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. Lucia's native Catania and nearby Mt. Etna are way cooler. If you really have to 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 Capo Market or 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.
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. Savia is an institution for sweet and savoury treats.
Visiting the Southeast
On the way down 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 spots that isn’t quite good enough but the wine list is great.
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. While Noto, Modica, and Ragusa are inland, Siracusa is on the sea.
Also in the southeast, Marzamemi is super cute. Its tonnara (tuna processing plant) is no longer functioning but the sand-colored buildings have been repurposed as bars and performance spaces. On the waterfront, La Cialoma is nice for seafood, especially crudi. Take a dip nearby at Portopalo and the Isola di Capopassero. On the southern coast, the Faraglioni di Ciriga and surrounding seaside is beautiful for swimming. There’s also the Riserva Naturale Orientale just south of Lido di Noto.
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).