Best places to go on holiday in May 2023

Most travel experts will tell you that the shoulder season is the sweet spot if you want to reap the best holiday rewards, and May is no exception. Itís warm, but not too hot in Europe and there are bargains to be had on flights and accommodation before the summer holidays get going. Sailing and small ship cruises are at their balmy best in Croatia and Southern Europe, while in the mountains and along the coastline flowers bloom and temperatures are perfect for hiking. As the days get longer, rail holidays in Scotland come into their own. And in the Arctic the sea ice has melted, leaving open waters to cruise through, with migrating whales breaching the chilly surface.
Make the best of Mayís dry, sunny weather with outdoorsy fun Ė whether thatís kayaking in the Azores or searching for orangutans in the jungles of Borneo.
For far flung fun, the best places to go in May include Malaysian Borneo, where itís the perfect time to see orangutans, or Japan, where the landscape is a riot of green and the legendary Nakasendo Trail calls both walkers and history buffs. For something really adventurous, follow the Silk Road on an extended small group tour. Read our guide to find out more about the best places to go on holiday in May.

May holiday activities

Activity holidays

Activity holidays ramp up a gear as the weather gets warmer and the days longer. You could opt to work up a sweat in serious comfort with a luxury fitness and wellness holiday in Spain or explore Croatiaís rugged trails on a self guided biking tour. Or, to bung some learning into the mix, an archaeology holiday in Greece will deliver both walks and talks.

Railway holidays

Rail holidays become a more pleasing prospect as the weather gets warmer and the days longer, with Scotland a popular choice. Not only do you get spectacular Highland views from your window, itís perfect walking weather when you do get off the train. Itís also an excellent time to whip out the binoculars to spot nesting birds on the west coast and islands.

Small ship cruises

The weather at this time of year is made for small ship cruises or sailing holidays in Croatia Ė the waters are clear, the weather is warm but not scorching, and the summer holiday hordes have yet to appear. Egypt hots things up further, with Nile cruises the most elegant way to take in the countryís top ancient relics. If you like your boat trips to be on the bracing side, then sailing the Arctic on a tall ship spotting whales and icebergs is the stuff adventures are made of.

Our top Best places to go on holiday in May Holiday

Amalfi Coast walking holiday, Italy

Amalfi Coast walking holiday, Italy

Walk in lemon groves and hillside villages

From £1579 to £2249 8 days inc UK flights
Small group travel:
2023: 17 Jun, 24 Jun, 1 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug, 26 Aug, 2 Sep, 9 Sep, 14 Oct, 28 Oct, 4 Nov, 11 Nov, 18 Nov, 23 Dec, 30 Dec
2024: 10 Feb, 17 Feb, 24 Feb, 2 Mar, 9 Mar, 16 Mar, 23 Mar, 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct ...
Travel Team
If you'd like to chat about Best places to go on holiday in May or need help finding a holiday to suit you we're very happy to help.


May is a lovely time to make for the southern European countryside, whether youíre rambling through Romania or soaking up salty breezes on the Amalfi Coast. Thereís less rainfall and itís usually warm enough to wear short sleeves during the day, though jumpers and jackets may be required when the sun goes down. In Japan, warmer temperatures and bursts of greenery make this a good time to tackle the Nakasendo Way, once one of the countryís most important feudal highways.

Wildlife watching

The annual migration of blue whales brings them to the Atlantic waters around the Azores in April and May. The seas are choppier than in high summer but there are fewer crowds. Itís also dry season in Borneo, so this is the time to head into the wild to see orangutans with an expert guide and conservationist, either on foot or by boat. Prefer something cooler? Then Alaska is a good bet. May is an excellent time for bird watchers and itís also the cusp of grizzly bear season
Written by Nana Luckham
Photo credits: [Page banner: v2osk] [Wildflowers, Dolomites: daniel plan] [Yoga: Kaylee Garrett] [Hiking, Romania: David Marcu]