Home Away From Home: Sicily’s Most Extraordinary Summer Villas

The Thinking Traveler welcomes Homeworthy to a week in its Sicilian villas

When it comes to vacationing, few places can rival the charm and elegance of Sicily. This Mediterranean gem offers a unique blend of history, culture, and breathtaking landscapes. Homeworthy’s founder, Alison Kenworthy, and her family recently embarked on an unforgettable journey to explore some of the island’s most exquisite vacation villas, offering a glimpse into the world of luxurious living.

This episode is the first installment of our new series Home Away From Home, where we’ll be opening the doors to the world’s most extraordinary vacation villas and hotels. This season, we’ll take you on the road to our favorite sanctuaries in Jamaica, Switzerland, Italy, and California. Thanks to The Thinking Traveler, we kickoff our series in one of the world’s most storied summer escape:

Our Sicilian adventure began with a partnership with The Thinking Traveler, Europe’s most prestigious villa rental company. This collaboration granted us access to two of their most incredible properties, located less than an hour’s drive from the city of Catania. These villas, run like luxury hotels with full staffs and top-tier chefs, provide an experience that rivals even the finest five-star accommodations.

The first villa we visited, Don Arcangelo All’Olmo, is nestled within a sprawling lemon orchard, surrounded by a garden that feels like paradise. Owned by the same family for over 400 years, this villa is a treasure trove of antiques and history. The owner, Marina, welcomed us with unparalleled warmth and hospitality. Every meal at the villa, from lavish lunches to cozy dinners by the fire, was a feast for the senses.

As we explored the villa’s rooms, we uncovered fascinating stories and met the artist behind some of the stunning artworks adorning its walls. The villa’s pool, one of the most magnificent in Europe, offered breathtaking views of the surrounding landscape. Walking through the Eden-like garden, Marina shared anecdotes about her family’s history and the extensive collection of antiques sourced from around the globe.

Our stay culminated with a special birthday lunch, where we got to savor local delicacies and wines from Mount Etna. The villa’s dining room, with its vibrant orange walls and eclectic collection of plates from around the world, provided a stunning backdrop for our meal.

Our Italian journey continued to Rocca Delle Tre Contrade, a villa perched atop its own hill, offering stunning 360-degree views of the Ionian Sea and the majestic Mount Etna. The owner, John, transformed a crumbling vineyard into one of Italy’s most glamorous vacation villas – and it’s no wonder that it’s become one of the crown jewels of The Thinking Traveler’s collection. With an infinity pool, clay tennis court, and a state-of-the-art Italian kitchen, the Rocca Delle Tre Contrade estate is a haven of luxury and comfort. We even had the opportunity to hone our cannoli-making skills in this exquisite setting.

As we explored the estate, we marveled at the panoramic views and the meticulous attention to detail in every corner of the villa.

Beyond the villas, we explored the renowned cities of Taormina and Syracuse. We met the woman who played a key role in shaping the last season of HBO’s “White Lotus,” filmed around the island, and sat down with the co-founder of The Thinking Traveler, Rossella Beaugié. She and her husband Huw created the company that now exclusively represents over 300 of the Mediterranean’s top villas and has been named the best villa rental company in the world eight years in a row.

If you’re looking to venture further into Italy, The Thinking Traveler also has stunning villas in Puglia – like this beachside home with expansive terraces and gardens, and this all-stone estate that sleeps 10. Or head to Greece and stay at the luxurious Meli on the Island of Patmos before hopping over to the laid-back villa Simone in Mykonos. Francophiles will be delighted to know there are also dozens of beautiful stays on the island of Corsica.

Alison’s Sicilian adventure offered a glimpse into the magic of these extraordinary vacation villas, each with its own unique charm and history. From the warm hospitality of the hosts to the breathtaking beauty of the surroundings, this journey was a celebration of the art of living well. Join us as we continue to explore more of the world’s most exquisite vacation homes in our new series.