Where to go in

May

Where to go in

May

You know how sometimes the starter is better than the main course? That’s how we

feel about May holidays – the tantalising appetiser of summer. So close you can

taste it but without the scorching temperatures and mass crowds. We think it’s the

best time of year for Stateside adventures with pretty much perfect temperatures to

be hitting up the Southern states and happening cities like LA and Chicago. As for

Europe, it’s May when the social season starts. Discover our guide to the best places

to visit in May 2026 - and where to stay across The Dis-loyalty Collective when

you’re there.

Los Angeles

There are a lot of reasons to love visiting LA in May, not least because it’s before the main summer vacation when suddenly everything gets very hectic with residents and tourists alike. The weather, too, is pretty much perfect. OK, so it’s not exactly a shocker to expect blue skies in LA but in May the temperature will feel good on the beach in Malibu, but also allows you to hike or sight-see without getting offensively sweaty. As for culture, you’re spoiled for choice. We’re loving the sound of Netflix’s Everything Is A Joke Fest with 350+ comedy shows at venues across the city - see Larry David, Jerry Seinfeld, Kevin Hart, Ali Wong amongst hundreds of others. May 5 is another key date for your LA diary with the largest Cinco de Mayo festival in the US. You may also catch WeHo Pride celebrations kicking off toward the end of the month, bringing music, parties and parades to West Hollywood.

Cannes

You might have heard of the Cannes Film Festival? Well - newsflash - that’s happening for a good stretch of the month, from May 12- 23. Needless to say, it’s all très chic and the chances of bumping into a Hollywood A-lister whilst you saunter stylishly down the Croisette is pretty high. The film festival also means there’s a massive buzz around town, lots of parties to crash, and people to watch. Back from the glitz of the promenade, Cannes Old Town (Le Suquet) really comes to life in May, with people dining outside on the pretty cobbled streets. Foodies will be spoiled for choice with everything from upscale French dining to casual bistros, tapas bars, and cafes. Beyond the film festival, it’s the true start of the season, the sun is shining, the Provencal Rosé is flowing and the business of everybody living their best lives on the Riviera has started in earnest. P.S. With Monaco just next door, you might want to swing by for the Grand Prix between the 5-7 June, too.

Rome

Say Ciao Roma to the Eternal City in May, an eternally brilliant time to visit this southern Italian city. With some of the world’s most compelling history and devastatingly good food, Rome at any time of year will be magical, but is it a little too hot and busy in August? Yes, it is. May, on the other hand, the sun is shining in a friendly way, the flowers are in full bloom and the city is smelling sweet - hello Azaleas on the Spanish Steps and the opening of the Roseto Rose Garden. Dates for your travel diary include a couple of freebies on the big-hitting sites – with the Colosseum offering free entry on the first Sunday of the month, and the Vatican Museums (home to the Sistine Chapel and that Michaelangelo ceiling) opening their doors for free on the last Sunday. Another best thing to do in Rome this month is ‘Nights of the Museums’ when a huge number of museums, monuments, and archaeological sites are open to the public for the symbolic price of €1 on Saturday night, May 16, from 8pm–2am. Finally, not that we’re blowing our own tromba, but Mama Shelter's rooftop bar and restaurant has a surreal view of the dome of St Peter’s Basilica in the Vatican.