Ultimate weekend in Anguilla

The last place one would think to head for an extraordinary weekend getaway is Anguilla. Its under the radar status has a lot to do with that, and I’m sure the island’s celebrity visitors would prefer for it to stay that way.

A longtime hideout for A-listers, Anguilla is one of those secluded spots that are easy to overlook. The Caribbean island, a British overseas territory a mere 20-minute ferry ride from busier Sint Maarten, has only six traffic lights.

There are no cruise ports, casinos or high-rise hotels, just laid-back luxury and five-star hospitality teeming across this sandy paradise.

I’ve been into Anguilla since I visited for the first time some years ago. I’m a seasoned content executive and former magazine editor who’s lived abroad and traveled to over 60 countries solo, coupled, with girlfriends, and with my eight-year-old son, Journey, close by my side. But it wasn’t until my most recent trip that the island's subtle appeal really registered.

Yes, its white sand beaches are some of the most gorgeous in the world and the culinary scene is impressive, but Anguilla’s true charm exists in the ability to indulge in the art of doing the most or absolutely nothing.

Similar to the restorative energy I’m able to tap into on Jamaica’s less-traveled south coast or in Soufriére, a lush fishing village on the southwest end of Dominica, Anguilla conjures chill. It’s low-key and uncrowded, even during peak season when travelers descend on the island for Moonsplash and Carnival. 

When the allure of chill has lost its luster, dive, boat, dine or flaunt a flamboyant Moke around town. Or don’t. The island’s intimate atmosphere may leave you in a transient lull. 

Here’s my guide to experience an extraordinary weekend in Anguilla, on and off the scene.

When to arrive: My rule of thumb for weekend jaunts is to arrive late afternoon/early evening on Thursday, leaving two full days on the ground to explore. Settle in, then enjoy a fresh seafood dinner and tropical cocktail at a local bistro. Touring will commence the following morning so don’t stay up too late. 

How to get from the airport: The most affordable and efficient way to access Anguilla is by traveling through Sint Maarten's Princess Juliana International Airport. Once you land at SXM, hop on a shared or private sea shuttle, public ferry or seven-minute flight to the island where you’ll be greeted by a friendly hotel concierge and transported to your resort. Tradewind Aviation, Cape Air and Seaborne Airlines offer nonstop daily flights from San Juan, Puerto Rico; Antigua; St. Barth’s and several other Caribbean countries. You’ve got options.

Getting around town: Anguilla is dry, flat and roughly 16 miles long from east to west. You can drive from point to point in 45 minutes, but taking your time to pull over and experience the island’s many wonders is highly encouraged. If riding around in style is low on your priority list, rent a car. There are several companies to choose from so do your research to secure the best rate. Given the goal for the weekend is extraordinary, a flashy red vintage Moke seems appropriate or an ATV for the off-road rugged types who prefer a more muted flash. 

Where to stay: Make Zemi Beach House your base. Situated on Shoal Bay East, one of the island’s most coveted beaches, Zemi does luxury without pretension. The nature-inspired guest rooms are comfortable and spacious with sleek wood furniture and generously sized bathrooms flaunting freestanding tubs that draw you in for a relaxing soak. Opt for a king ocean view with a private balcony, to curl up with a good book and glass of prosecco, and drift to the sound of crashing waves. Indulgent body treatments at Thai Spa House and dinner reservations at Stone – Zemi’s fine-dining joint – are necessary. 

What to pack: Anguilla’s dress code is coastal chic. Think breezy separates, matching sets, versatile swimwear, statement shades and a fun straw tote to lug the essentials. While your individual vacation aesthetic is personal, the category is resortwear, so pack comfortable pieces in vibrant prints, colors, patterns and textures that you can easily mix and match. Don’t forget to throw in a few sleek looks for dinner and dancing. 

Day 1 

Morning 

Anguilla has 33 beaches, so get acquainted immediately with the island’s main attraction. Start your day with a sunrise stroll on Shoal Bay East, a two-mile stretch of powdery white sand crowned by “the point,” where the beach bends out in the middle creating a breathtakingly beautiful backdrop that deserves a moment on the social media feed. 

Next, head to Straw Hat on Meads Bay for the Lobster Johnny Cake Benedict or Meads Bay Wake-Up Smoothie (iced coffee, banana, oat milk).

If you’re up for a swim after breakfast, take one. Meads Bay is a popular choice amongst travelers not only for its beauty but for the luxury hotels and random celebrity sightings.  

How to spend the day 

Afterward, hop in your Moke and head south to the famed Anguilla Arch, a natural sand and sea formation floating on the West End. Out of the water, explore historical landmarks like Old Salt Factory to stock up on distinct seasoning blends from local entrepreneurs and Ebenezer Methodist Church, the oldest house of worship on the island.

Stop for a cocktail and live tunes at Bankie Banx’s Dune Preserve, then head back east for lunch at Ken’s BBQ in The Valley. Order the grilled chicken drizzled in their signature sauce, with a side of potato salad and an ice-cold Axa Ale, Anguilla’s first local beer. 

Dinner 

When the sun sets, change clothes and do dinner at Stone for Asian and Caribbean fusion fare inspired by indigenous ingredients. Start with the curried mussels spiced with fresh turmeric, white wine and roasted tomato.

For your main, order the sea salt crusted sea bass to share and the Armagnac Flambé Prawns for a tableside spectacle and a bite of zest. You can’t go wrong with the chocolate lava cake à la mode for dessert. 

After dark 

Sandy Ground is as good as it gets when it comes to year-round night life in small town Anguilla. Johnno’s Beach Stop is known for its smooth Sunday Jazz vibes and Elvis’ Beach Bar is a local staple.

During peak season, this sleepy island stays rocking well after dark with reggae music festivals like Bankie Banx’s Moonsplash and epic beach fetes like Eyes Wide Shut during Anguilla Summer Festival. 

Day 2 

Morning 

Ease into your morning with a sunrise yoga session on your private balcony or on Zemi’s expansive outdoor yoga deck. Then walk over to Thai Spa House for raw pressed juice and indulgent body treatments.

Book a bespoke massage led by your therapist’s intuitive touch or Kobido, an ancient Japanese facial technique that improves circulation and relieves tension, giving your skin a bright, luminous glow. The Hamman room and heated vitality pool are not to be missed. 

When you’re done pampering, head to French bakery Le Bon Pain for buttery croissants and a classic café au lait. 

How to spend the day 

Sail to Sandy Island for snorkeling, sunbathing and a relaxed afternoon lunch. The grilled lobster, snapper, baby back ribs and stiff JoJo rum punch are a hit at the island’s beachside shack.

And since sunsets in Anguilla are dramatic, climb back in the boat close to magic hour, pour yourself a glass of something and meditate on the gradient pink sky glowing above the endless blue sea.   

Dinner 

Blanchards and D Richard’s should top your list of places to dine in the Caribbean’s culinary capital of cuisine but Veya is where we’re eating tonight.

Monday through Saturday, Veya diners are treated to live acoustic sounds from local musicians like Omari Banks, the talented son of Anguilla’s Bankie Banx, the legendary artist behind Moonsplash.

Veya’s food is as memorable as its entertainment: grilled octopus with white bean hummus and smoked paprika, five spiced roast duck breast, banana cheesecake parfait with dulce de leche and chantilly cream.

After dark 

If you’re feeling adventurous after dinner, take a night kayaking tour with Liquid Glow. The rare experience allows you to see Anguilla’s pristine waters and diverse marine life in a mystical light.

Look out for large turtles swimming beneath your transparent kayak, lobsters crawling on the ocean floor or jumpy ballyhoo fish trying to make their way onto your boat. 

Day 3

Before you go, enjoy one final feet-in-the-sand meal at 20 Knots on Shoal Bay East. Grab a table in the shade for unobstructed views of the Caribbean Sea and bid adieu to Anguilla – the perfect place for an extraordinary weekend getaway, after all.