I’ve only been to Jamaica once before, and that was a classic resort stay in Montego Bay, so this trip marked my first time in Negril, and specifically the West End. A quick heads-up: if you arrive on a Friday, island traffic is very real. It takes time to get where you’re going, but trust me, the wait is absolutely worth it.
Arrived! Night One:
We stayed on the rocky cliffs at a new residential property called West Signature, located in the West End of Negril. It’s not a hotel, it is a thoughtfully designed residential community that blends island living with sweeping views of Jamaica’s coastline. Our apartment was beautifully appointed: lots of space, a fully stocked kitchen, a large king-size bed, a pull-down dining table, and the cherry on top, a gorgeous patio with water views for days. And right on the property? Syd’s on the Rocks, which quickly became our anchor.
Once we arrived and unpacked (yes, I unpack everything before vacation officially begins), we headed upstairs to Syd’s on the Rocks. We were greeted by Paul with a very boozy rum punch and front-row seats to watch the sun dip below the horizon. (Swing seat for me). We snacked on cod-fritters and fried plantains, before being seated for a welcome meal crafted by Chef Kimsan Austin. As we settled in for dinner, we had the chance to spend time with Sydney Watson, the owner of Syd’s on the Rocks. Jamaican born and raised, Sydney is remarkably young and already leaving an outsized mark. She is one of the few Jamaican women to own resort-style properties on the island, and her story, rooted in vision and pride of place is as compelling as the setting she has created.
Day Two:
Day two started early with a trip to Negril’s famous Seven Mile Beach. Breakfast was at Miss Lily’s at Skylark. Traditional Jamaican breakfasts for my table included a bowl of sweet porridge, dense banana bread toasted and slathered with butter and The Jamaican Special (I mean, obviously)—> steamed callaloo, sweet plantain, ackee & codfish. And I had my first-ever Jamaican Blue Mountain coffee experience. Renowned for its mild flavor profile with almost no bitterness, it’s subtly sweet with hints of chocolate. It absolutely does not disappoint. Fueled up, we ditched the coverups and spent a couple of hours soaking up the sun Negril’s famous white sand beach.
Later that day, we stopped at Three Dives for a traditional Jamaican lunch of jerk chicken and goat stew. I mean that is the kind of meal that tells you exactly where you are. Not one to sit around, we then went on to Rick’s Café. It’s an iconic spot that everyone talks about. It’s a total scene, booming music, boozy cocktails, and people jumping off those very high cliffs. We watched the sunset there amid all the action.
Next stop: Ivan’s for a quieter, more reserved cocktail and cliffside scene. Then it was back to Syd’s on the Rocks for another on of Chef San’s dinner that blends Puerto Rican and Jamaican flavors, and this time we leaned all the way in: Whole fried snapper, the sweet plantains and the twice-fried green plantains and the rice and peas (always). But the standout? The Puerto Rican lasagna, a braised and pulled jerk short rib layered with cheese and plantains. Save room.
Final Day: Wah!
On our last day, we headed back to Miss Lily’s for more sun and those gorgeous turquoise waters. We walked along Seven Mile Beach, greeted by good music and those unmistakable Negril vibes.
That night, we returned to Syd’s one last time, snacking on those addictive plantain chips with a glass of rosé while watching the sunset yet again. Dinner followed at Rockhouse Hotel, right next door to Syd’s. We simply walked over and settled into one of their cliffside coves. Dinner included Caribbean lobster and (yes) more delicious rice and peas, with the ocean crashing underneath us.
Back Home (and Dreaming of Negril)
Now, back home, staring out at dreary weather, all I really want is to be looking out from West Signature, boozy rum punch in hand, watching the sun set over the cliffs at Syd’s on the Rocks.
