The concept was a great one for a teenager: getting thrown into the pool by flirtatious staffers, eating all the French fries I wanted at every single meal,watching grown-ups humiliate themselves during “talent night.” But those spring-break trips to all-inclusive resorts that I loved as an awkward adolescent were something I have avoided at all costs as an adult. Swapping bracelet beads for drinks, competing with the throngs lined up for soggy burgers, and watching people drink margaritas with breakfast is not my idea of a dream holiday. Nor is it my sister’s; we agree that her memories of our childhood trips are just as well left in the past.
But as soon as we walked into the Deco-chic lobby of Couples Tower Isle, on Jamaica’s northern coast, our distaste started to fade. With its white leather daybeds, vintage black-and-white photos of Hollywood glitterati, and a two-tiered dining room lined with murals from the 1940’s, the hotel looked like something straight out of South Beach. Not, as we’d worried, a flashback to the tackiest years of the eighties.
One of Jamaica’s first resorts, Tower Isle was built in 1949 by local businessman Abe Issa, who latched onto the then-novel idea of keeping a hotel open year-round. It quickly became a magnet for the Hollywood jet set, attracting guests like Eva Gabor, Debbie Reynolds, and Noël Coward. Some 30 years later, Issa had another brainstorm: reflag the hotel as Couples and introduce a fixed rate to encompass everything from meals to watersports. It worked: Issa’s Jamaican-based brand soon grew from one to four resorts.
The concept wasn’t new. Safari lodges had been luring travelers with a pay-one-price model for decades (It was Ernest Hemingway who popularized the safari on his first trip to Kenya in 1933). Club Med took the concept, merged it with French notions of joie de vivre, and opened its first fun-for-all-ages property, on Majorca, in 1950. And private island resorts and luxury hotels such as Antigua’s Curtain Bluff have cultivated loyal guests through a similar model for years. But as massive all-inclusives, some with 2,000 rooms, began to pop up on beaches everywhere, they earned a bad rap; their names became synonymous with booze cruises, bad buffet restaurants, and anything-goes behavior (swinger parties, anyone?). “All-inclusive was code for budget travel—budget lodging, food and beverage, and service,” says Lindsay Ueberroth, president of the Preferred Hotel Group.
The industry these days is renovating not only its properties, but its image. This past year, Couples Tower Isle poured $30 million into a makeover in an attempt to recapture its 1950’s glamour. And Couples isn’t alone. At Sandals Resorts, founder Gordon “Butch” Stewart has handed the reins of the company over to his children, most notably 30-year-old Adam Stewart, who has spent some $300 million over the past two years in an attempt to reinvent the brand. In addition to opening Fowl Cay Resort, in the Bahamas, where every villa comes with a boat for exploring the Exuma beaches, they’re building overwater bungalows—a first in the Caribbean—at their St. Lucia outpost. Adam is also overseeing a $20 million transformation of what was recently a Four Seasons into an all-villa, all-suite resort. “We could have stopped after we added three restaurants, a patisserie, and a swim-up bar, but we didn’t,” he says of the latest addition to the 22-property chain. “But we’re also upgrading the service, introducing white-gloved butlers, and adding indoor-outdoor showers.”

