Tucked behind the pilot in a tiny plane, I kept half an eye on the radar as we scudded along cotton wool clouds haloed by an orange sunset. Barely-seen islands slid past below – the kind once haunted by pirates and perhaps harbouring buried treasure. I could make out St Martin to the left before finally Anguilla came into view.

Having experienced Antigua’s bountiful beaches – and in the past, most other Caribbean destinations accessible via direct flights from the UK – I was curious to explore beyond the gateway islands. It’s a sentiment that seems to be echoed by tour operators, who report an increase in enquiries from clients keen to discover lesser-known Caribbean isles like Anguilla and St Kitts, with both places recently seeing a rise in visitors.

Thanks to fresh flights, reaching both Anguilla and St Kitts from Antigua is a cinch – with the direct British Airways service making a short stop there before flying on to St Kitts, and also offering an onward connection to Anguilla via Tradewinds on Saturdays and Sundays.

Low-key glamour

The three-times-per-week Anguilla Air Services connection from Antigua feels much more adventurous than a Boeing 777.

But despite its apparent isolation, the British Protectorate of Anguilla is far from being a castaway cay. On this pretty boutique island I travelled in vintage candy-coloured Mokes – like a weird cross between a classic car and a golf buggy – to gourmet restaurants and natural beauty spots with locals waving and shouting hello as I went.

With zero sprawling all-inclusives and no cruise terminal, its manicured lanes, private villas, small luxury hotels and beachside eateries infused with authentic island goodness give it an air of unpretentious exclusivity that’s vanishingly rare.

The Malliouhana embodies that spirit. Immaculate and effortlessly chic, it’s hard to believe the resort has been here for 40 years. Staff felt like a host family and the cabinet of curiosities and vintage diving helmets set into the lobby wall indicated it’s also a little quirky.

A divine Haitian art collection and heritage rum and chocolate pairing session by returning staff member Chesney quickly showed me this place has substance as well as style. “Malliouhana set the bar for tourism on the island and everywhere else tries to emulate it, but there’s only one mould,” Chesney tells me – he should know, as he has been connected to the resort for more than 30 years.

Centring on a lemongrass-scented lobby pool bar area, white two-storey villas containing a variety of boutique suites are arranged along low cliffs between a secluded cove and Meads Bay. At the latter I found some of the island’s best beach bars and restaurants including lovely Leon’s with lounger service for Malliouhana guests and live music at sunset, plus delicious French fusion seafood at Jacala.

The son of Malliouhana’s original owner was a Michelin chef in Paris, and he set the standard for dining on the island. An absence of all-inclusive hotels and a love of good food means Anguilla’s culinary scene is well developed with popular restaurants such as Veya leading the way. An annual culinary festival showcases its fine fare each May.

As one of the only coral sediment islands in the Caribbean, Anguilla is relatively flat, pitted with limestone caves and indented with 33 dazzling beaches including the supernatural platinum and crystal-cyan beauty of palm-tufted Shoal Bay.

At 16 miles long and just 3.5 miles wide, life on the island revolves around local beaches such as Sandy Ground where I boarded boats bound for snorkelling sites, a simple lunch on Sandy Island and some stellar shell-collecting. It’s also an evening hotspot for cocktails at Elvis’ or Lit bar with live music and beach-bar games.

Anguilla’s limestone caves make for some fun escapades too, such as the hike to Goat Cave. A gentle coastal saunter quickly turned to a careful climb along sea cliffs showered in salty spray from the waves crashing below. Descending to a natural pool, I followed my thankfully-competent guide Neil and swam into the cave, climbing up through smooth caverns to yet another plunge pool, where we whirled around as the waves from the outer ocean poured in through a window in the rock.

Kitt and caboodle

While Anguilla is a pocket paradise, St Kitts is twice the size, with a rich bounty of rainforests and reefs, heritage and culture that will suit clients who prefer a mix of rest and exploration, and another great option for those who want to move beyond the obvious (but well connected) Antigua. 

I stayed aboard my flight from London to Antigua for the 15-minute trip onto St Kitts. Though seemingly-secluded, the far south of the island at the Park Hyatt St Kitts is the perfect base for a luxury stay on the island. And sister-isle Nevis’ emerald cone gracing the southern horizon enhanced the sea view from my plush room was another bonus. 

From Reggae Beach – also known as Cockleshell Bay – little boats make the crossing there. A day trip to Nevis’ sleepy shores can be combined with snorkelling at White House and Shitten Bay on a private boat tour with Paradise Sun where I spied coral gardens teeming with tropical fish and a rusting shipwreck marooned on rocks. For clients keen on island-hopping, St Kitts has recently gained Makana ferry services to nearby Statia, Saba and St Maarten too.

Reggae Beach is also the setting for the second part of the Kittitian RumMaster experience in the mixology lab of newly renovated Spice Mill. I tucked into tacos with my toes in the sand before learning to rustle up mouth-watering hibiscus mimosas.The first half of the RumMaster experience had offered me a real taste of the original Caribbean at Old Road Rum on Wingfield Manor Estate. Positioned at the top of Old Road Town, which is the site of the island’s first settlements and oldest buildings, the rum distillery sits among the partially-excavated and restored ruins of an old sugar mill. It now contains Alfies bar serving delicious old fashioneds made with seven-year aged rum and coconut water ice cubes.

Showing me around, founder Jack Widdowson tells me he’s found evidence islanders were using sugar molasses to make rum on the site as far back at the 1600s. Archaeology is still emerging from the forest around the river, which disappears under the canopy of Central Forest Reserve National Park. Motioning to the jungle perimeter where a couple of long-limbed green vervet monkeys hung around in the shade, Widdowson adds that St Kitts is the only place in the world where the rainforest is expanding rather than contracting.

Tree hugging

Beyond Wingfield Manor Estate, trails lead into the rainforested hills of Central Forest Reserve, which covers most of the island’s rugged interior above 300 metres.

There, I joined veteran jungle guide O’Neil Mulrain for a hike along the river valley swathed in a veil of vines. He shared his extensive knowledge of the forest from fever grass to ancient ficus trees, swung like Tarzan on dangling tendrils and scrambled up cliff faces using a natural ladder of thick roots.

From sky-high Brimstone Hill Fortress north of Old Road Town, I gazed on an all-encompassing view of the area’s mountainous terrain and neighbouring volcanic islands. The fort clings to an ancient lava extrusion and its artillery stores, cells and lookouts are now used to house exhibits telling the island’s history.

While exploring St Kitts I discovered plenty of eateries serving wholesome, home-style food. At Serendipity in a sleepy backlane of Basseterre I spotted the biggest commendation of all – the island’s prime minister Terrance Drew lunching on the verandah, with views over the capital’s harbour. As he exited the restaurant, he greeted the other diners including us, displaying the warm inclusivity that many say marks out St Kitts as particularly welcoming to visitors.

How to book it

Inspiring Travel offers seven nights at Malliouhana staying in a Garden View Deluxe King room including breakfast, flights from Gatwick, inter-island flights between Antigua and Anguilla and private transfers, from £3,079 per person based on two sharing.

Seven nights at Park Hyatt St Kitts staying in a King Bed Room including breakfast, flights from Gatwick via Antigua and private transfers, is from £2,085 per person based on two sharing.