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Where to go on holiday in May

Molly Thompson

May-be a perfect month to travel! Summer is on the horizon; the weather is warmer and the days feel brighter. But where are the best locations during this month? Let our expertise guide you through the beautiful month of May.

See our where to go, when guide for destination recommendations throughout the year.


New York

Home to one of the most famous skylines in the world, New York has so much to offer: unmissable architecture, stunning skyscrapers, many of the world’s finest collections of arts and antiquities, seventy-five Michelin-starred restaurants, the legendary theatres of Broadway, the biggest names in shopping, and it’s vast, majestic parks. Between April and June, there are few crowds, it’s warm and those majestic parks are in bloom. Here we  highlight a few holiday experiences to enhance your visit to New York.

New York Full Day Pass

An all-in-one pass instantly accessible via your mobile phone with access to 100 top attractions such as the Empire State Building. Includes walking tours, sightseeing cruises, museums and attractions. From £98 per person.

Call 0800 047 1066

Helicopter tour

Travel from New Jersey and head north along the Hudson, passing over all the major sights of Manhattan with fantastic photo opportunities. See the bright lights of Times Square from a different angle.

Call 0800 047 1066

Boston Day Trip

Travel north to Boston, for a day of walks including Harvard Yard, part of the famous University campus. Cross the Charles River to visit Copley Square and Trinity Church. Walk the Freedom Trail, take lunch at Quincy Market and visit the site of the famous Tea Party.

Call 0800 047 1066

Sicily As the weather gets warmer, Sicily is a fantastic option for holidaying. May is a great time to visit its capital city, Palermo. You can tour several palaces and churches, such as the gilded Cappella Palatina. Or if you’d prefer you can visit museums such as the Pinacoteca Villa Zito.

Hotel Principe Di Villafranca

Located in Palermo’s chic shopping and dining area and a short walk from the historic centre, Hotel Principe di Villafranca is an elegant boutique hotel where sophisticated interiors feature Sicilian antiques and fine fabrics which blend harmoniously with contemporary elements.

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Hotel Plaza Opera

Surrounded by the wonderful boutiques of Via Liberta, 150 metres from Piazza Politeama and close to museums and theatres, the cosmopolitan Hotel Plaza Opera is well placed to discover all that Palermo has to offer.

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Sicily Self Drive

As Sicily is the largest island in the Mediterranean it’s difficult to see everything in a week. Our eight day self-drive itinerary acquaints you with all the highlights of Sicily’s east coast: Taormina, the Sicilian islands and Syracuse. Our six day self-drive holiday covers the west coast and takes in Palermo, Monreale and Cefalu.

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The Maldives The Maldives are an excellent travel destination for May. Rain may be more likely, but temperatures are still warm and there are usually long spells of bright sunshine. Meteorological anomalies are not uncommon in a tropical island nation as widely dispersed as the Maldives, and the seasons are less predictable.  Plankton in the water may reduce visibility for divers, but it does attract manta rays and whale sharks, and accommodation can be much better value in price. Remember the odd rain day in paradise can be equally as memorable as a sunny one.

Baros Maldives

Baros, being one of the first Maldives resorts to open, is something of a pioneer in luxury atoll holidays. Set on an intimate island, the natural beauty of the turquoise waters breaching the coral reef are complemented by the exquisite design of the resort’s handcrafted design and attentive personal service

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Constance Halaveli

This classic barefoot resort is located on an island of coconut palms dissected by sandy lanes, and with one long overwater jetty. The design of Constance Halaveli echoes the building traditions of the region with thatched roofs, polished wood and a nod to the curved Dhoni boats.

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Kandima Maldives

Kandima is an extremely appealing ultra-luxury resort with superb personal service and impeccable hospitality as its hallmarks. The property also embraces a regard for the wider community, its culture, and the stunning environment of which it is part.

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