The ‘90s were a time of all work and no play—at least, that’s how it looked in the movies. Films like Glengarry Glen Ross and The Associate (led by one Whoopi Goldberg) illustrated the strictly business nature of the time. But in the sea of suits and briefcases came 1998’s How Stella Got Her Groove Back, which gave permission for people—but especially Black women—to take a break. Angela Bassett starred as Stella Payne, an uptight, divorced stock broker in dire need of an escape from her daily routine and stagnant love life. Encouraged by her free-spirited friend Delilah (one Whoopi Goldberg), the two booked a vacation in paradise: at the five-star Round Hill Hotel and Villas in Montego Bay, Jamaica. While Stella first inspired Black women 25 years ago, her story reverberates to this day.
Earlier this summer, my friend and I followed in their footsteps by attempting to find our grooves at that very resort. Prior to the trip, Toni (a divorced attorney) and I (an over-scheduled freelance writer) rewatched the movie. It was my first time seeing it as an adult, and with the innocence of youth out of the way I found that my viewpoint aligned with that of Stella’s tired executive: We were over the grind—not to mention the nagging misogynoir that came with being divorced by 42. Being jaded fit us too well.
I imagine that, at its start, Round Hill was quite a bit like it is today—classic, quiet. Upon arrival, visitors descend a steep and winding hill to the white-sided lobby building, shielded from the sun by a striped green-and-white awning with glimpses of cerulean waters beyond. The furnishings reminded me of Ralph Lauren Home—preppy and patterned but bright and clean—which made sense when I discovered that Lauren himself, who owns one of the villas onsite, redesigned the hotel rooms (which sit in what’s called the “Pineapple House”) as well as the Grill, where photographs of the resort’s hallowed guests adorn the walls. It’s all very Jackie Kennedy-esque— fittingly, as this is where her husband came to write his inaugural speech. This is exactly the soft, quiet luxury that you crave when work is intense and you have the funds to splurge.
Speaking of a splurge: Toni and I took advantage of every amenity that the resort offered. Our routine was: heading to the beach in the mornings to watching the resort wake up from afar, hitting the spa, and Toni (while I enjoyed a back facial and a massage) took to the property’s winding hills for a three-mile run. Afterwards, we returned to our villa for egg-white omelets and ackee with saltfish, prepared and served on our patio. In the evenings, we delved into Caribbean fusion cuisine—like jerk snapper, and ice cream infused with spicy scotch-bonnet pepper. While I sampled the wine list, Toni danced along with a bridal party (the resort is becoming a hotspot for bachelorette weekends.)
Off site, we explored every corner of Montego Bay—slowly, with intention. We rafted down the Great River with Chukka, sticky from champagne and peeling mangoes with our hands. Toni lit up some bud that she purchased right along the river while our captain Aldean massaged our feet with limestone. Later, we shined up for dinner at the Sugarmill Restaurant, trying breadfruit gnocchi for the first (and probably for the only) time in our lives. We took a makeshift raft to the Houseboat Grill to gorge on escovitch and rice and peas.
But there were also times when we really wanted to stay put; play pickleball or get our groove on at the patio of the restaurant. Our trip was missing one thing: a Winston (played by Taye Diggs)—neither of us picked up a younger man, although the resort was not lacking in eye candy: I haven’t figured out if Toni actually struggles at pickleball, or if she just wanted the extra attention from Kevin, our instructor. And, speaking of instructors: Donavan, the resort yoga instructor who played himself in the film, is still just as sassy, and just as muscled as he was in the ‘90s—and we laughed through the sweat at his beachside yoga class.
