Private tours in Sicily
Seventeen private experiences across Sicily — Palermo, the western coast, Mount Etna, the southeast baroque, and the offshore archaeological sites. The Italian region most rewarded by a guide who can read the layers.
17 private experiences in Sicily
Hand-picked from Context Travel's catalog. Every CTA below books direct with Context, no markup, no agency fee.
Bespoke
Palermo in a Day with Monreale Cathedral
A long focused day on Palermo's centre plus a drive up to Monreale for the Norman-Byzantine cathedral with the largest mosaic-covered interior in Europe. The Palermo most travellers wish they'd had time for.
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From$664
Introduction to Palermo
A morning walk through Palermo's historic core with a Sicilian historian — the Quattro Canti, the Cappella Palatina with its Norman-Arab-Byzantine mosaics, the Ballarò market, and an espresso in a piazza you'd otherwise miss.
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From$761
Palermo Food Tour
Arancini, panelle, sfincione, cannoli, plus the Sicilian wine that everyone now knows about. A market-and-trattoria walk through Ballarò and Vucciria with a chef-historian.
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From$706
Introduction to Taormina
The cliff town that's been a resort since the Greeks — the theatre, the corso, the gardens, the view down to Isola Bella. The Romans, the Normans, the British White Lotus set, and now you.
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Bespoke
Mount Etna Half-Day Tour
Up Etna in the afternoon by 4x4, a walk around a recent lava flow, the cable car to the upper craters when conditions allow. The shorter Etna day, for travellers basing in Taormina or Catania.
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Bespoke
Mount Etna Full-Day with Sicilian Wine
A full day on Etna: morning hike on the volcanic slopes, an afternoon tasting at one of the new-wave Etna wineries (the volcanic soils make a wine unlike anywhere else in Italy), lunch at the cantina.
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From$632
Agrigento & the Valley of the Temples
Greek temples in a Sicilian field, the most photographed of which is the Temple of Concordia at golden hour. With an archaeologist who works the southern Sicilian sites.
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From$765
Syracuse: Ortigia & the Neapolis
Syracuse's medieval island core, Ortigia, in the morning; the Greek-Roman archaeological park, Neapolis, in the afternoon. The Sicilian city that was once larger than Athens.
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From$756
Selinunte Archaeological Site
The Greek city on Sicily's western coast, the second-largest set of temples on the island after Agrigento. Quieter, less visited, equally extraordinary. An archaeologist guide makes it land.
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From$756
Segesta Archaeological Site
A single unfinished Doric temple on a Sicilian hillside, with a Greek theatre on the next ridge. The Elymian site, oldest of Sicily's Greek-period ruins. Less than an hour from Palermo.
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From$747
Catania with the Duomo & Street Food
Catania's black-and-white volcanic-stone baroque, the fish market that fills the piazza every morning, the street food (arancini, polpette, horse-meat sandwiches the locals queue for). Sicily's second city, properly seen.
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From$871
Gibellina: Earthquake & Landscape Art
The Sicilian town flattened by the 1968 Belice earthquake and rebuilt as a single open-air landscape-art installation. Burri's Cretto is the headline — a quiet, haunting site for travellers who care about contemporary art.
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From$848
Introduction to Cefalù
The Norman fishing town on Sicily's northern coast — the Arab-Norman cathedral, the medieval streets, the long sand beach you can swim from. A half-day from Palermo with a coastal historian.
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From$695
Sunset Walk in Ortigia with Wine Tasting
Syracuse's Ortigia old town at golden hour, ending with a sit-down tasting of Sicilian wines — Etna whites, southern Nero d'Avola, sweet Passito di Pantelleria. The afternoon-into-evening tour.
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From$710
Modica with Chocolate Tasting
Modica's baroque on the hill, plus the city's distinctive chocolate — made the Aztec way, grainy and dark, unique to this Sicilian town. A workshop visit and tasting included.
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From$745
Palermo for Kids with Puppetry Workshop
A child-pitched tour of Palermo ending with a Sicilian puppet (opera dei pupi) workshop. The marionettes are UNESCO-listed; the kids make their own to take home.
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From$654
Introduction to Noto
The Sicilian baroque town entirely rebuilt after the 1693 earthquake — a single golden-stone vista the locals call the most beautiful in Italy. A half-day walk with an art historian.
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Doorways books the villa
We have 8 hand-picked villas in Sicily and the surrounding country, each walked through by us. Pair an experience with a villa week and we'll line up the rest.
See Sicily villas →Custom request
Want something not on the list?
A private cooking class with a Michelin chef in Sicily. A vineyard with the founder. A truffle hunt in November with the dog who actually finds them. Tell us the brief and we'll have our partner build the experience.
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