Welcome to Out of Office… Who What Wear UK's chic travel guide that provides you with the most stylish take on any given destination by tapping creatives who know where to stay, what to eat and, more importantly, which items to pack. This month, Who What Wear UK Contributor Harriet Davey shares her tips for a luxury trip to Jamaica.
There's some countries you visit that'll always have a special place in your heart long after you land back home, and for me, Jamaica is one of them. Having first visited the Caribbean island back in 2022 to style a shoot in Montego Bay, this time, I got to venture back to this same area along with also travelling around to Portland (via helicopter, casual) and finishing my week-long stay in Ocho Rios. And now I've seen more of this magical place, I love it even more than ever.
My favourite part of any trip – aside from planning what to wear, of course – is discovering places to stay and eat and also fun things to do. And after going rafting, having the best massage of all time and eating more jerk chicken than I care to admit along the way, I wanted to share my top tips on Jamaica so you don't have to spend hours on TikTok trying to plan your luxury Caribbean holiday. Consider this your guide to the chicest holiday to Jamaica.
1. Where To Stay
This time round, I was lucky enough to explore more of the island and ended up staying in Montego Bay, Portland and finished the epic week in Ocho Rios. Staying at hotels and villas, these are some of my recommendations that just so happen to be some of the most stylish accommodation on the island.
Montego Bay
Named 'Half Moon' after the 2-mile long moon-shaped beach that you'll have private access to, the resort has 210 rooms plus 19 villas. It's one of those places you could easily book and spend your entire trip there – mainly because of all the amazing restaurants (you can still eat at them without being a guest), the spa, gym, 9 tennis courts and 8 pickleball courts that'll keep you busy.
Ocho Rios
The hotel where Marilyn Monroe got married is of course as chic as you can imagine. With 55 suites to choose from (I had a sea-view room), all designed in blue and white to fit in with the beach-side resort theme, it's a hotel that so many celebrities choose to stay at while on the island. I had a massage in one of the open treehouse style rooms and I was the most relaxed I've ever been hearing the waves.
Oracabessa:
The former home of British writer Ian Fleming, GoldenEye is the 52-acre resort named after the James Bond book written by the author. Made up of villas and beach cottages, I saw people kayaking and paddleboarding up to their rooms (iconic) and it's also the perfect spot for snorkelling.
Portland
This has to be one of my favourite places I've stayed, ever. Owned by DJ and producer, Diplo, the 5-bedroom villa has to be rented as a whole property and with it you get access to the music recording studio, yoga pavilion, library, infinity pool, stables and there's a farm being built for farm-to-table food. The concrete building has the coolest interiors, the most chilled vibe and after staying in the main bedroom, I can confirm it's the best sunrise spot. I also haven't stopped thinking about the freshly-baked cookies in the kitchen-of-dreams since I've got back.
2. What to Pack
I'm a chronic overpacker, but I was very specific with packing for Jamaica as I knew we had a jam-packed itinerary so I wanted to make sure I had all the right outfits to take me from water rafting and spa days to chilled lunches and dressy dinners. The island is so colourful so it would be rude not to take inspiration from the surroundings and go for some vibrant looks. I packed quite a few printed co-ords – these are so easy to throw-on in the mornings and can also be broken up to create different outfits.
I wore these Zara toe-ring sandals every day, they're the most comfortable pair I own and go with everything but I also packed a few heels for evening. I also took an array of different sunglasses and statement jewellery to mix and match over the week. A big beach bag is also a must to keep your water bottle (it's super hot so stay hydrated, people), a beach towel and SPF. When it comes to swimwear, I rate Away That Day and I often end up wearing this swimsuit (below) as a top by adding a maxi skirt or shorts.
3. Where to Eat
I love food, so finding the best restaurants is always high up on my to-do list before any holiday. I was a fan of the food last time I visited Jamaica so I knew I would be in for a treat with jerk chicken, rice and peas, fried plantain and oxtail – something I never thought I would like but apparently oxtail ragu gets a firm yes from me.
Vanessa Foreman was booked as a private chef for us when we stayed at Pompey villa and she's also the resident chef at the local restaurant, Inn at the Cove. We went to try more of her amazing food using local ingredients for seafood dishes, salads and stews.
Sisters, chefs and cookbook authors Michelle and Suzanne Rousseau have just opened a new restaurant in the most colourful house high up on a hilltop. Creating culinary experiences for everyone to try authentic Jamaican food in the prettiest setting, we were treated to sausage and plaintain skewers, grilled chicken and homemade dips. It's now open to the public so I highly recommend a visit.
This vibrant restaurant is loved by locals, and I can tell why. The huge menu had everything from curried goat and jerk chicken pasta to shrimp salads and plantain and pumpkin stew. The restaurant is also such a vibe, and there's a nice garden to eat al fresco.
Even if you're not a guest at Half Moon hotel you can still visit the restaurants, and we ate at Hayward's. Here, you can eat the unlimited buffet and I recommend getting the freshly roasted chicken with gravy followed by the bread pudding with caramel sauce and a side of rum cake.
4. Where to Shop
Although a lot of the hotels and resorts have their own on-site shops, Main Street Rose Hall is the shopping mall with everything from designer sunglasses and jewellery to rum (because what's trip to Jamaica without getting some of the local drink?) and souvenirs made by local artisans in front of you. Here are some of the Jamaican brands I discovered.
Creating hand-woven straw bags using local, sustainable materials, I regret coming home without one.
This made-to-order brand has colourful co-ords, tops, dresses and kaftans.
I love discovering new swimwear brands and Jsea's bikinis and swimsuits looked so premium.
I rarely go home from a holiday without a new beaded bracelet or anklet, so I was happy to discover Swizzbeads.
5. What to Do
Whether you're an outdoorsy person, like to see the sights, prefer to chill on a beach or there for the nightlife, Jamaica has it all. We did a mix of water activities including sunset snorkelling on a private yacht – something I'll never forget. Along with some beach trips, lagoon swims, a visit to a haunted house and trips to any spa I could get access to.
Aristo Kat Tours sunset snorkelling:
Aristo Kat Tours has private yachts to hire (with full crew) and I was keen to get in the sea for a sunset snorkel. You can also choose different on-board catering and we had Mystic Thai who created jerk chicken sushi in front of us along with fruit sushi – both I'd never tried, but it was incredible.
There are of course so many beautiful beaches to discover but Frenchman's Cove comes highly recommended, and I get why. The white sandy beach with crystal clear waters and lagoon is somewhere you easily spend the whole day at.
Rafting is popular in Jamaica and although I tried it last time I was on the island, I was keen to go again. You basically sit on a bamboo raft and have a guide who will show you the picturesque sights. This one also had a stop where you got a foot massage using local limestone (it's supposed to be good for your skin) and although this wasn't on my bingo card for 2025, it was fun!
If you want to soak up some history then you can get a tour of the Rose Hall Great House, an 18th-century building where previous owner Annee Palmer was supposed to have murdered her three husbands and many slave lovers. You can also do a late-night ghost tour but I was even creeped out in the day so there's no way I was doing that.
You can visit the spa at Half Moon hotel without being a guest, and it's one of the prettiest spa areas I've ever had the privilege of visiting. I had a massage, followed by tea in the relaxation area and a dip in the pool with waterfall. Dreamy.
Jamica, I'll be back soon x
