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Small Group Tour

Ancient History of Southern Italy & Sicily

22 days · Small group · Up to 16 travellers

86% return to travel with us again 40+ years of small-group escorted touring 43,000+ travellers have toured with Odyssey

Tour Overview

From Bari to Sicily, discovering the stories of Southern Italy along the way.

Odyssey Traveller’s fully escorted small-group tours are designed for mature travellers, including solo travellers, couples or friends travelling together.

On this tour we explore the lesser-known islands and southern regions of Italy at a gentler pace. When people think of the country’s must-see sights, they often name Rome, Venice’s canals or Florence, the birthplace of the Renaissance. Yet there is much more to Italy than its northern cities. Travel south from Rome and the crowds begin to thin, revealing a different rhythm of life—and places such as the cave dwellings of Matera, the ruins of Pompeii, Mount Vesuvius and the beautiful Amalfi Coast.

This tour goes beyond the usual Southern Italy itinerary. We explore the rugged landscapes of the country’s southern “boot”, discovering ancient ruins, distinctive towns and the region’s cultural diversity. Along the way, we trace the influence of the Phoenicians, Greeks, Romans, Byzantines, Saracens, Normans, Angevins and Aragonese. We also enjoy local wine and Southern Italian cuisine.

In medieval times, religious houses offered travellers a safe and convenient place to stay. That tradition continues in Italy, and during the tour we sometimes stay in modern guesthouses housed in former religious buildings.

After arriving in Bari, we explore this picturesque port city, shaped by centuries of invasion and conquest. The journey also takes us through Calabria, whose rugged mountains stretch between the Ionian and Tyrrhenian Seas; Sicily, the Mediterranean’s largest island; and the Aeolian Islands, a beautiful archipelago scattered across the Tyrrhenian Sea.

Apulia (Puglia)

The heel of Italy’s boot, Apulia, is gaining recognition for its historic towns, beautiful scenery and relaxed pace of life. A major route between the ancient Greek and Roman worlds, the region has experienced repeated waves of settlement and conquest. Its history is reflected in a rich mix of architectural styles.

Our tour begins in Bari, Apulia’s capital and a lively university and economic centre with a striking historic district. We then base ourselves in Alberobello, a UNESCO World Heritage Site famous for its fairytale-like trulli: whitewashed stone houses topped with conical limestone roofs. Some trulli now serve as shops and tourist accommodation, while many remain homes.

We also visit Lecce, known as the “Florence of the South” for its abundance of Baroque architecture; Martina Franca, with its Baroque and Rococo buildings; and Ostuni, a whitewashed hilltop town with a history stretching back to the Stone Age.

Basilicata

Known in antiquity as Lucania, this small, mountainous region is one of Italy’s hidden gems. Matera is among the world’s oldest continuously inhabited cities. Its ancient cave dwellings, or sassi, create a landscape of stark beauty.

Once associated with poverty and known as Italy’s “national shame”, the sassi were closed by the Italian government in the 1950s. Since the 1980s, they have been restored and opened to visitors. Matera is now a UNESCO World Heritage Site and was named European Capital of Culture in 2019.

We also visit Metaponto, where an extensive archaeological site marks the location of the ancient Greek city of Metapontum. The city was once home to tens of thousands of people, including Pythagoras, who is said to have developed his famous theorem during his exile there in the sixth century BC.

Calabria

If Apulia is Italy’s heel, Calabria is its toe: a rugged peninsula with more than 800 kilometres (500 miles) of Ionian and Tyrrhenian coastline. The Greeks established settlements here in the eighth century BC, including at what is now Reggio Calabria. Successive Roman, Byzantine, Norman, Swabian, Aragonese and Bourbon rulers left their mark, while Greek words remain in local dialects and ancient ruins dot the landscape.

We visit Stilo, one of Italy’s most charming small towns and home to Calabria’s first Byzantine structure; Gerace, with its impressive Norman cathedral and well-preserved medieval centre; and Tropea, a picturesque seaside town.

Sicily

The autonomous island of Sicily has a distinct character. Like the rest of Southern Italy, it has been shaped by successive Greek, Roman, Byzantine, Arab, Norman, German and Bourbon influences.

The legacy of Magna Graecia, or Greater Greece, is visible in the ruins of Agrigento’s Valley of the Temples. In Palermo, Sicily’s bustling capital, Norman, Arab and Byzantine styles come together in magnificent architecture. We also visit Syracuse (Siracusa), where Greek dramas are still performed in an ancient theatre, and Taormina, with Greek ruins overlooking Mount Etna.

From Messina, we take a day tour to the Aeolian Islands, a beautiful archipelago in the Tyrrhenian Sea.

Campania

Home to Naples, Southern Italy’s largest city and Italy’s third-largest, Campania ranges from vibrant urban life to the exclusive resorts of the Amalfi Coast. The region was first inhabited by the ancient Greeks and later became a retreat for wealthy Romans. Naples grew into one of Europe’s largest cities: in 1600, its population of 300,000 made it the continent’s biggest.

Today, Naples is rich in history, art and architecture, from Pompeian frescoes and Caravaggio’s masterpieces to the Baroque grandeur of its historic centre. The haunting ruins of Pompeii live up to their reputation, while the region’s coastline offers famous beaches along the Amalfi Coast, hidden coves on the Sorrento Peninsula, and the contrasting islands of exclusive Capri and relaxed Ischia.

 

Tour highlights

  • 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.

Value built into your journey

What’s included

  • 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.
See all inclusions & exclusions →

The Odyssey difference

Small enough to experience more

One dinner table, shared experience

Our groups are deliberately small enough to dine together around one table—an intimate way to get to know fellow travellers, whether you join as a couple or on your own.

Access that larger groups miss

A smaller group can visit more intimate venues, stay in characterful places, and reach experiences that are often impractical for larger coach parties.

Time to understand a place

Expert Program Leaders and local guides add depth, while a considered pace leaves room to explore, rest, or follow your curiosity.

Discover why travellers choose Odyssey →
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Journey journal

Read, learn & explore before you travel

Expand your journey before departure with destination stories and carefully selected reading that bring the history, art and culture of this tour into sharper focus.

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What's Included:
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

Activity Level

Level 2 - Moderate
Participants must be able to carry their own luggage, climb and descend stairs, be in good health, mobile and able to participate in 3-5 hours of physical activity per day, the equivalent of walking/hiking up to 8 kilometres on uneven ground.
Learn about activity levels

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Prices shown per person

Prices displayed below are per person, twin share occupancy.
Departure Date Price Availability
20 Sep – 11 Oct 2027
$18,750 AUD
✓ Available Book This Date
18 Sep – 9 Oct 2028
$19,600 AUD
✓ Available Book This Date
20 Sep – 11 Oct 2027
$18,750 AUD
✓ Available
Book This Date
18 Sep – 9 Oct 2028
$19,600 AUD
✓ Available
Book This Date

A deposit of A$1,000 per person secures your place. Balance is due 120 days before departure. All prices are per person. View Terms & Conditions.

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Available dates & prices

Choose a departure and room type to see the current tour price. Every departure travels in a small group of up to 16 travellers.

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Prices shown per person, twin share occupancy. Select a departure to view booking details.

Small-group touring with up to 16 travellers Meals: 13D included Comfortable accommodation and expert local guidance A$1,000 deposit per person secures your place

How many travellers?

Twin share Sharing a room with a companion
Solo traveller A room of your own

0 travellers Deposit due today: —

Review your booking details next. Balance due 120 days before departure.

Small-group touring with up to 16 travellers Meals: 13D included Comfortable accommodation and expert local guidance A$1,000 deposit per person secures your place

How many travellers?

Twin share Sharing a room with a companion
Solo traveller A room of your own

0 travellers Deposit due today: —

Review your booking details next. Balance due 120 days before departure.

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Your route

From Bari to Sicily, discovering the stories of Southern Italy along the way.

Follow a carefully paced route through the places, stories and experiences that bring this journey to life. Open any day for the detail behind the itinerary.

Route map for this tour
⌖ 22 days · 10 stops
⌗ View larger map
1 1 day

Bari

You arrive in Bari and settle into your hotel at your own pace, allowing time to refresh after your journey. As evening approaches, you gather with fellow travellers and your tour leader for an introductory meeting, followed by dinner together—the perfect beginning to our shared adventure.

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.

2–6 5 days

Alberobello – Ostuni - Alberobello

We begin in Bari, where the Adriatic port city reveals its layered past through winding medieval streets, the venerable Basilica di San Nicola, and trattorias pulsing with local life. Then we journey south to Alberobello, our home for five days in Italy's heel—a region shaped by millennia of crossing cultures, invasions, and architectural legacies that

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.

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.

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.

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.

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.

7 1 day

Alberobello – Metaponto

We leave behind Apulia's distinctive landscapes and journey southwest into Basilicata, where ancient Greece meets the Ionian shore. Metaponto reveals itself in layers: a modern village and its seaside extension, with the haunting ruins of Metapontum nestled between them—a testament to the Achaean settlers who once claimed these Mediterranean shores.

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.  

8–9 2 days

Briatico – Stilo – Gerace – Briatico

We journey south through Calabria, Italy's storied toe, where ancient Greek settlements gave way to centuries of foreign rule that forged an independent spirit. Pausing in Cosenza, we venture into the wild beauty of Sila National Park, experiencing firsthand the rugged mountains and rural character that shaped generations of emigrants. Their traditions, carried across distant

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.

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.

10 1 day

Briatico – Troea – Reggio Calabria – Messina - Milazzo

We cross the Strait of Messina into Sicily, where centuries of conquest have woven together Greek temples, Roman relics, Byzantine mosaics, and Norman architecture into a rich cultural tapestry. Pausing in the elegant seaside town of Tropea and exploring Reggio Calabria's magnificent Greek antiquities, we ferry across to begin discovering an island shaped by successive

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.

11–14 4 days

Acireale – Etna area – Taormina - Acireale

From the Sicilian coast, we journey by ferry into an ancient volcanic landscape shaped by forces that still stir beneath the earth. The Aeolian Islands reveal themselves as a living laboratory of nature's power—seven islands born from fire, two still breathing with volcanic energy. We explore Vulcano Porto and Lipari before settling into the elegant

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.

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.

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.

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.

15–16 2 days

Agrigento

We journey southward through Sicily's heart, moving from the coastal elegance of Acireale toward the storied interior. In Caltagirone, we explore the town's treasures—its celebrated ceramics tradition and the remarkable Roman Villa of Piazza Amerina—before pressing onward to Agrigento, where ancient grandeur awaits.

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.

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.

17–19 3 days

Palermo – Segesta – Alcamo - Palermo

We journey westward across Sicily toward Palermo, pausing at Selinunte's remarkable archaeological park where ancient temples and weathered stones rest against the sea. Walking among residential ruins and unexplored zones, we encounter the layered history of a great Greek settlement. A brief visit to hilltop Erice punctuates our passage before we settle into Palermo for

Today we depart for Palermo. 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.

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.

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.

20 1 day

Palermo – Monreale - Naples

We conclude our Sicilian journey in Palermo, the island's vibrant heart, discovering its cultural treasures and bustling character. A brief excursion to nearby Monreale reveals the splendor of Norman artistry in its magnificent mosaic-laden cathedral. As evening approaches, we make our way to the port, embarking on an overnight ferry that carries us toward Naples

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.

21–22 2 days

Naples

We arrive in Naples where a local café welcomes us with breakfast before we explore the city's treasures on a guided half-day tour. The afternoon invites quiet reflection, and evening brings us together one final time to celebrate our journey over dinner. Tomorrow, as we depart after breakfast, we carry these shared memories forward.

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.

Our tour concludes today after breakfast at the hotel.

Plan with confidence

Travel Information

Everything you need to know before you travel, presented in one easy-to-read planning guide.

What’s Included

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

Traveller stories

What our travellers say

Real reflections from travellers who have experienced this journey with Odyssey.

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Ancient History of Southern Italy & Sicily
$18,750 AUD
per person · 22 days
Next departure
20 Sep 2027
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