A Cultural and Culinary Discovery of Sicily

Set in the middle of the Mediterranean, Sicily is a treasure trove of history and cultures. Sicily has no equal as a crossroads of cultures more than Sicily. On this 8-day luxury discovery of Sicily you’ll go beyond the obvious clichés as you also uncover the most iconic attractions as well. You’ll begin in Palermo, a seductive city of stark contrasts and captivating charms. You’ll then unwind for a couple of days in a beautiful olive oil estate and discover a totally different Sicily. Try your hands at traditional recipes and dine on the most authentic Sicilian food after walking among Greek temples and along cobblestone streets. Your grand finale will be Taormina for a taste of the good life. After all, this is an Italian holiday!


Where else to start this cultural discovery of Sicily than in Palermo? A unique patchwork of artistic remains, Palermo has been conquered over three millennia by whatever population happened to cross the Mediterranean. A guided walk through the city on arrival is essential to get a feel of this city and will immediately unveil its wonderful mishmash of cultures and architecture to you.

For your first dinner in town treat yourself to a delicious meal in the marina district and tomorrow get ready to go far beyond the usual stereotypes of Palermo and find out what makes it what it really is.

Let’s be clear: We don’t have Godfather’s tours, we want to tell you a different story. Guided by our local guide you’ll stroll around the town to discover how several shops and businesses have been rebelling against the pizzo, (the protection money demanded by the mafia). The motto is “I pay those who don’t pay”. Thus enlightened, you continue your walk to the Capo food market. By now it must be lunchtime and you are in the right place as Palermo is ranked number 5 in the world for street food. Which is fried, of course.

After a bit of relaxation pool-side or a spa treatment, we’ll arrange a boat transfer to the seaside neighborhood of Mondello to dine at Bye Bye Blues where their delicious dishes can be paired with any of the 350 wines on hand.

There are many places where you can really feel the city’s contrasts and the Kalsa district is one of them. You’ll see old men playing cards, drinking beer and eating babbaluci, next to creative spaces and art galleries. Right there the Italian collectors Francesca and Massimo Valsecchi bought an amazing 17th century palazzo in 2016 and initiated a colossal restoration for their art project.

You’ll take an exclusive visit to their private collection. It’s no surprise that in 2018 it was chosen as one of the venues of Manifesta, the European Biennal of contemporary art.

If you want to stay local tonight in the old district, your guide will take you to dine on fish grilled to perfection in a street trattoria and to check out together the local nightlife at the Vucciria market which takes on a new life at night in a colourful blend of artists, lawyers, students, rich and hippy people.

Day three will be a thrilling one. Marvel at the glittering mosaics of the Arab-Norman Cathedral of Monreale. Step into the Capuchin Catacombs where more than 8000 corpses and 1200 mummies of priests, aristocrats and rich bourgeois dating from the late 16th to the early 19th century and all wearing their best clothes are to be found lying underground. In the afternoon take a boat trip to swim in Mondello’s turquoise waters and wait for the sunset over a glass of Tasca d’Almerita sparkling rosé and panelle (the perfect Palermo combination).


Bidding farewell to Palermo you’ll take the scenic coastal Salt Road and cross the Marsala Wine DOC area. Few people know that this fortified wine is not just a dessert wine or worse a sauce with escalopes! A historical Marsala producer will teach you how to serve it as a surprising aperitif: a 2 year aged Marsala is a great combination with a tuna and lime croutons while a 10 year aged Marsala Riserva is perfect with blue cheese.

Your home for the next two days will be an elegant countryside estate producing olive oil where you’ll try your hands at old recipes and spend the evening preparing, chatting, sharing, and enjoying together good food and wine together.

Come in Autumn to catch the olive harvest. It’s a magical time in Sicily. The sun is warm, think of a pleasant summer when you can still bathe in the sea, the beaches are uncrowded and the countryside is simply gorgeous. Join your hosts and the workers in the olive grove, pick your olives and taste the just pressed oil straight from the press to your bruschetta. The traditional farmer’s lunch all together is clearly the moment everyone looks forward to!

The day after will start off in style with an amazing archeological walk among the eight Greek Temples of the UNESCO Valle dei Templi and the style continues as you sail along the coast towards the magnificent Scala dei Turchi.  

As you are unlikely to be around here often, don’t miss the chance to dine at La Madia restaurant, voted among the 50 best restaurants in the World.


Enjoy one more delicious homemade breakfast and depart for a final 3 nights in Taormina.

But before you settle down in the renowned town of Taormina, you’ll stop in Catania for a real gastronomic adventure at La Pescheria fish market. You’ll taste the freshest of fish at the fishmongers, the best “arancini” of your life and any amount of good food as you move further into the market through backstreets and a secret underground lava tunnel. If you still have room for dessert there’s granita with brioche… and the “minnuzza di Sant’Agata”.

By the afternoon you’ll be in Taormina. One of Italy’s most beloved towns for its charming history, stunning Greek theatre and unique panoramas, Taormina is, more than all others, the city in Sicily that embodies the good life. Oscar Wilde, Truman Capote, Pablo Picasso, Coco Chanel and Greta Garbo have all indulged in the pleasures of its outdoor cafés and restaurants.

The next day is devoted to Mount Etna. Known as Europe’s highest active volcano, Etna has a totally unique energy and is now home to world-renowned pioneers of natural wines.

Your guide will whisk you away on a fabulous day packed with stunning treks, lunar landscapes, natural wines and regional cuisine. On board of a first class 4WD vehicle you’ll cross the lava fields and the craters of ancient and recent eruptions, explore a lava tunnel and hike along seven small aligned eruptive cones with epic vistas. Unwind over lunch in a lovely winery and discover why the wines from Mount Etna are today considered some of Italy’s most intriguing.

Spend your final day in Taormina at the beach or perhaps stroll down the picturesque streets uncovering the best spots for a granita and dine by the sea at cosy Pietro d’Agostino’s restaurant, one of our favourites in town.

The present itinerary and the suggested accommodation are just examples to give you an idea of what your customised trip may look like. Get in touch to design together your very own trip to Sicily.

sicily journey
when to go


transport style

Private Driver / Self-drive


8 nights

with WHOM


sicily journey

where will you stay


In Palermo you will choose among some brand new boutique hotels in the historic centre or opt for Palermo's Art Nouveau grand dame, Villa Igiea, which is reopening its doors as a Rocco Forte property.


Set on a working farm, your home in the Agrigento countryside is a charming olive oil resort. Giuseppe and Silvia di Vincenzo, the proprietors of Mandranova, produce an excellent mono-cultivar olive oil and will teach you how to taste and smell the olive oil while touring the olive groves and the oil press. The “gebbia”, formerly used for agricultural irrigation, has been transformed into a small infinity pool set on a hillside above the farm with views of the olive trees.


Taormina offers a wealth of properties both on the water and in the old town. We have our selected favourites such as Belmond Timeo, where you’ll soak up the city vibe and enjoy views of the bay from your terrace . With a stunning view stretching from the waters of Taormina Bay to Mount Etna and the Greek Theatre just behind, the elegant and refined Grand Hotel Timeo has it all.

sicily journey


This is all about diving into Sicily’s lifestyle with lots of immersive cultural experiences and time with the locals. Get ready to explore so many Sicilies.  

"So many Sicilies, why? Because, over the centuries, Sicily has had the fate of being the hinge between the great Western culture and the temptations of the desert and the sun, between reason and magic, and between the mildness of sentiment and the heat of passion.” (G. Bufalino)

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