Imagine one country offering twenty vastly different holidays. This is the beauty of Italy.
Every one of the twenty regions has a different landscape, different food and traditions, different festivals. Puglia, the land of fifty million olive trees is a joy to discover with its whitewashed towns on the Adriatic coast and picture perfect villages like Locorotondo and Alberobello.
Just the names make you want to go there. Italy’s southernmost region has an 800 kilometre coastline where the blue Ionian sea dazzles spectacularly.
Itinerary
Rome x 2 days
There is never enough time to discover Rome, perhaps the iconic must-see landmarks, but not the secret Rome. Many years ago I met Ferdinando, a passionate guide and archaeologist, who told me “you could live in the historic centre of Rome for a year and still not see everything”. It is so true. On our first day we discover beautiful cobblestoned alleyways devoid of tourists, hidden corners and quiet neighbourhoods. You will hear the stories behind an imposing door, shuttered window, intriguing shop, ancient trattoria – in fact, the oldest in Rome, and where to find the best gelato!
The second day is full of quintessential Italian experiences for you to choose from to create your unforgettable memory of Rome.
Matera x 3 days
After breakfast we take the one hour train journey to Naples where our driver will be waiting to transfer us to Matera which is a three hour scenic drive. Rarely will you experience a place like Matera. First glimpse will take your breath away. It has a timeless landscape, almost biblical, that gives you a surreal feeling of having stepped back in time.
Unlike many hilltop towns that are built on rock, Matera is built into it. The rock cut dwellings of Sasso Barisano and Sasso Caveoso are stacked nine levels high, layer upon layer where one person’s floor is another person’s ceiling. We sleep and eat in old caves that have been painstakingly restored into boutique hotels and restaurants.
Matera is a dramatic story of rebirth from being known as the national disgrace of Italy in the 1950s to the pride of Italy as the winner of European Capital of Culture in 2019. It is a story you’ll want to hear.
Monopoli x 2 days
Leaving the region of Basilicata via private transfer, it takes just over an hour to arrive in our charming town of Monopoli in Puglia, located on the edge of the Adriatic sea. Like many towns in this part of the region, Monopoli’s historic centre is built of white stone and dotted with white-washed buildings which contrast perfectly with the vibrant blue sky and sea.
Less than ten minutes away is a great day out at the seaside town of Polignano a Mare, famous for three things: cliff jumping at the iconic Cala Porto; outstanding gelato and the birthplace of Domenico Modugno, who wrote the Italian hit song Volare.
Ostuni x 3 days
Known as the White City, this whitewashed medieval town sits on top of a hill overlooking a carpet of olive trees all the way to the Adriatic sea, eight kilometres away. Steps, staircases, arches and a labyrinth of alleys with hints of the Middle Ages make it a joy to surrender any sense of direction and wander aimlessly.
A big day out via private transfer is a visit to the towns of Locorotondo and Alberobello. Officially one of the Borghi piu belli d’Italia – most beautiful villages in Italy, Locorotondo is simply gorgeous. The historic centre, perched on the top of a hill, is circular and a whitewashed maze of little lanes lined with historic buildings, some humble and faded, others retaining rather grand baroque archways and detailed architecture.
Only ten minutes away is the fairytale town of Alberobello with its clusters of trulli, small dry stone huts with conical roofs. Declared a UNESCO World Heritage Site in 1996, there are two neighbourhoods to explore with more than 1000 trulli in Rione Monti and 400 in Rione Aia Piccola.
Gallipoli x 3 days
Driving down the coast, we stop in the beautiful city of Lecce for lunch. Lecce’s history dates back thousands of years and is known for its stunning baroque architecture and Roman amphitheatre built in the second century BC. On to Otranto, an enchanting town clinging to the south-easterly tip of Italy opposite Albania on the other side of the Adriatic sea. The historic centre is on a low promontory overlooking the bay and is still enclosed with fortification walls, preserving its ancient atmosphere.
Only 45 minutes away is Gallipoli, where we stay in the historic centre that is linked to the mainland by a 16th century bridge. Surrounded on all sides by the sparkling Ionian sea and home to an ancient fishing harbour, the old town is a network of narrow streets, historical buildings and lively piazzas. The perfect place to be on the water, whether swimming, kayaking or boating.
Naples x 1 day
After breakfast we depart Gallipoli via private transfer for Naples. Staying in the Spanish Quarter, you are in the heart and soul of the historic centre where life is noisy, vibrant and full of energy.
Tour Inclusions
Your Italian adventure includes:
Deb is your Tour Leader from the start of the journey to the end
Accommodation x 14 nights in a twin share/double room in boutique hotels or villas centrally located
Hotel city taxes
Breakfast every day
Taxis from Hotel Gregoriana to Termini Station
Train Rome to Naples
Transfers in private, luxury airconditioned minibus:
- Naples to Matera
- Matera to Monopoli
- Monopoli to Ostuni
- Ostuni to Locorotondo and Alberobello – full day
- Ostuni to Lecce, Otranto and Gallipoli – full day
- Gallipoli to Naples
Taxi transfers from Matera to the Sassi return
Train ticket Monopoli to Polignano a Mare return
Entry fee to Palombaro Lungo Cistern in Matera
Entry fee to the cave house of Vico Solitario in Matera
Gratuities for drivers
Dates & Rates
1st to 15th October, 2026
Package: 15 days / 14 nights
$6,650 per person for twin/double accommodation. Single supplement $1,550.
Email deb@ciaoitaly.com.au for full itinerary.
