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The jewel of the Mediterranean   



Beniamino & Anne


Sicily Grand Tour 
11 days (10 nights) 

NZ$11,975pp (small group max 10 people) 

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On this tour, you will: 

  • ​Traverse the land of the Cyclops in absolute comfort

  • Stay in high quality accommodation in attractive settings  

  • See the world famous “bikini ladies” depicted in stunning Roman mosaics

  • Find the ancient tomb of Archimedes but not the soap (or the ‘death ray’)

  • Visit the fabulous food market “La Vucciria” so lusciously painted by Renato Guttuso

  • Marvel at the monumental Doric temples standing proud against the sky      

  • Experience puppet theatre unlike any other you have seen

  • Practise your oratory skills in ancient Greek theatres

  • Tempt your palate with delicious Sicilian desserts

  • NOT have absolutely everything mapped out for you – there will be surprises along the way that you will want to tell all your friends about when you get home and MOST IMPORTANTLY you will have fun! -😊


Tour Outline:

Start date:   11 October 2024


End date:    21 October 2024

The tour starts and ends in Palermo 

Note: The tour package is a land package only. Flights to suit your individual needs can be arranged for you through us or you can make your own flight arrangements if you prefer. Palermo has an international airport for your inward and outward air travel.

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“To have seen Italy without having seen Sicily is not to have seen Italy at all, for Sicily is the clue to everything.”    J. Wolfgang (von) Goethe

Trinacria is the ancient Greek name and symbol of Sicily seen on coins minted in Siracusa from the 4th Century BC and still present on the flag and coat of arms of the region today.  According to Tiziana Manzetti, “the winged head of Medusa symbolizes wisdom, protection and freedom and acts as a protective talisman that wards off evil and brings good luck. The precise significance of the three bent legs is uncertain. They are usually described as emblems of the promontories or endpoints of Sicily. However, some scholars have also suggested they might represent time or the cycle of nature. The ears of wheat celebrate the fertility and agricultural richness of the island. They were added to the Trinacria by the Romans, as Sicily was then considered the granary of their empire.”

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We will start and end our tour in Sicily’s capital Palermo, one of the largest cities in the Mediterranean and home to one of the region’s seven UNESCO Heritage Sites.   

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On Day 1, after being collected from our accommodation, we will set off with a local guide for our introduction to this 2,758-year-old city noted for its history, culture, architecture, and gastronomy. Major highlights include the 12th-century Palermo Cathedral which houses royal tombs and the huge neo-classical Teatro Massimo, which is the third largest theatre in Europe and internationally known for its opera performances. Also in the centre of the city are the Palazzo dei Normani, a royal palace started in the 9th century, and the Cappella Palatina, with its glittering Byzantine mosaics. While in Palermo, readers and film buffs will be delighted to see the recently restored 18th Century villa that inspired the Prince of Lampedusa to write his masterpiece “Il Gattopardo” (The Leopard), immortalised in Visconti’s famous film of the same name.

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In the afternoon, we will travel to the Museo Guttuso at Bagheria, a short distance from Palermo. Here we will be able to see some of the stunning art created in the 20th century by the Sicilian artist, Renato Guttuso, whose art conveys the vibrant lights and colours of his homeland so effectively.  We will spend tonight and tomorrow night at leisure in the Palermo area.

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On Day 2, we will visit the famous street food markets of Palermo. As Plato said more than two thousand years ago, “Sicilians build things like they will live forever and eat like they will die tomorrow.” Dating back to the ninth-century Saracen rule of the island, Sicily’s outdoor markets share many characteristics with Arab souks. Meat, fish, fruit, and vegetables are piled high on the market stalls along with tantalising sweet and savoury dishes to tempt the locals, the visitors, and the gods!  Among some of the highlights will be Caponata, Arancini, Pasta alla Norma, Cannoli with ricotta combined with a variety of fillings, and Cassata with pistachio and chocolate, all of which have their roots in Palermo.


Later in the day we will visit the nearby hill town of Monreale located on the slope of Monte Caputo, overlooking the fertile valley called ‘La conca d’oro’ (The Golden Shell), where many varieties of citrus fruit including the thick skinned cedro are grown. We will visit the 12th century Duomo, which is one of the finest examples of Norman architecture and one of the most important attractions of Sicily. The town is also famous for its locally made jewellery and mosaics.

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On Day 3 we will leave Palermo driving first to the picturesque coastal town of Cefalu, which has been designated one of the 100 most beautiful villages in Italy. The town is dominated by a monumental rock which was known to the Phoenicians as the promontory of Hercules, on which stands the Temple of Diana and a cistern dating from the 9th Century BC. The town boasts an exceptionally fine Sicilian Romanesque Duomo dating from the 12th Century AD, which, like the Cathedral in Monreale, is a UNESCO heritage site.


After a stop for lunch, we will continue our journey into the hinterland of the island travelling along one of the most famous roads in Sicily which connects Palermo and Catania. We will pass by the highest provincial capital in Sicily, Enna, with its breathtaking views of the surrounding countryside before turning off the highway to reach our destination for the night near Piazza Armerina. The purpose of our stay here is its proximity to the magnificent Roman villa, Villa Romana del Casale, which we will visit at the start of Day 4.

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The Villa Romana del Casale is a large and elaborate Roman villa which was constructed in the early 4th Century AD. The site has been designated a UNESCO World Heritage site because it contains an extraordinarily beautiful collection of mosaics that have been excellently preserved due to the landslide and floods that covered the property until excavations began in the 20th century. We will have a lot to see here before we head back to the highway and then along the coast of the Ionian Sea to Taormina, which will be our base for three nights. On our way there, we will have a brief stop at the coastal town of Aci-Trezza to see the three rocky islands that are the result of stones thrown at Odysseus by the Cyclops in the book 'the Odyssey.'

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The famous 19th Century French writer Guy de Maupassant had this to say about Taormina: “Were a man to spend only one day in Sicily and ask, “What must one see?” I would answer without hesitation, “Taormina.” It is only a landscape but a landscape where you find everything on earth that seems made to seduce the eyes, the mind, and the imagination.”


On Day 5 we will  spend the morning exploring the many attractions of Taormina in the company of a local guide. Often described as the pearl of the Mediterranean, Taormina has been the most popular tourist destination in Sicily for over 200 years, ever since it became an integral part of the Grand Tour. Perched on a rocky promontory with dramatic views of Mt Etna, this town has beautifully restored medieval buildings and a network of winding streets full of shops, bars, and restaurants to attract the visitor. A major highlight is the famous Greek-Roman theatre, which started its life in the 3rd century BC and is still home to all manner of events including plays, concerts, fashion shows, and cinema festivals. The afternoon can be spent at leisure or swimming at Isola Bella or you may want to take a half day tour to see Mt Etna up close!

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On Day 6 we will head off for a day trip stopping first at Savoca, the location of the unforgettable Godfather films, where we will enjoy some refreshments at the famous Bar Vitelli. Regrettably we cannot confirm that Al Pacino will be there! We will then move on to the port city of Messina, commonly referred to as the Gateway to Sicily because of its proximity to the Italian mainland. From its mythological beginnings as the home of Scylla, one of the monsters that almost ended Odysseus’ fated voyage, like the rest of Sicily it was settled by the Greeks, dominated by the Romans, invaded by the Byzantines, subjugated by the Arabs, and occupied by the Normans! 


The historic centre of Messina is home to many architectural jewels, including the 12th-century Church of the Santissima Annunziata dei Catalani, the reconstructed Norman cathedral with its spectacular bell tower and astronomical clock, and the nearby Fountain of Orion. The Regional Museum houses some magnificent Renaissance and Baroque art and two dazzling works by Caravaggio: “The Adoration of the Shepherds” and “The Resurrection of Lazarus”. With a plethora of places to enjoy an excellent dinner in this fine city, we will not be hungry as we make our way back to Taormina.

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On Day 7, we will leave Taormina and have our first stop for coffee at the attractive seaside town of Giardini Naxos. We will then travel on to the 8th Century BC port city of Catania, which is home to the stunning Cattedrale di SantÁgata, the elegant Elephant Fountain and raucous fish markets. We will have plenty of time for lunch and sightseeing here before proceeding along the coast towards Siracusa, where we will be based in the area for two nights.

Siracusa was founded in 733 or 734 BC by Greek settlers from Corinth and Tenea. Described by Cicero as “the greatest Greek city and the most beautiful of them all,” Siracusa equalled Athens in size during the 5th Century BC. It later became part of the Roman Republic and was the capital of the Byzantine Empire in the 7th Century AD. The city is mentioned in the Bible in the Acts of the Apostles book as a place where Paul stayed.

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On Day 8 we will explore Siracusa and Ortigia island with a local guide, visiting the Greek theatre, the Temple of Apollo, and the Ear of Dionysus. We will also visit the Necropolis where the tomb of Archimedes is located. Siracusa was the birthplace of this legendary mathematician and engineer heralded for his famous scientific discoveries and (mistakenly) for his invention of a death ray machine utilising mirrors. Lovers of Caravaggio’s paintings will also be very keen to see his work, “The Burial of St Lucia,” in the Chiesa di Santa Lucia alla Badia, located close to the Duomo in the old city.  While in Siracusa, we will also look out for the famous Sicilian ceramics, the Testa di Moro, known as “Grasta”, depicting ancient Moorish art from around 1100 AD.

Siracusa is also famous for its Sicilian Puppet shows so attendance at one of these will be a must for us too. So will experimenting with some new gelato flavours as well as old favourites! We have the Sicilians to thank for inventing a machine for making and preserving gelato – in the late 1600’s.

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On Day 9, we will leave Siracusa and set off for Agrigento but we will stop off on the way to have a look around the Baroque towns of Noto and Ragusa. These two towns are part of a group of nine towns of medieval or pre-medieval origin located in south-eastern Sicily that were all rebuilt in a unique late Baroque style after the devastating 1693 earthquake that partly or totally destroyed them.

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Noto was described by the art historian Cesare Brandi as the “garden of stone”. Its honey-coloured limestone buildings ooze originality with the use of gargoyles, masks, ornate facades and balconies. Ragusa has a refined elegance of its own, found in its maze of narrow streets and many churches and palaces. While we are in this corner of south-eastern Sicily, we will also be certain to find time to sample the famous Nero d'Avola wine, which is produced locally. Then we will continue along the coast and as we approach Agrigento, we may catch a glimpse of the well-preserved Doric temples in the Valle dei Templi. We will stay in this area overnight.

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Day 10 will start with a wander around the seven temples in this world-renowned archaeological site at Agrigento, which Greek poet and writer Pindar described as “one of the most beautiful cities of those inhabited by mortals.”  The best preserved is the Temple of Concordia, which was converted into a Christian Basilica in the 6th Century dedicated to the apostles Peter and Paul by the then Bishop of Agrigento thereby surviving the destruction of pagan places for worship. 

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When we leave the Valley of the Temples, we will leave Agrigento and head off along the coast to Selinunte which boasts its own collection of Greek temples on an acropolis looking out over the sea as well as significant archeological sites stretching further inland. This was the location where the famous bronze statue, the Ephebe of Selinus was discovered.

We will continue further west passing the fishing port of Mazara del Vallo and the small town of Petrosino on our way to Marsala in the heart of wine country. This is the home of the world-famous fortified wine DOP, one of Sicily’s most renowned wines. Its intense aroma with hints of vanilla, burnt honey and roasted hazelnuts goes well with delicacies such as cassateddi with dried figs and mustazzoli in vino cotto. It sounds like a great place for dessert.  Marsala itself is an elegant town with an attractive baroque historic centre. It is famous in Italian history for the Landing of the Thousand, which led to the overthrow of the Kingdom of the two Sicilies and the Unification of Italy. The dark side of this was the death of feudalism that was written about in “Il Gattopardo” (The Leopard) and the expansion of property ownership eventually leading to the development of the Mafia as the vehicle for resolving disputes.

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From Marsala we will not have far to go before reaching Trapani, where we will stay for the last night of our tour. Many important naval battles have taken place at Trapani from ancient times but for the last few hundred years it has principally been a major port for fishing, especially tuna, and salt production. Today it is a pleasant seaside town with a charming historic centre.

Day 11, the final day of our tour, will take us to Erice perched on a mountain overlooking Trapani. Erice, which has been designated one of Italy’s 100 most beautiful villages, has very ancient origins. It was founded by the Phoenicians and later Hellenized, suffered badly at the hands of the Carthaginians and was under Arab control until Norman times, when it was renamed Monte San Giuliano. In 1934 the town retook its name of Erice.


Amongst the most visited sites are the two castles, Pepoli Castle and Venus Castle. The former was built by the Arabs while the latter was a Norman construction with imposing towers that derived its name from the fact that it was built on the site of the ancient Temple of Venus, allegedly founded by Aeneas. The medieval streets of Erice are a pleasure to wander around and the views are simply stunning.

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We must now make our return journey to Palermo. On the way there, however, we will make a slight detour to view the magnificent and unusually well-preserved Doric Temple of Segesta as our final farewell to this island’s magnificent Greek heritage.

We will drive you to Palermo International Airport, or the railway station depending on your onward travel plans, or your accommodation in Palermo if you plan to stay in Sicily for a little longer. For those who wish to delay their departure there will be plenty more to see and do in this ancient and culturally rich city.


It is always hard to reach the end of a tour, but we are confident this tour will have provided you with an unforgettable experience which we hope to replicate on our next adventure together. Grazie e buon viaggio!  

Tour inclusions

  • All accommodation costs including breakfasts

  • All tour travel costs 

  • Daily sightseeing as outlined in this itinerary

  • Pick -up and drop-off at prearranged locations in Palermo

  • One group dinner including beverages.

  • Expert local guides where appropriate

  • All entry fees

Tour exclusions

  • Meals and beverages other than those included

  • City taxes, room service meals and mini bar refreshments

  • Telephone/internet charges

  • Porterage and gratuities

  •  Individual or optional sightseeing not undertaken as part of the tour

  • Expenses incurred on sightseeing trips other than those provided as part of the tour including transport costs

We do not arrange TRAVEL INSURANCE. Comprehensive Travel Insurance is HIGHLY RECOMMENDED
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