It had been a while since I’d had a vacation vacation—the type where hours blend into nothing and your only responsibilities are to claim a lounge chair, choose a book, and try to remember where you left your sunglasses. A few days at the legendary Rockhouse in Negril, Jamaica, delivered just that and then some: think jerk chicken sandwiches off the grill, party vibes that start way before sundown, and an endless soundtrack of reggae and dancehall. Of course, I also needed to curate a packing list fit for the setting, one that included a swimsuit for making the most of my villa’s private ladder into the Caribbean sea, reading material guaranteed to immerse me in Jamaican culture and history, and a versatile tote bag that would look just as appropriate on the way to the spa as it would during a clifftop dinner come nighttime. Below, a few of my favorite items from the trip.