The Darling Social Club aims to redefine women’s leisure

Asocial calendar filled with Pilates, tennis, golf and a little pampering may sound like the perfect weekend escape, but for Annalisee Richards, the appeal goes well beyond the activities. Through The Darling Social Club, she is introducing a different approach to women’s leisure, one where trying something new, making friends and investing in oneself are all part of the experience.

That vision was recently brought into focus with The Darling Weekend, held from October 23 to 25, a celebration of wellness, recreation and socialising. The festivities kicked off on Thursday with an intimate launch at AB LAB Fitness Studio, welcoming specially invited guests, sponsors and supporters for an evening of movement, beauty and conversation. The gathering featured Pilates, refreshments and presentations from brand partners who shared in the club’s emphasis on wellness and self-care.

Among them was Lifespan, the weekend’s hydration partner, whose brand manager, Karonna Atkins, described the collaboration as one rooted in shared values. “We see this opportunity as more than just a sponsorship. We see it as a partnership built on shared values of health, wellness, self-care and empowering women to make better choices for themselves,” Atkins shared.

Beauty also featured in the evening’s conversations, with Shanique Ellington, founder and chief executive of Jamaican vegan make-up brand Le Champ Cosmetics, speaking about the relationship between beauty, wellness and confidence. Ellington encouraged the women to embrace the experience as an opportunity for personal growth. “I hope everyone leaves here with something more than just the experience. Leave with maybe a change in your mindset, even a little bit more confidence,” she said.

Dancehall recording artiste Stalk Ashley also made a special guest appearance, joining the women for Pilates. She described the session as a one-of-a-kind experience and expressed her enjoyment of the opportunity to connect with the other participants.

For Richards, the gathering reflected the larger purpose behind the club. “For me, it was never just about organising events. It was about creating a lifestyle and, more importantly, a sense of belonging,” she explained.

Three days, endless possibilities

Following Thursday’s launch, Darling Weekend was scheduled to continue with three days of recreation and wellness. Friday’s Darling Court was intended to combine tennis and Pilates, but inclement weather forced the cancellation of tennis, leaving Pilates as the day’s main activity. The weather also disrupted Saturday’s plans, resulting in the cancellation of Pickle & Plunge, which would have featured pickleball and contrast therapy.

The festivities continued on Sunday, with Darlings on the Greens at Caymanas Golf Club in St Catherine. Golf, Pilates and socialising brought the weekend to a close, with blush pink and Wimbledon green adding a fashionable touch to the afternoon.

Despite the weather-related setbacks, Richards was encouraged by the women’s enthusiasm and willingness to embrace the experiences.

“What stood out to me was the response from the women. They still showed up, participated, laughed, connected and made the most of the experience,” she recalled.

Particularly rewarding was seeing women who had arrived as strangers becoming acquainted through shared activities, reinforcing her belief that genuine connections can extend beyond any single event.

Making way for something different

Officially introduced in August 2026, The Darling Social Club emerged from Richards’ observation that women often place professional, family and personal responsibilities ahead of their own enjoyment. Although Jamaica boasts a vibrant entertainment scene, she recognised an opportunity to introduce experiences that deliberately combined recreation, wellness and meaningful female friendships.

“I envisioned a community where women could enjoy beautiful experiences, explore new interests, meet like-minded women and simply have something exciting to look forward to outside their everyday routines,” she shared.

The club made its debut with Darlings at Sea, a sailing experience that attracted more than 60 women, providing an encouraging introduction to the concept.

Richards hopes the club will challenge the tendency to postpone leisure until life’s demands become less pressing.

“As women, we often postpone enjoyment. We tell ourselves we’ll try something new when work slows down, when the children get older or when life becomes less demanding. But life is happening now,” she said.

While luxury remains central to the club’s identity, Richards believes its value extends beyond elegant settings, coordinated dress codes and thoughtfully selected details.

“For us, luxury is not simply about beautiful venues, elegant settings or exclusive experiences. It is about how a woman feels when she enters a space,” she explained.

That philosophy shapes the club’s approach to introducing women to unfamiliar activities, from sailing and golf to Pilates and tennis. Rather than emphasising expertise or performance, the experiences encourage discovery and interaction. Women are also welcome to attend independently, with the club’s House of Darlings community providing opportunities to maintain friendships beyond organised events.

“I never want someone to miss an experience simply because she doesn’t have a friend available to accompany her,” Richards shared.

The Darling Experience continues

With interest extending beyond Kingston, Richards is preparing to introduce the club to women across Jamaica. November’s programme includes Darlings on the Greens and an intimate wellness-focused sculpt session in Mandeville, alongside The Darling Equestrian Experience, scheduled for November 22 at the Kingston Polo Club. The latter will combine Pilates, equestrian activities, a scent atelier, floral experiences and brunch.

The club is also developing Cocktails & Conversations: The Wealth Edit, expanding its offerings to include financial wellness and personal development. December is expected to bring the introduction of a membership programme, providing access to exclusive experiences, preferred partnerships and continued opportunities for connection.

Plans for Montego Bay are also under way, with Richards envisioning an eventual presence across Jamaica and the wider Caribbean.

Yet, beyond the expansion plans, her ambition remains centred on helping women discover new interests, cultivate friendships and appreciate the value of making time for themselves.

“I want women to feel that investing time in themselves is not an indulgence but an important part of living a balanced, fulfilling life,” she said.

“Because being a Darling isn’t simply about where you go. It’s about how you choose to live.”

@nyoka.manning@gleanerjm.com