Self-Guided Cycling the Heel of Italy - Alberobello to Lecce

Self-Guided Cycling the Heel of Italy - Alberobello to Lecce

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Trip Fee

$ 2.450

Single Room Difference

$ 360

Date

08 - 15 October 2026

Trip Information

Activity Areas

Cycling
E-Bike
Self-Guided Cycling

Region & Country & City

Europe: Italy, Matera, Puglia

Included in the Price

7 nights in 3-star equivalent, 3-star and 4-star accommodation
- All breakfasts and 1 evening meal
- Bike hire included, plus bike fitting and briefing at the start of your holiday
- Luggage transfers between hotels
- Headwater navigation app

Not Included In The Price

Request a single room or e-bike upgrade if required, purchase travel insurance and arrange any visas and vaccinations. A compulsory solo traveller supplement applies to this holiday. The price excludes estimated local taxes/fees of 13 EUR.

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

08 - 15 October 2026 $ 2.450

10 - 17 October 2026 $ 2.450

12 - 19 October 2026 $ 2.450

15 - 22 October 2026 $ 2.450

17 - 24 October 2026 $ 2.450

19 - 26 October 2026 $ 2.450

22 - 29 October 2026 $ 2.450

24 - 31 October 2026 $ 2.450

26 October - 02 November 2026 $ 2.450

29 October - 05 November 2026 $ 2.450

31 October - 07 November 2026 $ 2.450

02 - 09 November 2026 $ 1.815

05 - 12 November 2026 $ 1.815

07 - 14 November 2026 $ 1.815

09 - 16 November 2026 $ 1.815

12 - 19 November 2026 $ 1.815

14 - 21 November 2026 $ 1.815

06 - 13 March 2027 $ 1.890

08 - 15 March 2027 $ 1.890

11 - 18 March 2027 $ 1.890

13 - 20 March 2027 $ 1.890

15 - 22 March 2027 $ 1.890

18 - 25 March 2027 $ 1.890

20 - 27 March 2027 $ 1.890

22 - 29 March 2027 $ 1.890

25 March - 01 April 2027 $ 1.890

27 March - 03 April 2027 $ 1.890

29 March - 05 April 2027 $ 1.890

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 $ 2.435

03 - 10 May 2027 $ 2.435

06 - 13 May 2027 $ 2.435

08 - 15 May 2027 $ 2.435

10 - 17 May 2027 $ 2.435

13 - 20 May 2027 $ 2.435

15 - 22 May 2027 $ 2.435

17 - 24 May 2027 $ 2.435

20 - 27 May 2027 $ 2.435

22 - 29 May 2027 $ 2.435

24 - 31 May 2027 $ 2.435

27 May - 03 June 2027 $ 2.435

29 May - 05 June 2027 $ 2.435

30 May - 06 June 2027 $ 2.435

31 May - 07 June 2027 $ 2.435

03 - 10 June 2027 $ 2.435

05 - 12 June 2027 $ 2.435

07 - 14 June 2027 $ 2.435

10 - 17 June 2027 $ 2.435

12 - 19 June 2027 $ 2.435

14 - 21 June 2027 $ 2.435

17 - 24 June 2027 $ 2.435

19 - 26 June 2027 $ 2.435

26 August - 02 September 2027 $ 2.465

28 August - 04 September 2027 $ 2.465

30 August - 06 September 2027 $ 2.465

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 $ 1.890

04 - 11 November 2027 $ 1.890

06 - 13 November 2027 $ 1.890

08 - 15 November 2027 $ 1.890

11 - 18 November 2027 $ 1.905

13 - 20 November 2027 $ 1.905

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