Puglia is often described as the “California of Italy,” but that doesn’t quite capture its ancient, sun-bleached soul. Occupying the “heel” of the Italian boot, the region is defined by a landscape of gnarled, centuries-old olive groves, dry-stone walls, and a coastline that alternates between rugged limestone cliffs and Caribbean-clear beaches. It’s a place where life slows down to the pace of the harvest, and the Mediterranean light makes the whitewashed hill towns of the Valle d’Itria practically glow against the deep blue of the Adriatic and Ionian seas.
For a cyclist, the attraction lies in a nearly perfect mix of terrain and atmosphere. While much of the Salento peninsula is refreshingly flat—ideal for coastal cruising and finding your rhythm—the inland Murgia plateau offers enough rolling hills and steady climbs to keep things interesting without being punishing. The weather is a major draw, with long shoulder seasons of mild temperatures and reliable sun that make cycling comfortable long after the rest of Europe has cooled down. You aren’t just riding between points; you’re navigating a network of quiet backroads that wind through a living museum of rural architecture.
The Route at a Glance
- Distance: 620 km (approx. 385 miles)
- Duration: 15 Days
- Terrain: Mostly flat coastal roads with rolling hills in the Itria Valley and a steady climb to the Murgia plateau.
- Elevation: Total ascent approx. 4,100 m.
Journey Highlights
Bari: The Living Gateway
Bari mixes grand boulevards with the tangled lanes of Bari Vecchia, where everyday life spills into the streets. Women hand-roll orecchiette outside their homes, food aromas fill the alleyways, and the lively old city makes a great starting point for the journey.
Matera: Stone Labyrinth
Just across the border in Basilicata, Matera is one of southern Italy’s great sights. Its ancient Sassi cave dwellings are carved into the limestone hillsides, creating a remarkable stone city with thousands of years of history.
Alberobello: Trulli Houses
Alberobello is famous for its Trulli — white limestone houses topped by distinctive conical stone roofs. More than 1,500 crowd the historic districts, creating one of Puglia’s most unusual and memorable landscapes.
Gallipoli: Island Fortress
Gallipoli’s historic centre sits on a limestone island linked to the mainland by an old bridge. Surrounded by defensive walls and the Ionian Sea, its narrow lanes, fishing harbour and waterfront are particularly atmospheric around sunset.
Lecce: Baroque City
Known as the “Florence of the South,” Lecce is filled with elaborate Baroque buildings carved from warm local limestone. Grand piazzas, a Roman amphitheatre and lively evening streets made it an ideal place for a rest day.
Ostuni: The White City
Ostuni rises dramatically above vast olive groves, its brilliant white old town visible from kilometres away. Inside is a maze of narrow lanes, stairways and whitewashed houses, with wonderful views across the countryside towards the Adriatic.
Puglia Cycling Itinerary
- Day 1: Arrive in Bari · Overnight: Bari
- Day 2: Bari to Matera — 65 km · Overnight: Matera
- Day 3: Explore Matera · Overnight: Matera
- Day 4: Matera to Alberobello — 75 km · Overnight: Alberobello
- Day 5: Alberobello to Taranto · Overnight: Taranto
- Day 6: Taranto to Manduria · Overnight: Manduria
- Day 7: Manduria to Gallipoli · Overnight: Gallipoli
- Day 8: Gallipoli to Santa Maria di Leuca · Overnight: Santa Maria di Leuca
- Day 9: Santa Maria di Leuca to Otranto · Overnight: Otranto
- Day 10: Otranto to Lecce · Overnight: Lecce
- Day 11: Lecce rest day · Overnight: Lecce
- Day 12: Lecce to Brindisi · Overnight: Brindisi
- Day 13: Brindisi to Ostuni · Overnight: Ostuni
- Day 14: Ostuni to Monopoli · Overnight: Monopoli
- Day 15: Monopoli to Bari · Overnight: Bari
- Day 16: Bike return and onward travel · Overnight Bari
Exploring the Heel of The Boot: a Three-Week Italian Odyssey
This June I’m heading back to Italy for what promises to be one of the great cycling journeys of my travels — a three-week adventure through the stunning southern region of Puglia before finishing with time in Naples and Rome.
The trip begins in Milan where I’ll catch up with my university friend Sam, now living in Torino, before flying south to Bari — gateway to Italy’s heel and one of the Mediterranean’s most fascinating regions. After a couple of days soaking up Bari’s old town atmosphere and preparing the bike, the real adventure begins.
The cycling route takes me deep into the heart of Puglia and neighbouring Basilicata, beginning with a challenging climb inland to the ancient cave city of Matera. From there the route threads its way through olive groves, vineyards, whitewashed hill towns and spectacular coastlines. Highlights include the UNESCO-listed Trulli houses of Alberobello, the seaside charm of Gallipoli, the dramatic southern cape at Santa Maria di Leuca and the magnificent Baroque city of Lecce — often called the Florence of the South.
One of the joys of Puglia is its slower pace of life. The region is famous for its endless ancient olive groves, quiet country roads, coastal fishing towns and extraordinary food culture. It feels very different from the busier tourist centres of northern Italy and promises the perfect blend of cycling, history, scenery and authentic Italian life.
The final stage of the journey heads north again through the brilliant white hilltop town of Ostuni before returning to Bari and then catching the fast train west to the vibrant chaos of Naples. After Naples comes a few final days in Rome, one of the world’s great cities and always a fitting place to end an Italian adventure before the long flight home to New Zealand.
It should be an unforgettable few weeks of cycling, food, history, coastal scenery and discovering another remarkable corner of Italy.
Wellington to Milan
Sunday 24th May 2026
It was another early departure from Wellington, this time flying through Abu Dhabi, which was under something of a cloud following the recent hostilities in the region. Fortunately, the journey was straightforward, with only a short stop before continuing on to Milan and arriving early in the morning. From the airport I caught the train into the city, found a café for some breakfast and coffee, and took a little time to regroup after the long flight.
Summer had well and truly arrived in northern Italy, with the temperature heading towards 30°C. With several hours to fill before I could check into my apartment, I hired a rideshare bike and spent the morning pedalling around Milan’s historic centre. My apartment was perfectly located in the heart of the city, only about five minutes’ walk from the magnificent Duomo. Jet lag was beginning to catch up with me, so being able to check in just after lunchtime was very welcome—a shower and a short rest made all the difference before heading back out to explore central Milan.
I had two days in Milan and was hoping to finally catch up with my old university friend Sam, who now lives nearby in Turin. The plan was for Sam to come down by train and spend the afternoon showing me some of Milan from a local Italian perspective while we caught up on old times. Unfortunately, Italy had other ideas. A breakdown on the railway line meant Sam couldn’t get to Milan, and once again our plans to meet were defeated.
Instead, I hired another rideshare bike and downloaded a self-guided cycling app that provided audio commentary as I travelled around the city’s historic sights. I’ve used this type of tour many times and really enjoy it. You can travel at your own pace, stop whenever something catches your interest and explore places that you might otherwise pass by. Milan is an easy city to discover this way, and it made for a very enjoyable second day.
If you like coffee, it’s hard to beat a visit to a Starbucks Roastery. As soon as you step inside, you are overwhelmed by the smell of warm coffee. Starbucks Roastery allows you to see the coffee be processed from bag of raw beans to cup. It’s a neat experience, especially if you are a coffee lover. It is almost like a mini coffee amusement park. The Milan Starbucks Roastery is a gorgeous Starbucks Roastery (the first one in Europe!) that is worth the stop if you are in Milan.
On Wednesday, 27 May, it was time to head south on a midday easyJet flight to Bari, the gateway to Puglia and the start of my cycling journey. I was up early to enjoy the city before the crowds appeared and stopped at the spectacular Starbucks Reserve Roastery Milano, housed in a grand historic building near the main square. Coffee and croissant in hand, I sat quietly for a while and FaceTimed everyone back home before catching the nearby airport bus. By mid-afternoon I was checking into my apartment in the historic centre of Bari, ready for the real adventure to begin.
Day 1 – Arrive in Bari
Thursday 28 May 2026
I was staying right in the heart of Bari Vecchia, the wonderfully atmospheric old town that occupies a small peninsula beside the Adriatic. It is a maze of narrow medieval alleyways, white limestone houses, tiny courtyards and bustling piazzas where everyday life seems to take place almost entirely outdoors. Washing hangs from balconies overhead, scooters squeeze through impossibly narrow lanes and around almost every corner there is another little church, café or doorway opening directly onto the street.
Not far from my apartment I discovered Antico Caffè del Carmine, a simple outdoor café tucked into a small local shopping and market area. It was open early and already busy with locals sitting around talking over their morning coffee. I liked it immediately and it became my regular breakfast stop—not only during these first days in Bari, but whenever I passed back through the city during the trip.
I spent much of the day simply wandering through Bari Vecchia, which is probably the best way to experience it. There are plenty of historic sights to visit, but much of the attraction is in the alleyways themselves—small shrines built into walls, ancient stone archways, neighbourhood shops and people sitting outside their homes chatting with neighbours. Eventually I found my way to one of Bari’s best-known sights, Strada Arco Basso, better known as Pasta Street.
Handmade pasta has been part of Puglian life for centuries, particularly orecchiette, the little ear-shaped pasta for which Bari is famous. Along Pasta Street, local women continue the tradition by sitting at wooden tables outside their homes, rapidly shaping pieces of semolina dough with their fingers and knives before laying the pasta out on trays to dry. The tradition has been handed down through generations and has become one of the symbols of Bari Vecchia—a working piece of local culture taking place in the same narrow streets where families have lived for centuries.
In Piazza Mercantile stands Bari’s unusual Column of Shame (Colonna della Giustizia), a stone column guarded by a small crouching lion. Dating from medieval times, it was used as a place of public punishment, where debtors and other offenders were tied to the column and exposed to the ridicule of the townspeople. Today it is a curious reminder of the rather unforgiving justice once handed out in the very heart of Bari’s commercial life.
Day 2 – Bari to Matera – 65km
Friday 29th May 2026
The Ancient Cave Districts Called The Sassi of Matera
Today’s Ride
BARI → MATERA
65 km · ↑ 740 m · 5–6 hrs
🚴 Surface: Mostly sealed roads
⛰️ Difficulty: Challenging
🛏️ Stay: Matera
⭐ Best moment: The first view across the Sassi of Matera
I hired my e-bike from Velo Service Bari and can highly recommend them for their friendly, helpful service and excellent bikes, well set up for cycle touring. Conveniently, they were located just a short distance from my accommodation in the heart of Bari’s old town.
Where I stayed and ate
Accommodation: Add the name and a short review.
Food: Add the best meal, café or local dish.
Rest Day and touring around Matera
