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Puglia: Round Italy’s Heel

Tour: IPuMTL9
Hotel To Hotel Cycling Holiday
Linear Cycling Holiday

Have a tip-top time cycling the Puglia peninsular. Discover cavernous, ‘Sassi’-filled Matera and the ‘trulli’ houses of Alberobello. Coast down by the Ionian Sea past Gallipoli to Salento’s very tip, then pedal alongside the Adriatic to finish at ‘Florence of the South’ - Lecce. It’s heady stuff exploring ‘The Heel’, with vineyard temptations like Itrian white wines, sun-kissed aperitifs and irresistible Mandurian reds, matched only by the region’s fresh and famous seafood, meat, olives and pasta treats of course. But whatever your tastes – piazzas, palazzos, ‘cittàs biancas’, beaches, Baroque churches, fortifications or even flamingos – it’s a vastly varied, superbly scenic area which delivers every time. Cycling Italy’s ‘heel’ is epic… we’re not pulling your leg! Read More


Europe, Italy

Start Day

Any Day

Board Basis

Bed & Breakfast

Prices from



9 Days, 8 Nights


Jan - Nov

Tour Grade

Grade 4 (More Challenging)

Read Overview
Home > Europe > Puglia: Round Italy’s Heel


Explore two wonderful Italian coastlines and all the best bits in between as you cycle right round

Puglia’s ‘heel’ of Italy from Matera to Lecce. Pedal through rocky gorges and mighty castle towns, alongside beautiful beaches and coastal cliffs. Highlights also include Alberobello, Gallipoli, Oranto and Santa Maria di Leuca. The terrain and some longer rides on this tour makes it perhaps less suited to people wishing to put a first toe in the water when it comes to a cycling holiday. The first day’s ride from Matera to Alberobello is more challenging than the others as it combines hills (nothing too big) with a longer ride. We believe that this tour will be best enjoyed by reasonably fit or more established cyclists, with other less challenging itineraries also available in Puglia should you prefer. As always, we are happy to talk through the cycling and / or the accommodation on this tour if you would like to give us a call.

Tour Code:
Hotel To Hotel Cycling Holiday, Linear Cycling Holiday
Europe, Italy
9 Days, 8 Nights
Board Basis:
Bed & Breakfast
Jan - Nov


Day 1 Arrive & explore

Matera’s an awesome introduction to this magical part of Italy situated on the border of Basilicata and Puglia. With its steep white rocky ‘tufa’ cliffs and spectacular deep Torrent Gravina gorge, it is renowned for its labyrinthine network of hilly alleys and streets and its ‘Sassi’ – the caves which burrow deep into the 300,000 year old history of this amazing city. The ‘Strada di Sassi’ is home to just caves used as homes, artists’ studios, shops and churches within this UNESCO World Heritage Site.

Matera’s cathedral has a impressive location, perched on the spur between two ‘walls’ of caves ‘Sasso Caveso’ and ‘Sasso Barisano’. The views over the gorge are breath-taking and Matera has more to fill a day (ask us if you’d like to stay an extra night!), but on the outskirts of town, the imposing towers and ramparts of the Castillo Tramontano reach other heights and the whole gorge has treasures along the popular Belevedere Path. Go exploring or find a perch at a piazza café where you can admire the rugged views with a glass of something deliciously local and bask in the in the sunshine.
Overnight in Matera.

Day 2 From Matera’s towers to Alberobello’s famous ‘Trulli’

Up early is the best way to start the day to make the acquaintance of your bike and the most of a great day’s cycling. Head out across the robust ‘Sassi’ landscapes and you’ll soon leave the rugged Basilicata province behind as you pedal through the southern part of Murgia and edge into the softer, more verdant valley countryside  of Puglia’s Valle d’Itria en route to Alberobello – the capital of indigenous ‘trulli’ houses and your UNESCO World Heritage Site number two.

Wooded slopes, vineyards and olive groves take over from the rocky landscape and clusters of the little limestone houses with grey conical roofs increasingly appear in the countryside, until Alberobello – a ‘trulli’ amazing sight. There are over 1500 of these single storey dwellings scattered around the Monti and Aia Piccola districts, making it surely one of Europe’s most unusual urban spectacles. A trullo looks like a cross between a kiln, tepee and an igloo and was traditionally constructed without mortar. The stone roofs often have strange finials with rather mysterious symbols. Be sure to take a  peek inside the tiny trullo church of Sant ‘Antonio or catch the only multi-storied trullo house, Trullo Sovrano, in the Piazza Sacramento.
Overnight in Alberobello.

Miles  47  Kms  76

Day 3 In search of the Città Bianca

Leave Alberobello through the colourful olive groves and vineyards, across the red soils of Valle d’Itria to find its ‘balcony’, ‘Locorotondo where you’ll find some rather different architectural delights. After the ‘trulli’, the local ‘cummerse’ seem almost Baltic in style – box houses with pointed gables, whose angular shapes contrast with the town’s hilly landscape and circular street plan (hence its name ‘loco rotondo’). The ‘balcony’ view is beautiful and certainly the place to try the local aperitif or white wine as you enjoy views.

Next up, Martina Franca has a delightful historic square and palazzi , followed by Cisternino, a tiny, be-towered and white-washed village that’s a great stop for lunch. Finally it’s on to Ostuni, the mighty medieval ‘Città Bianca’, named by the Greeks, but home to every kind of history imaginable form Baroque to Bourban and Byzantine. Check out the Baroque Palazzo Ducale which swallowed up the 12th century castle ruins and don’t miss the breath-taking view over the Rione Terra towards the Adriatic from the cathedral. Enjoy!
Overnight in Ostuni.

Miles   33 Kms  52

Day 4 An impressive crop of cosmopolitan castles  

Pedal out through gently undulating countryside towards the red wine (Primitivo di Manduria) region of Manduria and enjoy a really impressive of castles courtesy of all sorts of nationalities along the way. In Brindisi, the clue’s in the name at San Vito dei Normanni where Frenchman Bohemond de Hauteville had a hand in creating the square tower, although the town was sacked by Saracens, Venetians and the Ottoman Empire in its time. The area has a reputation for Greek influenced monastic ‘rock art’ too.

Next stop, Mesagne boasts an 11th century castle and a 7th century church and Oria lines up a bishop’s palace, cathedral churches and an impressive castle built by Frederick II Hohenstaufen in the 1200s. Finally, destination of the day – Manduria – really takes the biscuit with its Sant’ Angelo gateway to the historic town, its castle and of course, Garibaldi Square! Pliny the Elder described a well with an almond tree growing from it here some 2000 years ago. It has become the city’s insignia and unbelievably, both still survive today. See them with your own eyes at the Fonte Pliniano.
Overnight in Manduria.

Miles  45  Kms  74

Day 5 Cycling the Salento west coast

Enjoy the company of the Ionian sea as you discover resorts and historic ports en route to hugely historic Gallipoli. Put a toe in the water at popular Campo Marina or wander along part of the massive golden sandy beach of Porto Cesareo  – some 17 kms long! – which is protected by an archipelago of islands. Here, the marine reserves are a real draw, with excursions on offer to view the coral formations and sea life including sea horses and turtles. The port town has historic traces throughout, but nothing compares to Gallipoli’s impressive harbour ramparts. Named ‘Kale Polis’ – ‘beautiful city’ – by the Greeks, it seems to have more than its fair share of castle culture and baroque flourishes, noble palaces and churches, but it is deliciously down to earth (or should that be sea?) with fishermen selling their catch from quayside stalls and bars and restaurants serving up all sorts of cosmopolitan seafood dish with true Italian style.
Overnight in Gallipoli.

Miles  44  Kms  70

Day 6 Heading for the ‘Heel’

Plenty of head-turning beaches today. The sandy stretches at Torre San Giovanni are just classic. Clear waters. Fresh fish snacks to graze on at every corner café. You’d like to park up and stay for hours. Put a toe in the water at least maybe, before pushing the pedals on to the little harbour of Ugento on the Gulf of Taranto and Specchia, recognised as one of the most beautiful towns or ‘Borghi’ in Salento and even Italy. It follows a medieval circular street pattern, clustering around its castle with tiny lanes and courtyard houses which just invite you to go off the beaten track. It has plenty of things to discover underground too – like its famous olive oil mills! But Italy’s heel is calling, so its time to shin off and knuckle down to a few more gentle miles to reach destination of the day Santa Maria di Leuca at the eye-catching point where the Aegean, Ionian and Adriatic seas meet.

‘Leuca’ as the locals call it, is the southern-most tip of Salento and is spell-binding – so silent and colourful. The much-revered sanctuary – Punto Meliso – above the town is the place to head to get a feel for the rich wand riotous history of the place and to look out over the swirling currents created by the merging waters. If you’ve got your binoculars, you might even spot the Albanian mountains or hills of Corfu across the waves. There are less usual Moorish-style villas here, such as  Villas Daniela, De Francesco and Sangiovanni, plus ancient caves a-plenty here too in the soft, sedimentary rock, but near the port Grotto Portinara is one to look out for, covered in names and ‘graffiti’ showing ships and symbols, all carved by sailors and travellers passing the time before they set sail!
Overnight Santa Maria di Leuca.

Miles  44  Kms  71

Day 7 In the company of the Adriatic - Salento east coast

Setting out northwards from the Leuca tip, the Adriatic coast makes for great company. Enjoy discovering little ports and marinas full of bobbing boats like Tricase Porto also known for the fine façade of its Dominican convent, its castle and the ‘Quercia Vallonea’, an oak tree which reputedly dates back to the 13th century and ranking amongst the oldest trees in Italy – another one to see for yourself perhaps? Castro Marina is another colourful port where you could park up and canoe off a while if you wished. In these parts there are more caves to discover too (Grotta Palombara / Azzura/ Zinzulusa) reached by land or water and full of stalactites.

Despite all the eye-opening discoveries, the best is saved until last – Otranto is simply hugely impressive. Massively fortified and a huge melting pot of influences including Greek and Turkish, it’s pièce de résistance (literally!) is its dominating ‘Castello Aragonese’. The ‘Duomo’ (cathedral) reveals a different influence again – Norman this time with a famous crypt and stunning medieval mosaic floor to its name.
Overnight in Otranto.

Miles  38  Kms  60

Day 8 Along the flamingo coast (Alimini Lakes) to the ‘Florence of the South’

Just time to enjoy a little more of Italy’s most easterly city – or maybe see the macabre bones of 813 martyrs, if you missed them yesterday in the ‘Duomo’ Basilica Cattedrale di Santa Maria Annunziata… another of those things you need to see with your own eyes! Make sure you have your binoculars today though, to bring those herons and flamingos just a little bit closer as you pedal alongside the two interconnecting lakes known as ‘I Laghi Alimini’. There are towering cliffs, wide bays and sheltered coves at Torre dell’ Orso, where it’s hard to resist going for a swim in the Grotta della Poesie (Cave of Poetry), listed by National Geographic as amongst the ten most beautiful natural pools in the world.

Your final few miles through pine forests and past the round-towered castle at Acaya leads towards grand finale ‘Florence of the South’, Lecce. The university town is a masterpiece of the Baroque with opulent flourishes swirling about its many palazzi, churches and vibrant piazzas. Don’t miss the fantastic façade of Santa Croce Basilica in the Piazza Duomo or the history museum in the former Santa Chiara Monastery with its spectacular views of the town’s Roman amphitheatre.
Overnight in Lecce.

Miles  38  Kms  60

Day 9 Depart after breakfast

Depart after breakfast, or take time for a last wander around the lavish town of Lecce.


Extra nights can be booked at any of the overnight destinations included in this tour to allow more time to explore Puglia at your leisure.

Dates & Prices

Accommodation Options

In Matera, Alberobello, Ostuni, Manduria, Gallipoli, Santa Maria di Leuca, Oranto and Lecce.

is in Matera, Alberobello, Ostuni, Manduria, Gallipoli, Santa Maria di Leuca, Oranto and Lecce.   Selected properties include xxx 4 star hotels, xx 3 star hotels. We are pleased to discuss details on request.

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