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Where to go in May

The month we’ve all been waiting for. With bank holidays and rising temperatures, May is an all too fitting farewell to the year’s start and a warm welcome to the vastness of summer.

With international travel set to resume no earlier than May 17th, we’ve hand-picked the ideas below to get your mind racing about your options for the month. Whilst guidance on travel corridors, vaccine passports and testing continues to evolve and take shape, we’re on hand to give you the most up-to-date advice and expert suggestions in choosing your trip. And remember, we still have our super-flexible State of Flex cancellation terms up our sleeve.


Your destination inspiration for the month

Where to on holiday in May: Greece
Where to go on holiday in May: the UK
Where to go on holiday in May: Spain

100% refundable bookings should you cancel at any time up to 30 days before your departure.

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Experiences & Hotels

Our hand-picked recommendations for where to stay and what to do

Balearics to Barcelona

This is an island-focused foray into Spain’s Mediterranean culture, bringing together Mallorca, Ibiza, and a cultured dive into Barcelona. Yachts, helicopters and gastronomy. This high-end escape is perfect for couples and groups of friends.

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Macakizi, Turkey

A grown-up and glamorous resort with all of the energy of a sun-hot riviera. Stroll, swim, take in the music, prop yourself up at the bar. The surrounding countryside has a lot of history, and exceptional views.

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Luxury holiday to Greece in May

Mainland Greece

This is really our ‘alternative’ Grecian itinerary, with a big focus on history, food and culture. Perhaps it’s a bit more grown up, a touch more decadent. Sunrise at the Acropolis, sunset at the Temple of Poseidon. Art in Hydra, and extreme luxury at Amanzoe.

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Holiday to the Seychelles: Six Senses Zil Pasyon

Six Senses Zil Pasyon, the Seychelles

This is a firm Black Tomato favourite. All the exclusivity and facilities of a resort, albeit reserved for just 30 villas. A cinema beneath the stars. A duet of spa and infinity pool. Ecological sensibilities and (unsurprisingly) exceptional eating and drinking.

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Aman Sveti Stefan, Montenegro

Effortless in style and substance, this islet perched hotel sits amid one of Montenegro’s most exclusive – and visually arresting – settings. The 15th-century buildings, prettily fortified walls, and sparkling waters, meanwhile, offer a genuine slab of old-world romance.

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Le Manoir aux Quat'Saisons

Refined elegance meets family fun at the revered Le Manoir aux Quat’Saisons. Here, we’ll arrange foraging expeditions and Michelin-worthy cooking lessons for parents as well as quirky croquet games and magical tea parties for kids.

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Jumby Bay, Antigua

A Black Tomato favourite. This expansive private island off Antigua’s north coast has everything you could ever wish for. All-inclusive, incredibly private and totally family friendly. Trust us: you’ll love it.

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A Chic Portuguese Getaway

Here’s something special. The twin fantasy of Lisbon and Alentejo (and it’s ideal for a week-long getaway). Great for couples and families alike. The music of Fado, the baking of pasteis de nata, UNESCO-listed Sintra and the dark-sky reserve of Alentejo. Etc.

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Our notes from the field. Videos, guides, and stories to get your ideas flowing

Black Tomato Curated the Perfect Trip to Morocco!

“Our experience with Black Tomato has been outstanding. The accommodations, excursions, restaurants, and transfers were all top notch – the best of the best. Everything was seamless and so well planned. We had the most amazing time!”

Celia, Black Tomato Client

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Take the risk out of travelling

With State of Flex, all new bookings are now 100% refundable should you cancel at any time up to 30 days before your departure. Should you change your mind, we won’t charge you. Find true flexibility and peace of mind when you come with us.

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