Sicily has for many centuries soaked up influences from all over the Mediterranean, and these are the basis for the colorful and vibrant present day culture and cuisine. Our tour provides unique experiences covering the diverse aspects that the island of Sicily offers – the lifestyle and culture of the people, with visits to markets and a farm; the art and architecture, seeing several Sicilian baroque towns and Arab-Norman styles. And of course the history, with visits to ancient Greek and Roman sites including Segesta and Agrigento. We enjoy long lunches, taking time over the multiple courses to enjoy the atmosphere and to relax.
Our tours are a balance between being informative (examples of the culture and lifestyle, details of the fascinating history) as well as having time to explore by yourself and everything that makes for an enjoyable trip (long lunches in good restaurants, a relaxed pace, small group size). We plan the itinerary in the way that you would plan to travel yourself, or with a group of friends.
We invite you to join us to see beautiful Sicily.
Highlights
- Key locations such as Palermo, Agrigento, Siracusa, Taormina, Monreale, Erice, Segesta, Ragusa and Modica
- The tour includes UNESCO World Heritage archeological site of the ‘Valley of the Temples’ in Agrigento, the late baroque towns of Ragusa and Modica and the Arab-Norman architecture in Palermo
- The art and architecture of Sicily, where you find everything from Greek temples, Roman theatres through to Byzantine mosaics. Your guided touring adds a significant depth of understanding in these places, while you also enjoy the breathtaking views.
- We mix and mingle with the locals going about their normal daily lives, for example in the markets of Siracusa. Here all of your senses are stimulated; curious foods on sale, the aromas of ‘panelle’ frying, the vendors calling and chatting. A focus on off the beaten path experiences is an aim of this tour. This is the 'bucket list' trip that you've been looking for.
- Through the week we progressively uncover how the culinary traditions are intrinsically linked with the history of Sicily; Arab couscous, Spanish chocolate, pastries from the island’s convents, Palermo street food. We taste it all. We even make a full meal with a chef in our cooking class
- We stay for the week in good 4 star hotels in Palermo, the Ragusa area and Siracusa
Itinerary
DAY 1: PALERMO & MONREALE
Welcome to Palermo, with its many layers of civilizations and rich history. Once the largest city in Sicily, today it is a vibrant, living testimony to this cultural heritage. Our hotel is located alongside the historic centre of town, and the vibrancy of this diverse city is all around you.
We start our touring guided by a specialist local guide who has a depth of knowledge about all things Sicily and Palermo. We first look at a series of sights that provide an insight into both Palermo and Sicily – the Quattro Canti, the fountain Fontana Pretoria, and the exteriors of the Arab-Norman churches of San Cataldo and Martorana.
Together we travel a short distance to Monreale, a UNESCO World Heritage site. Monreale is on the outskirts of Palermo, a 30 minute drive.
We visit the cathedral at Monreale, with incredible golden mosaics. This is a UNESCO World Heritage site and is considered to be one of the finest Norman buildings in the world.
On returning to central Palermo we visit the Oratorio of Santa Cita. In this ‘oratorio’, a private chapel constructed in the 16th century, you will find sumptuous rococo stucco sculptures decorating the interior. The quality and detail of the sculptural elements are a wonderful surprise to many who visit here. This chapel really is a masterpiece of craftmanship.
Continue on to admire the façade of the largest opera house in Italy, the Teatro Massimo.
In the evening we dine together, sharing a meal of Sicilian dishes where we start to discover the unique flavours on offer here: vegetables that combine with Arabic influences to create this unique cuisine; seafood fresh from the Mediterranean Sea and distinctive local wines from grape varieties grown only in Sicily.
MEALS INCLUDED:
Dinner (3 courses including wine)
DAY 2: ERICE & SEGESTA
We depart for Erice, a charming town on a hilltop overlooking the western coast of Sicily. Erice is a medieval town, with beautiful cobbled lanes. There is a long history here, starting with a population that pre-dated the Greeks. We visit the site of the Temple of Venus, now a Norman castle. From this point there are awe inspiring views, looking out over the Tyrrhenian sea and the Egadi Islands where the traditional tuna fishing grounds are.
For lunch we enjoy the traditional dish for this part of Sicily, a hidden gem which some people are surprised to find out is couscous. This western end of Sicily was most influenced by the Arab rule and for many centuries their own take on couscous has been made here.
We have lunch in Erice, after which we continue on Segesta, where we have our first glimpse of the monuments that remain from when Sicily was part of Magna Grecia (the greater Greek empire).
Segesta boasts one of the most intact Greek-era Doric temples anywhere, and an excellent theatre, both from the 5th century B.C. In fact some performances continue to be held in this theatre during the summer.
We return to Palermo in the early evening, after your day exploring.
MEALS INCLUDED:
Breakfast & Lunch (3 courses including wine)
DAY 3: AGRIGENTO
Today we depart from Palermo and travel first to Agrigento, with its famous ‘Valley of the Temples’.
This UNESCO World Heritage site features the beautiful Temple of Concordia, one of the most photogenic spots in Sicily. We are shown around by an expert guide, who explains the phases of civilisation here, as well as the current discoveries that are being made.
Strolling through the archaeological area gives a sense of the gravitas of history, as well as a pleasant experience of continued traditions, surrounded by almond groves and olive trees.
For lunch we stop at a farm in the countryside, where we get an opportunity to taste good, wholesome rural Sicilian produce. Much of our lunch is grown right here on the farm. We enjoy a leisurely lunch in the courtyard of the farmhouse.
After lunch we continue on to our hotel near the town of Ragusa, arriving in the early evening.
MEALS INCLUDED:
Breakfast and Lunch (2-3 courses including wine)
DAY 4: RAGUSA AND MODICA
We drive to the nearby town of Modica. While Modica is another of Sicily’s famed baroque towns, here we also have an ulterior motive, and that is chocolate. Modica is an important centre for chocolate making, and has its own distinctive style known as ‘cioccolato modicano’. This is made using a different production method to regular chocolate, based on Aztec techniques brought in during the period of Spanish rule. We have a tasting where you can appreciate the unique qualities of this chocolate. Later in the morning, we visit the Cava d’Ispica, a site where early civilisations of the area used to inhabit, and we can see many examples of these ancient populations.
We continue on to have lunch just outside Modica.
We work our way through a range of specialities from the Ragusa and Modica area.
Next we visit the town of Ragusa where we first spend some time together to look at specific elements of the baroque architecture that are a feature of Ragusa. In Ragusa you can’t help but be charmed by the elegant palazzos and the picturesque winding streets.
After a walking tour looking at some specific points of interest together, we leave some time for you to wander around independently.
Ragusa is one of the best examples of the Sicilian baroque style, with ornate edifices and intricate detailing. Some of Sicily’s architectural gems are scattered through the beautiful city of Ragusa. The buildings we see in this style were built from 1693 onwards and feature elegant balconies and balustrades.
We return to our hotel in the late afternoon, once our day trips are complete.
MEALS INCLUDED:
Breakfast and Lunch (3 courses including wine)
DAY 5: SIRACUSA
Today we reach Siracusa, a treasure trove of ancient palazzi, a fascinating old centre, and many harbourside restaurants where good living and ‘la dolce vita’ comes first.
The old town of Siracusa is the island of Ortigia, the heart of Siracusa, with the remains of the ancient Greek city.
We first have a guided walk through the Ortigia markets. Here the particular specialty is seafood, with the fishing fleet heading out from the adjacent port and bringing the fresh catch here each morning – the huge swordfish are an impressive sight. It is in places like fish markets that you really get a good feel for the people and the lifestyle of Sicily.
We visit the Duomo (the main church), elegant and domineering in the beautiful central piazza. This church has an intriguing history, going right back to its origin as the Greek Temple of Athena. We still see the ancient Greek columns forming part of the structure of the current church.
Taking advantage of the natural beauty of our coastal location, lunch is in a restaurant that specialises in the seafood of the area.
We spend some more time after lunch exploring more of Siracusa, with some free time built into the day to let you wander around independently.
MEALS INCLUDED:
Breakfast & Lunch (3 courses including wine)
DAY 6: TAORMINA AND SICILIAN COOKING
We first visit the ancient theatre in Taormina, built first by the Greeks and enlarged by the Romans. This theatre continues to be a premier location for music and drama performances to this day.
The rest of the morning and lunchtime is free time in Taormina. Visiting Taormina is like visiting an elegant film set, such is the combination of stunning view (over the Mediterranean Sea and Mount Etna), beautiful old buildings, plus a touch of the ancient (both Greek and Roman). We take full advantage of all three aspects (the view, the town, the ancient ruins) as we enjoy our time here.
Located high on a hill, there is time available to take the cable car from Taormina down to the beach below the town, and the island Isola Bella. Around town, as well as the archaeological sites, there are numerous ceramic shops and cafes on the piazza.
We taste wines produced on the lower slopes of Mount Etna, benefiting from the unique microclimate and lava soils of this volcanically active area. Wine has been made in Sicily for over 2000 years, and the Mount Etna region is one of the key quality wine areas. Our tasting gives us a wine tour, starting with the predominant red grape Nerello – these wines are reminiscent of pinot noir – and the whites made from Carricante can be excellent.
We have a cooking class with a chef, where you take an active part in preparing a complete three course meal.
The dishes are typically Sicilian, a cuisine which has developed through the absorption of a myriad of influences through the ages. With today’s focus on Sicilian cooking, we have a local chef unlock some of the secrets and teach us the techniques used here. As well as this, we discuss the importance and provenance of the ingredients and produce used. Then we relax and eat!
MEALS INCLUDED:
Breakfast and Dinner (3 courses including wine)
DAY 7: ARRIVEDERCI
By now you know the local barista by name – and he knows which coffee you order – but we must say ‘arrivederci’ as you leave Italy’s largest island.
We organise transport for you to your departure point of Catania airport and bid you “buon viaggio”.
The tour finishes in Catania at 11 a.m.
Sicily Tour Dates 2025
- 4 - 10 May 2025
- 1 - 7 June 2025
- 15 - 21 June 2025
- 7 - 13 September 2025
- 28 Sept - 4 October 2025
- 12 - 18 October 2025
- See our Full Calendar
Cost and Inclusions
TOUR PRICE: €2750
* Price is denominated in Euros. Price listed is based on twin share
* Single supplement of €500 for solo travellers
- All accommodation is included in 4 star hotels with locations in Palermo, near Ragusa and Siracusa
- Meals as listed in the itinerary: breakfast every morning, plus a main meal each day including wine
- All costs/entry fees for activities listed in the itinerary are included
- All transport during the tour is included. Travel is in our minibus with a professional driver
- 'Italy With Pleasure' provides a tour leader who will be with you for the duration of the tour, on hand to provide any support that you need
- Contact us to book online for this group tour, we'd love to see you in Sicily
Accommodation
DISTINCTIVE CHARACTER, UNIQUE LOCATIONS
The high quality hotels we use for this tour are good quality hotels in Palermo, near Ragusa and in Siracusa. This makes it easy for you to spend time independently discovering these wonderful places. All of the hotels we use are 4 star rated.
In Palermo we stay in the Hotel Quintocanto. This hotel is conveniently located right in the centre of Palermo. Many of the key areas to see are in your neighbourhood.
Next we stay one of our boutique hotels in the countryside area near Ragusa, either the Relais Parco Cavalonga or the Eremo della Giubiliana. Both properties are immersed in interesting rural areas, and have their own restaurants and swimming pools.
In Siracusa we stay in either the Grande Albergo Alfeo or the Hotel Roma. The hotels are a short stroll from the centre of Ortigia, Siracusa.
Reviews
S O, AUSTRALIA 
My husband (Bill Griffin) and I had the great fortune to be on the Sicily tour 9-16 October this year. Our profession as geologists has taken us travelling around the globe as part of our job, but this was our first experience of a group tour and we were interested to see how it suited us.
The experience could not have been better! Ricky (Riccardo) was our tour leader and he was outstanding in this role – very outgoing, knowledgeable, organised but creating a very casual and inclusive atmosphere, and dealing very capably with any day- to-day potential/actual wrinkle. The limited size of the group was ideal.
We are very impressed by the range of key sites that we visited, and the expert guides who joined us for various visits. The mix of archaeology, food and culture was excellent and we appreciated the free time which created a great balance. The chosen hotels were perfect and gave extra depth to the experience of the regions we visited. We also consider the trip was great value.
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K M, CANADA
We are not tour people, but our small group Sicily tour was excellent. The whole tour was very well organized with a wide variety of sights and experiences. Our guide Mark was very conscientious and did an excellent job of managing all aspects of the tour agenda. I would highly recommend Italy With Pleasure.
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J H, AUSTRALIA
I really enjoyed my Sicily tour. We saw a lot of the island. The pace was excellent and the small group of 7 was perfect especially being able to spread out in the smaller buses which more easily navigated the windy mountain roads . Mark was a wonderful leader and adaptable to group requests with good suggestions for any free time. The leisurely lunches /dinners were a highlight.
My only suggestion would be to for the organisers to make it a smoother transition for any participants who move from one tour to the next. (This was a problem for a couple in my group)
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