Welcome to Sicily — an island where ancient history and modern-day charm go hand in hand.

From Greek ruins to Baroque beauty, this island is a living open-air museum. Whether you're cycling through centuries-old streets or wandering past sun-soaked vineyards, you'll quickly realize that every corner has a story to tell.

So, hop on, and let’s unravel the history of Sicily and its most fascinating ancient cities! 

History of Sicily (in a nutshell) 

The Greeks, Romans, and... pretty much everyone else. Sicily’s been the Mediterranean’s melting pot for over 2,700 years. First, the Greeks sailed over in the 8th century BC, establishing their colonies and leaving behind some of the finest ruins in the Mediterranean, including the ancient theatres at Catania and Segesta. Fast-forward a few centuries, and the Romans took control, making Sicily a key province in the Roman Empire and boosting its economy with agriculture (yes, Sicily’s famous citrus fruits and olive oil go back to Roman times!) 

But the island didn’t stop there — after the Romans, Sicily became a melting pot of influences, with the Arabs arriving in the 9th century and leaving their mark on the architecture, agriculture, and cuisine. The Normans followed in the 11th century, bringing their own unique blend of architecture and culture. And let’s not forget the Spanish, whose influence still lingers in Sicily’s food and festivals. In short, Sicily has hosted almost every major Mediterranean empire — making it the ultimate cultural buffet. 

In 1693, a massive earthquake (with a magnitude of 7.4, to be exact) hit southeastern Sicily, destroying entire towns. The rebuild? Baroque. It was ALL the rage at the time. That’s why many cities on our Sicily cycling tour, like Noto and Ragusa, are packed with over-the-top, jaw-dropping Baroque architecture. 

Fast forward to today, and Sicily’s still a blend of old and new. Ancient ruins sit beside modern vineyards, and centuries-old traditions simmer in every meal. It’s a place where sun, food, and culture have been mixing for millennia — and you can taste it in every bite. 

Sicily: What to see & do (ancient cities edition)

Sicily is practically one big open-air museum, and our Sicily bike tour is your rolling backstage pass to its ancient greatest hits. Here are six of our favorite ancient cities that'll have you cycling with wide eyes and even wider smiles. 

Palazzolo Acreide: Baroque with a side of bronze age 

Don’t let the fancy baroque façade fool you — Palazzolo Acreide has layers. Built on the site of the ancient Greek city of Akrai (founded in 664 BC), this hilltop town is a glorious mash-up of history. Think baroque balconies up top and buried Bronze Age secrets underneath — including tombs, temples, and a hillside Greek theatre that’s still standing (and stunning). Fun Fact: 

The entire town is a UNESCO World Heritage site — part of the “Late Baroque Towns of the Val di Noto”. 

The best way to take it all in? Hop on a bike and cycle the cobbled streets and quiet countryside, wander through ancient lanes, and, of course, sample a few plates of pasta-packed, cheese-crammed goodness, washed down with a caffè macchiato or two. 

The mountain city of Ragusa 

Ragusa isn’t just one city — it’s two. After the devastating 1693 earthquake, locals rebuilt both the old town (Ragusa Ibla) and a newer, more ''modern'' part (Ragusa Superiore) up on the hill. The result? A town rich in character that's all kinds of beautiful. 

On our Sicily cycling tour, you'll cruise through the Hyblaean highlands before diving into its winding lanes and secret courtyards. In Ibla, you’ll stroll past centuries-old churches, stone staircases, and noble palazzi that whisper of its pre-Roman and medieval past. Architecture nerd or not, this place will win you over. 

The mountain city of Modica 

"Oh my Modica!" — Set in a dramatic gorge and dripping in baroque beauty, Modica serves up more than just good looks. Beneath the balconies and churches lie layers of ancient history — with Greek, Roman, and even pre-Roman settlements once calling these hills home. Oh, and did we mention the chocolate? Don’t miss the chance to taste the town’s famously crumbly, grainy chocolate — still made using an ancient Aztec technique introduced by the Spanish in the 16th century.  

Fun fact: Modica’s signature chocolate is made without conching (that’s the step that makes most chocolate smooth). Instead, the sugar crystals stay crunchy, just like the Aztecs liked it. Add in a dash of chilli or cinnamon, and it’s basically ancient power food. Suitable for warriors… and cyclists (wink-wink.) 

Castelluccio Archaeological Site 

Long before the Greeks showed up with their temples and drama, the people of Castelluccio were already making their mark — literally — by carving tombs straight into the limestone cliffs. Dating back to the early Bronze Age (around 2000–1450 BC), this site is one of Sicily’s oldest and most atmospheric archaeological gems. 

Ride south through the sun-baked countryside to reach this remote and rugged site. Park the bikes, lace up your walking shoes, and take a short hike to explore the hillside dotted with ancient tombs. No ropes, no fences — just you, the view, and 4,000 years of human history. 

Marzamemi 

Tiny, sun-drenched Marzamemi might just be Sicily’s most charming seaside surprise. Originally established by Arab settlers in the 10th century, this fishing village became one of the island’s most important tuna ports — and you can still feel the salty, storied past in the air (and in the antipasti). 

The Arabs didn’t just bring tuna fishing to Sicily — they introduced mattanza, a communal hunting technique. Today, the old fishery buildings have been lovingly restored, and the village doubles as a film set (Inspector Montalbano, anyone?), food hotspot, and the perfect place to devour a tuna panino. 

Syracuse (obviously) 

Founded in 734 BC by Greek colonists from Corinth, Syracuse was the city. A cultural and military heavyweight, it became the most important city in Magna Graecia (Greater Greece) and rivalled Athens in power, intellect, and drama (both political and theatrical). Archimedes lived here, for Zeus’ sake! 

The best way to soak it all up? A guided walking tour through the historic streets of Ortigia. Explore a time warp of crumbling temples, underground aqueducts, and sunlit piazzas. Don’t miss the ancient Greek Theater (still used for performances today) or the Ear of Dionysius, a spooky cave with acoustics so sharp you could hear gossip from across the empire. 

Sicily Bike Tours with Grasshopper Adventures 

Whether you’re a history buff obsessed with ancient ruins or just here for the arancini (and let’s be real, who wouldn’t be?), on a bike, you’ll uncover a side of Sicily that no guidebook can quite capture. 

With our pro Tour Leader by our side, we won’t just skim the surface of southeast Sicily — we’ll be cycling, splashing, sipping, and snacking our way right into its heart. Get in gear... it’s time to go!