In 2010, I met my husband traversing the foothills of the Himalayas and sleeping on cowhides in rural Chinese villages. We saw, nay, lived in the heart of China for six months. That experience solidified my identity as a daring female explorer. It led me to hitchhike the island of Molokai, camp on the eastern coast of Iceland, and inadvertently delay an entire flight to Israel because the suspiciously small size of my pack. Since then, however, I’ve looked down upon seemingly cliché destinations, such as the Caribbean, and feigned interest in travel stories about these lesser exciting locales. Then I met Nevis. In 2018, my husband was starting a new business and I was submerged in the throes of graduate school. We needed an escape. Nevis was the winning destination after some quasi-sophisticated calculations involving credit card points, rewards status, and a timeshare plan. I was secretly embarrassed our only international trip for the foreseeable future was to the Caribbean, and I oscillated between choosing to enjoy the weather and pre-purchasing a Señor Frog’s t-shirt. We invited some friends to share our two-bedroom rental and figured we would, at least, enjoy some rum punch in good company. As we boarded the plane, I realized I had only seen one blurry photograph of the property on that sketchy timeshare website. Maybe, I thought, the house was a scam and we would leave with a good travel story after all! Our rental house did, in fact, exist. Upon arrival in St. Kitts (Nevis’ sister island), we rented a car and high-fived as we squeezed onto the last ferry to Nevis that night. We watched the sunset over the channel between the islands where the foreboding waters of the Atlantic Ocean met and awakened the relaxed spirit of the Caribbean Sea. I felt at home lounging on the car hood, watching the sun play with the water, and listening to a young American couple argue with the ferry operator about costs. Nevis continued to surprise me in that short trip. We went on a drive with our property manager who stopped his Jeep on the opposite side of the island to encourage his wandering goats to return home. Over lunch, he revealed with a sly smile that our unassuming rental house was owned by a high-profile American politician. We later found a checkbook in an unlocked drawer that corroborated his statement. A local took us snorkeling on his fishing boat and entertained us with increasingly dramatic shark tales. He laughed when we questioned their legitimacy, then emphatically insisted upon their truth. We came to appreciate the lack of concern in nearly all of our interactions. Upon recommendation, we embarked on an eight hour jungle hike that was described as “a nice morning walk,” and we received instructions to “just find me before you leave” when we didn’t have the cash on hand to pay a bill. We occasionally had more serious discussions about the slave history of the island and the influx of high-end tourism. Local opinions on the topic were nuanced, insightful, and always followed with a laugh. Needless to say, Nevis challenged my stereotypical impression of the Caribbean as I grew ever more intrigued by the Dalai Lama-like sense of omniscience that seemed to pervade the island. It was as if every Nevisian, native-born and expats alike, knew the same secret of life that infused them with a resounding sense of calm and quirky sense of humor. I was enchanted, and I wanted in. I would have many more of these lingering moments in my subsequent trips to Nevis. They presented as simple sunsets, drinks at bars with expats and locals, and visits to beautifully curated resorts that defined laid-back luxury. Each of these encounters embodied a sense of playful mischievousness, and that seems to be Nevis’ delicate way of dancing among the contradictions of local culture, a steady influx of expats, and tourists’ expectations. Those cheeky smiles, the evasive yet thought-provoking answers to deep questions, and the island-wide sense that everything will work out are what have me returning to this tiny Caribbean island time and time again that no one, and everyone, seems to know about.