The Very Best Five Day Sicily Itinerary

Italy’s largest island is one of those bucket-list destinations. As one of the most diverse and interesting places in the Mediterranean, there’s a lot to pack into this island escape. The experts here at Plum Guide have spent plenty of time on the island in the name of research and know a thing or two about travelling in Sicily. To help you make the most of your holiday, we’ve put together this Sicily itinerary for five days so that you don’t miss out on any of the best bits.

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The first day of your five-day Sicily itinerary will be spent exploring the island’s vibrant capital, Palermo. The city offers something for everyone, whether you’re interested in history, architecture, culture or food. The best way to get around is on foot, and you can get happily lost amongst the labyrinth of tight-knit streets. On your little adventure, you’ll come across landmarks such as the 12th-century cathedral, the Norman Palace and the accompanying Cappella Palatina, with its exquisite Byzantine mosaics. The many hidden squares provide a much-needed spot to catch your breath in between all that sightseeing.

For lunch, we highly recommend visiting Palermo’s bustling markets of Capo, Ballarò and Vucciria. The city is celebrated throughout Italy for having some of the best street food, so it would be rude not to test this claim to fame. Indulge in heavenly arancini (deep-fried rice ball filled with ragu sauce or beef, ham, peas and cheese), crispy crocche (deep-fried potato fritters) and finish off with cannoli (tube-shaped pastry filled with ricotta and garnished with pistachio).

Once you’re fueled up, head to the Antonino Salinas Regional Archeological Museum, one of Italy’s finest collections of antiquities. Those seeking something a little more macabre (no judgement here) can visit the eerie Catacombe dei Cappuccini burial catacombs. Deep underneath the city, the catacombs are filled with mummies, skeletons and corpses.

Come evening, culture vultures should be sure to catch a show at the Massimo Theatre. The largest in Italy, this opera house is renowned for its excellent acoustics and is the best spot for a night of Sicilian opera.

On day two, swap the city for the seaside delights of Cefalù. As soon as you set eyes on its golden sands and sparkling blue sea, you’ll find it difficult to leave. This is where you can live out your Sicilian dream, lounging under colourful parasols and floating in the warm waters.

When you’re not down at the beach, take a walk through the town’s charming cobbled streets. Follow your stomach to La Botte, which comes highly recommended, before continuing your explorations past the honey-hued stone buildings to the stunning Arab-Norman cathedral. Free to enter, you may as well head inside to see the intricate mosaics depicting Cristo PantocratoreI, or Christ All-Powerful. Another spot worth visiting is the Lavatoio or Medieval Laundry. This public laundry is a fascinating step back in time when women gathered to wash their clothing in a series of giant basins.

Sightseeing over, you have two options for the rest of the afternoon. The first option is to attempt the climb up La Rocca mountain, which rises 268 metres above the town. We promise that the workout is worth it for the spectacular panoramic views of the coast. Need more convincing? There are even some exciting stops along the way, such as the Temple of Diana dating back to the 4th century BC. The second option is a lot easier—simply find a seat at one of the cafes in the quaint Piazza Garibaldi and enjoy a Negroni and a spot of people-watching in the late afternoon sunshine.

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If you can’t get enough of relaxing on the beach, day three promises more of that. Sitting on a hill above the dramatic coastline, it’s easy to see why Taormina is one of the country’s most coveted summer destinations. The town is connected to the beaches below by cable car, where you can unwind on Spiaggia Di Mazzeo or enjoy the beauty of Isola Bella. Translating to ‘beautiful island’, there’s no better place to swim, snorkel, kayak and stand-up paddleboard.

Back in town, wander through the charming streets, admiring the views from the many terraces and squares—Piazza IX Aprile is one of the prettiest. Dine in open-air cafes, indulge in retail therapy in the many boutiques or discover historical architecture. The Cathedral of San Nicola dates back to the 13th century and is decorated with several medieval artworks. The three-storey Palazzo Duca di Santo Stéfano is worth a visit with its Gothic windows, fish-tail crenellations and detailed stonework.

However, the town’s crowning glory is its ancient Greek-Roman theatre (Teatro Antico di Taormina), initially built in the 3rd century. You can still catch shows today, and throughout the summer, the theatre plays host to plenty of dramas, concerts, symphonies, operas, ballet performances and music festivals.

When you just need a quiet moment, nab a bench in the shaded Villa Comunale, a lovely landscaped garden with picturesque views of the sea and the town.

The ancient port city of Catania sits in the shadow of Mount Etna. The city is unique for its ‘Black Baroque of Catania’, an architectural style inspired by its history. Lava, the same material that had threatened Catania for so long, was used to rebuild the city following an earthquake in 1693. It’s led to the nickname ‘the grey city’, and the best example of this is the Cathedral of Sant’Agata, in Piazza del Duomo. The piazza is also where you’ll see an elephant statue carved out of cooled lava with an Egyptian obelisk on its back—this is Catania’s symbol and is said to bring it good fortune. Other intriguing historical sights include Ursino Castle and Monastero dei Benedettini.

If all that lava has left you curious for more, you’ll be pleased to know that Catania is well-positioned for day trips to the volcano. Thrill-seekers can hike along one of the trails, passing sleeping craters, lava flows and hot springs along the way. There’s also the alternative of taking a cable car or a narrow-gauge railway ride to the top for epic views without breaking a sweat.

If you’d rather spend your day enjoying the local cuisine, we have just the place for you. Given its coastal location, you can find delicious fresh seafood here. Revel in the sights, sounds, and smells of the famous La Pescheria fish market, where you can see all of the Mediterranean delights before heading to the nearby seafood restaurants.

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On the final day of your Sicily itinerary for five days, venture into one of Sicily’s most remarkable areas. The entire Val di Noto valley is a UNESCO World Heritage Site, so wherever you turn, you’re bound to come across something special. It’s made up of eight delightful towns (Catania is one of them), each with a deep history and a wide array of things to do. Choosing which ones to visit is one of the most challenging decisions you’ll make.

Just outside of Catania is Militello, which was also largely destroyed in the 1693 earthquake. However, it was rebuilt with astounding Baroque-style architecture, and you can visit the many churches and palaces filled with art and beauty.

Head to Modica, a town with a rich history of chocolate making. Visit one of the many chocolate shops or the chocolate museum (you’ll find it hard to leave). Live out your dreams as a royal in the many elegant palaces dotted around Scicli, or immerse yourself in the greenery of Giardino Ibleo in Ragusa. This tranquil public garden boasts sweeping views of the valley below and fountains and various plant species.

In Caltagirone, get some interior design inspiration from the famously beautiful enamelled ceramics that decorate the buildings in the town. They pre-date Arab Sicily, so to come here is a privilege to see such well-preserved history.

Make your way to Noto to snap photographs of its famous San Nicolò cathedral, one of the best examples of Sicilian Baroque architecture. At the foot of the Iblei mountains, the town of Palazzolo represents the best of the Val di Noto—a wonderful mix of history (Greek archaeological heritage), tradition (Baroque architecture) and modern life.

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Explore our hand-picked collection of homes in Sicily.