Syracuse
The oddity of the title "the greatest Greek city and most beautiful of them all" for a Sicilian city is overturned the second you enter. Though you haven't left Sicily, you are transported back to a different time and place. Greek amphitheaters, fountains, and statues still dot the cityscape capturing the UNESCO World Heritage title. From its inception in the 8th century BC, the city was planned and mapped to rival all others including Athens. Today, the network of streets, wind their way through time periods long lost allowing you glimpses into the past.
Things to do
Once one of the most important cities in the Greek world, and later a royal home during the Kingdom of Sicily, Syracuse has quite the history. These historic sights make up much of the modern tourism scene though walks along the waterfront promenade and some gelato offer a nice reprieve from the history lesson.
Cathedral of Santa Maria delle Colonne
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Many Italian cities centre around a magnificent cathedral which hosts numerous events throughout the year and Syracuse is no different. The Cathedral of Santa Maria, on the island of Ortigia, is the crowning jewel of the main piazza. The 7th-century cathedral has been rebuilt numerous times, most notably after the 1693 earthquake but one unique feature has remained throughout each build. One wall of the cathedral is supported by the massive 5th century BC columns of the Temple of Athena. These columns along with their capitals are one of the main features of the interior offering a unique mix between Hellenistic and Catholic religions.
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Archeological Park
On the west side of Syracuse are the extensive archeological diggings of the Greek and Roman Amphitheatres. Started in the 5th Century BC, the Greek Amphitheatre was one of the most spectacular ever built and still retains much of its original qualities including incredible sound. Cut directly into the rock, the massive semicircle included intricate stage additions that allowed quick scene changes, people appearing in the middle of the stage, and a fantastic orchestra. It was likely one of the largest of the Greek era holding over 16,000 people.
Not far away is the Roman Colosseum built in the 4th century to fill the locals' wants and needs for gladiator fights and other spectacles. Both sites, along with a necropolis, quarries, and the Ear of Dionysius, make up the vast Archeological Park and can all be visited with just one ticket. While some may zoom through the park, it will likely take someone with moderate interest 4 or 5 hours to explore.
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Temple of Apollo
As you cross the bridge onto Ortigia, you are met by a beautiful piazza with the ruins of an old Greek temple. The Temple of Apollo was started in the early 6th century BC making it the first Doric (one of the most famous Greek building styles) temple built in Sicily. Based on its age and a number of unique architectural elements, it is likely the model most Greek temples would be based on including the famous Parthenon in Athens. While the site is mostly in ruins thanks to being used as a church, a mosque, and even a private house, the piazza that surrounds it is one of the main points of the island and is the perfect starting space for adventure.
Castello Maniace
Looking east into the open water stands the last of the major forts that kept the city safe over centuries of fighting. Built 800 years ago, it has been renovated numerous times and has been used as everything from royal palaces to a prison. Today, you can explore much of the castle including the barracks, the keep, and the upper fortifications which give you a great view towards the water or back onto the city.
Where to Stay
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With hundreds of hotels, it may be hard to figure out where to start looking to stay. Luckily, much of the city is residential leaving a much smaller section to investigate further. Syracuse is split into two major sections - the mainland and the island of Ortigia. Ortigia hosts many of the cities tourist restaurants, the Maniace Castle, a beautiful seaside premade, and of course just a few Gelato shops making it the perfect home base for the city. Spend your days checking out the cities fabulous Duomo, lounging in the park outside the castle, or walking along the seaside before sitting down for some fresh seafood or pasta overlooking the ocean. While you will need to spend at least a full day venturing out to the Amphitheater it makes way more sense to stay on the island rather than close to the Amphitheater. Remember to leave yourself a spare day for a trip out to Noto!
How to get there and around
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While the Sicilian train system may not be fast, it still connects much of the island and is likely your best option as a tourist. Though busses are possible, the terminals can often be confusing with a lack of signage and multiple companies to use. While you can make it to Syracuse by means of train or bus from most places in Sicily and even Italy as a whole, your most likely option will be Catania (roughly 1 hour to the north), Agrigento (6 hours to the west), or Palermo (5 Hours to the northwest).
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Once you are in town, staying on Ortigia makes travel by foot convenient with the exception of the Greek Amphitheatre. While it is a long walk, it is doable, but for the sake of time, your likely best option is on the local bus or by taxi.
Day Trips
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In the late 1600s, the most powerful earthquake to hit Italy leveled most of southwestern Sicily. With the majority of towns brought to rubble and over 60,000 people killed, an architect was commissioned to build up the Val di Noto (a Sicilian form of a province during the age). Building off of the Baroque style already popular, he designed the cities with beautiful main squares and with churches as street corner staples. The towns of Noto, Modica, Caltagirone, and Scicli are among the most famous and best-preserved. Noto is one of the most visited as the city becomes awash with orange light when the sun is setting making for one of the most picturesque places in Sicily!