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Getaway Guide

Sicily

Enchanting Italian island with ancient ruins and architectural wonders set amidst a stunning Mediterranean backdrop.

Private villas in Fontane Bianche offer the ideal escape for families and groups along Sicily's magical Ionian coast. Featured Haven No. 272646
Private villas in Fontane Bianche offer the ideal escape for families and groups along Sicily's magical Ionian coast. Featured Haven No. 272646

Ancient wonders amidst an enchanting island paradise.

With its cerulean waters, picturesque beaches, idyllic coastal towns, and famed cuisine, life on the island of Sicily is sure to enchant. Steeped in history, Sicily boasts ancient ruins and architectural wonders amidst a stunning Mediterranean landscape.

Sicily is packed with incredible beauty throughout the island, from the jewel of Taormina on the Ionian coast to the famous wine region of Trapani to the west. Art and history lovers will delight in visiting Sicily's UNESCO World Heritage sites, soaking in the exquisite mosaics of the 4th-century Villa Romana del Casale, the exquisite architecture of the late baroque towns of the Val di Noto, and the ancient seaside wonders of Syracuse and the Rocky Necropolis of Pantalica.

Among the most fascinating sites to see are Sicily’s famed castles and ancient wonders, a vast network of historical monuments sprawling across the island. In the west, take a cable car from Porta Tripani to Erice, the "City of a Hundred Churches" - a beautifully preserved hilltop town with two castles in the sky (Torretta Pepoli and the Castello di Venere) featuring breathtaking belvedere views. In the east, marvel at the stunning ruins of the Greek Theatre of Taormina, the pearl of the Ionian Sea, built from the rocks of Mount Taurus in the 3rd century B.C.

With so much to see and experience, Sicily beckons travelers to stay awhile and explore the many different possibilities.

The perfect home base in Taormina - a private paradise close to beaches, Mount Etna, the Greek Theatre & more. Featured Haven No. 272584
The perfect home base in Taormina - a private paradise close to beaches, Mount Etna, the Greek Theatre & more. Featured Haven No. 272584

Curated experiences to immerse in the magic of Sicily.

When you a rent a private villa or vacation rental in Sicily, a world of unique authentic local experiences opens up to you. While there is so much to see and do, there is a beauty in traveling slowly and serendipitously discovering the island's stunning scenery, vibrant colors, and rich flavors. Whether you're wandering the Baroque backstreets in the south, lounging seaside on a rocky beach, or watching the world go by in a historic piazza with an Aperol Spritz in hand, there's nothing quite like savoring the magic moments in the everyday.

For the active and adventurous, Sicily abounds with fantastic options for hiking, horseback riding, and cycling to explore the island's natural beauty. In the east, those seeking an adrenaline rush and fantastic views can take a guided trek or cable car day tour to the summit of Mount Etna - an active volcano dominating the skyline with otherworldly landscapes from volcanic craters to barren fields of lava. On the northwest coast, spend a day at the Riserva dello Zingaro, Sicily's beloved nature reserve where you can hike along the water's edge, exploring the island's rugged cliffs on natural coastal trails and stopping at hidden cove beaches and turquoise swimming holes to refresh along the way.

It goes without saying that food is a centerpiece of any Sicilian itinerary, and should you wish to dive deeper into an area of special interest, our network of local hosts can help recommend the best cooking classes, wine tours, private chef experiences, and more. Discover the best-kept secrets behind Sicilian specialties from a local Nonna in your own private kitchen, wander the markets tasting the best street food and gathering fresh ingredients for a divine evening feast, or spend a day at the vineyards sampling and learning how to produce Sicily's world-famous wines.

Discover the rich flavors of Sicily in Trapani, beloved for its fish couscous, almond pesto, and sweet marsala wine. Featured Haven No. 489955
Discover the rich flavors of Sicily in Trapani, beloved for its fish couscous, almond pesto, and sweet marsala wine. Featured Haven No. 489955

A coast-to-coast culinary adventure for all the senses.

Sicily is a food lover's dream, offering a delightful landscape of culinary specialities that vary from region to region. Sample some of the island's top flavors from coast to coast:

  • For scrumptious street food & open-air markets: Palermo. With a rich history dating back to 734 B.C., the Sicilian capital in the northwest is renowned for its mouthwatering street food and bustling outdoor markets set amidst ornate Baroque architecture. Visit Antica Focacceria del Massimo for a taste of Palermo's street snack standouts including panelle chickpea fritters, cheesy arancine, swordfish involtini di pesce spada, and potato crocché with cheese and mint. After working your way through the street markets of Capo and Ballarò, reward yourself with a decadent brioche con gelato at Gelateria Lucchese in the Piazza San Domenico.
  • For almond delights & sweet marsala wine: Trapani. The focal point of Sicily's western coast, the "City of Salt and Sail" is beloved for its unique culinary identity that speaks to its proximity to Northern Africa and its history as an ancient Phoenician trading center. Eat your way from Trapani to Marsala, indulging in the region's famous fish couscous alla trapanese, almond pestos, fresh tuna, and gourmet salts. Sample Sicily's famous sweet marsala wines and try a new wave of fortified wines using local grape varietals from Nero d'Avola to Inzolia.

  • For vineyard-studded hills & rare cheese: Agrigento. A lesser known gem in Sicily's southern coast, Agrigento province is an agricultural center and a destination for oenophiles. Visit the prestigious Planeta Estate, a family-run institution that has been honing its craft for over five centuries, and try artisanal cheese made from the milk of the native Girgentana goat, a rare breed numbering fewer than 600 throughout the island.

  • For sweets & chocolate confections: Modica. Known for its esteemed chocolatiers and beautiful UNESCO World Heritage sites, the island's southeast area of Modica and Ragusa is a sweet tooth's dream. Enjoy artisanal chocolates made straight from the cacao beans in small batches, sampling the area's traditional vaniglia, cannella, and spicy peperoncino flavors at the Antica Dolceria Bonajuto, the oldest pastry shop in Sicily.

  • For Mediterranean flavors with seaside views: Syracuse & surroundings. Once the foremost city in the Greek Empire, Syracuse in the southeast offers culinary delights with decadent views. Enjoy a cocktail at dusk in Ortigia's Piazza del Duomo as the sun sets over the historic landmarks, and feast on classic Sicilian seafood dishes in the idyllic seaside destination of Fontane Bianche overlooking the Ionian Sea. In the picturesque fishing village of Marzamemi nearby, visit seafood emporium Adelfio for a sampling of the area's specialty tuna delicacies and dine in the charming and colorful 18th-century piazza.


Experience the best of Sicily when you stay in an authentic private villa or holiday home on the island. Featured Haven No. 272584
Experience the best of Sicily when you stay in an authentic private villa or holiday home on the island. Featured Haven No. 272584

From sun-soaked countryside villas to seaside holiday homes, our experts are here to help you find your private haven in Sicily.

Our collection of private retreats in Sicily is designed to immerse guests in the island's singular charms. Find your haven in a quaint apartment nestled amongst ancient architecture and sun-drenched alleyways, or retreat to the hills at your own rustic-chic villa with a private pool, chef-prepared meals served al fresco, and breathtaking views of the azure sea below. Every stay is professionally managed and thoughtfully designed to provide the most magical Sicilian escape, inviting you to return again and again to this Italian island paradise. View some of our top picks at the links below.

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