Counting down the days until the first frost, there’s a particular kind of daydream that sets in around late October: white sand beaches, water so clear it looks fake, no calls to answer and absolutely nowhere to be. Four Seasons Resort and Residences Anguilla has built an entire identity around that daydream—and each year the property finds new ways to make it worth the flight.
Located in Anguilla’s famed Meads Bay, the Forbes Five-Star resort has long been a favorite among travelers who want the polish of a five-star property without the crowds that come with more heavily trafficked islands.
But what keeps guests coming back, year after year, isn’t just the setting. It’s the way the resort layers world-class food, wellness and entertainment on top of it—refreshing the lineup often enough that even repeat visitors find something new. Whether booking a couples-only getaway or a family trip with the toddler—and I’ve done both—Four Seasons Anguilla provides new reasons to return with each visit.
Dining Worth Planning Around
Anguilla has quietly become one of the Caribbean’s more interesting food destinations, and Four Seasons leans into that reputation by rotating in chefs and concepts that would otherwise require a trip to Miami, Los Angeles or even New York.
One of the standout offerings is Uchi at Home, a private omakase experience that turns the resort’s villas, penthouses and townhomes into intimate dining rooms. A dedicated chef from the acclaimed Uchi restaurant group prepares and presents a multi-course tasting menu built around the freshest seasonal seafood, available to just two parties an evening for those who want something truly exclusive. Guests who’d rather keep things low-key can still get a taste through a curated Uchi takeaway menu delivered via room service, no reservation drama required.
The resort also brings in guest chefs and mixologists throughout the year to put their own stamp on its restaurants. Korean cuisine has made its way to Sunset Lounge courtesy of chef and television personality Esther Choi, whose contemporary approach to Korean flavors pairs naturally with the venue’s sunset views. Latin American and Caribbean influences get their moment as well, with chef and author Mika Leon bringing vibrant, seafood-forward dishes to Salt, the resort’s signature oceanfront restaurant.
On the cocktail side, Sunset Lounge periodically hosts residencies from internationally recognized mixologists, including Valentino Longo of Miami’s ViceVersa, who brings modern aperitivo culture and inventive drink programs to the island.
Beyond the guest chef series, the resort’s built-in culinary traditions remain hard to beat. The Fish Market Experience, held regularly on Meads Bay Beach, lets guests pick out the day’s freshest local catch and watch it get transformed into a sea-to-table meal right in front of them. And Fire & Flavor, an immersive, market-style showcase of local chefs and artisans, is a great way to sample the island’s culinary talent in one sitting.
Wellness Beyond the Spa
Four Seasons Anguilla has also built out a wellness calendar that goes well past the standard spa treatments, though those remain excellent too. The resort periodically hosts a residency from Miss Lymph, whose lymphatic drainage treatments have developed a serious following among wellness devotees, offering customized therapies focused on recovery and rejuvenation.
Fitness fans should keep an eye out for Isaac Boots, the New York Times-recognized fitness expert known for his high-energy, low-impact workout method, who has returned to the resort to lead sessions that manage to feel like both a serious workout and a vacation activity. Tennis players, meanwhile, can look for clinics led by former ATP Tour professionals like Nick Monroe, which cover everything from match strategy to on-court drills for players at every level.
Even without a special guest on property, the resort’s standing wellness infrastructure is substantial: a 24-hour fitness center, a dedicated Reformer Pilates studio, a Strength Garden and group fitness classes that make it easy to maintain a routine without sacrificing vacation time.
Nights That Don’t Wind Down Early
When the sun sets, Sunset Lounge tends to become the heart of the resort, hosting live music and DJ sets that have, in past seasons, included Grammy-nominated performers and celebrated trumpeters bringing a jazz-meets-pop energy to the evening. It’s the kind of programming that makes an oceanfront cocktail feel like an event rather than a nightcap.
Built for Families, Too
What sets Four Seasons Anguilla apart from some of its adults-only competitors is how seriously it takes multigenerational travel. Kids For All Seasons, the resort’s complimentary children’s program for guests ages 5 to 12, keeps younger travelers busy with daily activities, outdoor adventures and creative projects, including periodic collaborations with New York City’s well-known Craft Studios for hands-on holiday-style workshops. Weekly stargazing evenings, complete with professional telescopes and celestial storytelling, give families a low-key way to spend an evening together under some of the clearest skies in the Caribbean.
Poolside parties, family-friendly fireworks celebrations and seasonal visits from Santa Claus around the holidays round out programming that manages to feel festive without tipping into chaotic.
The Everyday Extras
Even outside of special programming, a stay at Four Seasons Anguilla comes with a long list of complimentary experiences that make the resort feel generous rather than transactional. Guests have access to interactive cooking classes, chef demonstrations, wine and spirit tastings and mixology sessions at no extra charge. Non-motorized water sports, including kayaking, stand-up paddleboarding, sailing and windsurfing, are also included, as is access to the Sports Pavilion for tennis, basketball, volleyball and rock climbing.
The Takeaway for New Jersey Travelers
With direct and connecting flights making the Caribbean more accessible than ever from the tri-state area, Four Seasons Resort and Residences Anguilla makes a strong case for itself as a go-to escape, whether for a long weekend reset or a full week of doing absolutely nothing productive. The resort’s rotating calendar of chef residencies, wellness experts and entertainment means no two visits look quite the same, but the fundamentals, that impossibly blue water, that five-star service, that sense of unhurried luxury, remain reliably in place.
For reservations or more information, visit here.
Lifelong Jersey resident and Rutgers and FDU alumnus, Tom La Vecchia is publisher of New Jersey Digest, one of the state’s leading lifestyle media brands. When he’s not growing the Digest, he’s raising four kids, wrangling four cats and pretending it’s all under control. His mission: keep Jersey interesting and impossible to ignore.
