Postcards from… Jamaica

In our ‘Postcards from…’ series, we invite intrepid travellers and creatives to share their experiences from some of the world’s most fascinating destinations. This time, we venture to the tropical Caribbean island of Jamaica with Ian Pendleton, creative director at Show Media and friend of Globe-Trotter.

There’s a certain magic about Jamaica – its rhythm, its colours, the way the sea shimmers under the Caribbean sun. For those seeking both relaxation and adventure, few places rival Montego Bay and neighbouring Negril, each offering an idyllic yet contrasting slice of island life, all wrapped up in warm Jamaican hospitality.

Landing in Montego Bay, Ian’s journey began with a scenic hour-and-a-half-long drive along the coast to Negril, where Skylark hotel sits on the powdery shores of Seven Mile Beach. This boutique hotel is a sister property to the renowned Rockhouse (established in 1974) and embodies a retro-chic aesthetic with a playful, contemporary twist. With its pastel hues, vintage-style decor and lush tropical surroundings, Skylark exudes an easy-going, bohemian charm that instantly sets the tone for relaxation.

‘Days here are best spent between the crystalline waters and a sun-drenched lounger, with the soundtrack of reggae humming in the background,’ Ian advises.

And then, of course, there’s Miss Lily’s restaurant. Originally a New York institution, Miss Lily’s at Skylark is an explosion of flavour and colour. The beachfront eatery is a temple to bold Caribbean cuisine – jerk chicken that’s wonderfully smoky, curried goat that melts off the bone and plantain caramelised to perfection. The restaurant’s vibrant, neon lights combine with the scent of pimento wood smoke in the air – this is a place where rum punch flows freely, children fill up on sweet coconut treats and where Ian likes to savour the island’s finest seafood.

After spending a few sun-kissed days in Negril, Ian’s journey back toward Montego Bay led to Round Hill Hotel & Villas. This legendary retreat has drawn the likes of Grace Kelly, Jackie Kennedy and, most famously, Ralph Lauren, who owns a private villa here and designed the resort’s interiors in his signature crisp whites and nautical blues. Yet, despite its deep roots in old-world luxury, Round Hill remains wonderfully relaxed, making it perfect for a family escape.

Beyond the hotels, Ian was enticed by Jamaica’s natural beauty and vibrant culture. ‘A boat trip to Booby Cay is a must,’ he recommends. ‘It’s a tiny, uninhabited island where local fishermen grill fresh lobster over open flames. The experience is wonderfully rustic.’

For a more intimate taste of local cuisine, Ian headed to Murphy’s in Negril. Hailed as a hidden gem, this unassuming, family-run eatery serves some of the best seafood on the island. The setting is as unfussy as it gets – wooden picnic tables, twinkling string-lights and a kitchen that’s little more than a shack – but the flavours are nothing short of five-star.

Accompanying Ian on his 4,500-mile trip was his young family and the Globe-Trotter Centenary Carry-On case. Whether they were revelling in barefoot luxury at Skylark or enjoying the simple pleasure of cracking into fresh lobster on a secluded island, the case proved to be the perfect lightweight-yet-durable travel companion.

If not Jamaica, where will you take your Globe-Trotter this year?

Shop Ian's Centenary 2-Wheel Carry-On in Red/Caramel, £1,695.