No one goes to the Amalfi Coast or Capri hoping for bad weather, but there are few places I know of that bring such high aesthetic drama before a rainstorm. Count yourself lucky if you’ve ever experienced gray-black clouds intensifying the contrast of the coast’s green-hued terraced farmland just before bursting open. That was the scene that greeted me on my very first trip to Italy—or anywhere outside the US—as a high school Latin student in the early spring of 1996 (shout-out to public schools that value a classical education). It poured for most of our stay in Sorrento on the mainland, the sea air delivering the smells of damp pavement, orange blossoms, and jasmine as it gusted through the poorly insulated tiled halls of our pensione.

In spite of the weather, the ferries were running to Capri the next morning. This would be my first island experience during a trip brimming with firsts. The sea was choppy below an ominous sky of churning clouds, so only a few of us actually got on the boat. Others, preempting seasickness, stayed behind. I’m proud to say that I was one of the few who didn’t lose her morning cappuccino and cornetto on the way over. A little green around the gills, my classmates and I landed in Marina Grande, Capri’s main port, and took the funicular up to Anacapri, the village at the top of the island. It was nearly empty. It felt like we had been dropped into a movie set.

The buildings had been freshly painted white in anticipation of the impending tourist season, shops were open (I recall buying a Benetton dress in the most unflattering pea-green hue in the history of retail), and locals loitered in the town square, but there were no other visitors around.

Capri, a place that can be an overwhelming tourist hell during high season, was stunning and magical that day, and it felt like we were pioneers discovering a remote Italian village. It’s a feeling I have when I venture two blocks from downtown on most small islands in Italy. The Italian islands are universally beautiful, and their food, vistas, and lifestyles have obvious allure, but they also carry this promise of adventure and discovery that you can only fully grasp once you experience them for yourself.

My next island trip, five years later in 2001, was to Sicily, a much larger destination. I was a rising college senior and spending the summer in Rome courtesy of a generous fellowship I was awarded by Yale to fund travel for my college thesis. The paper was all about the Amazonomachy, the legendary battle between the Greeks and the Amazons, a scene the Romans enthusiastically carved in high relief onto their marble coffins in the mid-second century (turns out high school Latin is practical).

This was the era of guidebooks and calling cards and paper maps. There wasn’t much online about traveling around Sicily, but I had a copy of The Rough Guide to Italy, a thick tome of nearly one thousand pages describing Italy’s twenty regions in detail proportionate to their tourist appeal at the time. Both terrified and exhilarated by the lack of coverage on Palermo, Sicily’s largest city, I boarded a train from Stazione di Roma Termini to Stazione di Palermo Centrale.

I had booked myself into a ladies-only sleeping car that was scheduled to leave at nine p.m. and arrive at nine a.m. It was a hot and humid August night, and my fellow passengers were three Sicilian women, two of whom spoke only dialect and a third who spoke Italian with a thick Palermo accent. At the time, I had only a year of intermediate Italian class under my belt, and the language wasn’t yet clicking for me. I knew I was in for a confusing twelve hours.

The train was sweltering, so I reached up to open the window and was sharply reprimanded in the formal voi common in Sicily: “Eh, no! Non apritela! Un colpo d’aria ci farà venire un torciollo!” (Essentially: “Leave the window closed or a breeze will enter and give us a stiff neck.”) By that time, I had been in Italy for two months— but that was long enough for me to know that Sicilians possess a hysterical fear of drafts, attributing to them every imaginable ailment, and I wasn’t going to be able to negotiate for even a small sliver of open window. Unfortunately, two months was not long enough for me to have acclimated to Italy’s sweltering summer nights.

I made my bed with the folded sheets provided by the conductor while my fellow passengers unwrapped carefully prepared sandwiches, their dinner. Oops, I should have thought of that. Before hitting the lights, one of the women barricaded the door with her luggage, a stack of cardboard boxes. “Ladri,” she said—thieves—placing one finger beneath an eye and pulling gently downward, the Italian gesture for “watch out.” Yikes. The trip was off to a frightening start.

The train’s slow crawl toward Sicily was one of the more disorienting travel experiences of my life. We stopped at Campoleone, a town just outside of Rome, and inexplicably paused on the tracks for an hour. Farther along, not far past Caserta, we began a jerking crawl that lasted an hour. I almost fell asleep at one point and was jolted awake by the train’s screeching brakes. By six a.m., the train was gliding along the coast of Calabria, the last mainland region before Sicily. The rising sun cast a gauzy light over a sea that seemed just feet away. I dozed at last in this moment of calm.

What happened next was both scary and unexpected. I awoke to hollow clanging and metal thuds. We’ve derailed for sure, I thought. I’m going to die in this sauna on tracks. The other passengers in the car calmly got up, grabbed their purses, said a word I didn’t yet know—lo stretto—and left the car. Um, what about those thieves, ladies? I thought. I’m not going anywhere. I stayed put, and only when they returned 30 minutes later and the train chugged out of a dark tunnel past Messina train station did I realize THE TRAIN HAD GOTTEN ON A BOAT. We had crossed the Strait (lo stretto) of Messina, the narrow strip of sea between Calabria and Sicily on a boat. They had gone up to the deck to watch the approach to Sicily, which would have been over a bridge, had the public works projects dedicated to building it not been sidelined for decades by bureaucracy and fears of mafia interference.

Today, bizarre transportation glitches don’t faze me, but back then, that twelve-hour train ride taught me more than I had learned in years of studying Italy: among other lessons, bring a fan, pack sandwiches, and when everyone on the train does something, follow them. When I finally arrived in Palermo, I made my way to the pensione I had booked, only a short walk from where my great-grandfather Niccolò Cipollina was born and spent the first six years of his life. I was eager to explore my ancestral homeland— after a post-train shower and a nap with the pensione windows wide open, colpo d’aria be damned!

When I hit the pavement in the thick Palermo heat later that afternoon, I headed straight for La Cala, the neighborhood in which Niccolò was born, his mother died, his father remarried, and the new family packed all their belongings for a one-way trip to New York in 1906. Some other parts of Palermo were destroyed by bombing in World War II and razed afterward to make way for wide avenues, prestigious apartment buildings, and government offices, but La Cala, home to Palermo’s horseshoe-shaped port, was partially intact. Standing at the water’s edge, I wondered what Niccolò would think about me being there alone. Had he eaten panelle (chickpea fritters) from a street vendor’s stall on this very spot? Did he spend his youth playing in La Cala’s claustrophobic alleys? Had he watched Palermo recede into the distance as he set sail for America? I imagined him perched on his father’s shoulders, looking over the water as his home disappeared forever.

Niccolò never returned to Italy, and in his eighty-nine years barely left the confines of New York and New Jersey. But here I was, far from home, feeling sentimental for a place that was not my own, filled with a sense of connection that bridged the gap through time. My connection to Palermo isn’t just sentimental anymore. My Italian citizenship, which was granted to me through the country’s jure sanguinis (“by right of blood”) policy, is possible because my application named Niccolò as my ascendant. When he sailed from Palermo to New York, he brought his Italian citizenship along with him, and didn’t become a naturalized citizen until later in life—his naturalization papers feature a definitive and dramatic denouncement of Italy’s King Victor Emmanuel III—so he passed it along to his son, Anthony Cipollina, my maternal grandfather; then to my mother, Jo Ann (whom some of you know as “Joj”); and finally to me. My Italian birth certificate resides in Palermo’s vital statistics office.

I’m Sicilian on my dad’s side, too. My great- grandmother Giuseppina “Josephine” D’Antona was born in Villarosa, a village of fewer than five thousand people in the entroterra (rural interior) at virtually the geographical center of the island. I have fond memories of Sunday lunch at her house in Highland Park, New Jersey. She made ravioli, which she dried on a towel laid over her bedspread, and baked glazed cookies decorated with colorful sprinkles. I never met her husband, my great-grandfather Angelo Parlo (the surname was later changed to Parla), who died in 1960. The little I know about him comes from a newspaper article published about my great- grandmother to mark her ninetieth birthday. According to the article, he was from Villarosa, too. They met at the San Gennaro festival in Little Italy, and he didn’t consult her before moving the family away from New York to New Jersey in 1921 (which is why I’m not sure we would have hit it off).

Regardless, I inherited my curiosity and affection for Sicily from my ancestors, while my fascination with Italy’s dozens of other islands, large and small, is almost magnetic, an intangible attraction that draws me to their shores, at times in trains that board boats, at others on ferries or hydrofoils—and now even on a little fishing boat named Laura that I keep in Murano. I know that with each trip, adventure and discovery await, along with that warm embrace I felt when I first entered La Cala and walked in Niccolò’s footsteps.