Sicily is a beautiful and delicious layered cake of history. Just walking through the streets, you’ll witness a range of civilizations through its food, architecture and people.

Phoenicians, Carthaginians, Greeks, Romans, Byzantines, Arabs, Normans, Spaniards and more have made their mark on this island. Being strategically positioned and the largest island in the Mediterranean, Sicily was a valuable and fertile land source for cultivating and trading goods.

Its long and storied history began with indigenous tribes. Phoenicians then moved into Sicily in the 11th century BC. As empires rose and fell, Sicily served as a magnet and facilitator for power. It wasn’t until 1861 that Sicily became a part of the Kingdom of Italy.

Having explored and adored Italy five times before, Sicily felt like a deeper dive into a country we find ourselves gravitating toward every time we consider a European adventure. I’m so glad we decided to prioritize this island and give it the two weeks it deserves. Actually, we found ourselves having to scratch highlights off of our list to keep it to two weeks. You could easily spend a month here.

Boisterous and refined. Gritty and regal. Rugged and polished. Sicily is multifaceted with a unique personality that makes it stand apart from its home country, yet it feels comfortably familiar.

Here’s a snapshot of the itinerary we built over two weeks to hit the highlights of this cultural gem:

  • Palermo – four nights (visited Planeta Winery on the way to Agrigento)
    • Day trip to Cefalu via train
    • Day trip to Monreale via Uber
  • Agrigento – two nights (visited Villa Romana del Casale – a must-see on the way to Noto)
  • Noto – two nights
  • Siracusa – two nights (visited Catania on the way to Taormina)
  • Taormina – three nights
    • Day trip to Mount Etna and winery

I highly recommend the counter clockwise flow of this trip because it gave us lots of variety. If you wanted to shave off two days, skip Noto. In hindsight, I might add the two days to Siracusa and day trip to Noto. However, we would have missed staying in an 18th century villa at Seven Rooms Villadorato, which was a worthwhile experience.

To drive or not to drive

You absolutely do not need a car in Palermo, Siracusa or Taormina. We rented a smaller car at the end of our Palermo stay and returned it in Siracusa. In the larger cities, we walked and relied primarily on Uber, which typically was better priced than the taxis, to get around.

We had been warned that driving was difficult in Sicily. It’s certainly not for the faint of heart and you have to resign yourself to the fact you need to be on the lookout for merging cars, pedestrians and bikes at all times.

Sicilians also have another speed when it comes to driving on the highway. I think the speed limit signs are translated as speed minimums.

I’ve also never seen such aggressive passers.

Blind curve? No problem. Sicilian drivers throw up their hands to fate and go for it. Of course, I’m the complete opposite. I could have an opening the length of Texas and hesitate. Kudos to braver drivers.

Our hotels

Villa Igiea in Palermo is a heavenly escape. I have started falling for the Rocco Forte Hotel brand, which seems to run amazing properties rivaled by the friendliness and helpfulness of its staff.

The breakfast buffet and menu offerings were some of the best of our trip.

The only downside is the location required about a 15- to 20-minute ride into the town’s historic center, where we did most of our touring. With that said, it was a great nighttime escape to enjoy its signature drinks at the bar and dinner on the terrace overlooking the harbor.

A breakfast buffet highlight: heaping helpings of fresh ricotta

Villa Athena is all about its location. The hotel has its own private entrance into the Valley of the Temples, which is the main attraction in Agrigento. While the hotel seemed a bit tired, it offers a heavenly dinner among the stars overlooking the night-lit Temple of Concordia. An excellent live pianist enhances the drama and romance.

Carb lovers dream: the daily pastry tower that comes with breakfast at the Villa Athena

When we pulled up our car to Seven Room Villadorata and hit the buzzer, we weren’t sure what to expect. We thought, where in the heck are we going to park our car? Then the green double doors opened to the Palazzo Nicolaci.

As we steered toward our private parking in front of the 18th century palace, we knew we were in for a special treat.

We relished the spacious rooms and bathrooms, quiet, and balcony views over Noto.

We didn’t book a room with a terrace, but did have access to one from a communal living area. Next time, we’d choose a room with a private balcony.

The Grand Hotel Des Étrangers  ranked as one of our favorite hotels for its location on Ortigia Island, which is the place to stay when visiting Siracusa. We chose a seaside room with windows that opened onto a standing-room-only balcony.

Everything felt recently updated. My only complaint would be the slightly hard water. Definitely check out the rooftop bar and make reservations for a nice table from which to watch the sunset.

We refused to stay in the Four Season’s Taormina hotel made famous by its appearance in “The White Lotus.” How could we justify the premium when the Belmond’s well-located and old-world charm Grand Hotel Timeo offered so much better value? I guess we’ll never know for sure, but I wouldn’t want to take the chance to miss this gorgeous place that knows how to make every guest feel special with lots of perks.

First, there is the shuttle service to its sister beach hotel, Belmond Villa Sant’Andrea. Add to that the amazing treats, from the almond cookies at reception and the welcome amenity to the hearty breakfast options and complimentary evening gelato and granita cart service.

If nothing else, the views and location next to the Teatro Antico are enough to seal the deal.

Memorable meals

For my fellow meal planners, here’s a quick glance at the restaurants we’d revisit in Sicily organized by city.

Palermo

Florio Restaurant
It’s hard to leave the beautiful setting and grounds of the Villa Igiea. Fortunately, you can stay to enjoy an al fresco dinner with some excellent food.

The raviolis, steak and cannoli were some of the best of our trip, setting a high standard to follow. We loved this place so much we ate here twice for dinner.

Enjoy one of their signature cocktails beforehand at the adjacent bar. If you love martinis, try their “My Martini.” It’s secret? Counterintuitively, the addition of water to the gin, premixing and refrigerating the mix before assembly.

Far East (front cocktail), a Harrison Ford-inspired Manhattan with an oriental spice twist, and My Martini

Aperitivo spread delivered with your drink order

Villa Costanza
Clinging to a hillside overlooking the city makes this the perfect setting to reflect on a day of sightseeing. The homemade bread is a highlight and the pizza is good.

MEC Restaurant
Apple passion meets Michelin-star food at what I’d call the most unique restaurant experiences of my life. With Steve Jobs looming from the walls and old Apple computers set behind glass, you definitely feel the obsession of the collector who decided to create a culinary space in which to share his love. While we were turned off by what I’d call a fish-forward menu after the overpowering amuse-bouche and mackerel dishes, I could appreciate the remaining courses. If you love fish and all things Apple, this is the place for you.

Agrigento

La Terrazzaa degli Dei
This was one of our favorite restaurant experiences. Further setting the mood, a live pianist played while we admired the ancient temples and ate elevated classic Sicilian dishes. Eating their arancini served over a cream sauce ruined me for all other versions of this street-food staple.

Sal-8 
This restaurant on the main drag of the historic center was packed with locals and for good reason. The atmosphere outshines the food slightly, but we’d still highly recommend it.

Pistachio-topped ravioli

Eggplant caponata

Before or after dinner, be sure to stroll Agrigento’s city streets filled with what seemed like more locals than tourists

Noto

Viva il Bistrot
I would come to Noto just to eat at this restaurant. Trying new cocktails is always a risky affair, but the one they recommended was summer perfection in a glass. Each dish after that equally thrilled the eyes and palate.

Refreshing cocktail of rosemary gin, white vermouth, white myrtle and rosemary and lemon oil

Crocifisso
While we didn’t love our seating and the stark atmosphere of the restaurant, the food more than made up for it. We ordered the land tasting menu and didn’t regret it.

Sabbinirica
A casual lunch spot with delicious sandwich and salad options.

We tried the pizzolu, a cross between a pizza and sandwich

Siracusa (Ortigia)

Cortile Spirito Santo
This Michelin-star tasting menu was our best of the trip. Weather-permitting, book one of their outdoor tables. Every course blew us away with plenty of ingredient pairings that pleasantly surprised us. I’m always impressed with a chef who improvises. Every night he curates a different menu based on the ingredients he finds in market that day.

Beef tartare, veil of carrot, hazelnuts and butter

Egg, cream sauce, bacon, crispy potato on edges and Alba truffles shaved on top

Surprise dish of the evening: barbecue pork, potato and green beans with ketchup

Sicily map made with almond pudding, pistachio ice cream, peach and dessert wine sauce, and pistachio and almond crumbles

So glad we chose two different desserts so we could see and taste this chocolate cigar

Definitely not photo shy, the amazing chef and culinary team

Le Vin de L’assassin
This casual spot served one of the best gazpacho soups with creamy burrata cheese atop. We also loved the leg of pork.

Handwritten menus added to the charm

Taormina

Osteria Santa Domenica
This is a great local spot with ample personality and good Sicilian fare. I highly recommend the steak covered in truffles.

Bar Timeo
It doesn’t matter where were travel, at some point a good juicy burger is the only thing calling our stomachs. If you are craving some traditional fare, enjoy the live music, a stunning view, cocktails and some mainstream classics at this Belmond watering hole.

Otto Geleng
As if the setting wasn’t enough, the well-deserved Michelin-star food merits the price of admission at this Belmond restaurant. We saved the splurge for our last night and we are so glad we did.

Unfamiliar with the local gin to use for our martinis, our server excitedly brought out a few for us to try before committing to our choice in a full martini.

Every course was beautiful, delicious and interesting.

Bar Sant’Andrea
While we had some good pizza during our visit, this restaurant’s pie is reason enough to visit. In addition to watching the pizzaiolo working his pizzas, we also enjoyed watching the beach scene unfold with adventurous divers working up the courage to jump from nearby cliffs.

Our favorite experiences

Get a mosaic eyeful at Monreale Cathedral

You will have ample opportunity to cathedral gawk during a tour of Sicily. Even though you’ll get an eyeful of gorgeous churches in Palermo, take a 30-minute taxi ride to Monreale to see its cathedral and cloisters.

Built in the late 12th century, the Monreale Cathedral awes with its mix of Byzantine, Norman, Arab and Romanesque styles. What most impresses is its almost 70,000 square feet of gilded mosaics. Looking up and around the church, the Bible’s story unfolds.

The last Norman king, Williams II, chose the church’s site. As a result, a significant town now numbering almost 40,000 emerged.

Scenic overlook in Monreale

Day trip to Cefalù

While Palermo has plenty of harbor views, it’s worth a day trip to Cefalù to take in the beach scene and get lost in its beautiful streets. Save your appetite for plenty of street food options.

Its Norman-fortified cathedral is known to house one of the best mosaics of Christ. Unfortunately, it was covered for renovation during our visit, so we were left guessing at its grandeur.

We learned that Norman King Roger II chose the cathedral’s location when a storm led his ship to safely land in the shallow waters of Cefalù. His survival was enough to convince him of the town’s holiness. Of course, there also were political reasons behind his motives. Cefalù was the strategic halfway point between the Norman stronghold of Palermo and Byzantine Taormina. King Roger II planned to make Cefalù his capital city, but he died before that could happen.

Next time, I’d prioritize getting there in time to hike La Rocca for its views of the city and to see its castle ruins. We didn’t have the legs for it the day we visited.

Walk some of the best-preserved Greek temples at the Valley of the Temples in Agrigento

We’ve visited Athens and have been wowed by the Acropolis. Agrigento’s Valley of the Temples is equally transportive to a time some 2,500-plus years in the past.

Its well-intact Temple of Concordia built in 435 BC is considered one of the best-preserved Greek temples in the world. Thanks to Byzantine Emperor Theodosius’ call to end pagan religions, many temples like this one were converted to Christian churches, which ultimately helped them to stay better intact.

During its heyday, Agrigento had a population of 200,000 people and was the Greek’s third largest city after Athens and Siracusa.

When in Agrigento and if you have a few extra hours, visit the nearby Scala dei Turchi to see the dazzling white cliffs

On the way to Agrigento, drink in Sicily’s landscape

Although difficult to find, it’s well worth planning a visit to Planeta’s Menfi Winery, halfway between Palermo and Agrigento. It offered a great sampling of their Sicilian wines and accompanying treats. Definitely plan around lunchtime.

Our beautiful tasting room

Soil variety of Planeta’s wineries around the island

Delicious wine pairings

Our most-excellent wine guide

Just when we thought we had our fill, more food arrived

Feel like Roman nobility at Villa Romana del Casale

I have a fascination with mosaics, both small and large scale. It must be the puzzle-crazy girl in me. I love seeing how individual pieces of stone and glass can be pieced together in a myriad of conglomerations to create stunning images.

I was in heaven when we entered Villa Romana del Casale in the middle of Sicily.  This would have been my dream house in Roman times. Every room tells a story with its well-preserved mosaics.

Based on the dominant subject matter worked into 37,000 square feet of mosaics, some deduce that this rich villa owner probably was an exotic animal importer.

What kept this place from being plundered and pillaged like so many other Roman sites? Its remoteness and a landslide in the 1300s that keep it hidden from looters.

Some suspect the guy in the middle is a portrait of the villa’s owner

Go for Baroque in Noto

There’s nothing quite like Noto, dripping in Baroque loveliness. The downside is many others shared in our enthusiasm in seeing this city.

Take time to tour the many gorgeous rooms of this 18th century noble residence, Palazzo di Lorenzo Castelluccio

One of my favorite moments was trying my first tastes of granita on brioche at one of its famous cafes, Caffe Sicilia. I thought it would be strangely watered down in its iciness. On the contrary, it was full of flavor with none of the trappings of richness to get in the way of pure enjoyment. Add to that the touch of yeastiness from the brioche and it’s a match made in heaven.

My granita flavor choices: almond and fig

A spoonful of happiness

Be sure to duck into as many churches as possible and pay the extra Euros to climb their stairs for stellar views of the city. During the golden hour right before sunset, it’s magical.

Inside this church, I paid to climb its stairs for the city view below

Another church, another climb for this sunset view

Immerse yourself in the best of Sicily in Siracusa

After watching “The White Lotus” set in Sicily’s Taormina, I figured it would be my favorite city during our Sicily tour.

While I loved Taormina’s scenic overlooks and ancient Greek-turned-Roman theater, my favorite city, especially its historic center of Ortigia, was Siracusa. It has it all – Greek ruins, lively market, citidel, beaches, puppet wizardry and shopping.

In hindsight, I would have given this place an extra day or two.

Ortigia, which is actually an island connected by bridge to mainland Siracusa, has one of the most beautiful piazzas in Italy. Once again, you can see layers of history as you explore its baroque church built atop a Greek temple.

The lively market is just beyond these Greek ruins of the Temple of Apollo

Spices galore

Charismatic fishmonger

It’s easy to shop ’til you drop here

Beach outside the city walls

The elegant piazza duomo

Church built over Greek temple columns

Ruins of Siracua’s Roman amphitheater at the Neapolis Archae0logical Park

When is Sicily, especially Siracusa, check out its live puppet theater and museum

Savor the scenic overlooks of Taormina, but don’t miss the beach

Taormina is gorgeous and crowded in late September. There is no better view than the one from its ancient theater where concerts still take place. Sadly, we missed one by Andrea Bocelli just weeks before our visit.

While touring the town is worth a brisk walk, don’t miss venturing out. We loved watching the swimmers navigate the rocky promontory to dive into the Bay of Mazzarò. Next time, we’ll also be sure to allow time to head up to the hilltop village of Castelmola towering over Taormina.

Greek-turned-Roman theater

The smaller rock to the right and larger one straight ahead lured brave divers

Feel the power of Mount Etna

The highlight of our Taormina visit was checking out Mount Etna’s less touristy northern slope. It felt like we were entering a new and vast world blanketed in volcanic ash. The crunch under our feet added to the eerie feel of walking along craters walls that made you feel vulnerable and small.

A Mercedes Unimog helped us cover a lot of territory and get to the most scenic spots without investing a lot of time. We would highly recommend it.

After immersing yourself in the terroir, reward yourself with a wine tour.

We loved our stop at Fischetti Winery, which incorporates some of the winery’s original equipment into its beautifully designed tasting room. It was fun trying some of their main grape varieties of Catarratto, Nerello Cappuccio, Nerello Mascalese and Carricante – all new tasting territory for us.

A volcanologist led our Mount Etna tour

Our Unimog covered a lot of territory

Drinking in Mount Etna’s distinct terroir at Fischetti Winery

Formerly an old millstone, some original equipment adorns Fischetti’s tasting room

Taste of Sicily whets appetite for more

Sicily will delight all of your senses. It is a big island that deserves time to take it in. Regardless of how much time you allow, you’ll likely leave wanting more. That’s the sign of a special place and indeed Sicily takes the cake. Take the time to savor every layer one bite at a time.