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There’s nothing like that new hotel smell (one that, to me, combines wood, paint and hope!) But I’ve stayed at enough mediocre modern hotels to know new isn’t necessarily better. There’s a lot to be said for choosing a resort that’s a Caribbean classic. A resort where they’ve been welcoming guests for decades – sometimes even generations. A resort whose popularity has outlived fleeting hotel trends. A resort like one of these:

Round Hill, Jamaica

Round Hill.

Round Hill opened as a villa resort in 1953 with songwriter Noel Coward as one of its homeowners and now counts Ralph Lauren among them. I’d visited many times when I lived in Mo’Bay, but my stay this past April was my first. And I was pleasantly surprised to find that the vibe here is relaxed, distinctly Jamaican, and very warm. With black-and-white photos of past celebrities and royal guests decorating the walls, the hotel’s high falutin heritage was obvious. But there was no trace of stuffiness at the 36-room/27-villa retreat, which sits on what was Lord Monson’s colonial-era Round Hill estate, where pineapples (now featured in the resort’s logo) once grew. Many of the staff have been here for decades – which, in a town with so many hotels, speaks volumes about how happy they are to work here. It also explains why when you stay at Round Hill, whether for the first or 15th time, you truly feel like you’re being welcomed into someone’s home

Hamilton Princess & Beach Club, Bermuda

Hamilton Princess & Beach Club.

Established in 1885, this iconic Bermuda resort is named after one of Queen Victoria’s daughters and has welcomed an impressive roster of guests over the years, from Mark Twain to Muhammad Ali to King Charles. The “pink palace” is known its distinctive pink façade and elegant afternoon tea. But what I loved most about I when I visited in January was the collection of more than 300 pieces of contemporary art, which walk-ins as well as guests are welcome to browse. Work by Andy Warhol, Yayoi Kusama, Banksy, David Hockney and Kaws are casually displayed in the resort’s garden, lobby and other public areas, no piece considered too precious to be enjoyed close up.

The Buccaneer, St Croix

The Buccaneer.

Like many classic Caribbean hotels, the Buccaneer’s centerpiece is a colonial-era great house (this one built by the French in the 17th century) on what was formerly a plantation. A family-run hotel since 1947 (and a longtime favorite of President Biden), this sprawling estate exemplifies the Caribbean family-friendly retreat, with activities and amenities for everyone. There’s a golf course, eight tennis courts, three beaches and restaurants, two pools, a spa…take your pick!

The Hermitage, Nevis

The Hermitage.

No visit to Nevis is complete without a stay (or at least a nutmeg-dusted rum punch!) at one of the historic plantation inns that punctuate the landscape of St. Kitts’ little sister. The Hermitage is arguably the most charming of the bunch, comprising a collection of gingerbread cottages, villas and rooms on lush hillside grounds. Hermitage’s centerpiece is its dining room, bar and lounge, which is housed in a fretworked home that’s more than 350 years old and believed to be one of the oldest remaining wooden houses in the Caribbean. After sampling the delicious Wednesday-night Nevisian buffet (complete with a whole roast pig), you might be tempted to stay to confirm it.

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