Montego Bay, Jamaica. It’s famous for its gorgeous beaches, its awe-inspiring sunsets and being name-checked in that Beach Boys song. (Even if they did wind up going to Kokomo in the end.) And it’s just the kind of place where you’d love to find a posh island villa on which to descend en masse with a crew of your best frenemies, Real Housewives style, for a week’s worth of Champagne and air kisses.

We’ve found the setting: Round Hill Hotel and Villas. Opened in the 1950s on what was once a sugar plantation, the historic high-end resort boasts about two-dozen villas perched on a tropical flower-filled beachside slope. They’re all ideal for group getaways, and Round Hill—rather quiet, cloistered and refined—is what your posse will appreciate once (you can admit that) you’ve outgrown the nightclub scenes at those ultra-contemporary island properties that possess all the indigenous charm of an oceanfront Cheesecake Factory overflowing with Ed Hardy bathing suits. From the warm, grinning stewards in crisp cotton suits to the villas themselves—outfitted with tile-lined pool patios, lanais of slatted white woods and living rooms and bedrooms boasting rich finishes—Round Hill is the kind of storied Caribbean resort that offers whiffs of orchids and the ghosts of upper-crust guests who bore honorifics like Lord, Lady and Countess. (We don’t mean LuAnn.)

Take Villa 25, once owned by dancer Adele Astaire (Fred’s sister) and the site where a vacationing John F. Kennedy wrote and rehearsed his inauguration speech. (We’re pretty sure it started with “My fellow Americans—be cool, don’t be all uncool.”) It’s a 3,400-square-foot hideaway with three bedrooms, a pool and a full kitchen, where breakfast is made for you daily. During the Caribbean offseason, it can be had for $1,759 per night. Daunting, but do the math: That’s less than $300 per person if you round up three couples to share the pad, relatively reasonable by the standards of Caribbean oceanfront compounds.

In fact, all villa prices plummet through Oct. 31—so you and your cronies can book the same digs where flamboyant British playwright Noel Coward, Round Hill’s first shareholder, vacationed (Villa 3), where Oscar Hammerstein, a then-owner, wrote much of The Sound of Music (Villa 12) or even where Stella got her groove back. (Villa 11 was the setting for the movie, and star Taye Diggs later married Idina Menzel at Round Hill.)

Of course, you don’t have to splurge on the suite life. Steps from the beach and the infinity pool is the Pineapple House, which contains a series of sea-facing guest rooms for singles and couples, swathed in white linens and personally appointed by Ralph Lauren, who owns not one but two homes on the Round Hill property. You’ll crash here after a day of snorkeling, water skiing or cruising around the bay on a glass-bottom boat—and you’re that much closer to the beach bar pouring tropical tipples and the bi-level beachfront restaurant serving modern Caribbean cuisine. A meandering pierside path leads to the spa, where tropical showers and body scrubs with Jamaican coffee beans await, and the newly renovated yoga pavilion and fitness center, which is wrapped in glass walls so you won’t miss the ocean view while you’re on the elliptical.

When it’s time to explore the island, make the most of Round Hill-facilitated excursions around the lush, rainforest-filled Montego Bay region. You can take a dune buggy safari through mountains or zip line across them, dip in mineral springs or ride a 30-foot bamboo raft down the green waters of the serpentine Martha Brae River, hand feed native birds at Rockland’s Bird Sanctuary or frolic with Flipper at Dolphin Cove Jamaica (also home to sharks, snakes and various other friends of feather, fur and fin).

But the real must-visit has to be YS Falls. It’s worth the 80-minute drive inland to reach the seven-tiered waterfall that cascades into pools where visitors soak, splash and—for the cost of a few dollars as a tip—leap from rope swings given a good heave-ho by local guides in wait. There’s a zip line course, gardens for wandering and a small shanty slinging spicy jerk chicken for noshing at picnic tables. Kokomo could never.

Traveler’s Checks  

-Make a booze run at Appleton Estate, a distillery that’s been producing rum since the mid-18th century and is now home to 250,000 oak barrels aging the goods for up to 50 years. Tour, taste and take some home.

-Only an hour’s drive away is Negril, home to the world-famous Seven Mile Beach, Rick’s Cafe (a hopping cliffside bar where tourists gather liquid courage before jumping into the sea) and—if you, ahem, swing that way—the notorious nude resort Hedonism II.

Appleton Estate Nassau Valley, St. Elizabeth (876-963-9216)

Dolphin Cove Jamaica Ocho Rios, St. Ann (876-974-5335)

Hedonism II Norman Manley Blvd., Negril (631-588-4336)

Rockland’s Bird Sanctuary Rockland’s Road, Wiltshire (876-952-2009) Rick’s Cafe W. End Road, Negril (876-957-0380)

Round Hill Hotel and Villas John Pringle Drive, Montego Bay (800-972-2159)

YS Falls Cornwall (876-997-6360)


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