A Fashion Editor's Guide to Jamaica: Dining Recommendations, Accommodation Options, and Essential Packing Tips

      Welcome to Out of Office, the chic travel guide from Who What Wear UK that delivers stylish insights on various destinations by consulting creatives who know the best places to stay, what to eat, and, importantly, what to pack. This month, contributor Harriet Davey shares her recommendations for a luxurious trip to Jamaica. (Image credit: Harriet Davey)

      Some countries you visit will always hold a special place in your heart long after returning home, and Jamaica is one of those for me. After my first trip to the Caribbean island in 2022 for a photo shoot in Montego Bay, I was thrilled to return to the same area, explore Portland (via helicopter, no big deal), and conclude my week-long stay in Ocho Rios. Having experienced more of this enchanting destination, my affection for it has only deepened.

      My favorite part of any trip—aside from curating my wardrobe, of course—is discovering great places to stay, eat, and engaging in fun activities. After enjoying rafting, the best massage I've ever had, and indulging in more jerk chicken than I can count, I'm excited to share my top recommendations for Jamaica so you won't need to spend countless hours on TikTok planning your luxurious Caribbean getaway. Consider this your guide to the trendiest holiday in Jamaica. (Image credit: Harriet Davey)

      On this visit, I was fortunate to explore more of the island, staying in Montego Bay, Portland, and wrapping up the week in Ocho Rios. Here are some of my recommended stylish accommodations across the island.

      **Montego Bay**

      Half Moon: The resort, named after its private 2-mile moon-shaped beach, offers 210 rooms and 19 villas. It’s the kind of place where you could easily spend your whole trip, thanks to its fabulous restaurants (accessible even to non-guests), spa, gym, nine tennis courts, and eight pickleball courts that keep you entertained.

      **Ocho Rios**

      Jamaica Inn: This hotel, known as the place where Marilyn Monroe got married, is as chic as you'd expect. With 55 suites designed in beachside blue and white (I stayed in a sea-view room), it’s a favorite among celebrities visiting the island. I experienced a massage in one of the treehouse-style rooms and felt incredibly relaxed listening to the waves.

      **Oracabessa**

      GoldenEye: The former home of British writer Ian Fleming, this 52-acre resort is named after the James Bond book written by him. Comprising villas and beach cottages, I saw guests kayaking and paddleboarding to their accommodations (iconic), and it’s a fantastic spot for snorkeling.

      **Portland**

      Pompey: This villa has quickly become one of my favorite places to stay ever. Owned by DJ and producer Diplo, the five-bedroom property is rented as a whole, providing access to a music recording studio, yoga pavilion, library, infinity pool, stables, and a farm being developed for farm-to-table dining. With its stylish interiors and relaxed atmosphere, plus the main bedroom being the best spot for sunrise views, I can't stop reminiscing about the freshly-baked cookies from the dream kitchen.

      **What to Pack**

      I'm typically an overpacker, but for Jamaica, I was meticulous with my packing knowing we had a packed itinerary. I wanted outfits suitable for water rafting, spa days, casual lunches, and dressy dinners. The island's vibrant colors inspired my wardrobe, so I opted for a variety of printed co-ords that were easy to wear in the mornings and could be mixed and matched.

      I wore my Zara toe-ring sandals daily as they are super comfortable and versatile, but I also packed several heels for the evenings. I included an assortment of sunglasses and statement jewelry to interchange throughout the week. A large beach bag is essential for holding your water bottle (stay hydrated!) along with a beach towel and sunscreen. For swimwear, I highly recommend Away That Day, and I often wear their swimsuit as a top by pairing it with a maxi skirt or shorts.

      **Where to Eat**

      Food holds great importance for me, so locating the best restaurants is always on my pre-holiday checklist. I loved the food during my previous visit to Jamaica and was eager to enjoy jerk chicken, rice and peas, fried plantain, and oxtail—something I never expected to enjoy, but oxtail ragu proved to be a delightful surprise.

      Inn at the Cove: We hired Vanessa Foreman as a private chef during our stay at the Pompey villa; she is also the resident chef at the Inn at the Cove. We sampled her exquisite dishes created with local ingredients featuring seafood, salads, and stews.

      Two Sisters Experience: Sisters, chefs, and cookbook authors Michelle and Suzanne Rousseau have launched a new restaurant in a colorful house on a hilltop. They offer culinary experiences to showcase authentic Jamaican cuisine in a beautiful setting, and we enjoyed sausage