Self-Launched Cycling the Heel of Italy: Matera to Lecce

Fly into Bari (served by easyJet, Ryanair and British Airways from London). From Bari Centrale station, take a direct Ferrovie Appulo Lucane (FAL) train to Matera Sud — journey time around 1.5 hours, ~£6. Check into your guesthouse or B&B in or near the Sassi district. Spend the evening wandering the cave-house streets and hunting down a plate of orecchiette al ragù.

🚌Fly London to Bari (Ryanair/easyJet from ~£40 one way). FAL train Bari–Matera ~£6.

🛏B&B or guesthouse near Sassi di Matera (e.g. Le Monacelle Hostel or similar) ~£25–35/night

• →Arrive at Bari Airport and take the FAL train to Matera (~£6)
• →Check in to guesthouse near the Sassi di Matera
• →Evening stroll through the illuminated Sassi cave district

Spend a full day exploring the UNESCO-listed Sassi di Matera — one of the oldest continuously inhabited settlements on Earth. Visit the Casa Grotta di Vico Solitario cave museum (~£3), the Palomba Ravine viewpoints, and the rupestrian churches carved into the rock. Book a guided walking tour of the Sassi via GetYourGuide for around £15 if you'd like context. Pick up your hire bike today from a local rental shop (e.g. Ferula Viaggi or similar) so you're ready to roll tomorrow.

🚌On foot within Matera

🛏B&B or guesthouse near Sassi di Matera ~£25–35/night

• →Visit the Sassi di Matera UNESCO cave district (free to walk, £3 entry to Casa Grotta)
• →Optional: guided walking tour via GetYourGuide (~£15)
• →Explore rupestrian churches carved into the ravine
• →Collect hire bike from local rental shop (~£15–20/day)

Your first full cycling day. Head south-west through rolling wheat fields and wide open Murgia plateau panoramas. Stop in Laterza to admire the majolica pottery shops and pick up some of the town's famous baked goods. The final stretch brings you to Castellaneta, dramatically perched on the edge of a deep ravine. Load your route on Komoot before you leave — it's excellent for this region. Dinner is included at your accommodation tonight (book a B&B with dinner option).

🚌Cycle 60 km on quiet tarmac roads (self-navigated via Komoot app, free). Luggage can be sent ahead by taxi/shuttle (~£10–15 per bag, arrange locally).

🛏B&B or small hotel in Castellaneta ~£30–40/night

• →Cycle 60 km Matera to Castellaneta via Laterza
• →Browse Laterza's famous majolica pottery and bakeries
• →Walk to the viewpoint over the Castellaneta ravine
• →Dinner at local trattoria (~£12–15)

A spectacular day cycling through the Terra delle Gravine Natural Park, where rivers have carved deep canyons into the limestone over millions of years. The landscape then opens up into classic Puglia countryside: dry stone walls, ancient masserie farmhouses, and your first glimpse of trulli — those extraordinary conical-roofed stone houses built without mortar. Arrive in Putignano, famous since 1394 for its carnival tradition.

🚌Cycle 55 km on quiet roads through the Gravine park. Navigation via Komoot.

🛏B&B in Putignano ~£28–38/night

• →Cycle 55 km through Terra delle Gravine Natural Park
• →Spot dry stone walls, masserie and your first trulli houses
• →Arrive in Putignano and explore the historic centre
• →Aperitivo in a local bar in the main piazza (~£4)

A shorter, easier day — perfect for savouring the scenery. Leave Putignano's medieval centre and cycle through lush countryside to the Castellana Grotte, Italy's most impressive karst cave system. A guided underground tour lasts around 1–2 hours and costs £12–18 — book direct at the cave entrance or via GetYourGuide. Continue through almond, apricot and cherry orchards to Alberobello, the UNESCO-listed world capital of trulli. When available, try to stay in a trullo guesthouse — an unforgettable experience.

🚌Cycle 35 km on rolling country lanes.

🛏Trullo guesthouse or B&B in Alberobello ~£35–50/night

• →Cycle 35 km Putignano to Alberobello via Castellana Caves
• →Underground tour of Castellana Grotte (~£12–18, book direct or GetYourGuide)
• →Explore the UNESCO trulli district of Alberobello (free)
• →Stay overnight in a traditional trullo guesthouse if available

Cycle through the gorgeous Valle d'Itria, passing clusters of white-tipped trulli and terraced vineyards. Pass through Locorotondo, one of Italy's most beautiful villages — stop for a glass of its famous sparkling white wine at a local enoteca (~£3). Continue south-east towards the coast and up to Ostuni, the dazzling 'White City' whose whitewashed buildings cascade down a hilltop above the Adriatic plain. The views from the old town at dusk are extraordinary.

🚌Cycle 49 km on mostly flat-to-rolling quiet roads.

🛏B&B or guesthouse in Ostuni old town ~£35–45/night

• →Cycle 49 km through Valle d'Itria past trulli and vineyards
• →Stop in Locorotondo for local sparkling white wine (~£3)
• →Explore Ostuni's whitewashed hilltop old town (free)
• →Sunset views from Ostuni's cathedral terrace

Head inland through the colourful Salentinian countryside, characterised by ancient silver-green olive groves and the region's distinctive red soil. Pass through the walled town of Oria with its Swabian castle and then Manduria, famous for its Primitivo red wine — stop for a tasting at a local cantina (~£5–8). Arrive in Avetrana, a quiet agricultural town. Book a B&B that includes dinner tonight to enjoy genuine home-cooked Puglian cooking.

🚌Cycle 55 km on quiet tarmac roads.

🛏B&B in Avetrana with dinner option ~£40–50/night

• →Cycle 55 km through olive groves and red-soil countryside
• →Visit Oria's Swabian castle (exterior free, entry ~£4)
• →Wine tasting of Primitivo di Manduria at a local cantina (~£5–8)
• →Home-cooked Puglian dinner at your B&B (~£12–15)

A coastal classic. Head east to Torre Colimena on the Ionian Sea, then follow the coastline past beaches and medieval watchtowers south to Gallipoli — the 'Ionian Pearl'. The historic old town occupies a rocky island connected to the mainland by a 17th-century bridge, and rewards wandering: baroque cathedral, noble palazzi and seafood restaurants where a plate of crudo (raw fish) and a glass of local white is hard to beat (~£15–20 for dinner).

🚌Cycle 60 km, partly along coastal roads.

🛏B&B or small hotel in Gallipoli old town ~£35–50/night

• →Cycle 60 km along the Ionian coast to Gallipoli
• →Walk across the bridge to Gallipoli's island old town (free)
• →Visit the baroque cathedral of Sant'Agata (free)
• →Dinner at a local seafood trattoria (~£15–20)

Today you reach the very tip of Italy's heel. Cycle south along the Ionian coast through pine forests and past long sandy beaches towards Santa Maria di Leuca, where the Ionian and Adriatic seas meet at a dramatic promontory. Visit the lighthouse and the Basilica De Finibus Terrae (free). The village is dotted with elegant Belle Époque villas built by wealthy merchants. Take a dip — you've earned it.

🚌Cycle 50 km along coastal and inland roads.

🛏B&B or guesthouse in Santa Maria di Leuca ~£30–40/night

• →Cycle 50 km to the southernmost tip of Salento
• →Visit the lighthouse at Santa Maria di Leuca (exterior free)
• →Basilica De Finibus Terrae (free entry)
• →Swim where the Ionian and Adriatic seas meet

Pedal north along the spectacular Adriatic coast. Make time to stop at the Grotta Zinzulusa, a sea cave accessible by short boat trip (~£5), and the thermal baths of Santa Cesarea Terme for a look even if you don't take the waters. Arrive in Otranto, Italy's most easterly city — once a gateway to the Orient. Its 12th-century cathedral contains a remarkable floor mosaic depicting the Tree of Life, and the Aragonese castle overlooks the harbour.

🚌Cycle 53 km along the coastal strada provinciale.

🛏B&B or small hotel in Otranto ~£35–45/night

• →Cycle 53 km along the Adriatic coast from Leuca to Otranto
• →Boat trip to Grotta Zinzulusa sea cave (~£5, book locally)
• →Visit Otranto Cathedral and its extraordinary medieval floor mosaic (free–£2)
• →Explore Aragonese Castle of Otranto (~£4)

Your final cycling day follows the shoreline north through ancient olive groves before turning inland to the grand finale: Lecce. Known as the 'Florence of the South', Lecce's pale golden baroque architecture is simply stunning — over 30 churches, a Roman amphitheatre in the main piazza and a theatre from the time of Augustus. Return your hire bike and celebrate with a craft beer and a pasticciotto (Lecce's famous custard pastry). Tonight, splurge a little on dinner.

🚌Cycle 55 km on quiet roads into Lecce.

🛏B&B or hostel in Lecce historic centre ~£30–45/night

• →Cycle 55 km through olive groves to Lecce
• →Return hire bike at agreed drop-off point
• →Explore Lecce's baroque Piazza del Duomo and Santa Croce Basilica (free)
• →Roman amphitheatre in Piazza Sant'Oronzo (free exterior, £3 for excavations)
• →Celebratory dinner at a Lecce trattoria (~£20–25)

Make your own way home. Lecce has a well-connected train station with direct Trenitalia services to Brindisi (15 min, ~£3) for flights back to the UK, or you can take the train to Bari (1.5–2 hrs, ~£12) for a wider choice of flights. Alternatively, enjoy a final morning espresso and pastry in the sun before heading to the airport.

🚌Trenitalia train Lecce–Brindisi ~£3 or Lecce–Bari ~£12.

🛏N/A — departure day

• →Final morning stroll through Lecce's baroque streets
• →Train Lecce to Brindisi (~£3, 15 min) or Bari (~£12, 1.5–2 hrs)
• →Fly home from Brindisi or Bari