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Italy: Puglia

Cycling the Heel of Italy – Alberobello to Lecce

Trip code: C07PI

Average customer rating 4.7 / 5(55 verified reviews)

Self-Guided Cycling
7 nights hotel-to-hotel
Moderate
Flights available
CO₂ rating 1/5
Headwater Navigation app

Trip highlights

Alberobello’s fairy-tale trulli houses

Olive groves, towering limestone cliffs and Roman amphitheatres

The white city of Ostuni, the majestic castle of Otranto and Baroque Lecce

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Trip details

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

What's included

Included

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

Not included

  • Flights
  • Local taxes/fees
  • Travel insurance

Your bike

Hand-picked for the route, hire included

Cube, Nature Trekking or equivalent. Your bike hire is included in the price of your holiday and comes equipped with the relevant essentials, plus rear pannier and phone holder.

Travel options

Flights

Our air prices include standard flights and transfers.

Transfers

Transfers can be arranged at a supplement from Bari Airport at 14:20.

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 · —Arrive in Alberobello

Arrive in Alberobello

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

You stay at Trullidea

Trullidea
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Trullidea

Alberobello

  • Hairdryers
  • Wifi access

A unique and authentic experience staying in a trullo, a traditional 15th century Apulian stone building with conical roof.

Each trullo house is made up of a double bedroom, small bathroom with shower and living area with sofa and small kitchenette.

The trulli are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.

Day 2 · 49km/30.4miAlberobello to Ostuni

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.

Elevation

Alberobello to Ostuni elevation profile

You stay at Relais Sant’Eligio

Hotel SantEligiio, Ostuni
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Relais Sant’Eligio

Ostuni

  • Air conditioning
  • Hairdryers
  • Mastercard
  • Minibar
  • Shops
  • Television
  • Visa cards
  • Wifi access

Situated a stone’s throw from Ostuni’s Old Town, the Relais Sant’Eligio dates back to the first half of the 1500s when Queen Bona Sforza d’Aragona imposed all coastal cities from Naples to Otranto to have a resting station. The Resting Station of Camposada – as it was then – has welcomed many couriers and royal officials from yesteryear, whilst today, each of the 22 elegant and individually decorated rooms offer every comfort for the 21st century guest.

Day 3 · 65km/40.4miOstuni to Avetrana

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.

Elevation

Ostuni to Avetrana elevation profile

You stay at Masseria Strazzati

Masseria Strazzati
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Masseria Strazzati

Avetrana

Masseria Strazzati is an old farm estate and is set within 100 hectares of olive groves. Your evening meal is taken at the Masseria Bosco where the pool can also be used.

Day 4 · 61km/37.9miAvetrana to Gallipoli

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.

Elevation

Avetrana to Gallipoli elevation profile

You stay at Hotel Joly Park

Joli Park, Gallipoli
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Hotel Joly Park

Gallipoli

  • Air conditioning
  • Hairdryers
  • Mastercard
  • Safe
  • Swimming pool
  • Television
  • Visa cards
  • Wifi access

Located in the centre of Gallipoli and only a short walk from Corso Roma, Hotel Joli Park is modern and comfortable.

The rooms are well equipped and contemporary. The hotels offers guests a private shuttle service to take you to and from the private beach “Lido delle Sirene”.

Day 5 · 52km/32.3miGallipoli to Santa Maria di Leuca

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.

Elevation

Gallipoli to Santa Maria di Leuca elevation profile

You stay at Hotel Terminal

Bedroom at the Hotel Terminal, Sta Maria Leuca
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Hotel Terminal

Leuca

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Swimming pool
  • Television

Hotel Terminal is nestled among the eclectic villas on the central 19th century seafront dedicated to Cristoforo Colombo in the heart of town, with a beautiful view on Punta Ristola and Punta Melis. Rooms here are comfortable and well equipped and the hotel also benefits from its own private beach.

Day 6 · 53km/32.9miSanta Maria di Leuca to Otranto

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.

Elevation

Santa Maria di Leuca to Otranto elevation profile

You stay at Hotel Albania

Reception at the Hotel Albania, Otranto
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Hotel Albania

Otranto

  • Air conditioning
  • Hairdryers
  • Safe
  • Television
  • Wifi access

Located in the centre of Otranto, Hotel Albania owes its name to the majestic Albanian mountains which on a clear day offers guests breathtaking views and are visible from the hotel terrace.

Rooms are comfortable and modern.

Day 7 · 55km/34.2miOtranto to Lecce

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.

Elevation

Otranto to Lecce elevation profile

You stay at Eos Hotel

Outside the Eos Hotel, Lecce
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Eos Hotel

Lecce

  • Air conditioning
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Television
  • Visa cards
  • Wifi access

Situated just outside of the historic town of Lecce, Hotel Eos is a modern hotel with modern facilities.

Rooms are contemporary and fully furnished.

Day 8 · —Leave Lecce

Leave Lecce

Extending your holiday

Double room

Hotel Excelsior

Bari

  • Air conditioning
  • Hairdryers
  • Safe
  • Television
  • Wifi access

The Hotel Excelsior has large and bright rooms. There is also a bar and restaurant offering Mediterranean dishes.

What our travellers say

This was our first cycling holiday (we are in our seventies) We had the most enjoyable time, meeting up with fellow cyclist from other countries on route
The towns we stayed in and the hotel were all very good. The cycling was almost all on quiet roads. We would certainly like to book another trip. Mary and Tim

Mr Partridge

Excellent holiday with good hotels, great scenery and realistic riding days for the described activity level. The bikes were excellent and comfortable.

Mr Paul

It was a well thought-out itinerary which took in the high-lights of Puglia – rural rides to beautiful hill-top towns and coastal rides with lovely views over the Mediterranean.

Mr HALL

Our holiday was a celebration for our 30th wedding anniversary. In order to be consistent with the previous thirty years of marriage I left the planning until the last minute. I contacted Headwaters barely two weeks before the half term started yet they were able , as ever, to provide a first class service which totally met what we were looking for. From the moment we landed, where we met Mimmo our agent, until our departure from our gorgeous Lecce hotel on the final morning, we encountered nothing but an amazing service wherever we visited or stayed. We loved all of the accommodation as well as the stunning routes. Puglia is indeed an astonishingly beautiful region in Italy, as evidenced by the breath taking coastal routes to Gallipoli and Otranto. Likewise the climb to the hilltop town of Ostuni, as well the town itself, was simply stunning. I am running out of synonyms for brilliant but that is the adjective that I want to use to describe the everything about the trip. Thank you.

Mr WADE

An exceptional route – everything had been thought of. The first day is a long distance so it might be off putting for those who don’t cycle long distances regularly. The food everywhere is of a fantastically high standard. We recommend Le Bubbole in Matera, La Cantina in Alberobello and The Dish in Ostuni. Booking in advance recommended.

Mr Hrouda

Excellent. the App was easy to use for middle aged people who usually ask their children to work this kind of thing out. The Headwater emails were well timed and informative and when you passed us on to Gulia cycle tours, they were equally as efficient. The route was fantastic, the hotels just ideal for this holiday. The people we met from Puglia Tours delightful. We had 2 potentially big problems – A) one of our parties’ bags didn’t arrive from England on our flight. So we logged a missing bag form at Barri airport but it was difficult with language barrier and not knowing where we would be if and when the bag might catch up with us. Headwater were amazing and the bag caught us up 2 days later. And the driver from Puglio Tours took us from Barri airport to a hypermarket ( thank god open on a Sunday pm) to buy essentials. We also had a problem with a bike and again – fantastic backup and all sorted. Best holiday & when probs occurred the finest back up

Mrs Dudgeon

Fantastic way to see the glorious countryside, towns, cities and natural beauty of Puglia. Well organised, good bikes, good accommodation and we think the best way to immerse yourself in a location. As firstimers with Headwater would highly recommend to anyone.

Mr Becket

This cycling route through Puglia is a stunningly beautiful one – particularly in late May when the poppies and other wild flowers were in full bloom; the weather warm but not scorching and not too busy with other tourists. This was the first Headwater cycling trip I have done without ‘stay put’ days, and the overall mileage each day (at leisurely pace) did mean there was little spare time for sightseeing. However, it was absolutely worth the effort to visit each of the locations – they were wonderfully varied and I wouldn’t have wanted to miss out on any of them!
One of the days involves taking a train – it’s worth noting that not all the trains allow bikes, and we were lucky to have had help lifting up the bikes into the hanging racks on the train – a tricky manouevre for the vertically challenged!

Mrs Davidson

A great itinerary, a lot of variation in level of challenge.

Mrs Haddock

It was lovely to arrive at the end of a ride in the little towns of Puglia, all different and charming. Some of the cycling was really spectacular, particularly along the coast. I was pleased to have an e-bike as the temperature was way over 30 degrees everyday at the end of May. As someone not very tech-savvy, I needed help with the navigation app. Remember to download last-minute adjustments just before you go!

Ms Hall
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Positive impact

Carbon score for this trip

15.0

Kg CO₂e

per person, per night

Relative to other Headwater trips

We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more

Frequently asked questions

How demanding is this Puglia cycling route?

Graded Level 4, it offers gently varied terrain that suits fair-weather cyclists and more active riders looking for a relaxed trip. No special skills are needed, just reasonable fitness and good health. You ride quiet roads past Puglia’s archetypal olive groves and trulli, with the Headwater Navigation App guiding every turn and your luggage moved between hotels.

What are the cultural highlights?

You begin among the extraordinary conical trulli houses of Alberobello, a UNESCO World Heritage site, ride through the whitewashed towns and olive groves of the Itria Valley, and finish in Baroque Lecce with its honey-coloured stone. It is a wonderful blend of quiet cycling and rich Puglian culture, with all breakfasts plus one dinner included.

Is bike hire included, and can I ride an e-bike?

Yes, quality hire bikes are included with a bike fitting and briefing at the start, and e-bikes are available for a supplement if you would like assistance on the climbs. You are also welcome to bring your own bike. Panniers and a phone holder for the navigation app come as standard.

From£1,039per person