Premier Beach Suite at Jamaica InnWhile much of the marketing info that comes out of Jamaica these days is centered on giant all-inclusive resorts, two intimate, retro-chic properties with deep roots in the island’s glamorous, pre-mass-market past are perfect for a romantic escape. This vintage resort duo, Jamaica Inn in Ocho Rios and Round Hill Hotel & Villas in Montego Bay, epitomizes the star-studded appeal of the mid-20th-century when Jamaica was the preferred playground of such notables as John F. Kennedy, Oscar Hammerstein, and Noel Coward. I have visited both resorts twice – the first time 10 years ago and the second just last month – and can say that they are lovelier than ever. Plus, rates at both properties drop in April, making late spring a fabulous time to visit.

Jamaica Inn: The color is mesmerizing. I want to call it periwinkle, but the resort’s energetic and enigmatic manager, Mary Phillips, refers to the special-order tint as “Jamaica Inn blue.” It is never out of sight, coating the walls, both inside and out, and creating an aura that is both intensely soothing and addictively stimulating. It is a happy color for a happy, couples-oriented place (children under 16 are not allowed) that has been welcoming guests since 1950.


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Family-owned since 1961, Jamaica Inn specializes in old-school hospitality done right. Its 42 Verandah Suites (shown above at left) and Balcony Suites overlook a lushly landscaped lawn and 700-foot private beach, and each features a charming bedroom with sleekly renovated bathroom and a large living room-style verandah or balcony furnished with a crisp white sofa and dining table for two. Nine additional specialty suites and cottages range from the luxurious 2,000-square-foot White Suite, located on its own peninsula, to six cottages set atop a bluff (couples who can splurge should opt for the one-bedrooms, #3 and #4, with private plunge pools – shown at right – and incredible bathrooms). There are no TVs in the suites and cottages, but all have wireless access.

Not only is Jamaica Inn immaculately kept and welcoming, but its ambience echoes unapologetically with a sense of time and place. To get the scoop, take a seat at the beach bar and chat up head barman Teddy Tucker as he blends an icy cold Dirty Banana (the resort’s delicious signature rum drink). Teddy, who at a youthful 69 still rides his bike to work and likes to rattle off spellings of tongue-twisters like Nebuchadnezzar, has been mixing drinks here since 1958 and has served everyone from Winston Churchill and T.S. Eliot to Joan Collins and Kate Moss.

Infinity Pool in Jamaica Inn's Cottage 3A sense of place also prevails in the oceanfront KiYara Ocean Spa. KiYara, which means “sacred place of the Earth’s spirit” in the indigenous Taino Indian language, is a peaceful and intriguing bamboo and thatch structure, where balance and nature prevail. Book a 75-minute Couples Moonlight Serenade to sip Champagne by candlelight and be simultaneously soothed by locally sourced organic oils and the ocean’s lullaby, before heading back to your verandah for a private dinner.

The rest of your stay, you’ll enjoy Jamaica Inn’s open-air dining terrace, where talented chef Maurice Henry conjures flavorful interpretations of everything from local Jamaican beef patties and perfectly seasoned baby calamari to a delightfully sauced fresh catch and even an irresistible pesto pasta. Throughout dinner, a band serves up a musical feast – from Cole Porter classics to the jaunty (and deliciously naughty) Calypso ditty “The Big Bamboo.” Dancing is not required, but I guarantee your feet will feel inspired. Suites from $299/night.

Beachfront Room at Round Hill Hotel & VillasRound Hill Hotel & Villas: Not to be outdone in either the vintage or VIP departments, this 30-acre oasis, opened in 1953 and known for its crisp and timeless green-and-white striped window shades and black-and-white checkerboard floor tiles, is the past playground of John and Jackie Kennedy, Grace Kelly, and Paul Newman, among others, and the current winter vacation realm of fashion icon Ralph Lauren, who designed the resort’s hotel rooms and Polo Bar. Lauren (who was there during my last visit) owns a private cottage, as do 27 other shareholders, who when not in residence allow their two to six-bedroom cottages (21 of which have private pools) to be part of the rental program.

Individually and elegantly decorated, the villas are tucked amid lush foliage on a hill, providing panoramic water views. Favorites for couples are Villa Suite 97 in Cottage 25 (filled with antiques, including a fabulous king-sized mahogany bed, it once belonged to Adele Astaire, sister of Fred, and JFK practiced his inaugural address there) and Villa Suites 63 and 64 in Cottage 12 (where original owner Oscar Hammerstein wrote “The Sound of Music”).

More affordable, the 36 Lauren-decorated Oceanfront Rooms (shown above at left) feature white-on-white décor with vivid accents of blue and magenta; the upstairs rooms have vaulted ceilings, a four-poster bamboo bed and a large picture window with ocean views, while the downstairs rooms have identical décor and a patio. They overlook a two-tier infinity pool lined with comfy chaises and offer easy access to a recently expanded golden-sand beach washed by a tranquil and shallow bay. Tennis (on five courts, two of which are lighted), golf (on one of five nearby courses), and water sports (snorkeling, diving, sea kayaking, and more) are all available.

Guests staying in cottages will awake to the aroma of breakfast – from scrambled eggs and coconut pancakes to Jamaican ackee and saltfish – being prepared by their housekeeper. Lunch (the Cobb salad is terrific) and dinner (featuring a la carte menus and themed buffets, from Jamaican Night to Caribbean Curry Night) are served on an atmospheric Seaside Terrace and just-opened Grill at Round Hill, accompanied by musical entertainment.

The Spa at Round HillThe resort’s most recent addition is the Spa at Round Hill, featuring seven treatment rooms in a restored 18th century plantation house (shown at right) and a secluded hillside al fresco couples area. If you imbibe too much rum on Jamaican Night, schedule a side-by-side 60-minute Round Hill Signature Hangover Massage for the next morning and marvel as strokes of oil infused with toxin-clearing Jamaican Sweet Basil help you feel good enough to think about ordering rum punch with lunch. Rooms from $305.

See our Jamaica Travel Guide for more trip-planning information, then use our Travel Search price comparison tool to find the lowest prices on flights, hotels, packages, and more travel deals to Jamaica.

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