Hotel Name: Round Hill Hotel & Villas

Number of Rooms: 27 private villas + 36 hotel rooms

Location: Just outside Montego Bay, a 30-minute drive from Sangster International Airport

Forget the Montego Bay brouhaha clouded by cruise liners and college kids, Round Hill is the Jamaica of lore, where white gloved formalities are eased by genuine hospitality. A terraced hillside encircling a sandy cove, the property is the picture of Caribbean grooming, where the only blemish on its perfectly trimmed lawns is falling Frangipani petals and the occasional windswept palm frond. Expect your ackee and salt fish to arrive on fine china each morning and a chorus of “good afternoons” to follow you as you walk down to the beach before tea time. Round Hill’s 36 hotel rooms are designed by Ralph Lauren, but its truest expression of luxury lies in its collection of 27 privately staffed villas.

What We Loved: Old school Caribbean hospitality has made Round Hill an under-the-radar hideaway since it opened its doors in 1953. Over the years, the likes of Bing Crosby, John F. Kennedy, and Alfred Hitchcock have graced the tidy halls of Round Hill, giving the place a golden-age aura you won’t find elsewhere in Jamaica.

What We Didn’t Love: While Round Hill’s villas shine, its hotel rooms aren’t top tier.

Right For: Travelers looking for the feel of a private island villa, without the private island price tag

Wrong For: Those who’ve been to Mustique…

Best Time to Visit: November-April sport prototypical Caribbean climes, but if the sound of rain falling on a shingled roof has you mentally curled up with a dogeared copy of Wide Sargasso Sea, May-October is your prime time.

TLF Tip: Pack your clubs! The legendary Tryall Club is a 10-minute complimentary shuttle ride away.