Luxury Sicily Vacations

Sicily is one of Italy's most historically cosmopolitan regions. This enchanting island is full of art, history, breathtaking views, and exquisite cuisine.

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Palermo is the biggest city on the island and, as such, the main tourist hotspot, with its rustic winding streets, seafront restaurants, charming markets, and distinctive architecture. The equally beautiful, if not more sedate, towns of Siracusa and Catania are also worth exploring, and the spectacular sight of Mount Etna is a must, too.

You can't leave without sampling cannoli (fried pastry tubes with a sweet ricotta filling), wines grown in the fertile volcanic soil surrounding Mount Etna, or trying a Sicilian cooking class. And when the summer sun looms high, the sandy shores of San Vito Lo Capo, Cefalù, and Taormina beckon – with warm, inviting waters almost all year round.

Discover extraordinary Sicily vacations with Scott Dunn to experience the Italy you've dreamed of. Our travel experts are available to help plan your perfect Sicilian getaway.

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Things to Do in Sicily

Your time in Sicily should be spent getting to know the local culture. Learn the flavors of their cuisine, walk through the history and people who lived there, and wander amongst idyllic towns bursting with baroque and medieval architecture. With so much to do, here are some of our favorite activities in Sicily.

Walk Through History

Explore Sicily’s rich history starting in 5th century BCE at the Valley of Temples. Once the ancient city of Akragas, and now a labyrinth of incredibly preserved Greek temples, it’s a genuine look at how ancient civilisations thrived. Visit the Temple of Concordia and see how an ancient city moved back in 582 BCE with a private guide.

For 3rd-century BCE marvels, head to Taormina and the Teatro Greco. Taormina is a wondrous town and a tourist hotspot since the 17th century, however, just outside you’ll find the ancient Greek theater, the Teatro Greco, which is still used today. We can even help you plan a trip with a chance to see a starlit event here.

For a more literal walk through history, explore Literary Park, named for its connection to the author Giuseppe Tomasi di Lampedusa. Head from Palermo to Montecharo visiting the landmarks of Giuseppe’s journey and get an in-depth understanding of real Sicilian life.
Private Cooking Classes and Tastings

Sicilian gastronomy has a worldwide reputation and it’s well worth spending time indulging in it during your Sicily tour. Starting with a trip to the market with a private chef to learn about the ingredients that make up the Sicilian palate, then moving to an intimate venue where you’ll learn the techniques and tools used to create the region's decadent cuisine. In the town of Modica, a UNESCO World Heritage Site, see the famous Duomo di San Giorgio and the impressive Cathedral of San Giovanni before indulging in their best export, chocolate. Supposedly inspired by an Aztecan recipe, take part in a tasting session with a local chocolatier.
Traverse the Towns

While you could spend weeks traveling Sicily, uncovering the many charming towns that make up this island, there are a few that truly encapsulate the fascinating Sicilian life and its longstanding allure.

Ragusa, once marred by natural disaster but rebirthed as a symbol of art, is a hilltop city on the Sicilian countryside worth the attention. Less visited than the coastline, you get a new take on Sicilian culture with a private guided walking tour. Experience traditional cart masters, urban walks through historic buildings, local gastronomy and awe-inspiring architecture.

Over in Syracuse, Ortigia presents a unique view of ancient Greek ruins nestled against stunning Baroque features. Temples converted into cathedrals provide physical representations of history, alongside the vibrant artisan community where you can watch traditional theater and learn local crafts.

For an exquisite look at Sicilian life, take a private tour through Noto. Expect an elegant flair as you stroll the streets full of ornate structures and buildings. Work has gone into the incredible preservation of this city, and its varied history is one that will sit with you for years to come.
Hike Mt. Etna

Add some thrill to your luxury Sicily vacation with a hike up Mount Etna. An active volcano, this is for real enthusiasts as you traverse lunar-like landscapes thanks to the craters and hardened lava. You can also put your photography to the test with the unreal visuals you’ll see not only at the top but throughout the entire exploration.

Due to the active nature of Mount Etna access isn’t always guaranteed, but we’ll work with the experts at hand to ensure your best chance at this otherworldly adventure.

Walk Through History
Private Cooking Classes and Tastings
Traverse the Towns
Hike Mt. Etna

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When's the best time to visit Sicily?

For many people, the best windows are the shoulder seasons of spring and fall, bringing warm but manageable temperatures and smaller crowds than in the summer months. May sees wildflowers bloom along the coast, while September and October still offer warm seas for swimming.

With summer comes scorching temperatures, ideal for sunseekers and beach lovers. Our luxury accommodation options allow you to cool off when you need to. Plus, our exclusive experiences mean you can enjoy the sights and summer buzz without ever feeling rushed or crowded.

Read more about the best time to visit Italy.
What are the best places to visit in Sicily?

With its compelling mix of world-class culture, natural beauty and indulgent cuisine, Sicily has been a much-loved Mediterranean beauty for centuries.

Palermo is the cultured capital promising art, architecture and artisan feasts. A food tour here is a must, with local guides on hand to help you navigate hectic markets and bustling cafes, bars and restaurants.

The UNESCO World Heritage Valley of the Temples in Agrigento is Sicily's most spectacular archaeological site, topping the list for history buffs. For active types, Mount Etna towers above the city of Catania and can be scaled on foot or by bike, jeep or cable car.

If you're primarily looking for beach vacations in Sicily, Italy, Taormina is a glamorous choice. This coastal hilltop town offers stunning views of the sea and Etna, plus highly Instagrammable stretches of sand and pebbles.
Is Sicily good for family vacations?

Yes! Think miles of stunning coastline and sandy beaches, family-friendly stays and all kinds of food to discover, from high-end dining to famous street bites.

Accommodation options range from 5-star resorts to villas with private pools, perfect for slower days with little ones. Plus, our personalized itineraries feature guided tours of cultural gems such as the Valley of the Temples, capturing the imaginations of children and adults alike.