View from Hotel Villa Sonia, Castelmola

The Italian island of Sicily is a fascinating place to visit. A rich medley of ancient civilizations, Sicily offers Greek ruins, splendid cathedrals, and atmospheric street markets on one mountainous landmass. Here, you can visit Baroque towns clinging to hilltops, calm bays with sparkling blue water, and the decadent, dynamic capital of Palermo. But first, you’ll need to read our list of 12 mistakes to avoid -- Sicily is no place to show up like it’s amateur hour. Read on.

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Hotel Baia Azzurra

Hotel Regina

Hotel Villa Sonia

Artemisia Palace Hotel

Hotel Villa Schuler

1. Skimping on rental car insurance in Sicily.

Street at Artemisia Palace Hotel, Palermo

Visiting Sicily without renting a car is certainly possible. There are several bus and train systems across the island, and travel packages typically include transport. But if you want to optimize your time in Sicily, move at your own pace, or visit smaller towns in the interior and off the beaten track, then a rental car is the way to go. However, you should splurge on the highest amount of coverage. Driving in Sicily can be downright unnerving, whether you’re turning the 180-degree corners of the switchbacks; navigating a multi-lane roundabout, narrow road, or dark tunnel cutting through a mountain; or just trying to share the road with tour buses, motorbikes, and fellow drivers. This is European driving culture at its finest, and if you’re not used to it, it will definitely seem aggressive. And if you look around, you’ll notice that almost every car has a scrape, scratch, or dent of some sort. Chances are your rental car will join their ranks, and trust us, you’ll want maximum coverage.

2. Dressing like a slob in Sicily.

Street at Hotel Villa Schuler, Taormina

You may be going to Sicily for vacation, but this isn’t the time to wear faded muscle tanks, raggedy cutoffs, or baggy cargo shorts. Sicilians care about presentation, and you’ll do well to put a bit of effort into your look, if you don’t want to look like a tourist. Locals tend to wear smart, casual clothing and spotless shoes for everything from running errands to la passeggiata (evening stroll). For men, the look can even skew slightly formal — you’ll often notice neat outfits of collared shirts, sweaters, and hats. Women traveling to Sicily could consider packing midi sundresses, cropped palazzo pants, and woven strappy sandals; men could opt for light crewneck sweaters and slim-fit chinos. Clean white tennis shoes or sneakers are smart for either gender.

3. Forgetting toiletries on your Sicily vacation.

Street at Ambasciatori Hotel, Palermo

Don’t expect to find a 24-hour CVS, Boots, or the equivalent in Sicily. Most of the pharmacies, even in cities like Palermo and Catania, are quite small and offer a limited selection — much of it behind the counter. You’ll be able to pick up a toothbrush, but if you’re looking for something more specific, like facial sunscreen or dry shampoo, you might find yourself out of luck.

4. Only packing for hot weather in Sicily.

Beach at Wellness & Spa Hotel – Principe di Fitalia, Syrcause

Sicily is smack dab in the middle of the Mediterranean, so you may think that tees, tanks, shorts, and sundresses are all you need. Those items will certainly serve you well during the day, but you’ll need to bring warm layers for nights. Even in the spring and summer, nighttime in Sicily can get quite chilly (it dipped to the 40s most nights of our April trip). So, no matter what time of year you go, be sure to bring at least one sweater, one decent jacket, and good warm socks.

5. Trying to see too much in a short time.

View from Hotel Villa Diodoro, Taormina

It’s important to know that covering even short distances can be a challenge here. Driving can be slow-going, as many roads are extremely windy and full of switchbacks, so even going just 60 miles can eat up most of your morning. If you want to get from one coast to another, budget at least half a day of driving, and that’s with no major stops. And if you’re depending on buses and trains to get from point to point, then prepare yourself for a lot of travel time. Case in point: To get from Tusa (a beach town on the north coast) to Catania (the major city on the east coast) — a distance of 100 miles — we had to take three trains, totaling six-and-a-half hours of travel.

6. Skipping street food in Sicily.

Sicily is a long-simmering stew of cultures and civilizations from across Europe and the Mediterranean. On a single trip, you can feast on pasta alla norma (tomatoes, eggplant, ricotta, and basil), North African-style couscous, and the freshest seafood you can imagine. We say, for every two meals of pasta and fish at an enchanting little trattoria, make one meal out of delicious and ludicrously cheap Sicilian street food. Palermo is one of the great street-food capitals of the world; visit the souk-like street scene of Ballaro for a sense of Sicily’s Arabian heritage — and for panelle (chickpea fritters), sfincione (fluffy Sicilian pizza), and arancine (fried rice balls often filled with meat ragu).

7. Letting your wallet run low on cash.

Street at Hotel Regina, Palermo

Our advice: Withdraw as much as you can from the ATM at the airport in Catania or Palermo, and put half in your wallet and half in your money belt or an interior pocket of your suitcase. Restaurants, hotels, and shops accept credit cards, but you’ll want cash for street vendors and small purchases — including bus tickets — from a tabaccheria (deli/corner store/smoke shop). Train ticket kiosks accept plastic cards, but only those equipped with PINs. If you run out of cash, it may take a while before you find an ATM (this is true even in cities like Catania), and then you may have to pay ATM and bank fees a second time.

8. Focusing your trip around Taormina.

View from Excelsior Palace Hotel, Taormina

With ancient Greek ruins, alluring little streets, and stunning views of Mount Etna and the Ionian Sea, Taormina is one of the most beautiful destinations in Europe. It certainly deserves a visit. However, we recommend spending two or three nights in Taormina, and moving on. Almost everything you’ll want to do there — strolling Corso Umberto, sunning on the beaches during summer, hiking up to the Greek theater and even the hilltop town of Castelmola (if your quads can take it) — can be done in that amount of time. Traffic and crowds are inevitable, prices are high, and the food in Taormina isn’t the best because it doesn’t have to be — people are going to come here for the charming streets and incredible vistas regardless (and rightfully so). Soak it up for a couple of days, then seek out less splashy (and less crowded) destinations like Syracuse, Noto, Ragusa, and Modica.

9. Going to Sicily for an all-inclusive vacation.

Pool at Club Cala Regina, Sciacca

Some islands are famous for their pampering all-inclusive resorts. Sicily is not one of them. It does have some hotels with all-inclusive packages, but in general, they are tired properties with less-than-impressive buffet, drink, and entertainment options. Unless you are looking for a very toned-down and low-key version of the all-inclusive experience, stick to room-only or bed-and-breakfast rates, and plan to leave your hotel every day for excursions.

10. Not leaving suitcase space for Sicilian purchases.

Entrance at B&B del Massimo, Palermo

Hand-painted pottery, pom-pom baskets, coral jewelry, limoncello, olive oil, chocolate, and pistachios — you’re going to want to buy some of Sicily’s traditional crafts and food and drink products. Shipping is available at many ceramics stores and the larger souvenir shops in destinations like Taormina, but if you don’t want to add shipping costs to your travel expenses, then you’ll want to make sure you leave some negative space in your suitcase to fill with Sicilian goodies.

11. Expecting a contemporary hotel in Sicily.

Street at Hotel Romano House, Catania

There are design-driven boutique hotels in Sicily, but they are the exception, not the rule. The vast majority of Sicilian hotels are on the older side, so be prepared for dated decor and amenities (think chunky furniture, polyester bedspreads, and tile flooring). For a contemporary hotel, consider Monaci delle Terre Nere, an organic farm stay on the slopes of Mount Etna; Catania’s Hotel Romano House, an 18th-century private home for a noble family that now serves as a sleek boutique hotel; or Asmundo di Gisira, a truly one-of-a-kind urban art boutique where rooms represent stories from Sicilian folklore.

12. Neglecting to bring your best walking shoes.

Street at Il Principe Hotel, Catania

If you’re going to Sicily, you’re going to encounter hills, stairs, and uneven cobblestone streets. Bring your very best walking shoes — bonus points if they’re stylish and in great condition. On our April trip, we wore our Comfortiva Blossom sandals eight days out of 10. This included hiking up to the Greek theater of Taormina, climbing the 142 steps of Caltagirone, and walking the length of the lungomare (beach walk) in Cefalu. While you’re at it, pack a good pair of water shoes, too, as many of Sicily’s beaches are rocky or pebbly.

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