Cycling Puglia & Matera

Discover the heel of Italy by bike, taking a country-and-coast route from the cave town of Matera to baroque Lecce 

Cycling Puglia & Matera

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Trip Fee

$ 2.625

Single Room Difference

$ 540

Date

31 August - 07 September 2025

Trip Information

Cycle the captivating region of Puglia, riding through olive groves and along the winding coast to stay in some of the most spectacular cities and towns in Italy. The adventure begins in the cave town of Matera, officially in the Basilicata region and beloved by film directors for its ancient beauty, before progressing to the fairytale trulli houses of Alberobello, the White City of Ostuni, and seaside Gallipoli. It ends in Lecce, known as the Florence of the South for its extraordinary collection of baroque landmarks.  

Activity Areas

Cycling
Cycling Bestsellers
E-Bike
Road Cycling

Region & Country & City

Europe: Italy, Matera, Puglia

Included in the Price

— All breakfasts — All accommodation — All transport and listed activities — Tour leader throughout — Group arrival and departure transfers available — Local bike hire

Not Included In The Price

— Travel insurance — Single accommodation (available on request) — Visas or vaccinations — Local city taxes (approx. €10) — E-bike hire (available for an additional cost)

Accommodation Information

— Accommodation: 7 Classic nights (6 hotel, 1 agriturismo/farmhouse) — Six days cycling with partial vehicle support (limited seats) — Group normally 6 to 16, plus leader. Minimum age: 16

Map

Itinerary

Day 1 Start 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. Accommodation: Hotel Belvedere, Residence Casalnuovo, or Palazzo del Sedile (or similar)

Day 2 Ride past the historic Sassi houses of Matera before heading to Alberobello

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. Accommodation: Traditional trulli houses or Colle del Sole (or similar)

Day 3 Cycle through the lush Valle d'Itria, past the fairytale trulli houses to the hilltop town of Ostuni

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. Accommodation: Relais Sant’Eligio, Masseria Valente, or Ostuni Palace (or similar)

Day 4 Ride through quaint villages and country lanes to a typical masseria (renovated farmhouse) where we spend the night

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. Accommodation: Masseria Bosco (or similar)

Day 5 Cycle to the coast and swim in the crystal-clear sea before continuing towards Gallipoli with its old town on a rocky island

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). Accommodation: Hotel 33 Baroni (or similar)

Day 6 Head towards the Adriatic Sea and the ancient town of Otranto

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. Accommodation: Hotel Albània, Vittoria Resort, or Relais Valle dell’Idro (or similar)

Day 7 Continue along the shoreline to the beautiful baroque city of Lecce

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. Accommodation: Hotel Eos, Hotel delle Palme, or Hotel President (or similar)

Day 8 End Lecce

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.

Travel Dates

31 August - 07 September 2025 $ 2.625

07 - 14 September 2025 $ 2.700

14 - 21 September 2025 $ 2.925

21 - 28 September 2025 $ 3.075

28 September - 05 October 2025 $ 2.850

05 - 12 October 2025 $ 2.925

12 - 19 October 2025 $ 3.075

05 - 12 April 2026 $ 3.000

12 - 19 April 2026 $ 3.000

26 April - 03 May 2026 $ 3.000

03 - 10 May 2026 $ 3.000

10 - 17 May 2026 $ 3.000

17 - 24 May 2026 $ 3.000

24 - 31 May 2026 $ 3.000

31 May - 07 June 2026 $ 3.000

07 - 14 June 2026 $ 3.000

14 - 21 June 2026 $ 3.150

21 - 28 June 2026 $ 3.000

30 August - 06 September 2026 $ 3.000

06 - 13 September 2026 $ 3.000

13 - 20 September 2026 $ 3.000

20 - 27 September 2026 $ 3.000

27 September - 04 October 2026 $ 3.000

04 - 11 October 2026 $ 3.000

11 - 18 October 2026 $ 3.000

18 - 25 October 2026 $ 3.000

25 October - 01 November 2026 $ 3.000

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