Cycling the Heel of Italy - Matera to Lecce

Starting in Matera, the city of 'Sassi' and a UNESCO world heritage site, and through the local canyons, the 'gravine', you will enter Puglia, a unique landscape sandwiched between the Adriatic and Ionian seas.

Cycling the Heel of Italy - Matera to Lecce

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Trip Fee

$ 3.690

Single Room Difference

$ 459

Date

26 October - 06 November 2026

Trip Information

We explore the very best of this captivating region from Murgia to Salento. Your daily cycle routes allow you to explore a series of architectural and natural wonders, sites of immense historical and cultural interest, and of course, to be tempted by local culinary specialties! Cycle through the Murghe plateau, the Salento plain and along the coast through a landscape of ancient olive groves and vineyards and past traditional masserie, coastal watchtowers and splendid Baroque towns . This holiday is offered with a choice of mainly 3 Star, or mainly 4 Star accommodation. The 3 Star accommodation is listed on the hotels page. Stays are in the UNESCO listed towns of Matera and Alberobello; Putignano, known for its ancient carnival; white-washed Ostuni; Galipolli, where the historic centre is on an island; Santa Maria de Leuca, where the Ionian and Adriatic seas meet; Otranto, known as the gateway to the Orient and Lecce, known as the 'Florence of the South'. Stay also in Castellaneta and Avetrana where evening meals are included.

Activity Areas

Cycling
E-Bike
Self-Guided Cycling

Region & Country & City

Europe: Italy, Matera, Puglia

Included in the Price

11 nights in a mix of HHH, 3 and 4-star hotels
- All breakfasts and 2 evening meals
- Management by your local Headwater-appointed agent, plus the Headwater navigation app
- High-quality bikes
- Luggage transfers between hotels

Not Included In The Price

Request a single room or e-bike if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, you may also need to pay a solo traveller supplement (where only one person is travelling on a departure date)

Itinerary

Day 1 Arrive in Matera

Make your way to Matera, one of the oldest inhabited human settlements in the world.

Day 2 Free day in Matera

Explore the UNESCO-listed Sassi of Matera; a complex of houses built into the natural caves of the Murgia.

Day 3 Matera to Castellaneta

Your first cycling day takes you through a landscape of wheat fields and wide panoramas. Visit the town of Laterza, famous for its tasty bakery products and majolica pottery. Continue to Castellaneta, a small city perched on the edge of a ravine.

Day 4 Castellaneta to Putignano

Today you will cycle in the Terra delle Gravine Natural Park, amongst deep canyons, carved by rivers over millions of years. Leaving the ravines you will soon discover the iconic Puglia scenery: dry stone walls, old masserie (fortified stansteads) and trulli, rural houses with a conic roof typical to the area, built without any cement or mortar. Reach Putignano, known for its ancient carnival.

Day 5 Putignano to Alberobello

Leaving the medieval centre of Putignano, cycle in the lush countryside to reach Castellana Caves. It is the main karst site in the South of Italy and a visit is recommended.After the caves, continue along the rolling lanes of the countryside where olive, almond, apricot and cherry trees grow. Continue to the UNESCO heritage site of Alberobello, the world capital of Trulli.

Day 6 Alberobello to Ostuni

Cycle through the lush Valle d'Itria, passing more white-tipped trulli houses on the way. Boasting beautiful coastal views, the route takes you through the famous wine town of Locorotondo, regarded as one of Italy's most stunning villages. After sampling some of the local sparkling white wine, continue to the white city of Ostuni - so called for the dazzling effect of its whitewashed houses.

Day 7 Ostuni to Avetrana

Cycle through the colourful Salentinian countryside, characterized by olive groves and red soil towards the medieval towns of Oria and Manduria with their authentic historic centres.

Day 8 Avetrana to Gallipoli

Head to Torre Colimena on the Ionian Sea, then follow the coast alongside a series of beaches and the old coastal towers of Salento. Reach Gallipoli, known as the 'Ionian Pearl' with its Old Town situated on a rocky island. Take time to wander the narrow lanes of the historic centre to discover its baroque cathedral, elegant palazzi and enticing restaurants.

Day 9 Gallipoli to Santa Maria di Leuca

Cycle towards the most southerly point of Salento at Santa Maria di Leuca, where the crystal waters of the Ionian and Adriatic Sea meet. This village is home to one of the most important lighthouses in Italy, as well as numerous villas built at the turn of the century.

Day 10 Santa Maria di Leuca to Otranto

Pedal along the south coast of the Adriatic Sea, stopping off at the famous Grotta Zinzulusa and the thermal baths of Santa Cesarea Terme. Your final destination is Otranto, the most eastern point of Italy with a stunning cathedral and Aragonese castle.

Day 11 Otranto to Lecce

Follow the shoreline through olive groves to the Baroque metropolis of Lecce. Known as the 'Florence of the South', Lecce is home to over 30 churches, an amphitheatre and a Roman theatre dating back to Emperor Augustus.

Day 12 Leave Lecce

Make your own way back to the airport for your flight home.

Travel Dates

26 October - 06 November 2026 $ 3.690

29 October - 09 November 2026 $ 3.690

31 October - 11 November 2026 $ 3.690

02 - 13 November 2026 $ 2.745

05 - 16 November 2026 $ 2.745

07 - 18 November 2026 $ 2.745

09 - 20 November 2026 $ 2.745

12 - 23 November 2026 $ 2.745

14 - 25 November 2026 $ 2.745

06 - 17 March 2027 $ 2.865

08 - 19 March 2027 $ 2.865

11 - 22 March 2027 $ 2.865

13 - 24 March 2027 $ 2.865

15 - 26 March 2027 $ 2.865

18 - 29 March 2027 $ 2.865

20 - 31 March 2027 $ 2.865

22 March - 02 April 2027 $ 2.865

25 March - 05 April 2027 $ 2.865

27 March - 07 April 2027 $ 2.865

29 March - 09 April 2027 $ 2.865

01 - 12 April 2027 $ 3.070

03 - 14 April 2027 $ 3.070

05 - 16 April 2027 $ 3.070

08 - 19 April 2027 $ 3.070

10 - 21 April 2027 $ 3.070

12 - 23 April 2027 $ 3.070

15 - 26 April 2027 $ 3.070

17 - 28 April 2027 $ 3.070

19 - 30 April 2027 $ 3.070

22 April - 03 May 2027 $ 3.070

24 April - 05 May 2027 $ 3.070

26 April - 07 May 2027 $ 3.070

29 April - 10 May 2027 $ 3.070

01 - 12 May 2027 $ 3.675

03 - 14 May 2027 $ 3.675

06 - 17 May 2027 $ 3.675

08 - 19 May 2027 $ 3.675

10 - 21 May 2027 $ 3.675

13 - 24 May 2027 $ 3.675

15 - 26 May 2027 $ 3.675

17 - 28 May 2027 $ 3.675

20 - 31 May 2027 $ 3.675

22 May - 02 June 2027 $ 3.675

24 May - 04 June 2027 $ 3.675

27 May - 07 June 2027 $ 3.675

28 May - 08 June 2027 $ 3.675

29 May - 09 June 2027 $ 3.675

31 May - 11 June 2027 $ 3.675

03 - 14 June 2027 $ 3.675

05 - 16 June 2027 $ 3.675

07 - 18 June 2027 $ 3.675

10 - 21 June 2027 $ 3.675

12 - 23 June 2027 $ 3.675

14 - 25 June 2027 $ 3.675

17 - 28 June 2027 $ 3.675

19 - 30 June 2027 $ 3.675

26 August - 06 September 2027 $ 3.985

28 August - 08 September 2027 $ 3.985

30 August - 10 September 2027 $ 3.985

02 - 13 September 2027 $ 3.750

04 - 15 September 2027 $ 3.750

06 - 17 September 2027 $ 3.750

09 - 20 September 2027 $ 3.750

11 - 22 September 2027 $ 3.750

13 - 24 September 2027 $ 3.750

16 - 27 September 2027 $ 3.750

18 - 29 September 2027 $ 3.750

20 September - 01 October 2027 $ 3.750

23 September - 04 October 2027 $ 3.750

25 September - 06 October 2027 $ 3.750

27 September - 08 October 2027 $ 3.750

30 September - 11 October 2027 $ 3.750

02 - 13 October 2027 $ 3.750

04 - 15 October 2027 $ 3.750

07 - 18 October 2027 $ 3.750

09 - 20 October 2027 $ 3.750

11 - 22 October 2027 $ 3.750

14 - 25 October 2027 $ 3.750

16 - 27 October 2027 $ 3.750

18 - 29 October 2027 $ 3.750

21 October - 01 November 2027 $ 3.750

23 October - 03 November 2027 $ 3.750

25 October - 05 November 2027 $ 3.750

28 October - 08 November 2027 $ 3.750

30 October - 10 November 2027 $ 3.750

01 - 12 November 2027 $ 2.865

04 - 15 November 2027 $ 2.865

06 - 17 November 2027 $ 2.865

08 - 19 November 2027 $ 2.865

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