Sicily: Ancient History, Extraordinary Food and Hotels That Surprise
Published 21 September 2026
What Sicily is actually like for a holiday.
What is Sicily actually like for a holiday? In short: layered, generous with food, increasingly serious about its hotels, and not always as calm as the postcards suggest. Sicily rewards travellers who want to see how Greek, Roman, Arab, Norman and Spanish rule left physical evidence stacked on top of one another, sometimes on the same street, and who are happy to eat extremely well while doing it.
It is Italy's largest region and, for its size, one of the most historically dense places in the Mediterranean. A Doric temple built for a Greek colony can stand a short drive from a Norman chapel lined with Byzantine mosaics, itself not far from a baroque town rebuilt after a seventeenth-century earthquake. The food carries the same layering: rice and citrus from Arab rule, sweet-and-sour combinations from Spanish trade routes, and pastries whose recipes trace back centuries. The hotels have followed the history's lead too, with converted palazzos and grand seafront villas increasingly run to a genuinely high standard rather than simply traded on their setting.
None of this makes Sicily an easy or uniform holiday. It is a large island, best covered by car, hot for much of the summer, and unevenly developed: a handful of towns, Taormina chief among them, have become considerably busier in the past few years, while much of the interior and west remain quiet. A good Sicily holiday depends on knowing which version of the island you are booking.
A Greek temple, a Norman chapel and a Spanish balcony on the same street
Sicily's core appeal is that its history is not curated into a single museum quarter; it is worked into the fabric of ordinary towns. The clearest single site is the Valley of the Temples outside Agrigento, a UNESCO World Heritage property since 1997 covering roughly 1,300 hectares of Doric temples built between the sixth and fifth centuries BC, among the best-preserved Greek architecture anywhere outside Greece itself. A different layer sits in Palermo, Cefalù and Monreale, where nine Norman-era structures, dating from the Norman Kingdom of Sicily between 1130 and 1194, were inscribed by UNESCO in 2015 for the way they fuse Byzantine, Islamic and Latin craftsmanship into a single architectural language. Mount Etna, inscribed separately by UNESCO in 2013, adds a third, entirely different register: an active stratovolcano whose summit height genuinely changes with each eruption, currently reckoned at somewhere around 3,350 metres. Few destinations offer a natural World Heritage site, a Greek one and a medieval one within a single day's drive of one another.
Explore our multi-centre tour, the Antiquities of Rome, Naples and Sicily by train.
What a week on the ground actually feels like
The reality of visiting is more physical than the history books suggest. Sicily rewards early starts: the Valley of the Temples and Agrigento's ridge are considerably more comfortable to walk at 8am than at 1pm, and the same applies to most exposed archaeological sites in summer. Palermo's markets run on their own clock rather than a tourist one — Ballarò and Capo are loudest and freshest in the morning, while Vucciria is largely dead by day and only comes alive after dark, when the fry stalls and bars fill with locals rather than visitors. Distances between regions are longer than they look on a small map; a fly-drive covering Taormina, Siracusa, Ragusa, Agrigento and Palermo is comfortably a fortnight, not a long weekend. None of this is a complaint about the island so much as a note on pacing: Sicily works best at a driving-holiday rhythm, not a city-break one.
One of our most popular itineraries in Sicily is Splendid Sicily, a fly-drive tour of 12 nights.
Isn't Sicily just Taormina and crowds now?
This is a fair question, and the honest answer is that Taormina specifically has changed a great deal, while most of the rest of the island has not. Industry reporting on Taormina's hotel market shows bednights and average room rates both climbing sharply since 2022, a trend widely attributed in the hospitality trade press to the international exposure the town received after the second season of the television series The White Lotus was filmed at a hotel on its clifftop. Search interest in Taormina rose sharply in the months the season aired, and arrivals data for the town point to a marked jump the same year. The effect is real, concentrated, and worth planning around rather than ignoring — but it is a Taormina story, not a Sicily-wide one. Agrigento, western Sicily's wine country, Ortigia in Siracusa and most of the interior have not seen anything like the same surge, and a holiday that treats Taormina as one stop among several, rather than the whole trip, sidesteps most of the issue.
Stay at Taormina Mare, in a beach hotel, on the coast below the town which you can reach by cable car. The Belmond Villa Sant Andrea.
Where Sicily fits into a wider itinerary
Sicily works well as a self-contained touring holiday, typically ten to twelve nights covering Taormina, Siracusa's old town of Ortigia, the baroque towns of the south-east, Agrigento and Palermo by hire car. It also combines naturally with the Aeolian Islands to the north, reached by ferry from Milazzo, for travellers who want a slower, more remote coda after the mainland circuit, and can be extended further to Capri for a change of pace entirely. At the other end of the scale, Sicily can serve as the final leg of a longer fly-drive down through Naples and Calabria, crossing the Straits of Messina by ferry. The choice of role — standalone island tour, island-plus-islands, or final chapter of a longer Italian drive — changes the pacing considerably, and is worth deciding before hotels are booked rather than after.
Sicily by train is a perfect way to expeirence slow travel to Sicily.
How to do it well, versus how most people do it
Most first-time visitors fly into Catania, base themselves in Taormina for four or five nights, and see Etna and Siracusa as day trips, usually in July or August, when temperatures regularly exceed 35°C and the coast is at its busiest. It is a workable holiday, but not the one that shows Sicily at its best. A better-planned version moves the trip to April, May, September or October, when temples and gardens are considerably more comfortable to walk and hotel rates ease. It bases itself in at least two or three different places rather than one — a night or two in Palermo for the markets and Arab-Norman route, a stay near Agrigento to see the Valley of the Temples without a coach crowd, a wine estate in the west for a slower two or three days — and treats Taormina as a stop rather than a headquarters. It also builds in a guided food element, since Sicily's markets reward someone who already knows which stall is worth the queue.
Sicily suits travellers who want their history with some grit still on it: temples that are not roped off from ordinary streets, markets that operate for locals first, hotels that range from beautifully restored to charmingly uneven rather than uniformly polished. It rewards people happy to drive, tolerate real summer heat, and treat an average meal or two as part of an otherwise excellent culinary track record. It is less suited to travellers who want a single, entirely predictable five-star base with minimal logistics, who dislike driving on unfamiliar roads, or who are specifically hoping for the quieter, less-discovered Mediterranean experience that Sicily, in pockets, no longer quite is. For that kind of calm, other Italian regions — or Sicily's interior and west rather than its east coast — are usually a better fit.
How Expressions organises a Sicily holiday
We build Sicily holidays as bespoke touring itineraries rather than single-hotel packages, typically combining a fly-drive or private-transfer route across two to five bases depending on how much of the island a client wants to cover. Hotel selection matters more here than in more uniformly developed destinations: we favour properties such as Villa Igiea in Palermo, a Rocco Forte hotel in a restored Art Nouveau palazzo on the city's seafront, Villa Athena inside the Valley of the Temples archaeological park in Agrigento, and Grand Hotel Ortigia on the historic harbourfront in Siracusa, each chosen for a genuine sense of place rather than brand recognition alone. Every itinerary includes our concierge service and regional notes on timing, so clients know when to visit a site early and when a market is worth an evening detour.
Planning a Sicily holiday with Expressions Holidays
Sicily is one of the destinations where a little planning changes the holiday considerably: the same island can be a crowded coastal fortnight or a genuinely rich, well-paced tour, depending on timing, route and choice of base. Our team has planned Sicily itineraries for many years and can build a route — touring, single-base, or combined with the Aeolian Islands or the Italian mainland — around what a client actually wants from the island, rather than a fixed template.
Call us on 01392 441245 (Monday to Friday, 9am to 5.30pm; Saturday, 10am to 2pm) or email info@expressionsholidays.co.uk.
