Sicily’s Ultimate Road Trip

Sicily is one of Europe’s most enticing “fringe” destinations — still largely undiscovered, but well worth the journey. For Italy aficionados, Sicily is a fascinating “continuing education” in a place that’s somehow even more intense than the mainland (with all the highs and lows that entails). For first-timers, it’s a collection of delightful surprises and an exhilarating introduction to Italy. And for people who find mainland Italy a bit too much…could I perhaps interest you in Germany?

Our brand-new Rick Steves Sicily guidebook, published in April 2019, has been a real team effort: co-author Sarah Murdoch, contributing author Alfio di Mauro, contributions from Rick and from me, and the usual talented work by our editors, mapmakers, and graphics people. We’re thrilled with how the book turned out. Its publication has inspired me to share a few more of my favorite Sicilian photos and memories that haven’t seen the light of day yet.

These photos loosely follow the route I drove around Sicily to research the new book, starting and ending in Palermo and circling the island counterclockwise. It’s also the route of our recommended two-week itinerary by car from our Sicily book. Enjoy!

Stop #1: Palermo

Palermo’s main intersection — called the Quattro Canti (“Four Corners”) — features four fancy facades facing each other. Trying to capture this lovely space on film, I made full use of my fisheye lens. In addition to being a fascinating study in the theatricality of Baroque architecture — as the day goes on, the sun moves across female statues embodying spring (young maiden), summer, fall, and winter (elderly woman) — this intersection is the navigational center of town. I found myself passing through here again and again…and was always glad I did.

Stop #2: Segesta

Sicily — which was known as Magna Graecia (“Greater Greece”) back when the ancient Greeks outgrew their little islands and followed their own westward expansion — is the best place outside of Greece to see ancient ruins: Segesta (pictured here), Selinunte, and Agrigento (described later) are the “big three,” but seemingly every town has an old temple ruin or a theater carved into the hillside.

Stop #3: Trapani and the West Coast

Sicily’s often-overlooked west coast is a fine spot to settle in for a day or two of side-tripping. From the workaday but endearing port town of Trapani, you can head up to the hill town of Erice (this photo is taken from its castle), take a thirsty stroll through medieval salt pans, ride a boat to the isle of Mozia to see scant remains of the ancient Carthaginian civilization, sample some wines in a Marsala cantina, and set sail for the Egadi Islands. (Favignana has a surprisingly fascinating museum dedicated to the tuna fishing and canning industry that put this area on the map.) While not the most spectacular corner of Sicily, Trapani and the west coast are a fine kick-off for an island loop.

Stop #4: Agrigento

Sicily’s top sight from antiquity is the Valley of the Temples, in Agrigento. Slightly misnamed, it’s a half-mile-long ridge lined with temples (in various states of repair) from Greek times. Like the Roman Forum or Ephesus in Turkey, it’s one of those places that stokes your imagination for ancient times…you can’t help but mentally don a toga and picture when this was a thriving community.

While Agrigento is famous for its Valley of the Temples, its overlooked town center — which also lines up along a promontory —  is worth exploring. I stayed in an agriturismo in the nearby countryside, but I was glad I ventured into Agrigento one evening for a stroll up its main drag and a good dinner. Forking off Agrigento’s spine is the colorful “stairs of the winds” — a popular canvas for local street artists.

Stop #5: Villa Romana del Casale

While many of the great ancient sites in Sicily are from Greek times, it also has some of the best-preserved ancient Roman mosaics anywhere. Villa Romana del Casale, strategically located in the middle of nowhere, has elaborate floors decorated with painstakingly crafted murals that depict exotic animal hunts, cherubs on a fishing trip, and mighty female athletes who have acquired the unfortunate, persistent nickname “the bikini girls.”

Stop #6: Ragusa and Southeastern Sicily

Looking back on my Sicily trip, my favorite stop may have been mellow Ragusa, burrowed deep into the island’s southeastern hills. With houses blanketing two adjacent hills, Ragusa hits that perfect travel sweet spot: It’s big and bustling enough to be interesting and to serve its visitors well, but small and out-of-the-way enough not to be overrun by tourists. I saw quite a few out-of-towners here, but it seemed that almost all of them were Italians…a good sign.

I happened to be in Ragusa during an endearing little festival honoring the local Ragusano cheese. I expected the place to be mobbed. Instead, I strolled through a floodlit town where local people, and a handful of Italian tourists, were out enjoying their beautiful piazzas. The streets and squares of Ragusa are designed with a Baroque sense of theatricality and drama…church domes seem to be positioned just so.

Another reason to like Ragusa is that it’s an ideal home base for side-tripping to a delightful variety of low-impact, lovely towns dotting southeastern Sicily. Chocolate-crazy Modica (pictured here), valley-filling Scicli, and the Baroque beauty Noto are all within a short drive. This area was severely rattled by an earthquake in 1693 — and the reconstruction coincided perfectly with the high point of Sicilian Baroque. The entire region was rebuilt in this same style, using the luscious local sandstone, giving it an unusual harmony — especially in Noto. I found this to be the prettiest part of Sicily.

Stop #7: Siracusa

Siracusa may be Sicily’s most all-around entertaining destination. The mainland is dreary sprawl, but the historic center — filling a little island called Ortigia, surrounded by a nearly 360-degree bay — is magic: ancient Greek and Roman ruins, quality restaurants, characteristic back lanes, creative artisan boutiques, colorful puppet shows, hipster cafés, pebbly beaches, and my favorite square in Sicily — facing the town cathedral, which, like Siracusa and Sicily itself, is built upon layers of history. Ancient Doric columns still line the nave.

Stop #8: In the Shadow of Mount Etna

Catania — Sicily’s second city — gets a bum rap. It’s big, gritty, intimidating, and hard to navigate. While I wouldn’t put it at the top of my “must-visit” list, I was glad to spend the night here. Its old center is made of black lava rock from Mount Etna, which smolders on the horizon. Its center has been slowly rejuvenated — leaving the old core far more elegant than Palermo’s (which wears its charm with a patina of scruffiness).

Sicily’s glamorous poster child is Taormina, dramatically clinging to the edge of a cliff, with grand views to smoldering Mount Etna. Capping things off are the well-preserved ruins of a Greek and Roman Theater — built by the ancient Greeks, but later “upgraded” by the Romans. It’s hard to imagine a more scenic backdrop for a theatrical production. While I love the theater and the setting, I have to admit I was left pretty cold by Taormina. It’s a posh resort that — like most posh resorts — feels soulless, its authentic character plastered over in favor of amenities to please deep-pocketed tourists. (To be fair, I was primed not to like Taormina by many Sicilians and Sicily aficionados who had gravely warned me it was not “the real Sicily”…one of them used a perfect Italian phrase to describe it: “All smoke and no meat.”) Yes, you’ve gotta see Taormina. But you may find that other places stick with you longer.

We’re spoiled in the USA — with our long, broad, sandy beaches in California, Florida, and Hawaii. In Europe, a “beach” is rarely sandy — and more often, rocky and pebbly. Sicily is a great beach destination, but only for those who understand this crucial difference. The most memorable beach I saw here was Isola Bella, tucked just below the cliff-clinging center of Taormina (and accessible by a quick and scenic gondola). In the 19th century, an English noblewoman bought this island — tethered to the mainland only by a slushy pebble causeway just a few feet wide — and built a villa here. I went down to check out the villa…but the beach was the real star. It was packed with holiday-makers, basking in the hot Sicilian sun, splashing in the stunningly clear water (a fair trade-off for the lack of sand), and struggling to get comfortable on the rocks.

Mount Etna — the still-active volcano that gave rise to Sicily — is famous for its steaming profile. But what really blew me away was its stunning, fun-to-explore wine region. My favorite stretch was along its northern slope, between the villages of Linguaglossa and Randazzo. Regardless of whether you enjoy the wine, the scenery and dreamy countryside culture are divine.

Stop #9: Cefalù

My favorite beach town in Sicily is Cefalù…not for its fine beaches (though it does have those), but because it has the soul of an old fishing village — you still see fishermen pulling their boats up onto the beach, between the sunbathers. Its centerpiece is an insistently likeable Norman fortress-church, decorated inside with glittering golden mosaics. Cefalù is simply a fun place to be on vacation — it reminded me of my favorite island getaways on Croatia’s Dalmatian Coast.

The most satisfying hike in Cefalù is up to the top of “La Rocca” — the Gibraltar-like giant rock that rockets up above town. It’s a steep and rugged climb, but at the top you’re rewarded with stunning views over the town’s rooftops and hulking church.

On the day I summited La Rocca, with a sense of achievement and curiosity, I checked my Health app: 21,000 steps and the equivalent of 105 floors (plus another 105 on the way down). That’s like taking the stairs to the observation deck of Chicago’s Willis Tower. Yeah, I think I earned my gelato.

Stop #10: Back to Palermo

You know a city has gotten under your skin when you’re conspiring to get back there before you’ve even left the country. I started my trip in Palermo, then circled Sicily. As the end of my loop neared, I realized I really wanted one more crack at the island’s main city — partly for my guidebook work, but also just because I enjoyed it. I gave up a day off I’d planned in Taormina and added one more day in Palermo. I loved having another shot at the city, with the benefit of all I’d learned in the rest of the country. This strategy worked well for me in Iceland, too — where I had a few days in Reykjavík both at the start and the end of my trip. I like this approach so much, I’m going to start doing it on purpose.

Our new Sicily guidebook — with all of the details about everything mentioned here — is available now.

This itinerary works great by car. Sicily is a little crazy to drive in — but once you get used to it, it’s not so bad.

For my best advice on traveling in Sicily, check out my Top 10 Sicily Travel Tips.

And if you’re a foodie like I am, you’ll definitely want to sample Palermo’s street food.

We also have a wealth of free Sicily content on our website, including a recommended itinerary, links to two new episodes of Rick’s public television series about Sicily, several interviews from Rick’s public radio show about Sicily, more gorgeous photographs, recommended books and movies about Sicily, and much more.

And if you’d like to visit Sicily — but would love it if someone else did all the driving, took care of the hotels and half of the meals, and explained it all to you — well, then, we have a great 11-day tour for you.


15 Replies to “Sicily’s Ultimate Road Trip”

  1. Hi Cameron, love the article! I live here in my adopted city of Gela (between Licata & Vitoria). Wish we could have met up! Going to Palermo in a few weeks for the first time. Visited Taormina years ago & loved it, although like you said, it’s touristy. Will use this article for future overnight trip idea’s. Thanks! Stay well..

  2. Visited Sicily, the land of my ancestors from my mother side, a few years back, we spent a week there staying in the beach town of Giardini-Naxos, just under Taormina to explore de East coast and the rest of the days in Cefalu to explore Palermo and its surroundings, we drove everywhere by car and it was a pleasurable experience, we expect to go back soon.

  3. Taormina was the very best part of Sicily – we were there in April and loved it.
    Rick could not be more wrong in his opinion.

  4. It’s pretty much doctrine that Ragusa is wonderful, so I must play the heretic here. My wife and I found it to be the least likeable of the Southeast’s Baroque hill towns. Unlike Modica, Scicli, and Noto, where real life blends almost seamlessly with history and wonderful architecture, Ragusa feels sterile. Few people actually live in Modica Alta; the real working town, Modica Bassa, is a trail of tears back uphill. The insider tip here? Stay in Modica. Just wonderful, and most of the tourists are gone by dinner.

    You mentioned the lack of sandy beaches in Europe. If that’s true, then Sampieri is even more impressive than I thought. It’s a huge sandy beach that’s just a gorgeous short drive from Scicli. It also has the rather enigmatic and ghostly Fornace, a great and unusual spot to snap some wonderful photos.

    Our week in Baroque Sicily, capped by a long weekend in Siracusa, was unforgettable. We have at least 2 other itineraries planned for return visits to the island.

  5. I travelled through Sicily by train and bus. I really liked Taormina and Cefalu. Monreale’s cathedral near Palermo is one of Sicily’s jewels and not to be missed. Sicily was better than I expected and so glad I visited. Fascinating place.

  6. We just finished a driving trip in Sicily this May where you must have a car which is also your worst nightmare. We got our first traffic violation and rental car agency “Handling Fee” for their handing our information to the local policia in late August. Enjoyed the ZTL high fine restricted driving areas everywhere too.
    I hope your Sicily guide has extensive discussions about driving drama in Sicily.

  7. We went stopped in Taormina and arranged a nighttime trip around Stromboli. It was recommended to us by an old boat captain as the “searchlight of the Mediterranean.” Stayed at a hostel on one of the small islands where an evening cruise can be arranged. Delightful! An erupting volcano, a full moon. Met some lovely Italians who bought us lunch for my husband’s birthday.

  8. I loved Taormina, but I think the reason (in retrospect) was that I didn’t stay in the center of town, but above it. I woke up to glorious views down to the city and the water, then walked down through the “residential” areas to the center each day. Of course, this meant I had to hike up each night – but it was worth it.

    Before my visit to Taormina, I had read that famous people like Greta Garbo and Tennessee Williams would spend several months at a time there. I didn’t understand – until I visited. If I could do the same, I would. For me, it was magic – despite the daytime crowds.

    Of course, everyone responds to different places differently. Many seem to find San Sebastian, in Spain, as magical as I find Taormina. To me, San Sebastian was lovely, but not a place I needed to stay too long. Different strokes, as they say.

    I didn’t get to Catania, and would love to see it next time I go to Sicily.

  9. I spent a week in Sicily at New Year’s, 2007. My home base was Acireale, a sea-side Baroque town between Catania and Taormina on its east coast. Rented a car, and explored mainly the eastern part of the island with a day trip west to Agrigento. My favorite areas were the northern and eastern slope towns of Mt. Etna (magical at dusk with the sun setting over the volcano), and I loved the small historic town perched high above Taormina – Castelmola. Beautiful island, beautiful people.

  10. My husband and I were lucky enough to travel to Sicily on tour with Sarah. It was wonderful. I highly recommend it.

  11. Tour-guide-extraordinarie Stacy Gibboni led our Rick Steves Tour of Sicilia in 2016 and we were so amazed that we had to take our daughters there the next year (following much of the same route). One of the highlights was the Valley of the Temples in Agrigento. But could Cameron or someone in Edmonds double-check the photo above for Agrigento? I think it’s actually a second photo of the temple in Segesta.

    1. Wait—on second look, it really is Agrigento with the city of Agrigento on the hilltop in the background. It really is incredible how well the temples in Sicilia are preserved.

  12. You are absolutely right when you say that “we’re spoilt in the USA with our long, broad, sandy beaches”, as opposed to the pebbly European beaches. But at the same time no one usually speaks of the USA as of a resort – strange as it may seem. Tourists rather associate America with the Statue of Liberty and the Niagara falls than with marvellous beaches.

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