Unforgettable Travel Company

Luxury Sicily Tours & Vacations

Sicily, sitting off the southern toe of the Italian peninsula, is quite simply a different world. With a mid-Mediterranean setting at the crossroads of Europe, North Africa, and the Middle East, the island is a kaleidoscope of historic and cultural influences, more in common Morocco than Milan.

Former occupiers of the island include – to name a few – the Greeks, Romans, Saracens, Vikings, Normans, and Spanish, each of whom has left fingerprints all over the island’s architecture, culture, and cuisine. Nowhere else in Europe can you tour a Baroque cathedral before taking in an evening show at a Greco-Roman amphitheater, enjoy gelato for breakfast and couscous for dinner, or take in a modern art exhibition in a Norman town square flanked by swaying date and palm trees. 

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Contemporary travelers will delight in Sicily’s rich heritage, from Agrigento’s ruins to Palermo’s Norman palace. Art lovers can explore exquisite stuccos and mosaics in numerous churches, museums, and galleries. Adventure seekers can embrace Sicily’s rugged landscapes, including hill biking and climbing Mount Etna. Food enthusiasts will cherish this gastronomic paradise.

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Italy Specialist
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Our Trips to Sicily

All of our tours are custom built to you, below are example itineraries curated by our Italian specialists to provide you with inspiration for your luxury tailor-made Italy tour.

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Why we love private tours of Sicily

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Italy Specialist

Sicily’s historic cities Palermo and Catania are bustling Baroque hives, boasting beautiful stucco-clad churches, medieval commercial centers, and mouthwatering street food. Inner Sicily is breathtakingly beautiful, with rolling mountain passes, gently spewing volcanoes, and a carpet of food and wine production which includes some of the Mediterranean’s best wines. Each of its three coasts boasts fine pebbled and sandy beaches, lapped by gentle Mediterranean waves, with typically laidback terraces and bars to kick back in.

In spite of all this attraction, Sicily has yet to succumb to mass tourism and feels a world away from the dense crowds of Rome and Venice. You’ll find warm and truly genuine hospitality all across the island, and each day encounter a gallery, hotel, or cafe which feels you’ve stumbled across a hidden gem. One thing we guarantee is that the island won’t remain a secret forever, so contact our specialists today to set up your unforgettable custom tour of Sicily.

What to do in the Sicily

When visiting Sicily, be sure to explore its rich history, indulge in delicious local cuisine, and soak up the sun on its stunning beaches.

  • Climbing Mt Etna Sicily

    Climb Mt Etna

    Locally known as ‘Mongibello’, Mount Etna towers above the Ionian Coast of Sicily. It’s the most active volcano in Europe, with near-continuous low-level eruption, and is ripe for exploration. The 3,357m peak can be hiked in a variety of ways, from half-day trips which utilize a cable car to get at least one way, or multi-day camping adventures, all departing from the Rifugio Sapienza visitor center on the volcano’s southern flank. Make sure to bring good quality footwear for the trails, and an extra jacket as you’ll be above the clouds for much of the hike. 

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    Taste Sicilian Wines

    A bonus of Sicily’s volcanicity is that all that rich, fertile soil makes for some truly wonderful wines. With over 100,000 hectares in active cultivation, Sicily is one of the largest wine-producing regions in Italy and has a wine history going back some 6,000 years. Indigenous reds Nero D’Avola, Frappato, and Nerello Mascalese typically produce deep-colored, juicy, and fruit wines; Catarratto, Carricate, Grillo, and Inzolia (white) produce soft and dry whites. Malvasia, produced across on the idyllic Aeolian islands, is a beautifully sweet white dessert wine. 

  • Cannoli in Sicily

    Eat, eat, eat

    Great wine demands great food pairings…and Sicily certainly does not disappoint. With its kaleidoscopic history, and a setting on the edge of Europe, Africa, and the Ancient World, Sicilian cuisine is a mish-mash of influences and flavors, quite like anything else on the planet. Make sure to sample deep-flavored pasta all norma or caponata, delicate pastries (cannoli!), Arab-influenced couscous or cassata, fine meats and cheeses, granita, arancini, and some of the best ice cream on the planet. Dive into fabulous restaurants and cafes island-wide, or enjoy street food tours in Catania or Palermo – an absolute must. 

  • Valley of Temples. Agrigento Sicily 1

    Marvel at historic treasures

    Sicily’s history is truly unique. Over time the island has fallen under the Greeks, Romans, Byzantines, Saracens, Vikings, Normans, and Aragonese…to name a few. Graceful Baroque architecture sits in the shadow of date and palm trees; medieval alleys give way to airy palazzos or bubbling souk-like markets. The island is littered with historical marvels, from Greco-Roman amphitheaters to the towering ruins of Agrigento, and gorgeous churches, cathedrals, and palaces found on seemingly every corner. The only way to get to grips with Sicilian history is to join an expert guide and discover it for yourself.

  • View of Lipari Aeolian Islands Sicily 1

    Escape to the Aeolian Islands

    Sitting off the northern coast of Sicily, the Aeolian Islands are a group of seven volcanic outcrops which offer idyllic escapes amongst breathless scenery. The closest island is Vulcano, home to spewing Fossa di Vulcano, black sand beaches, and mud baths. Continue on to the glitzy, chic Lipari, or one island further to the staggeringly beautiful island of Salina, backdrop for Il Postino. By the time you reach far off Filicudi or Alicudi you’ll feel like you’ve reached the end of the world. On the horizon at all times is the gently smoldering Stromboli, nicknamed the ‘Lighthouse of the Mediterranean’.

Roman theater of Taormina, Sicily, Italy 670x400

When to visit Sicily

Situated off the very southern tip of Italy, Sicily’s Mediterranean climate is slightly warmer year-round than the rest of the country. It experiences four distinct seasons, but with markedly hot summers and mild winters. Temperatures in December & January range around 40-50F, hitting a peak of 65-80F in July & August. Summer months are also remarkably dry, with minimal rainfall from April through to October. We’d recommend timing your visit for the ‘shoulder’ seasons April, May, early June, and then September & October, at which time you’ll find comfortably warm temperatures and clear blue skies – ideal for the island’s culture, scenery, and great beaches.  

Your Sicily questions answered

How long does it take to tour Sicily?

Sicily is a very large island with plenty to see – you could spend weeks here and still keep on uncovering great beaches, mountain villages, and foodie spots! However, we typically find a tour of around 8-9 days is ample to cover the key spots such as Palermo, Taormina, Syracuse, and Agrigento.

What is the ideal Sicily itinerary?

As above, the most important places to visit in Sicily are the island capital Palermo, the chic mountainside resort town Taormina, history-rich Syracuse, and the graceful ruins of Agrigento. This itinerary leans heavily on Sicily’s rich and colorful history, but along the way you’ll doubtless encounter amazing food, fine wines, breathtaking scenery, and the wonderfully warm Sicilian people.

Is Sicily safe for tourists?

Absolutely. Thanks to glamorous film and TV portrayals (mostly of Sicilian diaspora on the other side of the Atlantic) Sicily has something of a murky reputation, but the reality is totally different. The island is just as tourist-friendly as anywhere else in Italy with a very low crime rate and warm, hospitable locals. 

How expensive is Sicily?

Generally speaking, Sicily is a cheaper destination for accommodation, food, and general travel expenses than the established tourist destinations of northern Italy such as Rome, Florence, or Venice. Furthermore, mass tourism has yet to take hold across the island, so you’ll find far fewer overpriced souvenir shops and tourist trap restaurants trying to part you with your tourist dollar!

What is the best way to travel around Sicily?

Sicily is a deceptively large island. Buses and trains take a long while to get from one city to the next, and while self-drive is certainly appealing learning to drive like a local is not necessarily the most relaxing way to spend your holiday! By far the best way to travel is on one of our private customized tours, with a private driver escorting you around the island and private expert guides accompanying for all sightseeing.

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