• Sicily Italy small group tour
  • Sicily Italy small group tour
  • Sicily Italy small group tour

Sicily Tour

Italy small group tour

Sicily is an absolutely fascinating place to visit, being a crossroads of civilizations with a range of diverse influences. With our 7 days in Sicily small group tour we provide a well rounded experience covering the diverse aspects that the island offers. Your Sicily Holiday includes wonderful food and wine, including a cooking lesson and winetasting; the lifestyle and culture of the people, with visits to markets and a farm; the art and architecture, seeing several Sicilian baroque towns. 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.

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Sicily Tour Highlights

  • Key locations such as Palermo, Agrigento, Siracusa, Taormina, Monreale, Erice, Segesta, Ragusa and Modica
  • The tour includes 4 UNESCO World Heritage sites: 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
  • We mix and mingle with the locals going about their normal daily lives, in particular 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
  • 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. We taste it all

Spectacular Amalfi Coast walking tour

7 Days Sicily Tour

  • Our tours are a balance between being informative (historical details, examples of the culture and lifestyle) as well as having everything that makes for an enjoyable trip (long lunches in good restaurants, a relaxed pace, free time in places we visit)
  • We stay for the week in good 4 star hotels in Palermo, Ragusa and Siracusa; always close to the centre of town so you can easily pop out for a gelato in the evening
  • Our Small Group Tour has a maximum of 14 people
  • You have our tour manager with you throughout the week, available to provide support and assistance when you need it. Many people appreciate having someone to turn to who is familiar with the local area, whether it be for help getting something from a pharmacy / drugstore, or simply where to find the best gelato!
  • This is the trip that you’d design for yourself. We are Italy... with pleasure
  • Our 7 days in Sicily tour starts in Palermo and finishes in Catania

Agrigento Sicily Italy small group tour

What our customers say about Italy With Pleasure

“Everything was perfect! They packaged the hotel, all meals, daily tours to a variety of very special and interesting sites, and handled all of the myriad of details seamlessly. The agency is very customer-service focused and was a pleasure to work with. I highly recommend this tour company. Italy With Pleasure gets 5 stars!”

“I am widely travelled and have never been on a tour before so went with some trepidation.It was the absolute highlight of my travels in Italy and definitely the best food I had the whole time. I cannot recommend Italy with Pleasure more highly don't even think about it just book with them you will not be disappointed I am sure.”

“Our time travelling with ‘Italy with Pleasure’ was our best experience. Believe all that they say in their brochure... family run, hands on and very professional. Their standards are high and they are very responsive to everyone’s needs. They source excellent restaurants... way beyond our experiences with other companies we travelled with. We highly recommend this company, have mentioned it to friends and fellow travellers”

“The itinerary was well organized and done at a comfortable pace: touring in the morning followed by mouth-watering lunch featuring the specialties of the area as well as fine wines of the area. All of the restaurants were excellent as was the food. It was a wonderful week and I will have many fond memories of my stay. This tour is a gem and I highly recommend it!”

“The tour group was quite small, 8 people all delightful. We were driven to some very interesting towns and other sites, where guides introduced us to the art and history... The tour was full but not too intense so we felt we had enough time to enjoyed the excellent food and wine which were highlights of the tour for us. I wholeheartedly recommend this tour.”

“The places that we visited were fascinating and very unique, and the food and wine was delectable. I didn't know what to expect of the trip, but it more than fulfilled any hopes that I had for a great week. Everything was well organised and the atmosphere was friendly and relaxed. I can thoroughly recommend the tour.”

See these and other reviews on Google Reviews, TripAdvisor and other review sites.
Agrigento Sicily Italy small group tour

Agrigento Sicily Italy small group tour

Ragusa Sicily Italy small group tour

Distinctive character, unique locations

The hotels we use for this tour are good quality hotels and all are centrally located in Palermo, Ragusa and 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.

In Ragusa we stay in the heart of the baroque historic centre of Ragusa Ibla, amongst the unique Sicilian baroque palazzi. Here we stay in either the San Giorgio Palace Hotel or the Hotel Antico Convento.

In Siracusa we stay in either theGrande Albergo Alfeo or the Hotel Roma. The hotels are a short stroll from the centre of Ortigia, Siracusa.

Taormina Sicily Italy small group tour

Some reviews of our tours:

“My daughter and I toured Sicily with Italy with Pleasure in 2019. It was the trip of a lifetime with professional and knowledgeable guides. I cant wait for life to return to normal so that I can once again book a tour! They are very easy to work with and booking was a breeze.”

“The tour was absolutely fabulous. I was able to see and experience things that created once in a lifetime memories. Riccardo was phenomenal. He made sure that our trip was perfect. Any question or request we had, he worked hard to answer/meet. He was so upbeat and fun while dealing with all of our varied personalities! Thanks again for a trip of a life!”

“Everything was perfect! They packaged the hotel, all meals, daily tours to a variety of very special and interesting sites, and handled all of the myriad of details seamlessly. The agency is very customer-service focused and was a pleasure to work with.”

“The tour was terrific as was the hotel accommodation, and Andy was the best! It was well organized and we didn’t skip a beat. That last night at the farmhouse was memorable and the perfect send-off. The tour guides in each of the cities we visited were well informed and did a great job explaining what we were seeing. I highly recommended Italy With Pleasure to people I know that might be interested in travel to Italy. The small group size, and in our tour, Andy, is what makes it happen.”

See these and other reviews on Google Reviews, TripAdvisor and other review sites.

Day 1: Palermo & Monreale

Welcome to Palermo, with its many layers of civilizations and history. The city today 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.

Starting the tour, 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.

At this point we team up for the afternoon with a specialist expert who has a depth of knowledge about all things Sicily and Palermo. 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 start by visiting the cathedral at Monreale, with incredible golden mosaics. It is said to be one of the finest Norman buildings in the world.

We go on to visit the cloisters at Monreale, a particularly evocative setting lined with marble columns. You’ll be amazed at the detailed carved marble and inlaid stone.

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.

After wandering through the Vucciria market area, we view the largest opera house in Italy, the Teatro Massimo (external only).

In the evening we dine together, sharing a meal of Sicilian dishes where we start to discover the unique flavours on offer here: Mediterranean vegetables that combine with Arabic influences to create this unique cuisine; seafood fresh from the Tyrrhenian Sea and distinctive local wines from grape varieties grown only in Sicily.

Meals included:
Dinner (3 courses including wine)

Accommodation Palermo:
The Quintocanto Hotel Hotel OR the Eurostars Central Palace (both 4 star)

Palermo Sicily small group tour Italy

Monreale Cathedral Sicily small group tour Italy

Santa Cita Sicily small group tour italy

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. The views from this point are stunning, looking out over the Egadi Islands where the traditional tuna fishing grounds are.

For lunch we enjoy the traditional dish for this part of Sicily, 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.

Meals included:
Breakfast & Lunch (3 courses including wine)

The Quintocanto Hotel or the Eurostars Central Palace (both 4 star), Palermo
Palermo Sicily small group tour Italy

Santa Cita Sicily small group tour italy

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 in the town of Ragusa, arriving in the early evening.

Meals included:
Breakfast and Lunch (2-3 courses including wine)

Accommodation Ragusa:
The San Giorgio Palace Hotel or the Hotel Antico Convento (both 4 star hotels)
Santa Cita Sicily small group tour italy

Agrigento lunch Sicily small group tour italy

Day 4 - Ragusa and Modica

On waking in Ragusa, you can’t help but be charmed by the elegant palazzos and the picturesque winding streets.

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. On our return to Ragusa we spend some time together to look at specific elements of the baroque architecture that are a feature of Ragusa. 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 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 afternoon.

Meals included:
Breakfast and Lunch (3 courses including wine)

Accommodation Ragusa:
The San Giorgio Palace Hotel OR the Hotel Antico Convento (both 4 star hotels)
Palermo Sicily small group tour Italy

Santa Cita Sicily small group tour italy

Day 5: Siracusa

Today we reach Siracusa, a treasure trove of ancient palazzi, a fascinating old centre, and many harbourside restaurants where good living 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 walk through the Ortigia markets. Here the particular speciality 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 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 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 in to the day to let you wander around independently.

Meals included:
Breakfast & Lunch (3 courses including wine)

Grande Albergo Alfeo or the Hotel Roma (both 4 star), Siracusa
Santa Cita Sicily small group tour italy

Palermo Sicily small group tour Italy

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 spectacular views (over the sea and Mt 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 Mt Etna, benefitting from Etna’s unique microclimate and lava soils. Wine has been made in Sicily for over 2000 years, and the Etna DOC (Denominazione di Origine Controllata) region is one of the key quality wine areas. The predominant red grape is called Nerello – these wines are reminiscent of pinot noir – and the whites made from Carricante can be excellent.

We have a session cooking 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)

Grande Albergo Alfeo or the Hotel Roma (both 4 star), Siracusa
Santa Cita Sicily small group tour italy

Palermo Sicily small group tour Italy

Santa Cita Sicily small group tour italy

Day 7 - Arrivederci

By now you know the local barista by name - and he knows which coffee you order - but we must say 'arrivederci'.

We organise transport for you to your departure point in Catania and bid you “buon viaggio”.

The tour finishes in Catania at 11 a.m.

Meals included:

Santa Cita Sicily small group tour italy

Sicily Tour Dates 2024:

13 - 19 May
27 May - 2 June
17 - 23 June
2 - 8 September
23 - 29 September
30 September - 6 October
7 - 13 October

Tour Price: €2500

* Price is denominated in Euros. Price listed is based on twin share
* Single supplement of €300 for solo travellers

Tour Price Includes:

  • All accommodation is included in 4 star hotels with central locations in Palermo, Ragusa and Taormina
  • Meals as listed in the itinerary: breakfast every morning, plus a main meal each day of 3-4 courses 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 van/minibus with a professional driver
  • 'Italy With Pleasure' provides a tour manager for the duration of the trip on hand to provide any support that you need

Some reviews of our tours:

“The Sicily Tour in 2019 was outstanding. All of the guides are so friendly, caring, knowledgeable and passionate about their country. This love comes through in every aspect of the Tour, and transfers to the group. The accommodations, the food, and the attractions were chosen with the care deserving of the area. Because of the “small group” identity, we were introduced to highlights of beautiful Italy that would not be available to larger groups, nor would they be available to independent travellers. It provides the opportunity to “get to know” your fellow travellers and share your love for exploring. I highly recommend “Italy with Pleasure” if you are wanting to explore the history and the character of the local people. You will come away with knowledge and fabulous pictures, but more than that you will come away with the feeling of having made new friends.”

“The history of different civilisations over time influencing architecture, agriculture and food, have created a cultural diversity that makes Sicily a very interesting island. From the busy streets of Palermo, the cobbled uphill streets of Erice, the winding, winding road to accommodation in a monastery overlooking a ravine at Ragusa, visiting the Valley of Temples near Agrigento, and from Taormina seeing Byzantine tombs and a 2nd century BC Roman theatre, our experience of Sicily was very varied and rewarding.”

“Believe all that they say in their brochure... family run, hands on and very professional. Their standards are high and they are very responsive to everyone’s needs.”

“We had an amazing trip with Riccardo (our tour guide). Ended up taking this tour for our honeymoon, and would do it over 1000x. Everything was planned to perfection. We are excited to do another one with Malcolm and his team soon!”

“Malcolm and Antonella are excellent tour guides, and all the dining and wine tasting they arranged on this trip were fantastic. They are very knowledgeable about the local area and had great advice on some side trips. The hotels chosen were well located and locally run. I had a wonderful time!”

“We had a fantastic time on this trip. Ricardo was wonderful and we all really enjoyed his company and knowledge of the area. Another fantastic Italy with Pleasure trip. I love this company for providing a small, private tour atmosphere, with attention to detail on food, logistics and educational site visits. You guys are amazing. Until next time.... thanks so much.”

“We had a most wonderful time and a most wonderful tour guide, Mark. He was personable, knowledgeable and accommodating. We would love him as our guide on another tour. Each town we visited had another guide specific to the that history and culture. Everything was beautifully planned out and well executed. Our room was beautiful, our view was breathtaking, we could not have asked for a more memorable trip!!”

See these and other reviews on Google Reviews, TripAdvisor and other review sites.

Sicily Map

Sicily small group tour map

Sicily small group tour