As we made our descent onto the Caribbean island of Saint Martin, beach goers eagerly awaited from Mako Beach with their arms raised high, in an effort to capture a photograph of our plane flying not much higher than their heads. Princess Juliana International Airport on the Dutch side of the Caribbean island holds an unusually short runway, and aircrafts get as close as possible to the runway, which neighbors the coast. It wasn’t long before we disembarked the plane and collected our luggage, keeping our eyes peeled for our butler Mickey, who would then transport us to our boat charter, the preferred method of island hopping between Saint Martin and the British overseas territory of Anguilla. Without missing a beat, Mickey greeted us in his tall stature with warm sentiments. “Welcome, Mrs. Sendor, I look forward to welcoming you and your family to paradise,” he said. This was the officially moment where I made it my personal mission to ‘break’ Mickey of formalities, insisting that he call me by my first name. Although we agreed to exchange communications on a first-name basis, in the five days I spent at ViewFort Estate, his professional yet personable manner was unwavering (no doubt ingrained in him from his days in butler academy—yes, that’s a thing).
The boat charter, which is arranged on a private or semi-private basis depending upon passenger preference, offers a comfortable transfer between the islands, surrounded by scenic water views, and equipped with refreshments during the ride. Following a 25-minute sea voyage, we had reached the beautiful isle of Anguilla, surrounded by crystal clear waters and shimmering white sands. At its widest point, the island is only 3 miles long, and it was a matter of minutes before we pulled up to the ViewFort Estate.
Upon arrival to the property, I was mentally transported back to the memory of how this all began. I must admit that I hadn’t originally held an interest in traveling to Anguilla, entirely out of my own negligence to its beauty and splendor. If there is one thing I have learned from my travels, it is that not all of the Caribbean was created equally; there are hidden gems between the islands, and Anguilla is the diamond among them. One spring day months prior, I had the opportunity to meet with Josephine Gumbs Connor, the owner of ViewFort Estate, during her brief visit in New York City. The meeting with Josie wasn’t unlike many I’ve had before to discuss potential destination features, but there was something different, dare I say special, about this place and this woman. As we parted ways, she asked, “So when will you come stay with us in Anguilla?” and I earnestly knew this would be an invitation I would soon take her up on.
Although I had several communications between the time I had initially met Josie and the moment we stepped foot on her property, I couldn’t quite gauge an expectation for the experience that would lie ahead. Upon arrival, the ViewFort Estate staff (a word I use with hesitation, as it became readily apparent this was more like an extended family) greeted us as the front entrance, equipped with cool towels and delicious refreshments served on sparkling silver trays. Josie then emerged in her aqua colored island attire, and she exuded an affinity that can only be described as what I would want my best vacation self to be. An attorney, activist, and villa entrepreneur, she is a woman of many talents. She was warm, beaming with love and sunshine, ready to welcome my family into hers, connecting with them as though she’s known us all our lives. Both tranquil and excited to have us, Josie gave us an inkling into the Anguillan way of life. Maybe she’s born with it, I thought. Or maybe it’s Anguilla.
The main estate, which is over 200 years old, and has been in Josie’s family for 150 years since her great grandfather assumed it, stands in its original limestone and is adorned by a blend of elegant heritage and modern touches amidst vibrant colors. A premier five-star private luxury retreat majestically rested atop Anguilla’s highest peak (214 feet above the sea), ViewFort Estate serves as the windows to 360-degree ocean views overlooking Crocus Bay beach. Guests of ViewFort Estate occupy exclusive use of the property and its nine luxury suites, never to be shared with any unfamiliar faces.
Although the estate emanates the atmosphere of an idyllic Caribbean home, it is fully staffed with an on-site villa manager, executive concierge, suite attendants, private butlers, a master chef, and groundsmen. In spite of its extensive staff, it never feels crowded; in fact, it feels just like our home (if our home were sprawled across four acres and equipped with the all the finest things). Unlike most traditional resorts, we did not have an assigned room or suite prior to arrival. Instead, we were invited to explore the entire property, and have our pick of the lot, boarding anywhere we fancied, on any night of our choosing. Each of the nine suites is aptly assigned names inspired by their unique characteristics. With spaces like Ocean’s Song and Secluded Bliss, deciding on where to lay rest would be a tough decision, and I would be lying if I said that we didn’t experience more than one during the course of our stay.
As we settled in to the estate, I took my rightful place in the hammock alongside the infinity saltwater pool and hot tubs that overlook the bay below. Enjoying a Pure Anguilla, one of the estate’s many custom-created tropical cocktails, and the most scrumptious hors d’oeuvres my buds have ever had the pleasure of tasting, I’d finally come to the realization of what paradise really means. As all dining here is al fresco, the fresh air both enlivens and enhances the senses with every bite.
As a robust welcome for our first night in Anguilla, Josie had arranged for the Mayoumba Folkloric Theatre to perform for us as we sat for a most exquisite plated meal consisting of local flavors and regionally-inspired cuisine. The Taste of Anguilla, as they call it, featured course highlights including Snapper Ceviche with Corn Bellini, Mahi Mahi with Coconut Curry Grilled Pineapple, and Lemongrass Chicken Medallion with Roasted Carrots. Each specially designed dish tasted distinct and remarkably fresh; a far cry from a frozen Trader Joe’s dinner I might pop in the microwave on a busy day back home. The Mayoumba folk band serenaded the scene with an infusion of joy, culture, and local flair, throwing in a few familiar tunes we could dance to.
Each morning presented a breakfast assortment that rivals the one that came before it. Warm baked croissants, farm-to-table delights (where the eggs are sourced right from the family’s own chickens, and produce from the on-site gardens), freshly squeezed juice, and local artisan brewed coffee were created and tailored to our tastes, creatively prepared by our private chef and skillfully served by our butler Mickey. Lunch is similarly prepared with delightful surprises with every plate before us, ready to be served at the timing of our choice.
Although there were many activities and excursions to explore throughout our stay, we never felt overscheduled, and enjoyed living life on island time. Much of the time, we were just happy to do nothing at all but soak up the sun and the surroundings. While exploring the island was certainly a thrill, it was also quite exquisite how often the island could come to us. Whether a Sip n’ Paint activity hosted on the grounds with Canita Ruan (think Paint Nite but better!), or an ahhh-mazing massage beneath the tented pavilion, we never had to go far to bask in all of Anguilla’s divine glory. In fact, each and every moment at ViewFort Estate is treated as though it is the most special occasion of one’s life; every dinner we enjoyed was adorned with distinct details and touches fit for royalty, dressed in different areas of the property by candlelight and catered to with finesse.
Guests of ViewFort Estate are invited to experience the 80-acre estate at Katouche and Katouche Bay Beach, regarded as one of the most diverse wildlife experiences on Anguilla. Adventure awaits at every turn, where active cave exploration down one of the deepest known areas of Anguilla (approximately 180 feet underground), with fossils, stalactites, stalagmites, and other unique rock formations lie. Guided by a personal tour guide and speleologist, private hiking and cave tours are available.
One of the days of our stay in Anguilla happened to be my birthday, where I was met with one special surprise after another. Without any inkling as to what the day would hold, the ViewFort family spent the early morning tirelessly arranging one of the most special days of my life. The day began with Mickey whisking us down to the beach to find a motorized boat waiting to bring us just a few minutes away over to Little Bay, a private nook beach with waters so clear, you can see right through to the bottom sea floor. As we approached the beach, it had been clear that Mickey must’ve been laboring on this all morning; waiting for us was an elaborate picnic facing the bay, with place settings, pillow cushions, and a full breakfast spread of pastries, sandwiches, coffee, and champagne. He had even packed us snorkeling gear, and anything we could want or need. Being a private beach, no one would have ever been the wiser if Mickey let his regal flair at ease, but even on a remote island beach with a population of zero, Mickey served with perfect posture and form, and a tea towel laid over his arm. After spending a couple of hours enjoying our breakfast and frolicking on the beach, we returned to the estate to laze some more, before a literal feast celebration that easily could have been the backdrop of an elegant intimate wedding appeared out of thin air. At the end of the night, my husband and I were invited to pack a small bag of whatever we would need to stay elsewhere overnight; Josie as it turned out, had arranged for Mickey to festoon the Green Flash Suite with tea light candles and rose pedals, and prepare a bubble bath for a most beautiful setting to close the evening.
More times than I can count, I envisioned what a majestic scene the estate must be for a celestial wedding. Between the deck and the lawn, up to 200 can be seated and accommodated, and the property strikes the perfect balance for all sizes leading up to it. With an ability to host up to 20 overnight guests, the versatile suites have something for everyone, and with lovely overnight accommodations available just down the road for excess guests, it is a most ideal wedding destination. Although the island of Anguilla is small in its size, it holds a great deal of talent and resources, where anything is possible. Drones, rentals, lighting, full-service catering—there is nothing that a wedding here can’t be had. Inventive cuisine is prepared by the villa’s talented Chef Shane Hughes, and upon availability, Chef George Hughes, whom is celebrated for his Michelin Star status. Sweet delights by Geraud’s Catering tickle the senses, as Pink Mako sets and captures the scene with comprehensive audio, lighting, photography, and videography services. The island runs like a tight-knit family, where together they make dreams come true, and I’m inclined to believe that Josie holds a big part in bringing them together. When she decided to turn ViewFort Estate into a vacation home and venue, she held the vision that every day should be a wonder-filled day as they experience Anguilla, and her trained staff should reflect her level of creativity, with service performed with exquisite precision. Even in the face of natural disaster, the property has rebounded from Hurricane Irma with grace. For everything humanly possible, Josie and her team have it made. Anguilla seems to take care of the rest, from the picturesque rainbows found in the day to the star-studded skies of the night, and the remarkable panorama all around.
If there is one word that wholly describes the ViewFort Estate experience, it is authentic, second only to the luxury it assumes. It is genuine in its desire to provide a superior hospitable experience, unpretentious in the best possible sense of the word, and serene in its natural beauty and landscape among the gentle island breeze. ViewFort’s Anguilla, in every respect, is heaven on Earth.
"Pure Anguilla" is a firsthand account story written by Samantha Sendor, originally appearing in the 2019 Edition of Sophisticated Weddings.