Introducing Anguilla, the Caribbean Winter Playground

Just like the Maldives, every island in the Caribbean has its own style. There’s often beautiful water and barefoot beachfront vibe, but in the Caribbean, contrasts between islands are far more noticeable.

Some Caribbean islands are about cruise ships and mega resorts. Anguilla is at the opposite end of the spectrum.

Quiet powdery beaches are connected by unmarked roads. Small five-star resorts are characterised by low-slung beachfront villas. There’s more space than you’d find on any Indian Ocean islet.

If we had to compare the Caribbean to the Maldives then Anguilla would be Soneva Fushi: slow barefoot luxury, privacy with all the amenities and activities. It’s unwinding on an island that goes under the radar.

Quiet barefoot luxury is the Anguilla way

Getting to Anguilla

Anguilla is exclusive, partly because it seems hard to get to. You need to fly to Saint Martin first, then transfer by light jet or private boat to Anguilla – it’s very similar to flying into the Maldives and taking a seaplane transfer from Male. The extra cost of the flight or boat has kept budget travellers away.

Belmond Cap Juluca awaits on an island with a clear focus on high-end tourism

Anguilla’s Superb Resorts

Anguilla is a high-end island and there are three excellent resorts we can recommend.

Belmond Cap Juluca

Reopened last month (October 2021) after a $121 million renovation by Lauren Rottet, who added very lavish interiors to a resort that felt a little dated. It’s now a 2020s imagination of Robinson Crusoe island vibes, with life in the open air and without shoes. Sea views from everywhere and a great degree of privacy should you wish, but also four restaurants and a new pool cocktail bar.

The redesigned villas at Belmond Cap Juluca

Staying at Belmond Cap Julaca means Bellini Club Benefits, such as complimentary upgrades and in-resort credit. Consider some very easy island hopping by combining Cap Juluca with a stay at La Samanna on Saint Martin.

The Four Seasons Anguilla

Another exemplary beachfront property

On a bluff between two dazzling beaches, the Four Seasons delivers their trademark service and Kids for All Seasons program to Anguilla. The villas are great, featuring their own infinity pool and hot tub.

Villas provide a huge amount of space for families

Plus there’s a massive array of activities, so it’s great as a one-stop holiday for families. It’s the largest property on the island with 120 rooms and suites, plus the villas.

Want Winter Sun in the Caribbean?

Aurora Anguilla Resort & Spa

The new Aurora Anguilla Resort & Spa

Spread across 300 acres, this vast resort opened in December 2021, after a complete transformation from its former guise as CuisinArt. It has its own fleet of jets, providing charter services for guests coming from anywhere in the Caribbean or the United States.

Beach suites are comfortable and the hotel is open all year around

Whitewashed villas are reminiscent of Greece and it has the only golf course on the island, by Greg Norman. We’re yet to try it out but you’ll be first to know when we do.

When to Visit Anguilla

Anguilla’s main season is from December to April, when the island has perfect beach weather – temperate days not exceeding 32℃, lower than usual humidity, and a famous cooling breeze blowing from the northeast. Hurricane season is June to November and some resorts close at this time.

So when you need some winter sun, it’s not that far to Anguilla and the Caribbean.

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