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Nearly the size of Massachusetts, Sicily is the Mediterranean’s largest island. Its many different regions offer a wealth of exploration, from the vibrant city of Palermo to the bucolic corners of the southeast.

Cheat Sheet

Lay of the Land

“For over twenty-five centuries we’ve been bearing the weight of superb and heterogeneous civilizations, all from outside, none made by ourselves, none that we could call our own.”
~Giuseppe di Lampedusa, 1958

Sicily’s different regions are incredibly varied in terms of landscapes, climate, food and culture. There are four main cities: Palermo, in the northwest, Messina, in the northeast, Trapani in the west and Catania in the southeast. International flights arrive either in Palermo or Catania.

Palermo

The capital of Sicily is a vibrant, crumbling, messy, fascinating place, with incredible churches, palazzi and atmospheric squares. It’s famous for its terrible traffic (if you can avoid driving, do) and for its bloody Mafia history, but there’s so much more to it. Some streets seem to be frozen in time, with sheets drying from balconies and Italian mammas shouting at vendors from their balconies before lowering buckets with coins to pick back up their selection of fruit and vegetables. The neighborhoods to know in the historic district are La Kalsa, La Vucceria, Il Capo and Il Ballarò, and all are easily explored on foot.

Southeastern Sicily

This is one of Sicily’s most glorious regions, composed of small towns that were built entirely out of yellow-golden stone; of bucolic countryside with wheat-covered fields as far as the eye can see; and the stunning Vendicari Nature Reserve fronting the turquoise Ionian Sea.

The towns to know in this region are Syracuse, the first Greek settlement dating to 733BC; the seaside village of Marzamemi (for a glorious lunch at La Cialoma); and the late-Baroque hilltop towns of Modica, Ragusa and Noto, with their unusual and soaring cathedrals. Travelers based here can also take advantage of their (relative) proximity to ceramics town Caltagirone and the stunning Villa Romana del Casale, which contains the world’s most complex collection of Roman mosaics (and is Sicily’s most-visited site). The Valley of Temples at Agrigento is about a 2.5-hour drive from Modica towards western Sicily.

Taormina & Mount Etna

Located in northeastern Sicily, the small resort town of Taormina is the island’s most well-known and most-visited destination. It’s also the most touristy and can get mobbed during the summer months, especially during the day. It pays, therefore, to stay at the Grand Hotel Timeo or the Villa Sant’Andrea and to only head into town before or after the day trippers arrive or after they leave. Taormina, with its ancient “Greek” Theater (it more probably hails from Roman times), should be on everyone’s Sicily itinerary. But as many guides and locals see it, “Taormina is not Sicily,” or rather, it’s not the whole story, so most travelers will want to plan in at least one more stop on their trip.

A 30-45 minute drive from Taormina, you enter the massive regional park that is Mount Etna. There are many small agriturismo and family run B&Bs in this part of Sicily, one of the most verdant in terms of landscapes.  Nothing is the same caliber as the Taormina hotels, but Monaci delle Terre Nere, opened in 2012, has a vineyard setting.

Western Sicily

Sicily’s most unexplored region is one rich with ancient history and small towns that barely see tourists. Starting at Agrigento, whose Valley of Temples is the most famous, you also have the Greek sites of Selinunte and Segesta in this part of the island. (The Rocco Forte-run Verdura is also based here, a bit off the beaten path but a true resort with amenities.) Closer to Palermo, on the north-western shore lies the pretty town of Erice, home to sweets made by cloistered nuns and with sweeping views. Since there is so much to see and do in the eastern and southeastern part of Sicily, the western part is usually recommended for return travelers.

A Note on Hotels

Sicily does not have the number of luxe accommodations as some of its Italian cousins, like Capri. The best ones are located in Taormina, on the east coast near Catania, most notably the Grand Hotel Timeo, San Domenico Palace and Villa Sant’Andrea. Travelers who can scale back expectations somewhat by staying in family run B&Bs or small, privately owned (and therefore, uneven) hotels, will enjoy exploring the wealth of discoveries in regions like the southeastern Baroque towns, Palermo and Mount Etna.

Approximate Driving Distance

  • Catania International Airport – Taormina: 1 hour
  • Catania International Airport – Syracuse: 1 hour
  • Taormina – Syracuse: 1h45min
  • Taormina – Noto: 2 hours
  • Noto – Villa Romana: 2h15 min
  • Noto – Caltagirone: 1h40min
  • Noto – Modica: 45 minutes
  • Noto – Vendicari Nature Reserve: 20 minutes
  • Noto –Marzamemi: 30 minutes
  • Noto – Agrigento: 3 hours
  • Modica – Ragusa: 25 minutes
  • Ragusa – Noto: 1 hour
  • Agrigento –Palermo: 2 hours
  • Palermo – Monreale: 20 minutes
  • Palermo – Erice: 1 hour 45 minutes
  • Palermo – Taormina: 3 hours

When to Go

Sicily’s high season runs from June through August, which coincides with the hottest temperatures and biggest crowds. The best time to visit is the spring (April and May) and early fall (September and October) when the temperatures are still warm, but the island is pleasantly crowd-free.

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