Sicily and Pantelleria, the Black Pearl of Mediterranean

This 10 day travel experience takes you to two of the most intriguing and unexpected places in Sicily, from the contrasts of Palermo, from time immemorial a melting pot of cultures, to the mysterious appeal of the island of Pantelleria.


Fly into Palermo and spend the first 3 nights at the brand new Rocco Forte property Villa Igiea. Day one will be all about chilling out by the pool, taking in the view from the terraces and dining al fresco.

Tomorrow morning you’ll be wisked away by your guide to get a feel of the city and discover its unique mishmash of cultures and architecture. From the Capo food market to the workshop of a puppet maker and from the Norman Cathedral that seems to be made of desert sand to the gorgeous renaissance Fontana della Vergogna, your guide will unveil to you Palermo’s unique patchwork of artistic remains and cultures.

This afternoon sail off at sunset to the turquoise waters of Mondello bay. Disembark at the beach neighborhood of Mondello and dine at Bye Bye Blues on delicious dishes paired with one 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 Kalsa 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.


Having got acquainted with Palermo’s contrasts, it’s now time to fly to the Black Pearl of the Mediterranean.  Lying just 45 miles east of Tunisia, and 60 miles south of Sicily, there is no place more suspended between Europe and Africa than Pantelleria.

A celebrity hideway, concealing gorgeous secluded villas, Pantelleria has a rugged coastline, black lava stone cliffs overlooking the bluest of the seas, zibibbo vineyards and African-hued sunsets. They say that when you fall in love with Pantelleria, it’s love at first sight.

Giorgio Armani was among the first to fall in love with the island and has owned a summer house here for forty years. Someone said that if you’ve ever wondered about the obsessive rigour of the designer’s palette, it’s all Pantelleria.

Your base from which to soak up the island’s mysterious appeal will be the Sikelia Luxury Hotel. On clear days the view at sunset reaches as far as Africa and after dark you will experience the most unforgettable starlit nights.

During your seven-night stay you’ll spend days on the water, taking out a boat with our skipper along the dramatic coast to crystal-clear water caves. Kayaking you’ll discover tiny coves and spectacular grottos.

If you feel like diving, either you’re a beginner choosing Pantelleria for your first experience in the underwater world, or you’re an expert taking an emotion-filled private archeological dive, you’ll go home with unforgettable memories.

After a day spent exploring hidden grottos and warm volcanic waters that are said to have been the love nest of Ulysses and Calypso, we’ll take you to a gourgeous wine estate to taste Passito, the “nectar of the gods”. With its dammusi surrounded by alberello vineyards, it is arguably one of Pantelleria’s most magical places where to gaze at the sea on the horizon, sipping a glass of wine at sunset and a passito later in the evening under a breathtaking starlit sky.


From Gadir’s hot springs and the Benikulà Cave natural sauna to the mud of the Lago di Venere, its volcanic origins make Pantelleria a natural open air spa.

Lying in the crater of an extinct volcano, the Mirror of Venus is an ancient caldera some 500 meters in diameter with mud and sulphurous hot waters for silky skin.

Legend has it that Venus stopped at this aquamarine-coloured lake to gaze at her reflection.

The good news is that we mere mortals can bathe in its sulfurous waters too.

Make the most of 100 km of trails along the coast and inland on a mountain bike or opt for a guided hike down a crater through deep, mysterious canyons to a remote shepherds’ hideaway, that was once a hiding place for the island’s infamous bandits.


After a morning unwinding poolside, set off in the afternoon on a private wine tour to taste dry whites made from Zibibbo grapes and discover two wineries that are key players in the island’s wine scene. A truly unique wine scene indeed, as unique as the farming techniques employed here where man is forced to bow to the will of nature. They call it “heroic” viticulture.

In fact, with its name coming from the arabic “Bent el rion”, daughter of the wind, Pantelleria does not make life easy. The giardini panteschi, circular garden walls “tailored” around one citrus tree create their own nano-climate and protect the tree from the wind. They date back thousands of years and of all agricultural systems, no other architecture involves so much work to grow one single tree! 

Meanwhile, it must be the perfect time to sip a passito Ben Ryé under the stars.

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


10 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.


Housed within typical white dammusi, Sikelia is a sophisticated yet effortless refuge. It is simply the essence of Pantelleria, a high-end place that fully respects and reflects the powerful style of the island.

sicily journey

About ISLAND HOLIDAYS Way of Travel

Who doesn’t love summer island vibes. From the Aeolians to the Egadi Islands and Pantelleria, the islands off Sicily are scattered around the blue Mediterranean sea, offering stunning landscapes, lovely villages, amazing properties and some of the best Italian food.

Here at Sicilian Journeys everyone has his own favourite isle and we escape there any time we can for a weekend with friends or a family holiday. There is no doubt that by the end of your island-hopping you’ll find your favourite and will want to come back again and again.

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