When I first visited Italy with my family when I was around twelve years old, we stayed in Montecatini, a small mountain town in Tuscany. The thing that stood out the most to me then was the way that people dressed up to walk around the town square in the evenings; women strode gracefully on mile-high stilettos, faces made up and hair curled beautifully, and I’m sure the men tidied up, too, but the women’s attire demanded all of my awkward, gangly, twelve-year-old adolescent self’s attention.
Now, upon returning to Italy nearly eighteen years later, this time to Taormina, Sicily, I noticed the same habit of people dressing to the nines once the sun went down. Walking through the town’s main drag on a Saturday evening, we passed a lot of couples in evening wear, women in long gowns and men in sharp tuxedos. Our group quickly felt underdressed in our jeans and cotton dresses.
This time around, however, I believe that most people were coming from an opera at the Greek Theater, which holds operas and concerts frequently throughout the warm months. If we ever return to Taormina, attending some type of show there will be at the top of our list.
Like Praiano, we owe our friend Michelle for choosing Taormina, Siracusa, and Modica, Sicily as travel destinations. Before, Sicily hadn’t really been on our radar; I think, for most people, it isn’t, which worked in our favor because it didn’t feel too touristy. Taormina, the biggest town on the island, was the busiest, but not overwhelmingly so. There were plenty of cafés and side streets and bars to find our own space in. And if it ever felt too crowded, we just returned to our Airbnb, the amazing Villa Mimosa.
The villa suited our group of seven perfectly; Michelle, Dave, John, Jackie, Garrett and I traveled together from Praiano and met Maya, our seventh, in Taormina. We made great use of its sprawling rooms and rooftop terrace, usually with a cocktail in hand. One of my favorite nights of this entire trip was when Garrett made homemade pasta at the villa and we dressed up to eat it al fresco by candlelight in the backyard. It was a beautiful evening.
Outside of the villa, we enjoyed hiking up to Castelmola, a small hilltop village with spanning views of the water and city below. It was a steep hike but worth it, especially as we were surprised by a marching band in the town square when we arrived. Their music made us feel all the more proud of our accomplishment of walking uphill in the Sicilian summer heat.
We also fell in love with Da Cristina, the best place for arancini in all of Sicily, according to our shuttle driver and now, all seven of us. We each ate a ragu arancini and slice of Diavola pizza from there at least once a day. For sweets and caffeine, we got cannoli at Roberto’s and cappuccinos at Bam Bar. My goodness, I would go back to Taormina for the food alone.
After three wonderful nights at Villa Mimosa, it was time to move on to our next Sicilian destination, and my favorite: Siracusa. Garrett said “I could live here,” as soon as we got there. The city lies flush with the waterfront; access to swimming and boating and fishing is easy, and the coastline is stunning. Locals and tourists make great use of swim platforms and rock beaches scattered around town.
Surprisingly, Siracusa made me feel like I was in Havana. The palm trees, the beautifully broken down buildings, the pink and the green and the white homes sticking out of the sea all made me feel like I’d been transported back to 1950s Cuba.
We stayed at the Grande Albergo Alfeo Hotel, which was comfortable, reasonably priced, and located just outside of Ortigia, the old town. I’d stay there again, but would check to see what was available in Ortigia first because that’s where we spent the majority of our time.
Most restaurants and businesses close between 2pm and 5pm in Siracusa, which worked against us when we first got into town hungry at 1:45. Luckily, the one place that had been recommended to us by fellow sailors was open and so good: Oz & Cappuccio Pesce Fresco. We ate fresh tuna steak sandwiches and calamari and it was the perfect, quick initiation meal to Siracusa.
That’s one of the biggest things we learned about Sicily: the street food and quick eats were much better than the sit-down meals. Our favorite thing to eat in Siracusa was a sandwich from Caseificio Borderi, located at the far end of the Old Market of Ortigia. You can go inside and order what you like at the counter, or queue up outside to have Andrea Borderi make you whatever he chooses. We did both options and were equally happy with both sandwiches, but watching Andrea make your sandwich is definitely an experience you don’t want to miss. And, if you buy a block of cheese from their family’s dairy, he might just sing to you.
In addition to the food, we loved getting out on the water in Siracusa (but of course). I can’t find the name of the company that we used, but their stand was right along the bridge to Ortigia and it was only 20 Euro per person per hour—easily the cheapest private boat hire we’ve had all summer. We got our own boat for the seven of us and extended it to two hours and it was so much fun. We swam, dove off of the boat, and drank prosecco lowered down to us in a bucket from the street above. It was magical.
After Siracusa, we went onto our final leg of our Sicilian tour: Modica. Modica, a small town in the southeast region of Sicily, was quiet and lovely, full of some of the most beautiful architecture on the island. The majority of our group stayed at Le Lumie, a small B&B with three rooms and a gorgeous patio overlooking the town. It was a short walk to the Duomo of San Giorgio and just a few flights of steps above the main stretch of town.
We took advantage of the quiet pace of Modica to wind down as our trip together came to an end. On that last full morning, people walked around the town alone or in twos, and I stayed back to read and write in the courtyard. We all came back together in the early afternoon to drink a round (or two or three) of Aperol Spritzes, take a chocolate tour at Antica Dolceria Bonajuto, the oldest chocolate factory in Sicily, have pre-dinner cocktails at Gli Orti di San Giorgio, and finally, get ready for our last group dinner at Accursio Ristorante.
I’m not sure if you’re supposed to belly laugh through a Michelin star meal, but we were giddy from having just spent a wonderful ten days together, and a little tired from the eight-course tasting menu, so belly laugh we did. For three and a half hours. The meal was lovely, but the laughter was memorable, and the perfect way to end our trip.
During that meal, we all took time to recognize how fortunate each of us were—and still are—to experience such a wonderful holiday with each other. The moments that we shared across Praiano, Taormina, Siracusa, and Modica will forever stay close to my heart. I’d go back to each of these places gladly, except…I don’t know if I’ll ever be able to capture what the seven of us had.
