Best Holiday Destinations For May 2026

May is an amazing time to go away, not only is it usually a transitional month meaning that the temperature is usually pretty damn warm still and there is not too much rainfall in most of our destinations but also you usually beat the crowds, which is pretty great! May 2026 will be no different and after the couple of years we've had, we wanna travel and we wanna travel HARD. If you wanna know our top destinations for May 2026, then scroll down! Keep on reading so you can get planning the most insane trip of your life. Here are the best places for your travels in May 2026!

We have created the ultimate guide for the best places to visit month-by-month. Everyone's availability for the year is different, so whether you'll be seeking sun in September or making plans for March, we have your back and we'll show you the top places you should consider visiting! The world is wide and the destinations are endless, but there's no need to be overwhelmed. Trust us and we will show how to get the best out of your holiday - no matter when you travel!

UP TO 40% OFF COLOMBIA THIS BLACK FRIDAY!

So most people say that it's best to visit Colombia between December and March as that's its dry season! BUUUT what people don't know is that in May, there are fewer crowds and it is still a lovely temperature (with highs of 32 on the Caribbean Coast, helllllo sunbathing) and with low levels of rain in most of the tourist hotspots such as Cartagena, so it's the perfect time to visit! So now that you know when you're going and where you're going, you wanna know the why? Well, with Colombia, the list is endless! Colombia has everything - you can soak up the history of Colombia's difficult past in Medellin and see how Communa 13 has been transformed by vibrant street art as well as visit Colombia's cultural hub, Cartagena, where you'll explore the old town and marvel at the stunning architecture.

COSTA RICA - 20% OFF THIS BLACK FRIDAY!

May is a great time to kick back and live that pura vida lifestyle in Costa Rica! While lots of people visit Costa Rica in their dry season (December - April), May is a transitional month in their so-called "green season" meaning that national parks are quieter than normal (woop to no crowds), the wildlife is out and about and the lush greenery is just that extra hint more vibrant since there are a few lil' showers to get them glowing again and the rivers and waterfalls etc are fuller and more impressive (water rafting anyone??). Not to fear though, May is still a relatively dry month with only a bit of rainfall and it is worth it to travel during this fantastic transitional period. As one of the world's adventure capitals, Costa Rica really packs a punch.

LIVE THE DREAM IN THE PHILIPPINES WITH UP TO 40% OFF!

The Philippines dry season is between November and April, and as a shoulder month, May is still a beautiful time to visit these stunning islands because not only is it still warm and very dry with the occasional shower before the proper rainy season starts but the islands are also generally less crowded, which is ideal for when you're wanting to relax on the white-sand beaches and snorkel in the vibrant seas. Can you think of a better way of spending your May than livin' it up on a Filipino Island, eating your body weight in Lechon (a quintessentially Filipino dish... but not suitable for vegetarians haha), sippin' on a Piña Colada and having the warm sand flow between your toes? Nope, we can't either.

There you have it - the best places to travel in May 2026! Now you know how to have the summer of dreams, book it and get something in the diary to look forward to! If you need any more travel inspo, feel free to send us an email at info@trutravels.com or check out our socials!