Luxury Caribbean Holidays & Adventure Tours

It’ll come as no surprise that Ian Fleming dreamt up James Bond while living in the Caribbean, where luxury travel first cut its teeth. After all, this jewellery box of 7,000 islands – with hedonism in Cuba and rum-punch in Jamaica – is all about big characters and easygoing exotica. But don’t write it off as ‘just beaches,’ because you’ve never seen beaches like the Cays of Tobago nor felt the rush of landing by Seaplane at Paradise Island (yes, it is a real place).

In Antigua, you’ll be spoilt for choice with one beach for every day of the year. That’s right, home to 365 beaches – letting you sunbathe, snorkel, dive, windsurf and boat around the island to your heart’s content. Touching down in St Lucia, adventure seekers can revel in countless opportunities for wild jungle hikes, coral reef dives and mountain climbs. If you’re looking for a romantic touch, just let us know and we’ll arrange a candle-lit dinner on the secluded beaches with you and your beau.

In between the unforgettable experiences and lavish hotel stays, take some time out to indulge in Caribbean cuisine. Get a taste for island life with freshly grilled lobster and kick back with a glass of rum and let the reggae float over you.

As a Virtuoso member, we’ve earned a reputation for our expertise in creating unbeatable bespoke trips and experiences. Something that’s more important now than ever before. We’ll put your mind at ease as we draw on years of access, knowledge, and insight to inspire you with innovative ideas on how to achieve the most COVID-secure holiday possible – without missing out on any of the experience. Throughout, you’ll benefit from up-to-date travel advice, 24/7 support and super-flexible booking conditions. So let’s get out there.

Countries List View

Anguilla

Anguilla could simply never be described as ‘just another island.’ With its rich ecology and expansive coral reefs, it&...

Antigua

Why should you travel to Antigua with us? You’ll be spoilt for choice with a different beach for every day of the year. An id...

Bahamas

Popping with colour and rich in the trappings of island luxury – you know the drill: pristine beaches, warm blue seas, ...

Barbados

Famed for its white sand beaches and turquoise waters, Barbados has forever been a favourite of those seeking an escape to pa...

Cuba

Why should you travel to Cuba with us? Pastel-hued villages, rum-scented squares and cigar-rolled plantations. Cuba is a favo...

Grenada

You need only step onto the powder soft shores, close your eyes and inhale the sweet scent of air laced with seasalt, nutmeg ...

Jamaica

An island brimming with colour and bursting with scent and sound, there’s more to a luxury holiday in Jamaica than powe...

Mustique

At just three miles long, Mustique is but a blip on the radar of many. But those three miles comprise untouched beaches lappe...

St Barths

A verdant island that rises up out of crystal clear waters to ooze a unique and independent personality, St Barths has not on...

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Explore our inspiring experiences in the Caribbean based on when you want to travel and how you want to feel.

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What the Press Say

Voted the world’s third best specialist tour operator in the Conde Nast Traveler Readers’ Choice Awards 2021

Voted as one of the top 10 best tour operators in the World’s Best Awards 2021

“The hottest company in luxury travel takes transformative trips to the next level”

“Black Tomato are one of the coolest things in the world. Don’t even try and live without them”

“Black Tomato, the people who bring you the coolest vacations you’ve ever heard of”

“Black Tomato is a super innovative company where the sky is the limit for their clients”

“Black Tomato prides itself on meeting customers every minor need or desires”

“Many companies brag about offering once-in-a-lifetime experiences. But with Black Tomato it’s not hyperbole”

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