Day 1 & 2 — Welcome to Puglia: Trani & Castel del Monte

Your Puglia adventure begins the moment you land at Bari Airport. A private transfer whisks you straight to Trani, one of Puglia’s most elegant Adriatic towns, famous for its luminous pink-stone cathedral rising directly from the sea. The afternoon and evening are yours to explore — wander the harbour, sip a local Primitivo, and soak in the atmosphere before your journey truly begins. Our team will meet you for a full briefing, answer all your questions, and prepare your bicycle for the road ahead.

On Day 2, a private transfer takes you to the starting point of the cycling route: the UNESCO World Heritage site of Castel del Monte, Emperor Frederick II’s extraordinary 13th-century octagonal fortress perched atop a solitary hill in the Alta Murgia. Here, your first pedals on the Ciclovia dell’Acquedotto Pugliese begin in earnest. The route descends through the wild, ancient landscape of the Parco Nazionale dell’Alta Murgia — a vast plateau of limestone, wildflowers, and deep silence, hauntingly beautiful and unlike anywhere else in Italy. After 34.2 miles of riding with 2,733 ft of climbing, you arrive in Cassano delle Murge, a quiet Apulian town at the foot of the Murgia escarpment, where a well-earned dinner and a comfortable bed await.

Day 3 — Through the Heart of the Murgia: Cassano to Alberobello

Today’s stage is one of the most evocative of the entire journey. Continuing south along the Ciclovia dell’Acquedotto Pugliese, you ride 40.6 miles through rolling Apulian countryside, passing through the charming hilltop town of Gioia del Colle — home to a magnificent Norman-Swabian castle and one of Puglia’s finest DOC wine zones, where Primitivo vines flourish in the rich red soil. The town’s weekly market and its celebrated aged local cheese, caciocavallo podolico, are not to be missed if timing allows.

The route then curves south toward the destination that needs no introduction: Alberobello, the fairytale town of the trulli. These ancient dry-stone dwellings with their conical whitewashed roofs and mysterious symbols are unlike any architecture on earth — and a UNESCO World Heritage Site since 1996. Arriving by bicycle, weaving in through the countryside where isolated trulli dot the fields, you experience the landscape exactly as it was meant to be seen: gradually, intimately, and at human pace. Spend the evening strolling the Rione Monti district as the golden hour light settles over thousands of cone-shaped rooftops. The climbing today totals 2,283 ft — a rewarding day that ends in one of Italy’s most iconic destinations.

Day 4 — Valle d’Itria to the White City: Alberobello to Ostuni

This stage is the scenic crown jewel of the entire itinerary. Departing Alberobello, the route traverses the incomparably beautiful Valle d’Itria — a pastoral mosaic of ancient olive trees, dry-stone walls, vineyards, and solitary trulli scattered across the undulating countryside like stone mushrooms. The village of Locorotondo, one of the Borghi più Belli d’Italia (Most Beautiful Villages of Italy), sits on a circular hill offering breathtaking panoramic views over the entire valley. Its perfectly round old town with whitewashed houses and flower-filled balconies demands a stop, a stroll, and ideally a glass of the town’s famously crisp local white wine.

Continuing south, you pass through the historic agricultural centre of Ceglie Messapica — quietly celebrated by food lovers as one of Puglia’s great gastronomic towns — before the route transitions from the Ciclovia onto quiet, low-traffic scenic asphalt country roads through the sun-drenched Apulian countryside. The final approach to Ostuni, the legendary “White City”, is a moment you’ll never forget: the gleaming labyrinth of whitewashed houses and the soaring Gothic cathedral rising above three olive-covered hills, visible for miles around, glowing against the deep blue Adriatic sky. At 38.1 miles with 2,234 ft of climbing, Day 4 is challenging and immensely rewarding.

Day 5 — Your Free Day in Ostuni

Today belongs entirely to you. Ostuni is the kind of place that rewards slow exploration — lose yourself in the labyrinthine medieval centro storico, duck into cool whitewashed churches and local artisan workshops, browse the morning market, or simply sit on a terrace and let the views of the Adriatic horizon wash over you. A rest day here is never wasted.

For those who can’t resist the saddle, we’ve prepared two optional loop rides departing directly from Ostuni, each offering a completely different flavour of the region.

Both loops are fully mapped with GPS tracks provided. Whether you explore on wheels or on foot, Day 5 is designed to recharge your spirit before the beautiful final riding stages ahead.

Day 6 — Along the Ancient Roman Road: Ostuni to Polignano a Mare

The penultimate cycling day is perhaps the most diverse and visually spectacular of the entire tour. Leaving the White City behind, today’s 35.8-mile route follows the ancient Via Traiana — the Roman road built by Emperor Trajan in 109 AD to connect Benevento to Brindisi — now reborn as a magnificent cycling path known as the Via degli Ulivi Millenari (the Road of the Millenary Olive Trees). You ride in the literal shadow of olive trees that are hundreds, some thousands of years old — gnarled, monumental, sacred presences in a landscape that has barely changed since antiquity.

The route passes through Monopoli, a lively port town with a beautiful historic centre, excellent seafood, and a handsome Aragonese castle right on the water’s edge — a perfect stop for lunch or a quick espresso before the final push north along the coast. The stage ends at one of Italy’s most photographed destinations: Polignano a Mare, the dramatic cliff-top town where whitewashed houses perch over vertiginous drops into the turquoise Adriatic far below. With only 847 ft of climbing on this relatively flat coastal stage, the legs feel fresh and the scenery is absolutely extraordinary. Arrive, check in, leave your bikes with us — we’ll collect them — and spend the evening exploring this sensational place.

Day 7 & 8 — Bari & Farewell

After the drama of Polignano’s cliffs, Day 7 offers a gentle, relaxed transition. You will reach Bari by train, Puglia’s vibrant regional capital, where the day is entirely your own. Wander the winding medieval lanes of Bari Vecchia, where elderly women still sit in doorways hand-rolling orecchiette pasta on wooden boards. Visit the magnificent Basilica di San Nicola, one of the finest examples of southern Italian Romanesque architecture, or simply meander along the seafront promenade as the Adriatic shimmers in the afternoon light.

Bari is also a superb city for food lovers — from street food stalls serving freshly fried panzerotti to upscale restaurants showcasing the region’s extraordinary raw seafood tradition. Browse the covered Mercato del Pesce, sip an aperitivo in Piazza Mercantile, and let the warmth and generosity of Apulian culture carry you through one final memorable evening in Puglia.

On Day 8, you can easily reach nearby Bari Airport by train for your return flight. You’ll leave with memory cards full, pleasantly tired legs, and a deep love for one of the most authentic and beautiful regions in Europe.