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

$ 2.225

Single Room Difference

$ 348

Date

30 August - 06 September 2025

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. The 3 Star accommodation is listed on the hotels page.

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 a mix of 3 and 4-star hotels — 6 days cycling — E-bike hire available on request (supplement applies) — Self-guided holiday. Min age 14 yrs

Map

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

30 August - 06 September 2025 $ 2.225

01 - 08 September 2025 $ 2.255

04 - 11 September 2025 $ 2.255

06 - 13 September 2025 $ 2.255

08 - 15 September 2025 $ 2.255

11 - 18 September 2025 $ 2.255

13 - 20 September 2025 $ 2.255

15 - 22 September 2025 $ 2.255

16 - 23 September 2025 $ 2.295

18 - 25 September 2025 $ 2.255

20 - 27 September 2025 $ 2.255

22 - 29 September 2025 $ 2.255

25 September - 02 October 2025 $ 2.255

27 September - 04 October 2025 $ 2.255

29 September - 06 October 2025 $ 2.255

02 - 09 October 2025 $ 2.165

04 - 11 October 2025 $ 2.165

06 - 13 October 2025 $ 2.165

09 - 16 October 2025 $ 2.165

11 - 18 October 2025 $ 2.165

13 - 20 October 2025 $ 2.165

16 - 23 October 2025 $ 2.165

18 - 25 October 2025 $ 2.165

20 - 27 October 2025 $ 2.165

23 - 30 October 2025 $ 2.165

25 October - 01 November 2025 $ 2.165

27 October - 03 November 2025 $ 2.165

30 October - 06 November 2025 $ 2.165

01 - 08 November 2025 $ 1.715

03 - 10 November 2025 $ 1.715

06 - 13 November 2025 $ 1.715

08 - 15 November 2025 $ 1.715

10 - 17 November 2025 $ 1.715

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