From Boston to Negril

When Sydney Watson left her consulting career in Boston to return to Jamaica in 2023, she knew she wanted to build something of her own. Three years later, the young entrepreneur is the co-owner of a cliffside restaurant in Negril, a property investor and the operator of a villa concierge business, having turned her ambition into a growing portfolio of ventures in western Jamaica.

Before returning home, Watson worked with a global consulting firm in Massachusetts, specialising in financial services compliance, including a major merger-and-acquisition transaction involving an investment bank. While the experience was invaluable, her ambitions extended beyond corporate life. “I learned so much in my consulting position, but I was ready to come home and translate those skills to my own business,” she shared.

For Watson, Jamaica was never simply a place to relocate. Having spent her formative years on the island between ages seven and 17, she developed a particular attachment to Negril, where she frequently spent weekends away from boarding school.

Her entrepreneurial journey began with a villa concierge service in Whitehouse, Westmoreland, offering private transfers, itinerary planning and other services to visitors. Recognising a gap in the area’s short-term rental market, she established a business that she continues to operate today.

However, it was an opportunity in Negril that would eventually become her primary focus. In October 2025, Watson opened Syd’s on the Rocks, a cliffside restaurant offering a fusion of Puerto Rican and Jamaican cuisine. Her interest in hospitality had developed years earlier while assisting a restaurant owner in Virginia with marketing, an experience that also introduced her to restaurant operations.

The venture is a partnership with Mcgarrit Franco, an experienced restaurant investor based in Washington, DC. Inspired by Watson’s time studying abroad in Italy, the restaurant features a Mediterranean aesthetic, while its menu celebrates the cultural backgrounds of both partners.

Despite the challenges of entering a new industry, Watson recalls the restaurant’s opening night as a defining moment. “It was raining all night, but I had over 120 guests dine and drink,” she recalled. “It was nice to see the place full of life after all the hard work went into getting it to that stage.”

Beyond hospitality, Watson has also ventured into real estate investment, with an opportunity that emerged directly from one of the earlier stagings of the Throp-X Investment Conference. During a November 2023 property tour attended by approximately 70 conference participants, her mother, real-estate professional Maura Watson, suggested that investors collectively purchase the former Coral Seas Cliffs hotel rather than pursue individual acquisitions.

The idea gained traction, eventually resulting in 26 investors purchasing the property, which was transformed into The West condominium development. Watson acquired and renovated a loft unit, now operated as a short-term rental property. “The details are crucial in carrying out the project to the end,” she explained, emphasising the importance of selecting qualified contractors and prioritising quality. “Sometimes the cheaper option ends up being the most expensive lesson.”

Her experiences in hospitality and property investment have also reinforced the importance of effective management. “Managing people, on the customer side and staff side, have been quite a lesson. But I’ve learnt that systems are your best friend,” she said.

Watson will share insights from her entrepreneurial journey during the Women in Business: Building Wealth in Jamaica panel at the sixth Throp-X Investment Conference, taking place from November 15–21, 2026, at Travellers Beach Resort in Negril. She will join fellow entrepreneurs to discuss their personal and professional experiences relocating to Jamaica and establishing businesses and creating opportunities on the island.

For Watson, the decision to return home has exceeded her expectations. “If you told me I would be operating a cliffside restaurant and own my own condo five years ago, I wouldn’t believe you!” she reflected.

Her advice to women considering a similar move is to begin building connections early, even from overseas. “Your network is extremely important,” she said, encouraging prospective returnees to use online communities to establish relationships before relocating.

lifestyle@gleanerjm.com