The Italian island of Sicily is filled with picturesque towns and villages scattered around the island. It can be difficult to decide which ones to visit. Sicilians themselves are known to get in heated arguments over the subject when travelers ask for recommendations. You could spend weeks exploring towns between ferry stop Messina in the northeast, Pozzalo in the south, and Marsala in the east.
On the magazine side of Perceptive Travel we have a story set in motion by this kind of conundrum. Our narrator Kirsten and her fiance planned on heading to Mount Etna, the live volcano, on their bikes. Their newly met companion, also a cyclist, insisted they ride instead to Trapani, where it would be quieter and have less traffic. (See Hiding the Cannoli for what happens when they all share a room…)
One filter that can narrow down the options is by looking at the UNESCO World Heritage list. While there are some gorgeous towns that aren’t on this list, plenty of those would be on the way between one UNESCO site and another. Since villa rentals in Sicily are so reasonable compared to ones in Tuscany or Umbria, your home base for exploration here won’t cost you a fortune.
Arab-Norman Palermo and Churches of Cefalú and Monreale
Since you’ll probably be coming in and out of Palermo anyway, this collection of structures is an easy add to the itinerary. They’ll be included on most any city tour. They got the designation based on the mixing of cultures in the time of 1130 to 1194. The mix of churches, palaces, and a bridge show influences from Muslim, Byzantine, Latin, Jewish, Lombard and French people.
Yes, the smoking volcano—the highest Mediterranean island mountain and the “most active stratovolcano in the world,” is a protected zone above a certain altitude. That means you can hike part of it or mountain bike on part of it, but you’re going to need to go way down to sleep near it. The mountain tops out at 3,350 meters (more than 10,000 feet) after all. Nicolosi is a good excursion base, while Randazzo on the other side is more lively and historic. It has managed to survive through many centuries of eruptions.
This is not the only smoking Italian cone: you can travel to Stromboli where the cone dominates the whole island. But there you can’t then hit the road and visit another UNESCO World Heritage center, such as…
The Late Baroque Towns of the Val di Noto
This is a rather spread-out UNESCO designation that includes eight different towns located in southeast Sicily (Caltagirone, Militello Val di Catania, Catania, Modica, Noto, Palazzolo Acreide, Ragusa and Scicli). What ties them together is that they were all rebuilt during the same period following a major earthquake in 1693. The aggressive rebuilding schedule meant that people constructed buildings in the prevailing style of the time: late Baroque architecture of the 17th century. One appointed man, Guiseppe Lanz, was in charge of the rebuilding, so he oversaw the designs across the region.
Since the earth hasn’t rumbled like that since, the eight towns look like they all went up at once, with a consistency you rarely find in urban centers that are hundreds of years old or more. Be sure to see the 26 frescoes by Olivio Sozzi at the Basilica di Santa Maria Maggiore in Ispica.
There’s more to do than gawk at municipal buildings and churches, however. Modica is a great place to eat some artisanal chocolate and Piazza Duomo in Ragusa is famous for its gelato.
Syracuse and the Rocky Necropolis of Pantalica
Known as Siracusa locally, the ancient Greek city of Syracuse contains one of the largest Greek theaters built anywhere. It has 9 sections, 8 aisles, and 67 rows of seats. That’s just part of the story, however, in an area that has been inhabited for some 3,000 years.
The Necropolis of Pantalica is the oldest part. It holds more than 5,000 tombs cut into the rock, most of them dating back to a period from the 13th to 7th centuries BC. Greeks from Corinth constructed ancient Syracuse, which they called Ortygia, back in the 8th century BC. Later remains show a mish-mash of influences and invaders from multiple lands a ship ride away.
Grand Villas Then and Now
One last UNESCO site is the Villa Romana del Casale, but this is not so much a place as a villa for a wealthy Roman. What makes it special is that nearly every room is filled with intricate mosaics and it provides insight into how the elite lived in the countryside.
You can act like a wealthy landowner yourself if you bypass the hotels and book a sprawling villa for your home base instead. Select Sicily villas provide stunning coastal views around the island, or in the countryside in the interior.
This villa pictured above has three bedrooms, four baths, and a pool for as little as $247 per night. Or spend a bit more and get a huge upscale farmhouse (but also with a pool) where you’re surrounded by almond trees, pistachio trees, and grape vines.
However you choose to tour Sicily, be sure to take your time. Smell the flowers, sip the earthy wine, enjoy all the fresh food. There’s a lot to see on this history-filled Italian island, but resign yourself to the fact you won’t be able to see it all.