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Puglia: From the Sassi Caves to the Salento Coast

Tour: IPuML9
Hotel To Hotel Cycling Holiday
Linear Cycling Holiday

Puglia’s just magic for a cycling holiday. There are the spell-binding ‘Sassi’ cave-dwellings in the rocky north; the mysterious ‘trulli’ houses of Valle d’Itria; mighty castle towns watching over rolling vineyards and olive groves or clinging to the coast, not to mention scores of beautiful Baroque treasures all basking close to the crystal waters of the Adriatic and Ionian seas in the warmth of the Mediterranean sun. Enjoy some really great time on two wheels exploring the coast and countryside of the heel of Italy from Matera and Alberobello to Gallipoli and Lecce, the Florence of the South. Read More


Europe, Italy

Start Day

Any Day

Board Basis

Bed & Breakfast

Prices from



9 Days, 8 Nights


Jan - Dec

Tour Grade

Grade 4 (More Challenging)

Read Overview
Home > Europe > Puglia: From the Sassi Caves to the Salento Coast


This superb tour around the heel of Italy touches the beautiful beaches of both the Adriatic and Ionian seas, although it is perhaps less suited to those 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 than normal. We believe that this option 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 chat through the cycling and/or the accommodation used 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 - Dec


Day 1 Arrive & explore

Literally piled high with history and carved out of the white rocky cliffs of a spectacular deep gorge, Matera makes for one awesome introduction to this magical part of Italy. Lose yourself a while with a wander round the clambering labyrinth of tiny alleyways and streets. Burrow deep into the history of this renowned UNESCO World Heritage Site along the famous ‘Strada di Sassi’, home to just a few of the time-honoured caves used as dwellings, artists’ studios, shops and churches. Or simply find yourself a suitable perch on a piazza café and sit back in the Mediterranean sunshine to sip in the rugged views, ably accompanied by a glass of local, full-bodied red.

Overnight in Matera.

Day 2 A gorge-ous day of cliffs, caves & churches

Time to get on top of things perhaps? Matera’s cathedral has a mighty fine location, right on top of the spur which divides the ‘Sasso Caveso’ and ‘Sasso Barisano’ – the caves deep in the steep tufa walls of the the Torrent Gravina. The views across the massive gorge are breath-taking and it’s easy to spend a day in Matera simply wandering and wondering, but on the outskirts of town, the imposing towers and ramparts of the Castillo Tramontano reach other heights and the whole of the rugged gorge has time-honoured treasures to share. Head out along the popular Belevedere Path or stride into the rocky hinterland on your own adventure to discover cave churches full of frescoes or maybe even the ‘Grotta dei Pipistrelli’, the haunting cave of bats!

Overnight in Matera.

Day 3 Off to Alberobello: from towers to trulli

An early breakfast is recommended so you are ready to receive your bikes. We recommend that you set out as soon as you can to make the most of a great day’s cycling as you cross the robust Sassi landscapes, leaving Matera’s towering ramparts and the Basilicata province for the softer green countryside of Puglia’s Valle d’Itria and Alberobello – the capital of indigenous trulli houses and your UNESCO World Heritage Site number two. Rugged rockscapes give way to wooded slopes, vineyards and olive groves as the countryside becomes punctuated by clusters of the little limestone houses with grey conical roofs. The climax comes in the town of Alberobello where over 1,500 of these fascinating single storey dwellings create one of Europe’s most unusual urban spectacles. A strange cross between a kiln, tepee or even an igloo to look at, the trulli were originally constructed without the use of mortar, their stone roofs topped with wonderful finials and often decorated with mysterious symbols. Experience the charm of these unique historic buildings for yourself with your overnight in Alberobello in an authentic trullo house.

Overnight in Alberobello

Miles: 47 Kms: 75

Day 4 All kinds of architecture along the Valle d’Itria

Pop in to the tiny trullo church of Sant‘ Antonio or catch the only multi-storied trullo house, Trullo Sovrano, in the Piazza Sacramento before setting off out of Alberobello to Locorotondo – the ‘balcony of the Valle d’Itria’ – for some rather different architectural delights. Here ‘trulli’ give way to ‘cummerse’, almost Baltic-style box houses with pointed gables, whose angular shapes seem strangely incongruous with the town’s curving hillscape and circular street plan which gave it the name ‘loco rotondo’. The view from the ‘balcony’ is a beautiful one of olive groves and vineyards through which your two wheels will take you en route to the tiny and be-towered, white-washed village of Cisternino, before reaching Ostuni, the mighty medieval ‘Città Bianca’, both wonderfully white and lavishly Baroque with helpings of every kind of history you can imagine from the Greeks who named it to Bourbons and Byzantines!

Overnight in Ostuni.

Miles: 22 Kms: 36

Day 5 Train transfer to Lecce, the 'Florence of the South'

Time for one last glimpse of the Baroque Palazzo Ducale which swallowed up the 12th century castle ruins or a final breathtaking view over the Rione Terra towards the Adriatic from the cathedral before letting the train take the strain and deliver you to even more wondrous things in Lecce, aka the ‘Florence of the South’. 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. Lecce can wow almost to the point of overwhelming. The tonic has to be a large bowl of gelato where you can make your own swirls as you sit back on the café terrace and just let the bustle of this gushingly Baroque place engulf you, safe in the knowledge that you’ll soon be back.

Overnight in Lecce.

Miles: 3 Kms: 5 (between hotels and stations)

Day 6 Coasting along the Adriatic: castles, coves & even flamingos

Today, the coast is calling, but just a short pedal from Lecce it’s hard to resist the impressive fortified village of Acaya with its medieval castle, ramparts and wide moat. As the Adriatic draws nearer, stretches of thick pine forests finally reveal wide bays and sheltered coves at Torre dell’ Orso, where the towering cliffs provide fortifications of a more natural kind. A brief pedal south and a wonderful world of flora and fauna unfurls along the two interconnecting lakes known as ‘I Laghi Alimini’. Be sure to have the binoculars at the top of the panniers to bring the herons and flamingos just a little closer, before continuing along the coast for your next overnight in Italy’s most easterly city. Massively fortified and a real melting pot of Greek, Turkish and Aragonese influences, Otranto is dominated by its ‘Castello Aragonese’ and its nearby Norman cathedral, renowned for its crypt and mosaic flooring.

Overnight in Otranto.

Miles: 34 Kms: 55

Day 7 Across Italy’s heel to the Ionian Sea

Steer inland for a day of coast to coast cycling as you head out right across Salento from Otranto to Gallipoli. Don’t miss Corigliano’s must-see castle with its beautiful Baroque façade around half way, but this is a day to enjoy Puglia very much at your own pace as you wind your way through vineyards, olive and almond groves, perhaps stopping off for bowl of ‘orecchiette’, Puglia’s famous little ear-shaped pasta or even a hearty serving of ‘maccheroni al forno’, an interesting pasta-meatball concoction served up under a pie crust! If you have more of an appetite for seafood, then be sure to save yourself for Gallipoli. Here amidst a world of bars and beautiful beaches, impressive harbour ramparts, noble palaces and churches, fishermen sell their catch from quayside stalls. Of course there’s a rich helping of castle culture and baroque flourishes too in the island heart of a town originally named ‘Kale Polis’ by the Greeks – ‘beautiful city’.

Overnight in Gallipoli.

Miles: 37 Kms: 60

Day 8 Gems of a golden age, en route to Lecce

Missed something on that ‘passeggiata’ last night as you strolled along harbour ramparts before settling for the freshest of fish suppers? Take time to explore Gallipoli just a little further, catch sight of the Palazzo Senape De Pace perhaps or just weave your way through its labyrinth of streets and alley ways. Heading north along the coast before steering inland, it’s not long until you reach Galatone, home to the exceptional Baroque church in the Piazza Santissimo Crocifisso. Just a little further and Galatina is another of Puglia’s many hidden gems. The town’s walls and gateways, the wall-to-wall 15th century frescoes inside St Catherine’s cathedral, the intricate doorways and balconies of the aristocratic ‘palazzi’ are each worthy of wonder in their own right, but are just a warm-up in a way when you know what’s up the road in Lecce. Linger, enjoy, then settle back in the saddle for the last northward stretch back to the ‘Florence of the South’.

Overnight in Lecce.

Miles: 35 Kms: 56

Day 9 Depart after breakfast

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

Dates & Prices

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For tour start days/dates, seasons and all prices, please click on the PRICES button above


Ensuite accommodation as described with buffet/continental breakfast (prices based on two adults sharing)

Hire of hybrid bicycle and ancillary equipment (single pannier and handlebar bag, pump, basic tools, spare inner tube)

Luggage transfer between hotels

Local assistance on call (although puncture repair is excluded)

Information pack with detailed joining instructions and daily route overviews sent out approximately 2 weeks before the start of your holiday

Easy to use GPS unit with pre-loaded cycle tracks

Overview notes and maps

Please note that the price EXCLUDES

City/tourist taxes in Italy

Costs of getting to and from the tour area

Accommodation Options

An unique un-rated Trullo house in Alberobello; selected 3 star hotels or better in Matera (2 nights), Ostuni, Lecce (2 nights), Gallipoli and Otranto.


Upgrade to mainly 4 and 5 star hotels.

We are pleased to discuss details on request.

More Information

Useful websites, travel information and tips to help you plan your journey to and from the country and location of your holiday.


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