The 'heel' of the 'boot' of Italy is a beautiful landscape known for its whitewashed hill towns, centuries-old farmlands and cave dwellings, and hundreds of miles of Mediterranean coastline.
Chapter 1: Puglia
DAY 1: Puglia Adventure Begins
One of our most asked-about itineraries begins in the heart of Polignano a Mare.
Discovery Walk: Heart of Polignano a Mare
This afternoon, join your Now Journey Tour Captain for a Discovery Walk through stunning Polignano a Mare — birthplace of Mr. Volare himself, Domenico Modugno. Explore seaside terraces, dramatic cliffs, and the iconic Lama Monachile bridge on this unforgettable stroll.
Welcome Dinner
Tonight enjoy entertaining your palete with cuisine from the land and sea at one of the most iconic locations in all of the south of Italy. Your Journey Tour Captain welcomes you to Puglia.
Now Journey Cuisine is authentically Italian: Now Journey’s dining is as authentic as Italy itself — featuring family-owned restaurants with farm- and sea-to-table cuisine. Enjoy premium beverages and full menu choice at every dinner. In Puglia, savor fresh pasta, seafood, local vegetables, and homegrown flavors rooted in tradition.
Where We Stay in Polignano a Mare,2 Nights with breakfast
Now Journey Hotels Collection —
Covo dei Saraceni or Villa Stay on Select Departures, or Similar Properties
— Our hotels feature 4 to 5-Star properties including entry-level room categories in 5-Star, and one category above entry-level in 4-Star. Final hotel assignments are made at around 60 days prior to the adventure.
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DAY 2: POLIGNANO A MARE
Breakfast included daily
Today's Adventure: Tasting Polignano a Mare
This morning (some itineraries feature an afternoon experience) we enjoy exploring Polignano a Mare. Tastes in Town: The traditional Panzerotto stuffed with mozzarella and tomato sauce are a local favorite as well as the typical Apulian cold cuts with Focaccia.
After the experience, enjoy the balance of the day at leisure.
Tonight, consider joining your Tour Captain to an optional dinner or explore at your leisure.
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Chapter 2: Basilicata
DAY 3: ALBEROBELLO & THE TRULLI HOUSES TO MATERA
Today's Adventure: Alberobello, Trulli and Sassi
After a delicious breakfast, set out with your Tour Captain on a scenic drive through the rolling countryside of Puglia — olive groves, dry-stone walls, and wide Mediterranean skies guiding the way.
Our first stop is Alberobello, a storybook town unlike anywhere else in the world. Recognized as a UNESCO World Heritage Site, Alberobello is famed for its whimsical trulli — whitewashed stone homes crowned with conical roofs that seem lifted from folklore. With our Local Guide, wander through the Rione Monti district and discover the symbolism behind the painted roof markings, the history of these ingenious limestone dwellings, and the charm of the Trullo Sovrano, the only two-story trullo in town. We’ll also visit the distinctive Church of Saint Anthony of Padua, built in trullo style — a rare architectural treasure.
After time to explore and enjoy lunch at your leisure — perhaps a rustic osteria featuring local burrata and handmade orecchiette — we continue onward.
This afternoon we arrive in Matera, one of Europe’s most extraordinary cities. Carved into limestone cliffs, Matera’s ancient cave dwellings and dramatic ravines create a landscape both haunting and beautiful. As you settle in, you’ll feel it — the sense that you’ve stepped into another era.
Here, among stone pathways and candlelit courtyards, the next chapter of your Journey begins.
Welcome to Matera – Apericena
Tonight join your Tour Captain and fellow travelers for the new Italian meal, Apericena! Is it a snack? Is it dinner? No, it’s apericena! A combination of aperitivo and dinner - most of all, it’s fun! We will enjoy apericena in a picturesque location in Matera.
Where We Stay in Matera - 2 Nights with Breakfast
Now Journey Hotels Collection —
Quarry Resort, Aquatio Cave Luxury Hotel & Spa, Sant’Angelo Luxury Resort or Similar
— Our hotels feature 4 to 5-Star properties including entry-level room categories in 5-Star, and one category above entry-level in 4-Star. Final hotel assignments are made at around 60 days prior to the adventure.
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DAY 4: EXPLORING MATERA
Today's Adventure: Secrets & Treasures of Matera
After breakfast, step into a world that feels suspended in time. Together with your Tour Captain and expert Local Guide, you’ll explore the extraordinary Sassi di Matera, a UNESCO World Heritage Site unlike any other in Europe.
Set within the ancient city of Matera, the Sassi are a labyrinth of stone dwellings carved directly into limestone cliffs — homes, chapels, cisterns, and passageways layered over thousands of years of human history. As you wander narrow alleys and sweeping viewpoints, you’ll discover how generations once lived in these cave homes, adapting ingeniously to the rugged landscape.
We’ll step inside restored cave dwellings to understand daily life of the past, and visit remarkable rock-hewn churches adorned with faded Byzantine frescoes — quiet spaces that still hold a sense of reverence and mystery. The views across the Gravina ravine are breathtaking, especially as the morning light illuminates the honey-colored stone.
Matera is not simply a place you visit; it’s a place you feel. Today’s exploration reveals resilience, beauty, and the enduring spirit of one of the world’s oldest continuously inhabited settlements.
Then enjoy some time at leisure to explore this amazing destination.
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Chapter 3: Lecce
DAY 5: TO LECCE
After breakfast, we bid farewell to Matera in Basilicata and travel to Lecce, our home for the next 3 nights. We travel further into the “heel of Italy” and discover more beauty, amazing people and, of course, delicious cuisine and vino.
Today's Adventure: Making our Way to Lecce: 'Florence of the South'
On arrival in Lecce in mid-afternoon, we check into our beautiful resort hotel and have time to freshen up before joining the Tour Captain for an orientation Discovery Walk in the Baroque city center. Later join the Tour Captain and your fellow travelers for a traditional Apulian dinner.
Welcome Dinner
Tonight enjoy a traditional Apulian dinner in Lecce with your Tour Captain and fellow travelers. Perhaps you will try the signature regional pasta shape, orecchiette.
Where We Stay in Lecce, 3 Nights with breakfast
Now Journey Hotels Collection —
Risorgimento Resort and Spa or Patria Palace Hotel or Similar
— 4 to 5-Star properties including entry-level room categories in 5-Star, and one category above entry-level in 4-Star. Final hotel assignments are made at around 60 days prior to the adventure.
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DAY 6: EXPLORING LECCE
Today's Adventure: Tour of Lecce
Today we step into the golden glow of Lecce, often called the “Florence of the South.” With our expert Local Guide leading the way, you’ll discover why this elegant city is considered one of Italy’s great Baroque masterpieces. Wander through honey-colored streets sculpted from Lecce’s soft pietra leccese stone, allowing extraordinary detail to flourish on every façade.
We’ll admire the exuberant artistry of the Basilica di Santa Croce, whose intricate carvings seem almost theatrical in their expression. In Piazza del Duomo, one of Italy’s most harmonious cathedral squares, you’ll feel the quiet grandeur of centuries past as we explore the cathedral and its surrounding palaces.
Our journey also reaches deeper into Lecce’s Roman roots with a visit to the remarkably preserved Roman Amphitheatre of Lecce, where echoes of ancient spectacles still linger beneath the modern city. Along the way, expect moments to pause — perhaps for a café in a sunlit piazza, or to admire artisan workshops carrying on traditions that define this soulful southern city. Lecce isn’t just beautiful; it’s atmospheric, intimate, and proudly distinct.
We take our time today. Look up. Notice the details.
Lecce rewards the curious traveler.
Tonight, consider joining your Tour Captain for an optional dinner or explore at your leisure.
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DAY 7: OPTION TO OTRANTO OR DAY AT LEISURE
Today's Optional Adventure: Secrets & Treasurse of Otranto
After breakfast today, we invite you to join the Tour Captain to travel to Otranto for a day of exploring (no additional charge). We will visit the picturesque town of Otranto where we will have time to walk and explor its fascinating architecture and history and free time for shopping or just wandering. Following lunch on our own, we continue our exploration of the Salento peninsula as we make our way back to Lecce.
Our Special Now Journey Finalé
Meet tonight for our special Apericena to celebrate our time together. Our days have been filled with new sights, tastes and discoveries - tonight enjoy reflecting on the incredible journey we've had together.
It has been a Journey of adventure and discovery, along with making new friends! Until our next Journey — Arrivederci!
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DAY 8: DEPARTURE DAY: Arrivederci Italy!
We say Arrivederci to Lecce today or perhaps you extend your stay to the Amalfi Coast.
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