22 days
Level 2 - Moderate

Ancient History of Southern Italy & Sicily: small group tour for seniors

Join Odyssey Traveller on this Southern Italy tour as we traverse the lesser known islands and southern regions of the country. When you ask people about the must-see sights for tours of Italy, more often than not one of the first places they mention is the capital city, Rome, or the submerged streets of Venice, or the sights of Florence, birthplace of the Renaissance. But there is more to Italy than its northern region. Head further south from Rome into the region called “Southern Italy” and the crowds will begin to thin and life will start to move at a slower pace. Here you will see the cave dwellings of Matera; the ruins of Pompeii; Mount Vesuvius, the only active volcano in mainland Europe; and the gorgeous Amalfi Coast.

We go beyond the typical Southern Italy itinerary on our trip. During our educational tour, you will witness the dramatic, rugged countryside of the lower part of Italy's "boot" as we explore the ancient ruins, unique treasures, and diversity of Southern Italy. We learn about the influence of the early Phoenicians, Greeks, Romans, Byzantines, Saracens, Normans, Angevins and Aragonese while we search for evidence of their colonisation. We will also go on a cities tour and enjoy wine-tasting and a sampling of Southern Italian cuisine.

For the medieval traveller, religious houses provided a safe and convenient refuge. This tradition still exists in Italy and, as travellers, participants in this tour will sometimes stay in the modern-day version of these ancient religious houses.

Small Group Tours Southern Italy Itinerary

After arriving in Bari, we explore this picturesque port city, shaped by an almost continuous stream of invasion and conquest. The tour also includes Calabria, its brooding mountainous terrain stretching southwards between the Ionian and Tyrrhenian Seas; Sicily, the Mediterranean’s largest island, epitomising centuries of successive waves of colonisation; and the Aeolian Islands, steeped in antiquity and scattered like a string of pearls in the Tyrrhenian Sea.

After meeting in Bari, our escorted small group tour begins in earnest in Apulia. Here we take a walking tour of the city and explore the distinctive food and wine of the region. From there we head to the nearby Alberobello. Because of its location, Apulia was a major thoroughfare between the ancient Greek and Roman worlds and has been subjected to constant colonisation and invasion, which has shaped the very nature of its people. This heritage has resulted in a rich mixture of historic architectural styles. Now a secluded off the beaten tourist track part of Italy, Apulia has many surprises on offer. Our next stop is Calabria, before Sicily, where we spend ten nights exploring the region. We then head back to Naples, where our educational tour concludes.

Other destinations and highlights of this small group tour include wine tasting in Alcamo, visiting the rock dwellings and “Sassi” of Matera, and discovering the culture and countryside of Sicily, from the ancient citadel of Lipari on the Aeolian Islands to the superlative Greek remains. We also experience the 12th century mosaics in the cathedral of Monreale, and take in the Norman Capella Palatina in Palermo, with its Byzantine artistry. Another highlight is the chance to explore Apulia, with its peculiar conical-roofed, stone trulli church and houses.

For more details, click the ‘Top 5’ or ‘Itinerary’ buttons above! If you’re keen to experience this tour, please call or send an email. Or, to book, simply fill in the form on the right hand side of this page.

You can also begin by reading our articles on Southern Italy:

Frequently Asked Questions About Southern Italy and Sicily

When you are asked about tourism nightmares, the big-bus tours usually come to mind: 40 to 50 people descending upon a place and by their very presence wiping out the adjectives that the tourism brochures may have used to describe it: “charming”, “cozy”, “idyllic”. In search for more “authentic” experiences, where one can feel more like a person travelling with friends than a sheep in a herd, more and more people are gravitating towards smaller groups–and the smaller, the better. Odyssey Traveller specialises in crafting unforgettable experiences for senior or mature-aged travellers, providing adventure and educational programs to small groups since 1983. A “small group” for Odyssey is typically up to 18 travellers. This is a comfortable alternative to big-bus tours for large groups. You can read more about why we do small group tours here (https://www.odysseytraveller.com/articles/join-small-group-tour/).

Travellers seeking a more laid-back pace (and a thinner holiday crowd) fly to Southern Italy to bask in its sunshine, try its diverse cuisine, and view its historic sites. One of our Top 5 for Southern Italy is Matera in Basilicata, famous for its sassi or cave dwellings, a network of human settlements carved into limestone, first inhabited during the Paleolithic. Later dwellings consisted of homes, shops, churches, and monasteries built into the natural caves of the Murgia Plateau. The Sassi of Matera are included in the UNESCO World Heritage List. In the 1950’s the caves housed the city’s poorest, until the government moved them out of the virtually uninhabitable dwellings and did major renovations in the area. Now travellers can stay in cave B&B’s and eat in cave restaurants offering exceptional views of this ancient settlement.

Southern Italy has a Mediterranean climate, which means warm dry summers and relatively mild winters. You’ll be comfortable in light clothing, but if you are joining our September and January departures it might be best to pack outerwear, like a light jacket, for use in the evening and in case the weather turns. Sun protection is essential, so please include sunscreen, hat, and sunglasses on your list. Modest clothing should be worn when visiting religious buildings and sites as well as smaller, traditional communities, so keep this in mind when you pack.

PDF of Tour PDF of Reading List

Overview: On arrival in Bari, you will make your own way to the hotel. Having had time to unpack and settle in, you will get the chance to meet the tour leader and the rest of the group during an introductory meeting, followed by dinner at the hotel.

Accommodation: Hotel Adria or similar.

Overview: In the morning we enjoy a guided tour of Bari. Bari is a port city on the Adriatic Sea, and the capital of southern Italy’s Puglia (Apulia) region. Its maze-like old town, Bari Vecchia, is on a headland next to the port. Urban Bari offers a lively atmosphere full of culture and tradition; Trattorias line the streets, and the Basilica di San Nicola is said to house the bones of St Nicholas.

In the afternoon we travel southwards to Alberobello, which will be our base for the next five days. Located in the heel of Italy’s boot, the strategic significance of the region over several millennia has left behind a rich and varied history. It was a major thoroughfare between the ancient Greek and Roman worlds and has been subjected to constant colonisation and invasion since, which has resulted in a remarkable range of architectural styles and ruins. The region has a distinct feel from the Northern Italian hot-spots that many tourists are accustomed to, and was only integrated into what we recognise as modern Italy towards the end of the 19th century.

We will conclude our day with dinner at a local restaurant.

Accommodation: 5 nights at Hotel Lanzilotta or similar.

Overview: Our destination today is Matera, located approximately one and a half hours from Alberobello. Matera is a striking and atmospheric town located in the remote southern region of Basilicata (also called Lucania). It’s famous for its extensive cave-dwelling districts, the sassi. The old town is a UNESCO heritage site, and we will have a guided tour to really make the most of its fascinating past. We visit the Chiesa San Pietro Barisano, Matera’s largest rupestrian church dating back to the 12th century. We learn about the district and its history at the Casa Noha Museum, and visit the distinctive Aragonese-style Castello Tramontano.

Later in the day we will explore the Palombaro Lungo, the underground cistern, and the Museo Nazionale a’Arte Medievale e Moderna della Basilicata. We will then drive back to the hotel, where we will have a group dinner.

Accommodation: Hotel Lanzilotta or similar.

Overview: Today we will meet our local guide for a full day tour of the area including a visit to the towns of Locorotondo and Martina Franca. Locorotondo is known as one of the most beautiful villages of Italy, with its whitewashed cone-roofed trulli houses as well as its wines, the historic centre is on a hill with lovely views over the Valle d’ Intria. Martina Franca is another picturesque town with winding alleys, whitewashed houses in its old quarter but also features lovely baroque and rococo buildings and airy piazzas. Here, we view the Basilica of San Martino and visit Acropoli di Puglia – a traditional olive store.

Accommodation: Hotel Lanzilotta or similar.

Overview: After breakfast we travel to Lecce, also known as “The Florence of the South” due to the rich baroque architecture of the city. We enjoy a guided tour of the main sights, including the Roman Ampitheatre and Basilica di Santa Croce, followed by some free time to explore before returning to Alberobello.

Accommodation: Hotel Lanzilotta or similar.

Overview: Ostuni, another small hilltop town is perhaps one of the most well-known in the region. The area has been inhabited since the Stone age, destroyed during the Punic Wars, and later rebuilt by the Greeks, who named it Ostuni, from the Greek Astu neon (“new town”). We have plenty of time to explore the town before returning to our hotel.

Accommodation: Hotel Lanzilotta or similar.

Overview: Today we depart Apulia region and travel southwest to the town of Metaponto, in the Basilicata region.  The town is located by the Ionioan Coast and is composed of the main village and Metaponto Lido, the beach area. Between them lie the ruins of Metapontum, an ancient Greek Achaen colony.


Accommodation: Borgo Ritrovato or similar.

Overview: En route to Briatico we pause at Cosenza, where we visit Sila National Park on a guided tour. Calabria, the “toe” of Italy, was occupied by the Greeks. Ever since those living in this part of Italy supported the cause against the Romans, the region has been dominated by foreign powers: Romans, Saracens, Normans, Swabians, Aragonese and Spanish. This has given rise to a proud and independent culture reflected in the magnificence of the environment. From this rugged and dramatic land of rural villages and mountainous terrain, many Italian emigrants brought to the Antipodes their traditional culture that has helped shape the persona of their new home.

Accommodation: 2 nights at Popilia Resort or similar.

Overview: In the morning we transfer to Stilo, a small town that has been named one of the most beautiful hamlets of Italy. The local economy is based on the agriculture, mainly the production of wine, cheese, olive oil and cereals. Here, we visit the main sights and then continue to Gerace, a town that stands on a hill formed of clusters of 60-million-year-old sea fossils. The main attractions of Gerace are the remains of the old Norman Castle and the perfectly preserved medieval town. Later, we return to Briatico.

Accommodation: Popilia Resort or similar.

Overview: After breakfast we depart Calabria and head to Sicily. On the way we stop at Tropea, a lovely seaside town. The most famous view of Tropea is the large rock outcrop jutting into the sea opposite the centre of town. We continue to Reggio Calabria where we visit the Museo Nazionale Della Magna Grecia. Later we make our way to the port to board our ferry to Messina, Sicily.

The Mediterranean’s largest island suffered, like Calabria, from its strategic position near “the middle of the world”. Its history recounts stories of constant invasion and colonisation and its cultural heritage has been shaped by the many different peoples who have occupied it over centuries. Its natural features range from the lofty, smouldering Mount Etna to the tiny volcanic Aeolian Islands where we discover many examples of former civilizations: from Phoenician and Carthaginian cities to Greek temples, Roman relics, Byzantine mosaics, Saracen domes and Norman castles and churches.

We stay in Milazzo tonight.

Accommodation: Eolian Milazzo Hotel or similar.

Overview: We start our day by travelling by ferry to the Aeolian Islands: seven small inhabited islands off the northern shore of Sicily. The archipelago was formed by volcanic activity and two of the islands still have active volcanoes. We visit the Vulcano Porto, as well as the city of Lipari, before transferring to Acireale.

Accommodation: 4 nights at Santa Caterina Hotel or similar.

Overview: Today we explore Siracusa, located approximately one-hour drive south of Acireale. Siracusa is a large town including island and mainland districts. Many of its attractions are archaeological and historical. It was home to Archimedes and its Greek theatre still stands, with classic dramas performed there each year.  We visit the main sights with our local guide and also explore the island of Ortygia, the historical heart of Siracusa.

Accommodation: Santa Caterina Hotel or similar.

Overview: Our local guide will spend the day with us visiting the Etna area and Taormina, with its famous Greek theatre high above the sea and facing Etna.

Accommodation: Santa Caterina Hotel or similar.

Overview: After breakfast we enjoy a city tour of Catania, the birthplace of composer Vincenzo Bellini. The town is situated between the Ionian Sea and Mount Etna. Here we visit the ruins from the ancient city and see the wealth of fine baroque architecture. There will be some free time to discover the city at your leisure before we return to our hotel in Acireale.

Accommodation: Santa Caterina Hotel or similar.

Overview: Today we depart for Agrigento via Caltagirone, where we visit the town’s main sights including the Roman Villa of Piazza Amerina. We also visit the Museo Regionale della Ceramica, before continuing on our way. We spend the next two nights at:

Accommodation: 2 nights at Hotel Agrigento or similar.

Overview: In the morning we visit the UNESCO World Heritage site of Valle dei Templi (Valley of the Temples), one of the greatest legacies of ancient Greece. The ruins are what remains of the ancient Greek city of Akragas. The town’s archaeological museum is also on our list of places to explore today; it holds a wide range of exhibits from the area. The afternoon is free for your leisure.

Accommodation: Hotel Agrigento or similar.

Overview: Today we depart for Palemo. En route, we stop for a guided tour of Selinunte, home of one of Sicily’s great Greek archaeological sites. The archaeological park encompasses temples, ancient town walls, ruins of residential and commercial buildings as well as zones not yet excavated. As it’s set next to the sea in the south-western corner of Sicily, it also offers stunning views. We continue on to Erice for a short visit before arriving at Palermo: our base for the next four nights.

Accommodation: 3 nights at Hotel ibis Styles Palermo or similar.

Overview: Our travels take us to Cefalu today; a charming historic seaside town where we take a guided tour. The remainder of the day is free to enjoy at your leisure here, and then back in Palermo.

Accommodation: Hotel ibis Styles Palermo or similar.

Overview: Today we travel west to the town of Segesta, originally founded by the Elyman people – one of the three indigenous peoples of Sicily – and later integrated with the Greeks. The archaeological complex is set up high in the mountains, where we visit the Doric Temples and Hellenic Theatre. Later we drive back via Alcamo where we have the opportunity to visit a local wine producer and sample their drop.

Accommodation: Hotel ibis Styles Palermo or similar.

Overview: On our last day in Sicily we explore Palermo on a full day tour of Sicily’s cultural, economic and touristic capital. We also take a short trip to Monreale, a town just outside Palermo and famous for its mosaic-adorned Norman cathedral. Later, we transfer to the port for our overnight ferry to Naples.

Accommodation: Overnight cabin on the ferry.

Overview: On arrival, we are picked up at the port and taken out for breakfast in a local café. This is followed by a half-day tour of Naples. The afternoon is free to relax and, in the evening, we gather for the last time as a group for our farewell dinner.

Accommodation: Naples Hotel or similar.

Overview: Our tour concludes today after breakfast at the hotel.

Visit the rock dwellings and “Sassi” of Matera.
Discover the culture and countryside of Sicily from the ancient citadel of Lipari on the Aeolian Islands to the superlative Greek remains.
Marvel at12th century mosaics in the cathedral of Monreale and the Norman Capella Palatina in Palermo, with its Byzantine artistry.
Calabria in the ‘toe’ of Italy with cliff-hugging Tropea and Byzantine Gerace.
Explore Apulia with its peculiar conical-roofed, stone trulli church and houses.

What’s included in our Tour

  • 20 nights hotel accommodation
  • 1 night on board overnight ferry from Palermo to Naples (Single cabins may not be available)
  • 20 Typical local breakfasts at hotels.
  • 13 dinners at the hotel or local restaurants.
  • Touring by comfortable and modern coach.
  • Transport, lectures and field trips as indicated.
  • Applicable entry fees and services of local guides.
  • Services of a Tour Leader.
  • Service Charges and Gratuities.
  • Detailed Tour Information Booklet.

What’s not included in our Tour

  • International airfares and taxes
  • Airport transfers
  • Meals not included in the itinerary
  • Comprehensive travel insurance
  • Items of personal nature like laundry, phone calls, etc
Ancient History of Southern Italy - Island Procida near Naples, Italy
Island Procida near Naples, Italy
Matera, Southern Italy
Polignano al mare, Puglia, Italy
Italy, vintage, travel
Cefalu, Sicily
Noto Sicily Southern Italy
Fontana Pretoria in Palermo
Piazza Pretoria, Sicily, Italy
Cathedral of Palermo, Sicily Italy
Harbour in Cefalu, Sicily, Southern Italy travel
Agrigento Temples
Palermo Sicily
A street in Palermo, Sicily
Sicilian people
Southern Italy
Ostuni white town skyline, Apulia, southern Italy.

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