Travel

The Essential Itinerary: Anguilla, “a true gem of the Caribbean”  

A slow, sun-soaked journey through this tropical island’s famed beaches, eclectic food scene and pristine landscapes, where luxury is understated and tranquillity is the norm

  • Published Feb 04, 2026
  • Updated Feb 05
  • 1,771 words
  • 8 minutes
"Tranquility wrapped in blue" is the official slogan for Anguilla — it's easy to see why.
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In the roughly one hour it takes to drive from Anguilla’s East to West End, you’ll pass every stoplight on the island — all six of them. It’s a small detail, but one that speaks volumes about the pace of life here.

There are no casinos, cruise ships or sprawling shopping centres. Instead, Anguilla has built a reputation around low-density luxury, authentic island culture and beaches that feel untouched, even at the height of the season. And then there’s the vibrant food scene — Anguillian cuisine is widely regarded as some of the best in the Caribbean.

Formed from coral and limestone, the island of Anguilla is relatively flat, but there are some impressive viewpoints.
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Just 25 kilometres long and six kilometres wide at its widest point, this British Caribbean island is renowned for its white sand beaches and turquoise waters. But unlike some other tropical destinations where “Instagram versus reality” shows that not everything is as idyllic as it appears online, Anguilla is truly picture-perfect.  

Quiet, unspoiled and serene, Anguilla is “a true gem of the Caribbean,” says Accelyn Connor, an Anguillian local who operates Premier Taxi & Tours. “In a nutshell, Anguilla is tranquillity wrapped in blue, like you’ve never seen before.” 

That serene spirit is revealed almost immediately. Upon arriving at Aurora Anguilla, a year-round resort overlooking Rendezvous Bay, I’m handed a cool towel and a refreshing welcome drink infused with lemongrass and ginger — ingredients both cultivated on the property’s hydroponic farm. Each staff member greets us with an enthusiastic smile, a warm gesture that embodies a pride and welcoming manner that is repeated by locals across this island.

With 33 public beaches, one-of-a-kind properties, a variety of beachfront bars and a food scene that blends classic Caribbean fare with international influences, Anguilla is truly a unique destination.

At Aurora Anguilla, guests are treated to luxurious rooms, many of which boast expansive balconies with picture-perfect views.
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Across Anguilla, there are more than 33 public beaches for visitors and locals to enjoy.
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DAY ONE

10 a.m. | Beach hop

Anguilla is home to some of the most tranquil coastlines in the Caribbean, with more than 30 pristine white-sand beaches dotted around the 9,100-hectare island. But, aside from their beauty, what sets these sandy paradises apart is their exclusivity. “You can go to any of the beaches and you won’t feel crammed,” says Amelia Vanterpool-Kubisch, Chair of the Anguilla Tourist Board. “We are spoiled as locals. If I see 30 people on the beach, it’s too much.” 

At Maundays Bay (arguably one of the Caribbean’s most picturesque stretches of coastline), the crescent-shaped beach remains blissfully free of crowds and chair set-ups. On the opposite side of the island, Meads Bay offers the same unspoiled calm. Exploring Anguilla’s beaches is the perfect introduction to the island’s greatest pleasure: effortless, unhurried beach hopping.

Liquid Glow offer unique kayak tours for visitors to appreciate and enjoy Anguilla from a different perspective.
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5 p.m. | Night kayak 

As the sun dips below the horizon, transparent-bottom kayaks equipped with LED lights illuminate the ocean below, creating a portal into the world beneath the surface. Departing from Crocus Bay, Liquid Glow operates one-of-a-kind kayak tours that combine beautiful scenery with active adventure. On the Sunset Tour, guests explore Little Bay (about a 10-minute paddle from the departure point), where green sea turtles come to rest for the evening. The two-person kayaks are constructed with a wide base to ensure they’re extremely stable. Whether joining a morning, day, sunset or night tour, Liquid Glow showcases Anguilla from a new perspective: beneath your seat.

The lobster risotto at Sharky's Restaurant is a local favourite.
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7:30 p.m. | Sharky’s Restaurant 

When it comes to food, Anguilla knows how to do it right. From freshly caught crayfish and lobster to tender jerk chicken and Johnny cakes (a beloved Caribbean staple), there is no wrong choice. But for visitors seeking a local, authentic and grounded experience, Sharky’s Restaurant is the answer. Tucked in Anguilla’s West End, Sharky’s is a local favourite, known for its mouthwatering meals and heartwarming story of resilience. In September 2017, Hurricane Irma (Category 5) struck the island, causing widespread damage. In the wake of the disaster, Chef Lowell Hodge faced a decision: wait for normal to return or rebuild. He chose the latter. From the porch of his home, just one month after the hurricane, Hodge opened his doors to what would soon become Sharky’s. Today, it remains one of the most popular restaurants in Anguilla, a dining destination that draws locals and tourists alike.

Madeariman Bar and Restaurant in Shoal Bay Village is another great dining option for travellers seeking authentic Caribbean cuisine.
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The impressive views from the patio of Malliouhana.
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DAY TWO

10 a.m. | Time to unwind

Relaxation comes in many different forms, from soothing massages and aromatherapy to splashing beneath the Caribbean sun or speeding down a waterslide. At Aurora Anguilla, “unwinding” means choosing your own kind of bliss. For those seeking serenity, Sorana Spa offers a quiet retreat where guests can drift through steam and sauna rooms, relieve stress with a little hydrotherapy, or visit experienced therapists for exceptional treatments, including age-defying facials, beach stone massages, body scrubs, and more. Afterward, sip herbal tea in the relaxation lounge or add a manicure and pedicure for an extra glow. 

Want something a little different? Check out Aurora Anguilla’s Entertainment Park, which boasts an expansive water park, featuring a 400-metre lazy river, twisting waterslides and a lagoon-style pool. “My favourite thing is the waterpark,” says Montré Edwards, Aurora Anguilla’s marketing specialist. “Adults have fun here, too!”

The swordfish nicoise salad from Malliouhana's Bar Soleil is made with edamame, olives, potatoes, boiled egg and a passionfruit dressing.
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12:30 p.m. | A cliffside classic 

Perched on a cliff with sweeping views of Turtle Cove and Meads Bay, Malliouhana is arguably Anguilla’s most luxurious getaway. Since 1984, the oceanfront boutique hotel has welcomed guests who crave an intimate, upscale Caribbean stay. “Hospitality in Anguilla is as old as Malliouhana,” says Feliz Pina, Malliouhana’s general manager. “We believe in the exchange of culture and storytelling.” 

Named one of Travel + Leisure’s Readers’ 25 Favourite Resorts in the Caribbean of 2025, Malliouhana offers a tranquil escape with some of the most delicious food in the Caribbean. The resort’s culinary director, renowned Anguillian chef Kerth Gumbs, guides the culinary program, showcasing Caribbean ingredients in deliciously unexpected ways. For casual dining, Bar Soleil offers a chic, relaxed setting where guests can admire the stunning view while surrounded by a large collection of Haitian art.

Offering British-inspired fare, Roy's Bayside Grill is a friendly dining option at Sandy Ground Beach.
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7 p.m. | Dinner at Roy’s

After a relaxing day in the sun, wander down to Roy’s Bayside Grill, a beloved seaside eatery featuring British-inspired fare: bangers and mash, scalloped potatoes and drool-worthy fish and chips. But don’t worry, there are also plenty of Caribbean favourites to choose from, including conch fritters, curried lobster and, of course, Johnny cakes. This open-air restaurant, which has been serving Anguillians and travellers since 1982, boasts a laid-back charm that makes it feel more like a friendly local haunt than a tourist stop. Originally opened by Chef Proprietor Roy Bossons and his wife, Mandy, today Roy’s is managed by the couple’s daughter, Claire Lynch, and her husband, Patrick.

Approximately 250 metres long and only 75 metres wide, Sandy Island is a must-visit stop during a trip to Anguilla.
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Aurora's farm manager Rohan Maynard shows some of the produce grown in the property's greenhouses.
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DAY THREE 

10 a.m. | Learn about the land 

For nature lovers, Anguilla is alive with vibrant colours and vegetation found nowhere else on Earth. Endemic flora, such as Anguilla bush (Rondelitia anguillensis) and Statia morning glory (Ipomoea sphenophylla), alongside 132 other native plants, support a wide variety of wildlife, from manatees and green sea turtles to ground lizards and iguanas. At Aurora Anguilla, guests can explore this natural abundance on a Flora and Fauna Resort Tour to learn about the island’s ecosystems and the ways the resort works in harmony with the land.

The property also features the Caribbean’s leading hydroponic farm, the backbone of Aurora’s dining experience. Nearly 90 per cent of the resort’s produce is grown on its 10,000 square feet (929 square metres) of farmland. “Everything we grow is for the restaurants,” says Rohan Maynard, the farm’s manager. “Lettuce, kale, butterhead, romaine… We grow the plants using nutrients dissolved in water from a large reverse-osmosis desalination plant. All the elements are combined to properly grow everything.”

Drunken coconut shrimp and bite sized fish traps from Sandy Island's restaurant.
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Noon | Sandy Island

A trip to Anguilla is not complete without a visit to Sandy Island. Approximately 250 metres long and only 75 metres wide, this small spit is home to only one restaurant, which also happens to be one of the best beach bars in the Caribbean. Known for its drunken coconut shrimp, tender crayfish and freshly-caught lobster, Sandy Island is open daily and also offers an eclectic array of drinks and cocktails. “No straws!” says Star, one of the island’s restaurant staff. “They kill the turtles,” he explains, setting down a bright blue mocktail. 

Departing from Sandy Ground Beach on Anguilla’s northern coast, the Sandy Island shuttle offers a quick and convenient way to get to this picturesque spit. Lounge chairs and umbrellas await, beckoning visitors to soak up the sun and enjoy the turquoise waters and white sand in style.

Guests enjoying fire dancers on the beach during Aurora's Thursday night Lobster BBQ.
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7 p.m. | Lobster BBQ 

Few places in the world offer all-you-can-eat freshly grilled lobster — but Aurora Anguilla is one of them. Every Thursday night, the resort’s C-Level Restaurant hosts an epic barbecue, featuring live music, DJs, s’mores-making and fire dancers, all in a beachfront setting. With sand in your toes and a plate full of Caribbean delights, guests can truly let loose at this highly sought-after culinary event (reservations are recommended). The buffet wraps around the main floor of the restaurant, showcasing an eclectic array of choices:  paella, ribs, a salad bar, dozens of sides, a dessert station and, of course, freshly grilled lobster and crayfish. This heady celebration of sights, sounds and flavours is designed to awaken your senses and serve as the ultimate way to wrap up your stay in Anguilla.

Where to stay: Aurora Anguilla 

With 178 rooms across two properties, Rendezvous and Merrywing, Aurora Anguilla’s expansive beachfront accommodations blend Caribbean ease with modern touches. Originally opened in 1999 as CuisinArt Resort & Spa, Aurora Anguilla was reopened in early 2022 after extensive renovations following Hurricane Irma. Today, the resort boasts the island’s only golf course, seven restaurants, an amphitheatre, tennis and pickleball courts, a climbing wall and basketball courts, just to name a few additions.

The light-filled rooms and multi-bedroom villas are designed to reflect the island’s gentle energy. Large soaker tubs with jets make the ultimate end-of-day relaxation ritual and, if you’re feeling peckish, dig into the minibar for a late-night snack. And don’t be surprised if you return to your room at the end of the day to find a delectable mango pudding or chocolate mousse waiting for you, courtesy of the exceptional housekeeping staff. 

For families or extended stays, Aurora’s Estates and Villas offer larger living areas, private pools, and services such as a butler, a personalized concierge, and housekeeping.

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