Sample Itinerary for 2 Weeks in Sicily

It’s hard to believe that I was just returning from Sicily nearly two years ago today! The memories got me reminiscing about all the beautiful sites, delicious food and wonderful beaches on the island. An under-rated Italian destination, here is my ideal itinerary for two weeks in Sicily to encourage you to explore this amazing island!

Day 1-2: Palermo

Palermo is the city where most international arrivals come in to, and is usually the most logical place to begin your tour of Sicily (although there are an increasing number of flights to Catania). However, it was probably my least favorite city I visited, because it is all kinds of chaos. If you’re not into the hectic city culture, you might consider staying somewhere else. Nearby Terrasini is a nice alternative!

The streets of Palermo roads are pretty crazy (think Rome but crammed into old city walls), so I might recommend not renting a car until after you’re ready to leave the city. But if you’re feeling ballsy, this would be a fun place to rent a motorbike and scoot around. The city is undoubtedly Sicilian and has some worthy stops – Pretoria Square, Zisa Castle, Catacombs of the Capuchins, Jesus Palermo Church, Botanical Gardens – that can easily fill 1 day.

Day 3-5: Agrigento

Once you head out of Palermo, you will immediately feel more calm and relaxed. The rest of the island has a much more comfortable and laid back culture. Agrigento is a wonderful next stop to consider, although there are plenty of small towns along the way which might be worth stop depending on what you’re interested in, such as Selinunte, Segesta or Ribera.

Agrigento is a coastal city that is home to the amazing Valley of the Temples ruins. These are some of the best preserved Greek ruins in Europe and are deserving of at least a half day tour. Old town Agrigento is charming, located up on a bluff making for beautiful views and is a wonderful stop for a nice dinner and sunset. The beaches in southern Sicily are less picturesque than some on the North, but far less crowded, and I’m glad we checked them out!

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Day 6-8: Ragusa & Modica

Known as sister cities, Ragusa and Modica are just plain beautiful. They are built on the top of cliffy scrags of jagged rock divided by deep valleys. Ragusa is even considered a UNESCO world heritage site! The views are probably the most impressive parts of the city, but I also enjoyed the beautiful Cathedral of San Giorgio and the other Baroque churches in the cities. It’s easy to spend a day or two exploring around the old architecture and winding streets of these picturesque cities!

Day 8-10 Syracuse

This was my favorite stop of all, and I could have easily added a few more days here! We stayed on the peninsula of Ortigia, which I really enjoyed because it is so quintessentially Italian, with narrow cobblestone streets, fresh food markets and ocean front views. It’s a fun place to just wander around and explore. There are lots of galleries, shops, restaurants and museums to check out, so leave yourself some free time!

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Oritigia’s most famous attraction is Duoma de Siracusa on the central square. There are lots of little restaurants along the square, and it’s a fun place to spend an evening. There is also have a delicious farmer’s market that I highly recommend. I spent nearly 200 euros at one of the butcher shops getting meat & cheese for a rooftop picnic!

Greater Syracuse also has some great tourist attractions I would recommend. The archeological park is quite impressive, especially the natural acoustics in the Ear of Dionisa and the amphitheater. Walking along the waterfront and seeing all the fishermen is also quite nice!

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Day 11: Mount Etna

The largest active volcano in Europe, Mt. Etna is visible from much of the Eastern coast of Sicily. Depending on the time of year, you may be able to hike it. It’s a pretty awful hike, if I’m being honest. It’s all volcanic soil so lots of slipping and loose gravel to deal with. There is little scenery on the volcano itself, so you’re really just hiking for the views. Those are pretty nice, but make sure to pack lots of water since there aren’t really refuges on the volcano itself. I would say this is not a great hike for beginners, and it is good to be prepared for the experience.

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Day 12: Wine Region

Like many other parts of Italy, Sicily has excellent conditions for growing grapes. The slopes of Mt. Etna are where a lot of the vineyards and wineries are located, so it’s a natural next stop (or only stop if you’re not so into the hiking). I could have easily spent more time here, it’s really a beautiful area! There are lots of different winery options to check out, including Gambino Winery, Enoteca Etna Wine and Benanti. Some of these vineyards even have onsite accommodation, so if you get a little too into the tasting, you don’t have to worry about making it back to your hotel.

I would definitely suggest one with a tour & tasting, so that you can get the full experience. But certainly the tasting is the best part. We opted for a tasting at Gambino and had a really lovely time, especially since they plied us with stiff pours and delicious food.

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Day 13: Taormina

Like many of the towns on this list, Taormina is a scenic seaside town located on some towering rocky cliffs. If you go all the way up to the Saracen castle, you can get an incredible panoramic. The main archeological site in town is the ancient amphitheater, which is more unique and cool than the one in Sircausa. So if you’re not much of a history nut, opt for this one. It’s better preserved, still has it’s façade and overlooks the city.They happened to be preparing for a fashion show while we visited!

The central town square is another great stop in Taormina and is definitely the hub of activity in the evenings. There are live musicians, delicious restaurants, touristic shops and great people watching to easily fill your evening! We stayed just on the north side of town in along the coast, which I really enjoyed. You kind of get the best of both worlds!

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Day 14: Cefalu

Lots of European tourists visit Sicily for the beaches. They are excellent, so it makes sense! I liked having this as our last stop, a relaxing way to end your trip on the island. Although we visited a few different beaches while in Sicily, the beach in Cefalu was my favorite. It falls in the shadow of a massive mountain, and is just really beautiful. Unlike any other beach towns I’ve seen before.

It’s popular, so expect tourists, but it also has an authentic and cute vibe. You can swim right off the docks or beach, and there is a beachfront walk that stretches for miles, so you can eat and drink you way along the water all day!

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Most people don’t think of Sicily for their first choice in Mediterranean stops, which I guess behind Greece or Spain makes sense. But I think it is absolutely worth the stop, and I loved my 2 weeks exploring the island. The culture is markedly different than mainland Italy, and it offers many of the great beaches, scenery and unique history that you’d see in other parts of the Mediterranean.

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Author: Megan Arz

I am a travel and food obsessed Midwesterner living in Chicago and dreaming of the world. I work as a full-time program manager for Greenheart Travel, but I am also committed to integrating the travel lifestyle into my every day routines. I am passionate about ethical travel, meeting new people, creating unique memories and eating local cuisine!

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