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.

  • Perfect for
    Art Lovers | Families | Romantics | Soul Searchers
  • When to go
    June-August | September-November
  • Ideal length of stay
    1 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.

  • 10 Days: Essential Sicily-LP
    Courtesy Grand Hotel Timeo

    10 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.

    • taormina sicily italy

      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.

    • agrigento sicily italy

      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.

    • palermo sicily italy

      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.

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.”

What To See & Do

Ready to go and in need of expert trip planning? Contact us today.

What To Read

Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.

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