I visited Sicily for a week in late May. We stayed in Syracuse, an ancient town on the southeast side of the island, in a home overlooking the Greek Theatre and the island of Ortigia. Unlike other hot spots in Italy, Sicily still feels very authentically European and not overly Americanized or too touristy at all. In my opinion, the island is best explored on a week (or so) long road trip, allowing you to pop in and spend a few days in each of the tiny towns that line the coast. Here are some of the places I explored, things I loved, and recommendations I would provide to anyone planning to visit this special place.
WHEN TO GO
Late May-early June, or early September, for perfect weather without the peak summertime crowds.
TOWNS TO VISIT
Palermo: a vibrant city rich in history and culture.
Cefalù: a charming beach town outside Palermo, known for its turquoise waters and picturesque streets.
Taormina: perfect for shopping, upscale dining, and luxe accommodation, plus a breathtaking view of Mt. Etna.
Syracuse and Ortigia: spend a few days and enjoy an authentic, local feel and a great home base to visit smaller, southeastern towns like Noto.
Agrigento: worth a detour to see the Valley of the Temples, one of Sicily’s most iconic ancient sites.
STAY
DO
Have lunch at Four Seasons San Domenico Palace in Taormina to check out where White Lotus was filmed.
Visit the Greek Theater in Syracuse.
Stop for lunch at a family-owned winery in the Sicilian countryside (we did this about 1 hour outside of Syracuse).
Spend a day window shopping (or not) in Taormina along Corso Umberto I. Stop in at the various Dell'Oglio boutique locations for a unique selection of designer brands.
If you're feeling adventurous, climb Mt. Etna at sunrise.
Enjoy a day or two at the beach in Cefalù.
Take a tour of each town, including Noto, Palermo, and Syracuse, to learn about each area's unique history.
Watch the sunset from a sailboat in any of the coastal towns.
Visit Taormina and take the cable car between the ocean and the cliffside shops and restaurants.
Stop in for happy hour at Ristorante Sant'Andrea at the Belmond Villa Sant'Andrea.
Do a bike tour to visit tiny towns scattered along the countryside.
Visit the local market in Ortigia and then take a cooking class with the ingredients you pick up.
EAT
One of my favorites was Ristorante Sant'Andrea at the Belmond for sunset drinks and bites. The vibes, service, and food were amazing. Otherwise, we mostly stumbled into local spots, which did not disappoint!
WHAT I WORE
What is your go-to airport look?
In the summer, the Artless Drew Pants and a t-shirt, with a sweater tied around my shoulders or tossed in my carry-on bag. In the winter, always a cashmere set!
What’s in your bag (travel edition)?
At least three lip balms (I love Summer Fridays and Rhode), noise-cancelling headphones, a sweater, an eye mask, melatonin gummies, a mini Dedcool fragrance, and my laptop and notebook so I can work the whole flight.
What piece did you wear the most on this trip?
The Reese Tee from Artless! It’s the perfect white t-shirt, is buttery soft, and literally goes with everything. I love the versatility of a t-shirt. You can wear it with trousers and flip flops for a chic daytime look, or dress it up with a silk midi skirt and kitten heels for an al fresco dinner.
Artless Forever has timeless capsule pieces … what are some of your favorites currently?
So hard to choose! I literally live in my brand, but my current fixation is the Romy Mini. It’s chic, long-sleeve, and backless. I’m obsessed!
Xx,
Villa Igiea is a longtime favorite of mine ❤️
I'm now adding Sicily on my Notes list of places I want to visit. <3