This small-group journey through Sicily is designed for travelers who want to experience the island as it truly is—layered, expressive, and deeply rooted in tradition. Over eight nights, you’ll travel from the volcanic slopes of Mount Etna to the salt-lined shores of Trapani, discovering Sicily through its food, wine, landscapes, and the people who call it home.

The journey begins in eastern Sicily, where life unfolds in the shadow of Mount Etna, Europe’s tallest active volcano. Stay at a winery resort surrounded by lava-stone vineyards and dramatic landscapes, and enjoy a warm welcome that sets the tone for the days ahead. Walk among the vines, taste wines shaped by volcanic soils, and share a first evening together over a thoughtfully prepared dinner paired with estate wines and local olive oils.

From Etna, explore the vibrant city of Catania, built from black lava stone and alive with movement, markets, and Baroque architecture. Wander through its historic center and bustling fish market, where daily life is loud, colorful, and unapologetically real. Shop for ingredients alongside a local chef before rolling up your sleeves for a hands-on Sicilian cooking class, preparing classic dishes and enjoying them together over wine and conversation.

A scenic drive brings you to Taormina, perched high above the Ionian Sea, where ancient Greek and Roman history meets sweeping coastal views. Stroll its elegant streets, visit the iconic Greek Theatre, and enjoy free time to linger in cafés or browse artisan shops. Later, slow the pace in the seaside town of Cefalù, known for its golden beach, medieval lanes, and magnificent Norman cathedral overlooking the water.

In Palermo, Sicily’s bold and complex capital, dive into the island’s multicultural soul. Discover Arab-Norman architecture, lively piazzas, and one of Europe’s most celebrated street food scenes on a guided walking and tasting tour. Sample arancine, panelle, sfincione, and sweet cannoli while learning how centuries of cultures shaped the city’s cuisine. Balance the energy of Palermo with creative time in a ceramic workshop, where you’ll hand-paint your own piece using traditional techniques—an authentic keepsake with a personal story.

The western part of the island reveals a quieter, poetic side of Sicily. Visit a countryside winery for a relaxed brunch and tasting, including the island’s iconic sweet passito wine, before ascending to the hilltop village of Erice. Wander cobblestone lanes, admire sweeping views over the sea, and pause for almond pastries made using centuries-old recipes. Continue on to Trapani, where historic windmills and shimmering salt marshes reflect the sky in soft hues of pink and gold at sunset.

Your journey concludes with a boat excursion to Favignana, a serene island surrounded by turquoise waters and known for its unhurried rhythm. Spend time exploring on foot, enjoying the sea air, or simply slowing down before returning to Trapani for a farewell dinner shared under the stars—a final moment to reflect on the friendships formed and the depth of experiences shared.

This is not a checklist-style tour, but a carefully paced exploration designed for a small group, allowing space for meaningful connections, hands-on experiences, and genuine encounters. Sicily reveals itself gradually here—through flavor, landscape, conversation, and time well spent.