Luxury Sicily Tours made for you
Discover the wonders of Sicily with our private, tailor-made tours
A cultural crossroads
Sitting off the toe of Italy’s boot, Sicily has long been a melting pot of Mediterranean culture, a ruggedly beautiful island surrounded by sparkling seas.
Sicily’s long history has seen it at the heart of great civilizations and often under foreign rule. Of the ancients, the Greeks loved Sicily most and left a monumental mark on the island, almost as great as the island itself made on classical culture. The great cities of Syracuse, home to Archimedes, Selinunte and Agrigento are still strewn with vast ruins and towering doric temples. The iconic amphitheatre at Taormina overlooks sea and smoking Mount Etna, as impressive a view now as it was two millennia ago.
Next came waves of Romans, Byzantines, Moors, Normans, Spanish and Bourbons, each adding to the identity of Sicily, from golden cathedrals, imposing castles and Baroque palazzos, to the islanders’ generous hospitality and rich cuisine. Even with Italy unified under today’s Republic and a tough twentieth century, Sicily proudly retains its own distinct culture.
When Goethe wrote ‘to have seen Italy without having seen Sicily is not to have seen Italy at all, for Sicily is the clue to everything’, he was not far off the mark, but truly seeing Sicily would take many months. As well as the great Greek ruins, beautifully Baroque Noto, Ragusa and Modica all deserve time to be explored, as does seaside Cefalù and lofty Erice. After re-emerging from years of poverty, Sicily’s two biggest cities can each captivate for days, Palermo as a cultural centre and Catania with a heady nightlife at the foot of Mount Etna.
And that’s before exploring the glorious interior, a hinterland home to sublime mountainscapes and a rural patchwork of gently crumbling villages, sleepy olive groves and basking vineyards. There’s also miles of quiet beaches and dozens of off shore islands.
From our experts
Experiences picked by our Sicily specialists
Wander Noto, Ragusa and Syracuse
Get lost wandering through the streets of the impossibly pretty cities of Noto, Ragusa and Syracuse
Hunt for the best cannoli in Sicily
Sample Sicily’s incredible cuisine and enjoying finding your favourite place for cannoli
Spend an afternoon city sightseeing
While away your time in the beauriful city of Taormina
Feel the energy of Palermo
Enjoy the frenetic energy of Palermo
A word from one of our experts
Sicily has it all: natural reserves, a live volcano and secluded islands for adventurous types; stunning panoramic spots for photographers and romantics; and Greek temples and baroque architecture for history lovers. Plus, everyone agrees on Sicilian cuisine – simply irresistible.
Murray Mitchell
Luxury accommodation in Sicily
There are many incredible places to stay in Sicily. Here are some of our favourites, handpicked by our travel designers:
Why book with Jacada?
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Personalised design
We’ll plan your trip around your specific interests, tastes and preferences, providing helpful tips and honest advice based on first-hand knowledge of the destination.
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Authentic experiences
Our expert guides and brilliant travel concierges are hand-picked to provide a genuine experience, bringing your destination to life with care and passion.
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Responsible travel
Our luxury trips are designed with responsible travel principles that prioritise travel experiences that are both good for you and good for the planet.
Trip Inspiration
Get inspired with our Sicily example trips and then get in touch to plan your own adventure
Grand Tour of Italy
A country of incredible diversity, beauty and history, Italy is one of the world’s most fascinating and rewarding holiday destinations. This 21-day Italian adv…
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The Charms of Southern Sicily
Discover the essential beauty of Southern Sicily on this eight-day journey, which begins in the enchanting seaside city of Taormina. This remarkable island sho…
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Amalfi Coast
Draped along the cliffs on the southern side of the Sorrento Peninsula, between Salerno and the city of Sorrento, the Amalfi Coast is one o…
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Capri
Approach by sea from Naples, and as you come to the landmark of the Faraglioni rocks, you’ll know you’ve reached the fabled hed…
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Dolomites
Soaring peaks, tooth-like crags and lush verdant slopes, the Dolomites are some of Italy’s most dramatic scenery. Nestled in the north east…
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Emilia-Romagna
Emilia-Romagna is a region in northern Italy sandwiched between the Apennines and the River Po, the Adriatic Sea lapping at its eastern sho…
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Florence
Surrounded by rolling Tuscan hills, the beautiful city of Florence is one of Europe’s most enchanting and historically influential cities.…
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Lake Como
Lake Como has been a popular retreat since the time of the Roman Empire, and its popularity shows no signs of waning. Everyone from aristoc…
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Lake Garda
Italy's largest lake.
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Matera
Basilicata forms the instep of Italy‘s boot and has transformed itself from one of the country’s poorest regions to one frequen…
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Milan
An arbiter of international style, Milan is Italy’s financial and industrial heart, a thoroughly modern European city with a great history…
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Piedmont
Nestled in the north west of the country, Piedmont is one of Italy‘s most naturally beautiful regions. Its name means ‘at the foot of the m…
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Portofino and Cinque Terre
The magnificent Italian Riviera has been attracting rich and beautiful since the days of Byron, Shelley and Keats who spent time here swimm…
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Puglia
A 400km strip of land that makes up the heel of Italy’s boot, Puglia is one of Italy‘s most charming regions. Known for its never-ending co…
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Rome
Rome, Italy’s capital and largest city, needs little introduction. One of the most historied locations in the world, we can help you discov…
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Sardinia
With exquisite beaches lapped by crystal-clear waters, stunning scenery and its own unique identity – Sardinia, off the west coast of Italy…
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Tuscany
Few scenes are more evocative of Italy than that of rural Tuscany: undulating hills dotted with stoic stone farm houses, dark green cypress…
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Umbria
Located in central Italy, this hilly region is dotted with historical towns like Perugia, Assisi and Terni. The scenery is delightfully pas…
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Venice
Sat within a shallow lagoon between the mouths of Po and Piave rivers, Venice comprises 118 islands formed by some 170 canals connected by…
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Verona
A splendid city of art inextricably associated with Shakespeare’s Romeo and Juliet, straddling the winding Adige River where ancient and mo…
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Meet your Europe team
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Alice Cosso
Europe Concierge
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Dan Rhodes
Travel Designer
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James Wakelin
Senior Travel Designer
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Kirsty Brand
Travel Designer
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Kit Wong
Senior Travel Designer
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Luisa Armandine
Travel Designer
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Marta Silva
Client Experience Manager
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Meg Simpson
Senior Travel Designer
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Melania Siriu
Senior Travel Designer
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Murray Mitchell
Senior Travel Designer
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Rita Pinto
Senior Concierge – Europe
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Symmone Anderson
Europe Concierge
When to visit Sicily
The best time to visit Sicily is in the late spring and autumn months. April to June or September to October bring beautiful, mild days. The summer months (July-August) are fine for those seeking high temperatures, but the region can get very busy.
Peak Season
May - Sept
History
April - May, Sept - Oct
Coast Trips
April - Nov
When Is the Best Time to Go to Italy?
Italy Travel Guides
Our Guide to a Family Vacation in Italy
Everything you need to know for a seamless family trip
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Our Guide to the 8 Best Mediterranean Islands
From stunning beaches, delicious cuisines and spectacular sunsets - the Mediterranean islands have so much to offer
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The Most Romantic Honeymoon Destinations in Italy
Italy is made for romance. Every view, meal and moment becomes a shared memory. Explore the country’s most beautiful honeymoon destinations with our expertly (…
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The Ultimate Guide to Italian Cuisine
Universally beloved dishes including pizzas, pastas and sweet treats, all made with fresh, seasonal ingredients
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“We enjoyed our first trip with Jacada…”
We enjoyed our first trip with Jacada and it surely won't be our last! Every detail and moment of our trip was perfectly planned. We were met every step of the way with courteous and knowledgeable drivers and guides. We really appreciated the local guides and the commitment they had to make every day special. Thank you Jacada for the…
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We had a wonderful trip planned through Jacada. We enjoyed the venues and the excursions. This is a beautiful place we'd recommend to anyone who wants to go on a new adventure.
Your trip, your story
We craft trips deeply personal, delightfully surprising and entirely one of a kind. Every Jacada journey begins in conversation with a travel designer, a specialist in their destination of expertise. Behind each journey is a wealth of insight, gathered over years of on-the-ground exploration.
Once you’re booked, you’ll meet your concierge. Based in the region you’re visiting, they’ll take care of all the details so your mind is at rest. They make the trip truly special – and truly yours.