A journey into the island through the people who call it home.

8 Days · 7 Nights
October 13–20, 2026
May 13–20, 2027

Small Group Journey by Italy by Experts

ENTERING SICILY was born from a belief at the heart of Italy by Experts: luxury travel is built on relationships, not reservations.

THREE NIGHTS

THE BAROQUE SOUTHEAST

Our first home is a traditional Sicilian baglio in the countryside of southeastern Sicily.

From here we enter the world of Ragusa Ibla and Modica — Baroque towns, country roads, local producers, chocolate, wine and long Sicilian tables.

PEOPLE BEFORE PLACES

Meet the people behind Sicily's traditions — from a local cheesemaker to wine producers, artisans and families who allow us into their world.

MODICA & ITS CHOCOLATE

Discover Modica through one of its most distinctive traditions, with time to understand why its chocolate is unlike any other in Italy.

WINE, LAND & THE SICILIAN TABLE

Spend time in the countryside, walk through the vineyards, talk with the people behind the wine and experience food where it belongs: close to the land that produced it.

ACROSS ANCIENT SICILY

Cross the island through Agrigento and the extraordinary landscape of the Valley of the Temples, with a picnic along the way.

THE SICILY FEW TRAVELLERS SEE

Travel into the Madonie to Castelbuono, meet one of the people preserving the centuries-old tradition of manna and discover the flavours of Sicily's mountains.

PALERMO BEHIND THE SCENES

Enter Palermo through its market with a chef, cook together and later step behind the doors of a private palazzo for aperitivo.

CEFALÙ, SLOWLY

See Cefalù from the water, leave time for wandering and doing absolutely nothing, and end the journey around the table in the home of a local family.

A cheesemaker. A winemaker. A chef. A family.

The people we meet are not an addition to the itinerary.

They are the itinerary.

IN THE BAROQUE COUNTRYSIDE

3 nights in a traditional Sicilian baglio

A country home surrounded by the landscape of southeastern Sicily — intimate, rooted in the territory and the perfect place to begin our journey.
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IN CEFALÙ

4 nights in a sea-view hotel

Our second home places us between the historic town and the Mediterranean, with the sea becoming part of the final days of the journey.

Departure 1
October 13–20, 2026

Departure 2
May 13–20, 2027

Small Group Journey ( maximum 12 people)

ENTERING SICILY is for travellers who want to go beyond sightseeing.

For those who would rather spend time talking with a winemaker than visit another monument.

Who enjoy beautiful places but care just as much about the people behind them.

Who appreciate good food, thoughtful hospitality and a slower rhythm.

And who understand that sometimes the most memorable moment of a journey is the one that could never have been scheduled on a checklist.

THIS IS NOT SICILY SEEN FROM A WINDOW.

We begin the journey around a table.

Seven days later, we end around another.

Between those two tables lies our Sicily.

Come and enter it with us.