Your itinerary
Day 1
Adventure begins in Matera
The town of Matera is a real jewel of southern Italy, and our hotel is just a short walk from the historic centre. There is usually time in the afternoon to wander through the narrow alleys of the town’s Unesco-listed cave-dwelling district and enjoy the unique atmosphere of this enchanting city.For millennia, inhabitants of this region have carved dwellings directly into ravines and gullies made of tuff (or tufa), a characteristic honey-coloured soft stone. These houses are called Sassi and are a Unesco World Heritage site. Matera is the only place in the world where people still live in the same houses as their ancestors did 9,000 years ago.Around 6pm, say ciao to your tour leader and fellow travellers, when we gather as a group to get to know each other and learn more about the adventures ahead. Your tour leader then ensures a big welcome over a group dinner.Want more time in Matera? Speak to your sales representative about adding extra nights.
Meals: Dinner
Day 2
Ride past the historic Sassi houses of Matera before heading to Alberobello
On leaving Matera, we pedal through the area that makes this town so special. Today’s ride is mostly hilly with gentle ascents throughout, as we cycle on quiet rural roads among the picturesque Apulian countryside towards Alberobello. We’ll pass the lovely towns of Noci and Gioia del Colle plus fairytale trulli houses that have made the historic centre of Alberobello another World Heritage site.
Meals: Breakfast
Day 3
Cycle through the lush Valle d'Itria, past the fairytale trulli houses to the hilltop town of Ostuni
Today we cycle through the lush Valle d’Itria, one of the prettiest cultural and natural landscapes in southern Italy, to the hilltop town of Ostuni. The route is rolling throughout but much shorter than yesterday’s ride. This allows us to enjoy the views at a more leisurely pace with plenty of opportunities for rest stops. Along the way we pass the wine town of Locorotondo and Cisternino, both known for their historic centres filled with whitewashed houses, narrow streets, churches and elegant piazzas. In the afternoon, we reach Ostuni, known as the White City thanks to the dazzling effect of its white buildings.
Meals: Breakfast
Day 4
Ride through quaint villages and country lanes to a typical masseria (renovated farmhouse) where we spend the night
We continue pedalling through tranquil country lanes to the town of Francavilla Fontana and on to Oria. A popular destination among Apulians, Oria is famous for its 13th-century castle and delightful historic centre of cobbled streets, whitewashed walls and beautiful architecture. We continue through the countryside to a masseria, a typical Apulian converted farmhouse and our accommodation for the night. The masseria is still a working farm and most of the produce grown here, from vegetables to olives and wheat, is used daily for the preparation of local dishes. Before dinner we will have the opportunity to taste some organic olive oil produced by the family that runs the farm and accommodation.Upgrade to a junior-suite today – speak to your sales representative for more details
Meals: Breakfast
Day 5
Cycle to the coast and swim in the crystal-clear sea before continuing towards Gallipoli with its old town on a rocky island
From the masseria we cycle towards the Ionian Coast and the beautiful town of Gallipoli, known as the Ionian Pearl with its old town on a rocky island offering fantastic views both to north and south. The town itself has many churches and narrow alleys and was the largest exporter of lamp oil made from olives in the 17th and 18th centuries. There are plenty of opportunities for swimming in the Ionian sea near the popular seaside resort of Porto Cesareo (weather permitting).Upgrade to a suite today – speak to your sales representative for more details
Meals: Breakfast
Day 6
Head towards the Adriatic Sea and the ancient town of Otranto
Leaving the Ionian Sea behind, we head across the peninsula to the Adriatic sea and the ancient Messapian town of Otranto, the easternmost point in Italy. Before dinner there will be time at leisure to explore the medieval town centre. Here the interesting architecture, views, sea-front restaurants and white sandy beaches make it one of the most picturesque towns in Puglia.Upgrade to a superior or deluxe room today – speak to your sales representative for more details
Meals: Breakfast
Day 7
Continue along the shoreline to the beautiful baroque city of Lecce
Today we follow the shoreline through innumerable olive groves to Lecce, the baroque masterpiece of southern Italy, in the heart of Puglia. Sometimes described as the Florence of the South, the city is an architectural gem, with sumptuous palazzi and churches. Today’s ride is relatively short and easy, giving us time to stop for a last swim (seasonal) in Torre dell’Orso, a lovely bay surrounded by limestone cliffs with many ancient caves to discover. In Lecce, there will be free time to explore the historic centre before an optional farewell dinner.
Meals: Breakfast
Day 8
Adventure ends in Lecce
We enjoy our final breakfast of the adventure this morning. But if you’d like an extra day in Lecce to soak up the atmosphere of this elegant baroque city, speak to your sales representative about extending your stay.
Meals: Breakfast
What’s included
What’s not included
Additional information
Food
The included breakfasts usually consist of a continental-style buffet. A typical hotel breakfast consists of toast/bread with jam, cereal, cheese and ham (occasionally), served with coffee, tea, milk, orange juice, fruit, cake and yoghurt.
Lunches are normally arranged as picnics or taken in small cafes along the route. You may opt in to a lunch kitty (€50-€80, depending on the weather/season) to cover the cost of these lunches. The tour leader will collect cash at the welcome meeting and the kitty also covers local city taxes. If you choose not to opt in, the local city taxes should be paid directly to each hotel on check-in.
Vegetarians and people with special dietary requirements can be catered for but please inform us of your requests prior to travel.
In Puglia, you will find authentic regional cooking with strong links to the land and sea – think orecchiette pasta served with a turnip-tops sauce or fresh tomato and sheep’s ricotta cheese, cavatelli with pulses, grilled fish and seafood, burrata, and excellent wines. This region is a paradise for food lovers.
Ionian Coast Ride, Porto Cesareo Swim & Gallipoli Old Town
Follow sunlit lanes toward the Ionian, where dunes and pine scent the breeze. Weather permitting, swim in the crystal-clear waters near Porto Cesareo, a cherished stretch known for gin-clear shallows and soft sand shoals.
Roll into Gallipoli’s old town, perched on a rocky island linked by bridge. Explore fishermen’s lanes, the sea-battered castle, and churches that recall the port’s olive-oil trade—once lighting Europe—before you pause for photos and reflection along the ramparts.
Optional Farewell Dinner in Lecce
Celebrate the journey’s finale with a convivial meal in Lecce, choosing trattoria specialties such as orecchiette alle cime di rapa, silky burrata, and Adriatic seafood, paired with Primitivo or Negroamaro wines. This experience is available at additional cost and bookable on tour.
Between bites, admire baroque facades glowing in evening light and toast to miles ridden and friendships forged—a fitting close in the “Florence of the South.”
Valle d’Itria Cycle & Ostuni ‘White City’ Visit
Pedal through the Valle d’Itria’s vineyards and olive groves, rolling between hill towns famed for their gleaming stone. Locorotondo’s circular lanes and Cisternino’s butchers’ grills scent the air, while trulli punctuate the countryside like giant chalk pebbles.
Climb to Ostuni, the ‘White City’, where sunlit alleys and limestone ramparts spill toward the Adriatic. Admire facades carved from pale local stone and a cathedral skyline etched against cobalt skies, capturing the essence of Puglia’s high-ridge settlements in one evocative panorama.
Oria & Francavilla Ride to Masseria Stay with Olive Oil Tasting
Cycle tranquil backroads to Francavilla Fontana and Oria, where lanes of whitewashed houses wind beneath the silhouette of Frederick II’s 13th-century castle. The route blends pastoral calm with glimpses of Apulian baroque and medieval ramparts.
Settle into a working masseria, then taste organic extra-virgin olive oils pressed from centuries-old trees. Expect grassy, almond-tinged notes and a primer on olive varieties and harvest traditions—an intimate window into Salento’s agricultural heartbeat.
Adriatic Traverse to Otranto Old Town & Cathedral
Cross the Salento peninsula by bike to Italy’s easternmost shore, feeling the landscape shift as olive groves meet wave-cut limestone. The Adriatic breeze guides the final approach to Otranto’s harbor and crenellated walls.
Stroll the lanes to the cathedral to view the famed 12th-century mosaic ‘Tree of Life’ and recall the city’s turbulent past within the Aragonese Castle. The blend of sea air, Byzantine echoes, and Latin stonework gives Otranto a quietly magnetic character.
Coastal Ride to Lecce & Baroque City Highlights
Trace the shoreline past innumerable olive groves, with chances for a seasonal dip at Torre dell’Orso’s limestone bay. Gentle gradients and sea views create an easy, photogenic finale as the Salento sun warms pale cliffs.
Arrive in Lecce and explore its baroque heart: the lacy facade of Basilica di Santa Croce, Piazza del Duomo’s theatrical skyline, and a Roman amphitheatre in golden Lecce stone. Artisans of cartapesta (papier-mâché) keep traditions alive in vaulted workshops.
Hosted Welcome Dinner in Matera
Meet your tour leader and travelling companions for a convivial introduction to the journey, then share a hosted welcome dinner that spotlights Basilicata’s flavors—think Pane di Matera IGP, local cheeses, and dishes enlivened by peperoni cruschi, paired with Aglianico del Vulture.
Conversations flow as the cave-city’s evening glow settles over stone lanes. This warm, guided start fosters camaraderie and offers practical insights for the days of riding ahead.
Matera–Alberobello Ride & Trulli Town Walk
Ride quiet rural roads across rolling farmland toward the limestone plateau of central Puglia, passing stone-walled fields and olive groves en route to Alberobello. Arriving by bike lends a frontier-town feel as fairytale trulli houses begin to pepper the horizon.
Wander amid the Unesco World Heritage site of Alberobello, where whitewashed cones rise in tidy rows. Learn how these dry-stone dwellings evolved, spot mystical roof symbols, and enjoy the tactile charm of hand-hewn limestone before you pause for photos and reflection on a sunlit lane.
Matera Sassi Cave District Walking Exploration
Explore the Unesco-listed Sassi of Matera, a honey-colored labyrinth of cave dwellings carved into tufa. Thread through the rock-hewn lanes of Sasso Barisano and Sasso Caveoso, pausing on terraces that open to ravine views and sun-warmed stone.
Encounter echoes of monastic life in rock-cut churches adorned with medieval frescoes and note the ingenious cisterns and courtyards that sustained this community for millennia. Expect a contemplative mood as you pause for photos and reflection amid one of Italy’s most cinematic urban landscapes.