Daydreaming in the Mezzogiorno | Round trips Italy

Southern Italy was also called 'Magna Graecia', 'Great Greece', in ancient times. Starting in 750 BC, the Greek colonised the mainland coast and the islands around it. Later the rule of the region fell into Roman hands, and even later numerous other rulers followed, whose traces can still be found today in this fascinating region.

This experience trip combines the best of what Southern Italy has to offer: Pompeii - the buried city - with a wealth of culture and history, Puglia with its unique cone-shaped 'trulli' and its baroque towns, the unspoilt Basilicata with the cave dwellings of Matera, protected by UNESCO, and Campania with its impressive temples and its unspoilt coastlines.

DAY 1: Departure to Naples

Your journey begins at the airport, anticipation building as you board your flight to Naples. Upon arrival, you collect your rental car and drive towards one of our favourite locations near Sorrento.

DAY 2: Pompeii and Herculaneum

You visit the archaeological remains of two cities buried by Mount Vesuvius in AD 79, where everyday life still feels remarkably tangible. Caractère arranges a local guide who brings these ancient cities to life and explains how people once lived here.

DAY 3: Capri

From Sorrento, you take the ferry to Capri. A short crossing with endless views brings you to this iconic island. Ride the funicular to the top, wander through lively streets, or explore the island from the sea by boat.

DAY 4: Mount Vesuvius

Lace up your hiking shoes and prepare for a rewarding climb. At the summit of the dormant volcano, you see the traces of centuries-old eruptions. On clear days, the views are breathtaking. Later, unwind by the hotel pool or stroll through the charming streets of Sorrento.

DAY 5: The Amalfi Coast

Today you drive along the spectacular Amalfi Coast, stopping in Positano, in Amalfi with its cathedral, and in beautifully situated Ravello. Visit Villa Rufolo and Villa Cimbrone for their extraordinary views. Prefer a deeper dive? A private guide can accompany you along the coast.

DAYS 6 and 7: Sorrento – Matera

You leave the Bay of Naples and travel to Matera in Basilicata. You stay in the heart of the sassi, ancient cave dwellings protected by UNESCO. Explore Sasso Barisano and Sasso Caveoso and their many rock-cut churches.

DAY 8: Puglia

You swap the sassi for trulli as you continue to Puglia. You stay in the northern part of the region, an ideal base to explore the area. It is also possible to divide your final nights between the north and the region around Otranto.

DAY 9: Locorotondo / Alberobello

A fun fact: Locorotondo is the only town listed in the Guinness Book of Records with five “O’s” in its name. Above all, it is a welcoming, authentic village with excellent restaurants. Alberobello features the largest concentration of trulli, though it can be busy in high season.

DAY 10: Castellana Caves / Polignano a Mare

Visit the impressive Castellana Caves, Italy’s most renowned speleological site. Another Puglia highlight is Polignano a Mare, where the sea crashes against dramatic cliffs. Explore the old town, or head out on a sea kayak for a touch of adventure.

DAY 11: Monopoli

This charming coastal town is known for its historic centre, narrow streets filled with shops and atmospheric squares. Its rich past, dating back to Greek and Roman times, shows in landmarks such as the Castle of Charles V and the cathedral of Maria Santissima della Madia.

DAY 12: Lecce

You drive to the far south to visit Lecce, the baroque highlight of southern Italy. Alongside the magnificent Basilica of Santa Croce, the lively Piazza Sant’Oronzo and Piazza del Duomo invite you to linger.

DAY 13: Return home

You return to Naples airport and hand in the rental car. During the flight home, memories of this Italian journey linger on.

Frequently asked questions

Do I need a rental car for this journey through Puglia?

Yes. A rental car is essential. Distances are manageable, but the real beauty lies in the stops along the way: abandoned trulli in the Valle d’Itria, a masseria pressing its own olive oil, or the harbour town of Otranto with its Byzantine mosaics. Routes take you through landscapes untouched by public transport. All hotels provide parking, often shaded by vine-covered pergolas.

What is the best time to visit Puglia?

May, June and early October are ideal, with temperatures between 24 and 28 °C. The Ionian Sea reaches a pleasant 22–25 °C. September stands out, with grape harvests, local festivals and a warm, golden light. July and August are best avoided due to heat and crowds.

What atmosphere can I expect across these regions of Puglia?

Ostuni enchants with whitewashed streets and quiet corners. Lecce feels more vibrant, animated by students, artisans and late-night wine bars. The Ionian coast moves at a slower pace, with fishing villages, olive groves and peaceful beaches. The journey unfolds from picturesque to cultural to contemplative.