After years of traveling for both leisure and business, I’ve come to appreciate the kind of places that leave a lasting impression. Not just because they’re beautiful, but because they get the little things right. So when the chance came to visit the Four Seasons Resort and Residences Anguilla, I was genuinely looking forward to it. Situated on one of the island’s most breathtaking stretches of sand and surf, this 35-acre resort feels like the Caribbean at its most peaceful and polished. Anguilla, with its 33 beaches and laid-back vibe, has quietly become a go-to for travelers who want luxury without the crowds—and this Four Seasons might just be the crown jewel.
Getting There: Surprisingly Easy
Getting to Anguilla feels like a mini adventure, but in the best way. After landing in St. Maarten from Newark Airport, the Four Seasons team whisks you away on a smooth, climate-controlled private boat ride that lasts just 25 minutes. The process was seamless including customs, passport control, so by the time you arrive at the dock in Anguilla, you’re already in vacation mode, sipping a perfectly chilled welcome cocktail upon arrival as your luggage magically appears in your room.
Where You’ll Stay: Like Your Dream Beach House (But Better)
We stayed in an oceanview suite that genuinely felt like home—if home came with floor-to-ceiling windows overlooking Barnes Bay and a massive marble bathroom that made you want to live in it. The room blends indoor and outdoor living beautifully, with a private terrace and outdoor shower that invites you to slow down and soak it all in.
It’s the small touches that make a big difference: Egyptian cotton sheets, daily restocked minibar with fresh fruit and top-shelf goodies, and deck furniture that’s actually comfortable (not just Instagram-worthy).
Food Worth Writing Home About
While the dining scene on the island is diverse, two standout spots capture completely different vibes and flavor profiles. Sunset Lounge offers a more refined experience with Asian-inspired flavors, where dishes are artfully presented and infused with subtle complexity—think miso-glazed seafood and aromatic herbs that transport your senses. In contrast, Half Shell Restaurant brings the party with its bold Caribbean and Mexican-inspired dishes. From fresh ceviche and jerk-seasoned entrees to vibrant tacos and house-made salsas, every plate bursts with flavor. Both restaurants provide something memorable—whether you’re craving elegance at Sunset Lounge or vibrant energy and spice at Half Shell, you’re in for a treat.
Salt, their breakfast spot, deserves its own standing ovation. Think warm pastries straight from the oven, tropical fruits that taste like sunshine, and the best French press coffee I’ve had outside Manhattan. The team even remembered our coffee orders by day two. Little things like that make you feel truly looked after. We also went to Salt for their dinner service as it didn’t disappoint. There is virtually no reason to leave the resort as the on-site food and beverage program is second to none.
Poolside service is just as on point—drinks show up when you need them, not when you’ve given up and gone to find someone.
The Beach: Postcard-Perfect
Barnes Bay is what you imagine when you picture the perfect Caribbean beach. Soft white sand, calm turquoise waters, and—best of all—no crowds. The resort manages to keep it pristine without making it feel over-managed. There are plenty of loungers and umbrellas spaced out for privacy, and the staff strikes that perfect balance of being helpful without hovering.
The People: Service That Feels Natural
One of the biggest reasons Four Seasons Anguilla stands out is the people. Everyone—from the servers to housekeeping to the concierge—seems genuinely happy to help. No script-reading here. Want a great local excursion off-property? The concierge doesn’t just rattle off the top three spots from a brochure—they give real, thoughtful recommendations and handle every last detail.
What To Do (If You Feel Like Moving)
If your version of vacation includes more than just lounging, the resort has plenty to offer. The spa is world-class, with ocean views and treatments that don’t feel rushed. The gym is well-equipped, and even the tennis courts are tournament-ready.
Water sports? They’ve got it all—snorkel gear, paddleboards, kayaks—and everything’s in good shape. Even the Wi-Fi is solid enough for Zoom calls (if you absolutely have to take one). I attended my weekly meeting with my team flawlessly. Although I’d rather have been in one of their three majestic pools.
Luxury Done Right
Here’s the thing—Four Seasons Anguilla doesn’t try too hard. It doesn’t need to. It nails the basics and beyond: stunning location, thoughtful service, great food, and total relaxation. It’s not trendy; it’s timeless.
If you’re based in New Jersey and looking for a Caribbean escape that delivers real value and five-star execution, this is it. It’s a splurge, sure—but one that actually feels worth it.
After four nights here, I left not just relaxed but impressed. That’s a rare combination.
Learn more or book your stay here.
Tom is a lifelong New Jersey resident, Rutgers and FDU alumni and the publisher of The Digest.
