Cycling the Heel of Italy - Alberobello to Lecce

In the heart of the Mediterranean lies Puglia, a unique landscape sandwiched between the Adriatic and Ionian seas

Cycling the Heel of Italy - Alberobello to Lecce

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Trip Fee

$ 1.760

Single Room Difference

$ 348

Date

07 - 14 March 2026

Trip Information

We explore the very best of this captivating region from our start point in Alberobello, known for its UNESCO-listed Trulli houses, to the end point in Lecce, known as the 'Florence of the South'. The daily routes take you through the Murghe plateau, the Salento plain or along the coast. Discover a landscape of ancient olive groves, long fields of grain and vineyards.The architecture of the region takes you from the conical Trulli houses in Alberobello, the white city of Ostuni, past traditional masserie, coastal watchtowers and splendid Baroque towns. The region is filled with spectacular views; beautiful coastline and mouth-watering cuisine. This holiday is offered with a choice of mainly 3 Star, or mainly 4 Star accommodation.

Activity Areas

Cycling
E-Bike
Self-Guided Cycling

Region & Country & City

Europe: Italy, Matera, Puglia

Included in the Price


- All breakfasts and 1 evening meal
- Management by your local Headwater-appointed agent
- GPS Route directions and maps
- Headwater navigation app
- High Quality Bikes
- Luggage transfers between hotels

Not Included In The Price


- Travel insurance
- Single accommodation (available on request - compulsory supplement)
- Solo traveller supplement (where only one person is travelling on a departure date)
- Visas or vaccinations
- Arrival & departure transfers
- Hotel Upgrades

Accommodation Information


- 7 nights in 3 star hotels
- 6 days cycling
- E-bike hire available on request (supplement applies)
- Self-guided holiday. Min age 14 yrs

Itinerary

Day 1 Arrive in Alberobello

Make your way to Alberobello, famous for its Trulli houses.

Day 2 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 3 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 4 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 5 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 6 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 7 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 8 Leave Lecce

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

Travel Dates

07 - 14 March 2026 $ 1.760

09 - 16 March 2026 $ 1.760

12 - 19 March 2026 $ 1.760

14 - 21 March 2026 $ 1.760

16 - 23 March 2026 $ 1.760

19 - 26 March 2026 $ 1.760

21 - 28 March 2026 $ 1.760

23 - 30 March 2026 $ 1.760

26 March - 02 April 2026 $ 1.760

28 March - 04 April 2026 $ 1.760

30 March - 06 April 2026 $ 1.760

02 - 09 April 2026 $ 1.925

04 - 11 April 2026 $ 1.925

06 - 13 April 2026 $ 1.925

09 - 16 April 2026 $ 1.925

11 - 18 April 2026 $ 1.925

13 - 20 April 2026 $ 1.925

15 - 22 April 2026 $ 1.965

16 - 23 April 2026 $ 1.925

18 - 25 April 2026 $ 1.925

20 - 27 April 2026 $ 1.925

23 - 30 April 2026 $ 1.925

25 April - 02 May 2026 $ 1.925

27 April - 04 May 2026 $ 1.925

28 April - 05 May 2026 $ 1.965

30 April - 07 May 2026 $ 1.925

02 - 09 May 2026 $ 2.285

04 - 11 May 2026 $ 2.285

07 - 14 May 2026 $ 2.285

08 - 15 May 2026 $ 2.325

09 - 16 May 2026 $ 2.285

11 - 18 May 2026 $ 2.285

12 - 19 May 2026 $ 2.325

14 - 21 May 2026 $ 2.285

16 - 23 May 2026 $ 2.285

17 - 24 May 2026 $ 2.285

18 - 25 May 2026 $ 2.285

21 - 28 May 2026 $ 2.285

23 - 30 May 2026 $ 2.285

25 May - 01 June 2026 $ 2.285

28 May - 04 June 2026 $ 2.285

30 May - 06 June 2026 $ 2.285

01 - 08 June 2026 $ 2.285

04 - 11 June 2026 $ 2.285

06 - 13 June 2026 $ 2.285

08 - 15 June 2026 $ 2.285

11 - 18 June 2026 $ 2.285

13 - 20 June 2026 $ 2.285

15 - 22 June 2026 $ 2.285

18 - 25 June 2026 $ 2.285

20 - 27 June 2026 $ 2.285

24 - 31 August 2026 $ 2.300

27 August - 03 September 2026 $ 2.300

29 August - 05 September 2026 $ 2.300

31 August - 07 September 2026 $ 2.300

03 - 10 September 2026 $ 2.375

05 - 12 September 2026 $ 2.375

07 - 14 September 2026 $ 2.375

10 - 17 September 2026 $ 2.375

12 - 19 September 2026 $ 2.375

14 - 21 September 2026 $ 2.375

17 - 24 September 2026 $ 2.375

19 - 26 September 2026 $ 2.375

21 - 28 September 2026 $ 2.375

24 September - 01 October 2026 $ 2.375

26 September - 03 October 2026 $ 2.375

28 September - 05 October 2026 $ 2.375

01 - 08 October 2026 $ 2.375

03 - 10 October 2026 $ 2.375

05 - 12 October 2026 $ 2.375

08 - 15 October 2026 $ 2.375

10 - 17 October 2026 $ 2.375

12 - 19 October 2026 $ 2.375

15 - 22 October 2026 $ 2.375

17 - 24 October 2026 $ 2.375

19 - 26 October 2026 $ 2.375

22 - 29 October 2026 $ 2.375

24 - 31 October 2026 $ 2.375

26 October - 02 November 2026 $ 2.375

29 October - 05 November 2026 $ 2.375

31 October - 07 November 2026 $ 2.375

02 - 09 November 2026 $ 1.760

05 - 12 November 2026 $ 1.760

07 - 14 November 2026 $ 1.760

09 - 16 November 2026 $ 1.760

12 - 19 November 2026 $ 1.760

14 - 21 November 2026 $ 1.760

06 - 13 March 2027 $ 1.850

08 - 15 March 2027 $ 1.850

11 - 18 March 2027 $ 1.850

13 - 20 March 2027 $ 1.850

15 - 22 March 2027 $ 1.850

18 - 25 March 2027 $ 1.850

20 - 27 March 2027 $ 1.850

22 - 29 March 2027 $ 1.850

25 March - 01 April 2027 $ 1.850

27 March - 03 April 2027 $ 1.850

29 March - 05 April 2027 $ 1.850

01 - 08 April 2027 $ 2.030

03 - 10 April 2027 $ 2.030

05 - 12 April 2027 $ 2.030

08 - 15 April 2027 $ 2.030

10 - 17 April 2027 $ 2.030

12 - 19 April 2027 $ 2.030

15 - 22 April 2027 $ 2.030

17 - 24 April 2027 $ 2.030

19 - 26 April 2027 $ 2.030

22 - 29 April 2027 $ 2.030

24 April - 01 May 2027 $ 2.030

26 April - 03 May 2027 $ 2.030

29 April - 06 May 2027 $ 2.030

01 - 08 May 2027 $ 2.405

03 - 10 May 2027 $ 2.405

06 - 13 May 2027 $ 2.405

08 - 15 May 2027 $ 2.405

10 - 17 May 2027 $ 2.405

13 - 20 May 2027 $ 2.405

15 - 22 May 2027 $ 2.405

17 - 24 May 2027 $ 2.405

20 - 27 May 2027 $ 2.405

22 - 29 May 2027 $ 2.405

24 - 31 May 2027 $ 2.405

27 May - 03 June 2027 $ 2.405

29 May - 05 June 2027 $ 2.405

31 May - 07 June 2027 $ 2.405

03 - 10 June 2027 $ 2.405

05 - 12 June 2027 $ 2.405

07 - 14 June 2027 $ 2.405

10 - 17 June 2027 $ 2.405

12 - 19 June 2027 $ 2.405

14 - 21 June 2027 $ 2.405

17 - 24 June 2027 $ 2.405

19 - 26 June 2027 $ 2.405

26 August - 02 September 2027 $ 2.435

28 August - 04 September 2027 $ 2.435

30 August - 06 September 2027 $ 2.435

02 - 09 September 2027 $ 2.510

04 - 11 September 2027 $ 2.510

06 - 13 September 2027 $ 2.510

09 - 16 September 2027 $ 2.510

11 - 18 September 2027 $ 2.510

13 - 20 September 2027 $ 2.510

16 - 23 September 2027 $ 2.510

18 - 25 September 2027 $ 2.510

20 - 27 September 2027 $ 2.510

23 - 30 September 2027 $ 2.510

25 September - 02 October 2027 $ 2.510

27 September - 04 October 2027 $ 2.510

30 September - 07 October 2027 $ 2.510

02 - 09 October 2027 $ 2.510

04 - 11 October 2027 $ 2.510

07 - 14 October 2027 $ 2.510

09 - 16 October 2027 $ 2.510

11 - 18 October 2027 $ 2.510

14 - 21 October 2027 $ 2.510

16 - 23 October 2027 $ 2.510

18 - 25 October 2027 $ 2.510

21 - 28 October 2027 $ 2.510

23 - 30 October 2027 $ 2.510

25 October - 01 November 2027 $ 2.510

28 October - 04 November 2027 $ 2.510

30 October - 06 November 2027 $ 2.510

01 - 08 November 2027 $ 1.850

04 - 11 November 2027 $ 1.850

06 - 13 November 2027 $ 1.850

08 - 15 November 2027 $ 1.850

11 - 18 November 2027 $ 1.850

13 - 20 November 2027 $ 1.850

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