Countries

Anguilla coastline | Black Tomato

Anguilla

Anguilla could simply never be described as ‘just another island.’ With its rich ecology and expansive coral reefs, it’s easily our favorite destination for days spent beneath the surface. Whilst on land, its tranquil air makes for an addictive antidote to the pressures of everyday life. Whether perched atop a clifftop bluff or cocooned by warm waters, a luxury vacation in Anguilla offers the perfect viewpoint on a carefree getaway.

Sunset in Antigua | Black Tomato

Antigua

With a different beach for every day of the year, a luxury vacation in Antigua should feature on every bucket list. You’ll be entranced by island magic, carried on the same warm breeze that used to hoist the sails of trade ships. Today, it carries windsurfers and luxurious schooners into tranquil bays with only the slightest rustle of palm trees. It’s a veritable paradise.

Swirling sands in the Bahamas | Black Tomato

Bahamas

Popping with color and rich in the trappings of island luxury – you know the drill: pristine beaches, warm blue seas, and sizzling scents – the Bahamas, the super tropical neighbor of nearby Florida, are a luxury traveler’s dream. And with more than 700 islands and 2,400 cays, this is a true Caribbean playground.

 

 

Palm trees in Barbados

Barbados

Famed for its white sand beaches and turquoise waters, Barbados has forever been a favorite of those seeking an escape to paradise. On a luxury vacation in Barbados, live life in the slow lane or embark on an island adventure. Surf the Soup Bowl, swim with native Hawksbill Turtles, soak up the charming blend of West Indian and colonial traditions – all before retreating to idyllic boltholes and luxury hotels.

Cayman Islands - Black Tomato

Cayman Islands

Grand, Little and Brac; luxury, isolation and rugged charm. Each of the three Cayman Islands offers a distinct flavor, all the while dripping with the requisite good looks of this glistening patch of waters. Cocooned by the vibrancy of the Caribbean on one side and the culture of Central America on the other, a luxury vacation in the Cayman Islands offer an insatiable taste of tropical living.

Streets of Havana

Cuba

With its faded glamor and colorful history, Cuba is a destination that will confound and amaze in equal measure – and that’s exactly why we love it. Blending Latin and Caribbean influences in a heady cocktail of arts, music and gastronomy, a luxury vacation in Cuba will take you from the rum-scented squares of Old Havana’s Vedado to the cigar-rolled plantations of Vinales and on to pretty pastel-hued Trinidad.

Grenada Beach - Black Tomato

Grenada

You need only step onto the powder soft shores, close your eyes and inhale the sweet scent of air laced with seasalt, nutmeg and mace to know that you have arrived in Grenada. A place where miles of untouched beaches run into thick virgin rainforest, we can’t help but channel our need to explore here. Hiking to secret waterfalls, dining with locals at Gouyave; a luxury vacation in Grenada is a whole new Caribbean.

Views over Falmouth, Jamaica | Black Tomato

Jamaica

An island brimming with color and bursting with scent and sound, there’s more to a luxury vacation in Jamaica than power-soft sand. This is a place where the rhythm of the steel drum is carried on a breeze scented with creole spices, and where hummingbirds kiss the gaudy flowers in the afternoon heat. Jamaica offers every bit of the effervescent island life you might imagine. Kick back on Runaway Bay, or hit up the Bob Marley Museum. There’s no rush.

Sail around Mustique - Black Tomato

Mustique

At just three miles long, Mustique is but a blip on the radar of many. But those three miles comprise untouched beaches lapped by clear waters and drenched in Caribbean sun (and just one gorgeous hotel). A luxury vacation in Mustique becomes an easy choice to make. We’ve decided that this is the purest definition of an island getaway. It’s the kind of place people point to from other, busier islands and exclaim, “I want to be there.” Well, you can.

Romantic beach in St Barths - Black Tomato

St Barths

A verdant island that rises up out of crystal clear waters to ooze a unique and independent personality, St Barths has not only garnered a reputation of exclusivity and luxury – but of stunning natural beauty. Home to perspectives that change around every cove, admire it all from the glamor of St Jean Bay to the rugged isolation of Colombier. A luxury vacation in St Barths will leave you wanting for nothing.

The Piton Mountains St Lucia

St Lucia

Set apart by a dramatic landscape of twin coastal peaks that overlook vast rainforests filled with birds of paradise. St Lucia is luxury island living at its best and most laid-back. Join locals on banana plantations, lay eyes upon vibrant wildlife and hike atop the island for one of the best views in the Atlantic. Trust us on that one.

St Vincent and the Grenadines - Black Tomato

St Vincent and the Grenadines

Turks & Caicos Beach - Black Tomato

Turks and Caicos

A place that embodies everything you think of when you think of the Caribbean, a luxury vacation in the Turks & Caicos offers all the beauty of these tropical isles – with none of the crowds. Thousands of acres of white sand beaches speckle the seas creating a feeling of seclusion and privacy whilst luxurious hotels settle on the shores, hidden from view by tall palms that droop under the weight of fresh coconuts. Bliss.

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