The city of Siracusa (or Syracuse) near Sicily's southeastern tip has been around and thriving for 2700 years, which can only be a good reason to visit. As you might expect, this metropolis of the ancient world - Syracuse was quite possibly the largest city in Europe in the 5th century BCE - offers an agreeable jumble of ancient remains, Sicilian Baroque architecture and art (find the Caravaggio) and contemporary Italian lifestyle. Palermo may be bigger and livelier, but Siracusa gets the mix just right.
The core of Siracusa is formed by the largely pedestrianised island of Ortigia (linked to the mainland by bridges), where a beautiful Baroque warren of narrow streets and squares surrounds the odd ancient ruin. Highlights are:
Cathedral Square (Piazza Duomo): beautiful set-piece urban space surrounded by palaces and churches, not least the Cathedral itself, which nicely blends into the ancient Temple of Athena from which it was converted.
Temple of Apollo: impressive ancient ruin that was inhabited by everything from a mosque to a Spanish army barracks, but now mostly by cats.
Maniace Castle: medieval fortress on Ortigia's southernmost tip, with impressive views in all directions.
Unsurprisingly for a continuously inhabited city, much of Siracusa's ancient cityscape remains buried beneath contemporary residential areas, but you can get an impressive insight by heading out to the Archeological Park in the Northwest of the city: it contains an interesting array of ancient buildings, among which the highlight is the well-preserved Greek Theatre.
It also includes a network of ancient limestone caverns, including the so-called Ear of Dionysius, which was allegedly used by ancient tyrants to spy on their prisoners (almost certainly a figment of the medieval imagination).
As you can imagine, Siracusa's food includes seafood in all shapes and sizes. We mostly frequented Pizzeria Don Carmelo (not online, Via C. M. Arezzo 9) near the central Piazza Archimede, which does amazing pizza as well as seafood dishes.
A foodie series on Sicily could not be complete without mentioning Pasta alla Norma, and as it is a speciality of Catania (a city we didn't visit) we will drop it in here: this vegetarian pasta dish with tomato, aubergine, salted ricotta cheese and basil is ubiquitous and delicious.
Which other historic seaside cities would you recommend?