I asked my mother where she would like to go for her 70th birthday, and her answer was quite simple: Lie on a beach with a fruity drink in hand. The actual task of choosing a place was not as easy. That is, until I revisited a list, buried deep in my iPhone called “Places I’d Actually Go Back.” As a travel writer and enthusiast, it’s rare to go to the same place twice. But occasionally, a destination is so perfect that you bypass the desire to visit something new and instead take your family along for the experience. Jamaica Inn ticked all the boxes. A quick non-stop flight from NYC? Check. Gorgeous private beach? Check. Small, boutique property with a great staff? Check. Resident dog? A huge bonus for my pup-obsessed mother.
The property exudes old Hollywood glamour, likely a result of being run by the same family for nearly 70 years, and playing host to the likes of Marilyn Monroe; Ian Flemming; and Meghan Markle. And it’s easy to see why: the staff offers genuinely warm service combined with privacy and loads of personal touches. As soon as you step through the airy entryway of Jamaica Inn, you’re immediately welcomed home. The staff is quick to call you by name, cheer on your football team, and have your favorite beverage before you even get the hint of thirst.

Located just outside of Ocho Rios, on a private beach, the 52 guest rooms are spread over eight acres, including eight cottages with private plunge pools and plenty of space to spread out. The verandah suites are classic and what we came for this time around, featuring palatial outdoor living rooms complete with a comfy sofa, chairs, coffee table, and dining table–in addition to ceiling fans and a mini fridge. It’s where we spent most of our time.
Other than lounging on the verandah, days were exactly as my mother requested: Lying on the beautiful beach with a topical drink in hand (the staff comes around at 11am each day to pass out complimentary fruit smoothies or Planter’s Punches). Dining is an elegant affair, with cocktails and hour d’oeuvres served around 7pm, following a more formal (but not-at–all-stuffy) dinner. For those who want a more casual experience, the beachside grill serves traditional Jamaican meals and wood-fired pizzas. Guests can often be found dancing post-dinner to the live house band.
No stay at Jamaica Inn is complete without visiting The Ocean Spa. The retreat is nestled into the cliffs of Cutlass Bay so that guests can hear the ocean waves crashing, nearly to the same rhythm of the massage. The spa uses locally sourced botanical ingredients during treatments that take place in open-air treatment huts overlooking the sea. Our fantastic complimentary Sunday morning yoga class took place here, as well.
If there’s one negative about Jamaica Inn, it’s–quite honestly–having to leave. Nearly every guest we met on the trip had been coming for decades, and most of the staff had been here even longer. But as each person hugs you goodbye, you know you will return again just like I did. And just like my mom will.

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