My great grandfather Niccolò Cipollina was born in the Cala, Palermo’s ancient port, in 1899. My great grandmother was born in Villarosa in the Enna province at around the same time. My Sicily roots run deep and it’s one of my favorite places to travel. It’s also a frustrating place to dine out since so many restaurants exist mainly to cater to tourists (too often demanding ones from Milan so you can imagine…) and can be mind bogglingly disappointing. Sicilians generally eat at home and cook, transforming fresh ingredients into tasty dishes. I HIGHLY recommend you find an apartment with a kitchen and use it as a base and cook. Sicily’s market ingredients are amazing and the bakeries and pastry shops are outstanding so you will eat very well if you aren’t married to the idea of three meals a day at a restaurant table. Also bear in mind Sicily is the largest island in the Mediterranean and if you’re planning a visit I would either suggest 2 weeks or more for exploring the whole island; if you have a week or less choose one side (fly into Palermo to explore the west, Catania to explore the east). The roads are fine but it takes time to cross the island, so save yourself hours driving between destinations and embrace the chill atmosphere of the island.
Let's get this out of the way
If you're loaded, sure, go stay at the hotel from White Lotus for a couple days. Otherwise, I would skip Taormina. It was developed for Anglophone tourists 150 years ago and that's exactly what it feels like. Catania and nearby Mt. Etna are way cooler. Every second you spend in Taormina is a second robbed from another part of the island. No one listens to this advice, though, so when you go, eat at Osteria Divino Rosso.
Don’t Skip Palermo & Its Environs
This is seriously the most vibrant city in Italy and it just keeps getting more interesting. Rent a place near the Ballarò market and shop and cook and you’ll have an incredible time. Eat lots of street food like pane ca meusa (spleen and lung sandwich) at Pani ca’ Meusa di Porta Carbone or Nino U Ballerino. Also head to Piazza Ballarò and you'll find loads of stalls frying things (the panelle and potato croquette sandwiches are the best things there). There are a bunch of stalls there including a frittularu (a dude selling fat and cartilitdge and random veal trimmings either in a paper cone or on bun). There is a full Palermo guide here.
Spend a couple of days near Palermo at the Tonnara di Scopello, hike and swim every day in the Riserva Naturale dello Zingaro. Pop down to Segesta to see the 5th century BCE Doric temple then drive over to Erice for pastries at the legendary Pasticceria Maria Grammatico.
Go to Catania
Catania is magic. The black volcanic buildings from nearby Mt. Etna are visually striking and the city has fantastic energy. For food and drinks, check out: Fud (donkey and horse burgers are the specialty), Trattoria N'ta Za' Carmela (horse steaks on via Plebescito!), Le Tre Bocche, and of course, the fish market near the Duomo. Scirocco is the spot to grab a bite with a view of the fish market. Savia is an institution for sweet and savoury treats and Forno Biancuccia is great for breads and savory pies. Nelson is a great bottle shop with a huge natural wine selection. A few blocks north, Vermut serves vino and cocktails.
Visiting the Southeast
On the way down from Catania and Etna, stop at I Rizzari in Brucoli for an excellent fish meal. Choose a base in or around Modica, Noto, Siracusa, or Ragusa and explore these baroque towns. I’m partial to Noto since it’s the home to Corrado Assenza’s Caffe Sicilia. Since this perfect pastry shop was immortalized on Chef’s Table the crowds have become a bit unpleasant, but Assenza’s excellent pastries and cookies (not to mention the most pure and life altering almond milk) just keep getting better. The pasta at Il Crocifisso in Noto is relatively solid. Il Crocifisso’s sister restaurant Dammuso TRIES SO HARD. It’s one of a growing number of wannabe contemporary Càssaro on the main drag is good enough and the wine list is amazing. If you're just in town for a snack, hit Panificio Maidda for bread and savory treats.
In Modica, Caffè Adamo is great for granita and sweets in general and Enoteca Rappa is great for wine. In Ragusa I like I Banchi for baked things, especially breads, and cheeses and cured meats. I’m not wild about the dishes that come out of the kitchen but, as the name suggests, the stuff from the banco (counter) is the move. My favorite place to eat and drink in town is Delicatessen in Drogheria. They have it all-cheeses, cured meats, vegetables, pasta, meat, and groceries. It's fantastic.
A very spectacular and very overlooked inland town is Palazzolo Acreide, which has a cool theater ruin and overall baroque appeal. Estro (no relation of the place of the same name in Venice!) is a bit on the fancy/cucina revistata side but the ingredients are great. Trattoria del Gallo is on the simpler side but they go HAM with the squirt bottle decorations especially on desserts. I mean the whole island does. In spite of being very early 90s, it’s not disqualifying. Lo Scrigno dei Sapori has absolutely the wackiest decor but the pasta and fried things are very good. They even do some fine pizza. It's my favorite spot in town.
Just outside of town, Giannavì is a big farm and they make their own cheese, raise their own pigs and make awesome salumi. I suggest doing lunch there on a Sunday. It’s kind of a classic sicilian scene: country meal, you get hammered with food and don’t have to make any decisions it just all comes to the table, all for around €30 per person. Mental. It’s also a good place to get a crash course in the food of the surrounding Hyblaean Mountains.
Siracusa and Ortigia are hard. They're so beautiful but the restaurants are mostly very bad. This is true for most of the southeast, actually. I'd love to hear if you find some great foods. HMU! My favourite place in Ortigia for vino is Enoteca Solaria. The list is incredible. Grab sandwiches to take to the beach at Fratelli Burgio then eat dinner that Latteria Mamma Iabica.
Visit Sicily in mid-September to November or During Holy Week
Sicily is a MAJOR destination for Italian and European tourists but those crowds thin after kids go back to school in September. The water is still quite warm into October. If hanging by the beach isn’t your top priority, visit during Holy Week when religious festivals abound.
Obviously Sicily is an island, but it also has lots of little islands around it. The Aeolian Islands are the most heavily trafficked and they lay just off the north coast of “mainland” Sicily. Off the west coast, Marettimo, Favignana, and Levanzo are an easy trip from Trapani. Trapani port and Palermo’s airport offers year-round connections to Pantelleria (which otherwise can be challenging to reach given the season nature of its transport).
Pantelleria is my favorite. Stay in a dammuso (traditional dwelling or agricultural building), ideally on the western part of the island so you can eat daily at Osteria Il Principe e Il Pirata and swim at Cala Tramontana and Arco dell’Elefante. If you’re not on a budget, stay at one of the Tenuta Borgia villas (the Villa Grande and its pool was immortalized in Luca Guadagnino’s 2015 film A Bigger Splash and it’s €€€€€ but some of the smaller villas also have their own small private pools).