point in Italy. Before dinner there will be time at leisure to explore the medieval town centre. Here the interesting architecture, views, sea-front restaurants and white sandy beaches make it one of the most picturesque towns in Puglia. Stay: Hotel Albània, Vittoria Resort, or Relais Valle dell'Idro (or similar) (B).

Today we follow the shoreline through innumerable olive groves to Lecce, the baroque masterpiece of southern Italy, in the heart of Puglia. Sometimes described as the Florence of the South, the city is an architectural gem, with sumptuous palazzi and churches. Today's ride is relatively short and easy, giving us time to stop for a last swim (seasonal) in Torre dell'Orso, a lovely bay surrounded by limestone cliffs with many ancient caves to discover. In Lecce, there will be free time to explore the historic centre before an optional farewell dinner. Stay: Hotel Eos, Hotel delle Palme, or Hotel President (or similar) (B).

We enjoy our final breakfast of the adventure this morning. But if you'd like an extra day in Lecce to soak up the atmosphere of this elegant baroque city, contact your sales representative to arrange post-tour accommodation (B).