Indagare's Simone Girner
“Sicily challenges you, gets under your skin, invades your dreams and ultimately makes you accept that you will never know it fully. All you can do is plan a return trip to peel back one more layer.”
Nearly the size of Massachusetts, Sicily is the Mediterranean’s largest island. Its many different regions offer a wealth of exploration, from the vibrant city of Palermo to the bucolic corners of the southeast.
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Perfect forArt Lovers | Families | Romantics | Soul Searchers
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When to goJune-August | September-November
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Ideal length of stay1 Week
Designing Your Journey
Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.
Courtesy Grand Hotel Timeo10 Days: Essential Sicily
As the Mediterranean’s largest island, Sicily offers a huge range of experiences, from antiquities to glorious seaside. Touring with a great guide is key, especially if you’re not comfortable navigating the small hilltop towns with a car on your own. Here is just one example of what our destination experts can create for you.
Days 1-4: Southeastern Coast
Between historic Syracuse, the Baroque hilltop towns and the glorious seaside, the southeastern part of Sicily packs a punch. Antiquities fans will love touring the Greek theater of Syracuse, Italy aficionados will love the bucolic charm of Noto, Ragusa and Modica, and everyone should get out on the water for a half-day boat charter. Days finish at incredible authentic restaurants recommended by Indagare.
Day 5: Agrigento
The Unesco Heritage site of Agrigento deserves a stop, especially when based at a hotel that sits within the archeological site with spot-on views of the Valley of Temples. This history-rich area comes to life with a great guide, recommended by an Indagare specialist. After an extensive tour, return to your hotel and enjoy such amenities as a lovely pool and a terrace restaurant with fabulous views.
Days 6-10: Road Tripping
Make your way to Taormina via a one-night stop in Palermo. Crumbling but fascinating, the city has incredible churches, palazzi and atmospheric squares, all best toured with an insider who can navigate through the crowds. The final days of any itinerary should be spent at seaside Taormina, which is in easy distance to Mount Etna national park. Cooking classes and olive oil, wine and marmalade tastings can be organized in this verdant part of the island.
Where To Stay
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities, including upgrades, early check-in, breakfast, spa credits and more. Look for the Indagare Plus logo in the reviews.
Courtesy BelmondRead MoreGrand Hotel Timeo, A Belmond Hotel, Taormina
At a Glance As bold and beautiful as its location, Grand Hotel Timeo is set high in the rocky hills of Taormina, adjacent to the ancient Greek Theater and facing the rainbow hues of the coastline, with majestic Mount Etna...
Beach view, courtesy Belmond Villa Sant’ Andrea, Sicily, ItalyRead MoreBelmond Villa Sant’ Andrea
The more casual sister property to the Grand Hotel Timeo, this lovely villa is located right on Taormina's pebble beach, making it a perfect enclave in which to end a busy Sicily itinerary.
