Jeannine Connor-Gittens was recently sitting on the rooftop deck at Sheriva Estate in the Caribbean country of Anguilla. It was a clear day and she was so taken by the view that she had to pull out her phone and call her husband, Tiger Gittens to share the moment – the nature below, the sky above, the ocean beyond.
Jeannine has been on this rooftop countless times but never ceases to be amazed at the view, whether on cloudy days or on that particular day recently when she could see Saint Martin across the Anguilla Channel.
She sat on this same land in 2004, not on the rooftop deck nor on a chaise longue by one of the seven pools, but on an overturned five-gallon paint bucket, with Anguillan-born entrepreneur Sheridan Smith sitting on another. Sheridan had drawn up plans for his 10 acres of undeveloped family land, located in the West End, some of the island’s most prime real estate. He wanted to convert it into a luxury rental property overlooking the water. Spreading out their papers on a piece of plywood, Sheridan and his wife, along with Jeannine started to plan out some of the ideas that still exist today, including providing guests private golf carts for getting to and from the beach and turning the nearby hotel Cap Juluca to their advantage, by giving Sheriva guests signing privileges at its three coveted restaurants – Pimms, Blu and Spice.
In the early 2000’s, Anguilla was becoming a popular travel destination, thanks to several developments that had sprung up. And every time Jeannine’s husband Tiger would come and visit, he found himself buttonholed by some old friend who had a project and was in need of some of his lumber business’ hardwood for, say, a pergola or a door or some decking.
At the same time, Sheridan was determined to show the world that when it came to accommodations, Anguillans could hold their own in catering for high-end travelers. Jeannine (who grew up in the US Virgin Islands but has a strong connection to the island, having been born to Anguillan parents) says Sheridan wanted to build something great in his home country. She says he was looking to debunk “the myth that only Europe and US can create something spectacular.” Besides, she says, many of the other developments on the island had a sterile, modern and museum-like feel, whereas Sheridan was creating something high end and traditional while still aiming for spectacular.
And spectacular it is. Sheriva is a sprawling three-villa, 22-room estate, designed and decorated with Caribbean flourishes. It boasts a view of Cove Bay and Maundays Bay beaches, and has seven swimming pools and shared gym and games room. It won the 2016 Condé Nast Johansens Awards for Excellence in the category of Best Exclusive Use Villa for the Caribbean and Pacific. Its height and architecture provide it with ocean views, while its distance from the beach offers privacy from the public for the many clients who crave that. That’s where those golf carts come in handy.
Jeannine, who had extensive experience in high-end tourism in Florida and Anguilla, had initially turned down the job of managing Sheriva. She and Tiger had moved back to the island to modernize his family’s five decade-old hardwood lumber business, which was now seeing a renaissance, thanks to all that development on the island he had been witnessing.
Included among their customers was Sheridan, who was making the company’s dark-stained, indigenous wood a signature décor element. It brings to the estate both a classic contemporary and distinctively cozy Caribbean feel. Dark wood runs throughout, on ceilings, doors and windows and on some furniture items like custom-made bed frames, contrasting with the light and breezy colour palette and the open-air feel of the estate.
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“This is not Greece or the Florida Keys; this is the Caribbean,” says Jeannine, who says there is a comfort that guests remark on. “One guest said ‘I walked in, took my shoes off and didn’t put them back on until I left.’”
With so much to do in her life and her husband’s family business, Jeannine would only agree to becoming a consultant for Sheridan and his nascent estate. While the lumber business occupied much of her time, as did raising two boys, the work of building Sheriva would eventually devour even more and, soon after, would become a passion. “It was my third baby,” she said, having found herself lured back into the hospitality industry for a “unique opportunity.” She agreed to take on the title of General Manager at Sheriva.
She comes by tourism honestly. One uncle ran one of the first car rental operations on the 35-square-mile island, and was one of the country’s first pilots, while and her grandfather was a celebrated ship’s captain. Her own background has given her experience in the airline industry and in bespoke hotels and villas. “I’m used to the luxury market and its discerning guests,” she says.
She was 32 when she began this job and her plate was more than full. “How did I do it?” she asks, looking back a decade. She tended to school activities for her kids such as PTA meetings, and worked on the lumber business, rebranding it to play up the family’s connection to the Arawak, the First Nations people found throughout South America and the Caribbean. Plus, she performed a myriad of tasks for Sheriva, including welcoming unnamed celebrities, royals and media types (Katie Couric and Glenn Beck the only ones she could name).
Her boys are now 15 and 17, having both spent years in the US Virgin Islands and Anguilla, with lots of tourism and time on the water. That seems to have shaped their career plans. One of her boys wants to major in hospitality at university, while the other is hoping to operate his own speed boat company and ferry travellers between different Caribbean islands.
Jeannine may be busy, but she definitely has time to talk up the estate’s attributes. “Sheriva is so versatile,” she says of its ability to accommodate different size events.“It can work for everything from honeymoons to corporate retreats.” Two villas, Harmony and Infinity have eight bedrooms, while Mystique offers six. The three villas can be rented as one estate for a large group, with rollaway beds and pull-out couches to fit in even more people. And one of the villas can even be broken up into individual rooms, with separate entrances.
This past December, the estate celebrated 10 years in operation. The three people who planned some of this from their overturned paint buckets are still there. Their plans have come to fruition as their country celebrates a jewel that has a distinctive Anguillan cut to it.
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