How to Have the Perfect Holiday in Sicily

Photo by Freeimages.com/Roger Johnson

by Lee Marshall and Sicily expert from The Daily Telegraph, April 14, 2016

How do you experience the best of the Mediterranean’s most alluring island in a two-week trip? By following the ultimate itinerary created by our expert Lee Marshall.

Though it’s one of the most ravishing places in the Mediterranean, one which can prove dangerously addictive for anyone with a taste for sweeping olive-strewn landscapes, starkly beautiful Greek temples, Byzantine mosaics and ricotta-filled pastries, Sicily is also an island that suffers from an inferiority complex.

Sicilians look back with some nostalgia to the two eras when they could have been a contender. When they were more than just a provider of grain (for the Ancient Romans), of alcohol-rich grapes (to bolster pale northern Italian wines), of manpower (for Australia, the US, and the Fiat factories in Turin).

These were, respectively, the flowering of Greek culture on the island beginning in the 7th century BC, and the brief but intense awakening between around 1100 and 1250 AD, when the island’s Norman rulers engineered a unique fusion of northern European, Byzantine and Islamic cultures.

These two high-water marks are the focus of a major exhibition, Sicily: Culture and Conquest, that opens at the British Museum on April 21. Around 200 objects will be on display, among them a cheeky terracotta Gorgon from a Greek temple front and a rare bronze battering ram from a Roman warship that was found on the seabed off the west coast of Sicily.

That was then; what is perhaps less well publicised is the fact that in the last 15 years or so, Sicily has started to get its act together once more. Sure, the Mafia still exists, as does a sometimes infuriating bureaucracy. But it would be an unfortunate visitor that had much to do with either. What you are much more likely to encounter are: a new breed of boutique hotels the equal of anything in Tuscany; passionately-run private tour companies like Passage to Sicily or Etna Finder that bring guidebook sights to vivid life; a wine scene that is currently among the most interesting in Italy; and a range of restaurants, from Michelin-starred temples to hip organic cafes, that simply didn’t exist when my wife and I made our first trip to the island, in a battered brown Simca we’d bought in Bristol for £150 cash, in April 1986.

Back then, we drove along the north coast from Cefalu with its beaches and glorious Norman cathedral, via Monreale - another golden mosaic cave of wonders - to Segesta, arriving at what for me is still the most stunning of the island’s Greek temples just as the setting sun was working its magic. This memorable drive has become a section of the anti-clockwise island route I’ve put together for an itinerary that, for me, distills the best of Sicily in a two-week tour.

Never under-estimate the sheer size of Sicily. It was inevitable, even on a two-week tour, that something would have to give - so you won’t find the far west, or the island’s agricultural heartlands, or (to my regret) Palermo, a chaotic but captivating city which deserves to be seen in a separate trip, and not from behind the wheel of a hire car. What I have tried to do is factor in enough downtime to offset all the driving. And take heart: another thing that’s improved in the last 30 years is the roads - with a few exceptions, left there, perhaps, for old time’s sake.

There’s also plenty of opportunity to explore, in your own time, the towns and villages that make the island so fascinating. Places like Sciacca, whose evening passeggiata is a sheer joy and deserves to be listed by UNESCO. Or Modica, a sandstone city that looks from a distance like a Baroque Spaghetti Western set, but turns out to be a vibrant, surprisingly young place with a cool line in Aztec chocolate (it’s also one of the locations for the Montalbano TV series that has done so much to alert visitors to the charms of the island’s deep south). Or Ortygia, the peninsular centro storico of Siracusa, where a hipster wine bar is just the turn of a corner away from a piazzetta where a fishermen sits mending his nets. It’s in contrasts like these that the soul of this resilient, irresistible island lies.

Day 1 

Fly into Catania - it’s an easy 40-minute drive from here to Relais Monaci delle Terre Nere ( telegraph.co.uk/terrenere ), a laid-back, eco-friendly boutique hotel on an ancient Sicilian country estate, with an excellent farm-to-table restaurant.

Day 2 

If you arrived on an evening flight, now’s your chance to take in the glory of these fertile lower skirts of Etna, a patchwork of drystone-walled vineyards, orchards and citrus groves sloping seawards. After breakfast, put yourself in the hands of the best guides on the mountain, Fabio, Guglielmo and Lorenzo of Etna Finder ( etnafinder.com ), who offer a range of customisable excursions. I recommend the half-day jeep-and-walking ‘Etna tour’ (€55 per person). It doesn’t reach the main crater but provides a fascinating introduction to the rumbling giant - whose cavernous entrails you explore at one point with ropes and flashlights - and how locals have learned to coexist with it.

Day 3 

Sometimes dubbed ‘the Burgundy of the Mediterranean’, Etna Rosso wine has come on apace in recent years. Explore its volcanic charms with knowledgeable American sommelier Benjamin Spenser of the Etna Wine School ( etnawineschool.com ), who uses the Relais’s own vineyard and ancient palmento wine and oil press as teaching props in his three-hour Etna Masterclass, which wraps with a five-wine tasting session.

After lunch - and perhaps a siesta - head for Taormina, Sicily’s most dolce vita hilltown. Time your arrival for after 4.30pm, when the coach parties have mostly decamped; in summer, this gives plenty of time to see the Teatro Greco (open until an hour before sunset), a paean to the Greek (and Roman) talent for location, location, location, and to splash out on a Bellini on the terrace of elegant Belmond Grand Hotel Timeo (gents, wear that linen suit for the full effect).

Day 4 

The spectacular four-hour drive’s the thing on this transfer day: take the high road to Linguaglossa via the ski resort of Mareneve, across petrified rivers of black lava, then head west to Randazzo on the panoramic SS120 A-road, via some of Etna’s top wineries (Passopisciaro, Graci, Fessina), before heading coastwards to Capo d’Orlando and Cefalu. If you started late, stop for lunch at Cave Ox ( caveox.it ) in the hamlet of Solicchiata, 10km west of Linguaglossa, where good-value pizzas help to absorb a stellar wine list. Stay at Kalura ( telegraph.co.uk/hotelkalura ) for the next two nights, a classic Italian seaside hotel that punches above its three-star rating, perched on a low cliff above a private beach.

Day 5 

Without Roger II, Cefalu would be no more than a pleasant gelato-stop on the road to Palermo. But the ruler of the European-Greek-Arabic cultural crucible that was Norman Sicily ennobled the town by giving it one of Sicily’s great cathedrals, its apse mosaic of Christ Pantocator perhaps the most striking single Byzantine image in Italy. Nearby, don’t miss the absorbing little Museo Mandralisca ( fondazionemandralisca.it ) with Antonello da Messina’s deliciously enigmatic Portrait of an Unknown Man.

Day 6 

Palermo is a treasure trove of Moorish, Norman and Baroque art but not one to attempt lightly in a hire car. But one sight - handily placed on the ring road - is worth a stop: Villa Tasca ( grandigiardini.it ), a grand aristocratic residence belonging to the Tasca d’Almerita wine family that is today a green enclave amidst encroaching suburbs, one that conjures up the spirit of twilight-of-the-Sicilian-aristocracy novel The Leopard. Book ahead for a private tour of the landscaped park with its cycads, palms and bamboo-fringed ‘Swan Lake’, which can be followed by a light lunch in the villa. 

Next stop is Monreale Cathedral on the heights above Palermo, another refulgent Norman masterpiece of mosaic art. Afterwards, head to Partinico, then west on the A23 motorway towards Trapani, exiting at Segesta, where a splendid, unfinished Doric temple stands in glorious seclusion. It’s just an hour from here to your lodgings for the next three nights at Foresteria Planeta ( telegraph.co.uk/planetaestate ) near Menfi, a bright, contemporary hotel surrounded by the vines of the Planeta estate, with an inviting infinity pool.

Day 7 

Continue the Greek theme by taking a tour of nearby Selinunte, its history intimately linked to that of Segesta, which brought allies from Carthage in to end its rival’s glory days in 409 BCE. Selinunte’s tumbled ruins (the only standing temple is a reconstruction) are best visited with a guide - I recommend one of the highly qualified art, archaeology and history specialists from island-wide network Passage to Sicily ( passagetosicily.com ). If you decide to go it alone, don’t miss Cava di Cusa a short drive away - the city’s abruptly-abandoned quarry, where part-hewn and carved column sections stand in a romantic flower-strewn landscape.

Day 8 

Downtime. When the pool palls, head for the beach in the nearby nature reserve of Foce del Belice, take a cooking course with the Foresteria’s talented chef, Angelo Pumilia, or do the evening passeggiata in nearby Sciacca, a lively port town with a glorious Baroque centro storico. In nearby Porto Palo, beachside seafood trattoria Da Vittorio is one of Giorgio Locatelli’s favourite places to eat in Sicily (+39 0925 783 81, no website).

Day 9 

Start early for the longest driving day of the trip, taking in two of Sicily’s most awe-inspiring UNESCO world heritage sites. A 7am departure from Menfi will allow you to arrive at the Valle dei Templi in Agrigento in plenty of time for the 8.30am opening. Park at the Temple of Juno entrance at the top to beat the crowds. Don’t bother with the uninspiring official audio guides; you’ll get all the context you need from the first chapter of John Julius Norwich’s erudite yet entertaining Sicily, published in 2015. On arrival at Piazza Armerina, a 90-minute drive from Agrigento, gourmet restaurant Al Fogher (+39 0935 684 123;  alfogher.net ) makes for a suitably decadent lunchtime prelude to the vast patrician Villa Romana del Casale a few miles south, with its marvellous Roman mosaic floors (including those much-reproduced female gymnasts working out in their bikinis). Note that you can download the official guidebook for free at  villaromanadelcasale.it . From here it’s under two hours to Casa Talia ( telegraph.co.uk/casatalia ), where you will be staying for three nights. Belonging to two Milanese architects, this is a delightful design-hotel conversion of a series of partly rock-hewn dwellings and terraced gardens that eye downtown Modica from across a gorge.

Day 10 

Welcome to the Baroque triangle of Sicily’s deep south, its honey-coloured sandstone towns the result of enlightened reconstruction by the island’s Spanish rulers after the devastating 1693 earthquake. Modica drapes its splendours across two valleys and their confluence; Ragusa piles its treasures on a rocky spur. Modica is celebrated for its grainy-textured chocolate, made according to what locals claim is an Aztec recipe brought back by the conquistadors. Groups who phone at least a couple of days in advance can visit the chocolate-making workshop of oldest and best producer, Antica Dolceria Bonajuto ( bonajuto.it ; 00 39 0932 941 225; prices vary), followed by a tasting session.

Day 11 

Head seawards towards Marina di Ragusa for a breezy jaunt through landscapes made famous by Inspector Montalbano. Fields of gnarled olives and prickly-pears criss-crossed by drystone walls lead down to a series of family resorts - among them Punta Secca, where you’ll find the house (now a B&B) used as the location for the fictional cop’s waterfront abode. Lunch at reliable, old-fashioned seafood restaurant Da Serafino in Marina di Ragusa ( locandadonserafino.it ) before heading back to Modica via the town of Scicli, a Baroque diamond in the rough which also bristles with Montalbano locations (its town hall served as the series’ main police station).  

Day 12 

No need to rise early, as it’s little more than an hour’s drive to Borgo Alveria ( telegraph.co.uk/borgoalveria ), an ancient walled farmstead that has become a hip boutique hotel without forfeiting the warmth of what is very much a family-run concern. Spend the afternoon exploring Noto, the most visionary of the area’s resurgent Baroque burgs because it was built ex novo on a site miles away from the earthquake-struck old town. Refuel with an almond, lemon or coffee granita (water-ice) at historic Caffè Sicilia in Corso Vittorio Emanuele.

Day 13 

Chiudere in bellezza, as Italians say: end on a high note with a day-trip to one of Sicily’s most absorbing and attractive cities, Siracusa. My recommendation is to arrive at the Neapolis archaeological site by 10am at the latest (it opens at 8.30am) for a 90-minute tour with enthusiastic local guide and archaeology graduate Enrica de Melio ( viaggioasudest.it ), who brings alive the Greek Theatre and surrounding quarries (like the echo-chamber known at the Ear of Dionysius). Then head for the sea-girt old town, Ortygia, wandering through its tight warren of lanes and piazzas, admiring a cathedral that was built simply by filling in the spaces between the columns of the Greek temple of Minerva, and joining the queue for a made-to-order gourmet panino at popular local deli Caseificio Borderi in Via Emmanuele de Benedictis, 6 (00 39 0931 463253).

End your final full day in town with a boat excursion around Ortygia’s harbour, the Porto Grande, site of a great sea battle between Siracusans and Athenians in 413 BC. The cheap-and-cheerful way of doing this is to take the pleasant 90-minute tourist cruise (€15 each) run by Compagnia del Selene ( compagniadelselene.it ). But if you’re in the mood for something really special, let Enrico Marletta ( touristboatservice.it ) take you for a four-hour evening cruise on his beautifully restored 1923 sailing ketch Fiesta; from €650 for two, drinks and dinner included.

Day 14 

Depart from Catania. 

When to travel

Sicily has a long, warm spring and autumn, but summer is roasting hot. March-June and September - November are the best times to travel.

Sicily tour bigLa Foresteria Planeta Estate Menfi, Sicily, ItalyTelegraph expert rating 8

Anyone keen to explore the beaches, historic towns and Greek temples of this seductive south-western corner of the island will be well-placed at La Foresteria, a countryside boutique hotel. It's also a boon for those wanting to sample the local wine as the hotel overlooks the Planeta family's Menfi vineyards. Read expert review

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From £145inc. tax

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Monaci delle Terre Nere Zafferana Etnea, Sicily, ItalyTelegraph expert rating 9

With its sapient design mix, organic food, stellar wine list and verdant grounds, Monaci delle Terre Nere appeals most of all to stressed city-dwellers in need of some rural detox. Many guests go nowhere but spend their days lounging by the pool, a cool blue splash amidst citrus and olive groves. Read expert review

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From £137inc. tax

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Casa Talìa Modica, Sicily, ItalyTelegraph expert rating 9

A couple of Milanese architects fell in love with a tumbledown property just across the gorge from downtown Modica, and have transformed it into one of Sicily’s most unique and characterful boutique hotels. Read expert review

From £121inc. tax

Borgo Alveria Noto Antica, Sicily, Italy Telegraph expert rating 7

Simple and chic, Borgo Alveria is the perfect bolthole for travellers who love to be left to their reveries undisturbed, in a marvellously secluded setting amid the ruins of Old Noto. Located in superbly sparse Sicilian countryside at the end of a drive which is not for the faint hearted. Read expert review

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From £96inc. tax

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Kalura Hotel Cefalù, Sicily, Italy Telegraph expert rating 8

Perched above a gorgeous stretch of Mediterranean just outside Cefalù, the 72-room Kalura is a welcoming beach hotel offering sporting activities and a marvellous bathing platform on a private rocky beach. Singles to multi-room accommodation are available – some of it self-catering – making it ideal for families. Read expert review

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From £48inc. tax

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This article was written by Lee Marshall and Sicily expert from The Daily Telegraph and was legally licensed through the NewsCred publisher network.