I’ve Been to 12 Caribbean Islands. Here’s What Makes Anguilla My New Favorite
Pristine beaches, standout dining, laid-back luxury—and new nonstop flights—make this award-winning island easier to experience than ever
The gate at Logan Airport in Boston looked more like a party than a boarding area. I was surprised to see balloons, catered food, and people mingling as AnguillAir, operated by BermudAir, marked its inaugural nonstop flight from Boston to Anguilla. When we landed in Anguilla, the celebration continued with a live band and remarks from Premier Cora Richardson-Hodge and other island officials.
New seasonal nonstop flights also connect Anguilla with Baltimore/Washington and Newark, making the island more accessible to travelers across the Mid-Atlantic and Northeast. Previously, reaching Anguilla often required a connection or a flight to St. Martin followed by a ferry. The new routes may introduce Anguilla to travelers who once considered the journey too complicated.
A British Overseas Territory, Anguilla sits at the northern end of the Leeward Islands, about 200 miles east of Puerto Rico and just north of St. Martin. Amerindian people reached the island about 4,000 years ago and called it Malliouhana, or “arrow-shape sea serpent.” European explorers later renamed it Anguilla for its long, eel-like shape.
Beyond the resorts, Anguilla’s culture comes alive through steel pan, reggae, calypso, and soca music; art made from canvas and driftwood; and boat racing, the national sport. These traditions help give the low-lying island a personality all its own.
Travel + Leisure magazine recently named Anguilla the "Best Island in the Caribbean," marking the fifth time it has topped the list since 2017. Having visited 11 other Caribbean islands, I now understand Anguilla’s appeal: powdery beaches, standout food, low-key luxury, and a relaxed pace.
Where to stay
During my December 2025 visit, I stayed on both sides of Anguilla. The quieter East End offers a residential feel, uncrowded beaches, and access to nature, while the West End is known for luxury resorts and calm bays. Experiencing both revealed more of the island than staying in one place would have.
On the East End, I stayed at the Zemi Beach House, a AAA Four Diamond property on Shoal Bay East. Tropical flowers and lush greenery frame the resort, but the beach is the star: a broad, uncrowded stretch of pale sand where I took long walks and watched pelicans skim the turquoise water. I also loved visiting the spa, housed in a 300-year-old Thai house brought here in the 1980s. From the beach-level infinity pool, the water seemed to merge with the sea.
A 30-minute drive took me to Malliouhana Resort, also a AAA Four Diamond property, on the West End. In contrast to Zemi’s beach-level setting, Malliouhana rises above Meads Bay on a coral bluff. Its Art Deco-inspired design recalls 1960s Caribbean glamour, and its tiered infinity pools appear to spill over the cliff. Beach access is a short walk or golf-cart ride downhill. At dusk, the elevated perch offered a dramatic view of the sky turning deep red above the water.
Where to dine
Anguilla’s dining scene was another highlight. At Veya Restaurant, owned by chef Carrie Bogar and her husband/restaurant manager Jerry Bogar, the open-air, second-floor dining room explains its nickname: The Treehouse. Bogar blends Caribbean ingredients with flavors from India, North Africa, and Southeast Asia. The duck—one of the best dishes I’ve ever had—paired sweet and savory spices with a tropical fruit reduction, while warm Johnny cakes arrived crisp on the outside, dense in the middle, and accompanied by spiced butter.
At Cip’s by Cipriani at Cap Juluca, A Belmond Hotel, on Maundays Bay, classic Italian dishes meet Caribbean ingredients. The restaurant is a sister to Cip’s Club at Hotel Cipriani in Venice, and it delivered the same sense of gracious Italian hospitality I had recently experienced there. Hand-rolled pasta incorporated fresh local seafood, and wood-fired bread came with regional olive oils. Large, open-air windows framed the turquoise water so perfectly that it felt as though I were dining in a gondola.
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Anguilla now ranks among my favorites for its beaches, food, views, and warm hospitality. With new nonstop flights simplifying the journey, it’s easier than ever to discover why this Caribbean island inspires so many repeat visits—and why I’m already planning my return.
Just putting it out there: writer willing to work for a permanent lounger on an Anguilla beach.