My earliest memories of Jamaica are visiting as a little girl, in an era when locals walked the streets with baskets on their heads. The rare sight of this today calls to mind the essence of the island: a place where pockets of exotic glamour exist amid an eccentric culture.
I call myself a “Jamerican” and split my time between Jamaica, New York and Nantucket. My Jamaican home is at Round Hill (villas, from $950; John Pringles Dr.; 800-972-2159; roundhill.com), long the blue chip of resorts in Montego Bay, on the island’s southwest point. My family owns Cottage 12, one of the resort’s 27 villas that can be rented. I’ve been a guest in all the cottages. Cottage 9, with its sexy outdoor showers, is a favorite, along with Cottage 16, which has two private pools. There’s a stylishness to Round Hill, the kind that, even being in the Caribbean, makes you want to dress up at night.
A typical day begins in our pool, fresh coconut in hand—though it’s worth throwing on a caftan for the breakfast served by our chef, Nora. Come lunch, we join the social scene at Round Hill’s beach bar. Active afternoons might entail waterskiing at The Caves (cottages, from $660; 144 One Love Dr.; 876-957-0270; islandoutpost.com), a resort 40 miles to the west in Negril, or stopping by Montego Bay’s boutique Schatzie (Fairview Town Centre; wrightinstyle.com). I like to drive across the island to Jakes Treasure Beach (rooms, from $95; Calabash Bay, St. Elizabeth; 877-526-2428; jakeshotel.com), or down the coast to visit Chris Blackwell, owner of the recently renovated GoldenEye Villas and Spa (cottages, from $560; Oracabessa Bay, St. Mary; 876-622-9007; goldeneye.com).
If I’m not having dinner at Round Hill’s Seaside Terrace, I’m at one of the local spots: Sky Beach (Hopewell, Hanover; 876-956-5006; skybeachgrill.com) for jerk anything (fresh fish, chicken, pork) and Lobster Trap ($ Sawyers Beach Rd., Hopewell; 876-783-5046) for seafood. No visit is complete without singing at Round Hill’s cocktail bar, where pianist Brimsley has shared his ivories with no less than Paul McCartney. It is, in a word, jammin’.
$ Establishment accepts no charge/credit cards or accepts cards other than the American Express Card.