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Where to go in May

With brighter days and rising temperatures, May sits neatly between the year’s start and the vastness of summer. And you won’t always have to travel far to find something rare and unknown.

We’ve hand-picked the ideas below to get your mind racing about your options for the month. As ever, we’re on hand to give you detailed guidance and expert suggestions in choosing your trip. And remember, we have our super-flexible State of Flex cancellation terms up our sleeve.


Your destination inspiration for the month

Where to go on vacation in May: USA
Where to go on vacation in May: Italy
Where to go on vacation in May: Croatia
Where to go on vacation in May: Turkey
Where to go on vacation in May: Jordan
Where to go on vacation in May: Morocco

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

Vacation in May: Charleston USA

A charming cultural journey in Charleston

A journey built around the people and stories of this extraordinary region. May is the perfect moment to experience Charleston before things get too hot. Canoes, waterways, historic towns and motorboats. A night campout on Capers Island is a must.

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Vacation in May: Italy

An Italian grand tour

Here’s a trip featuring some of Italy’s greatest icons and most legendary hotels. From Lake Como and Tuscany to Rome and Amalfi. We’re very close with the hotels and properties, ensuring you’ll be exceptionally well looked after. There’s a vintage Alfa Romeo with your name on it, too.

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Vacation in May: Croatia

A luxury holiday on the Adriatic

Combining Croatia with its lesser-visited (and stupendously picturesque) neighbor, Montenegro. Ultra-luxury in Aman Sveti Stefan. Split, Korcula, and Dubrovnik. Private islands and secret dinners.

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Vacation in May: Greece and Turkey

A duet of Greece and Turkey

A world of difference right next door to neighboring Europe. This itinerary includes Greece (with Mykonos and Santorini) before hopping across the Aegean for Istanbul and surreal, beautiful Cappadocia (with its balloon rides and iconic ‘fairy’ chimneys).

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Vacation in May: Jordan

See it all in Jordan

This ‘best of’ itinerary takes in all the greatest sights (and some secret surprises). The highlight is Petra by night, a rare experience including music performances, candlelit tours, and tea ceremonies. Magical.

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Vacation in May: Morocco

The best of Morocco

Our quintessential Moroccan experience, bringing together Marrakech, the Agafay Desert and the Atlas Mountains. Sidecars, street-food, hot air balloons and Kasbah Tamadot. You can easily spread this trip across one or two weeks.

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

Our third trip with Black Tomato...

“This was our third trip with Black Tomato, and we could not recommend them more! They take every trip to the next level, we trust their advice implicitly. Their knowledge and network of local guides across the world is unparalleled. We are now in the process of planning our fourth trip!”

Anon, Black Tomato Client

Meet the ‘taxi’ drivers of Madeira

In remotest Portugal, a 200-year-old mode of transport is still going strong

What our clients say

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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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