Where to Travel in May Before the Summer Crowds Hit
Let’s be honest—summer travel is fun, but everyone and their abuela is at the airport from June through August. If you’re anything like me and prefer your adventures with a little more peace, fewer lines, and no screaming toddlers at the pool (bless them, but no), then May is chef’s kiss the perfect time to escape.
Here are my top picks for where to travel in May before the summer madness kicks in—and yes, they’re all adult-travel-friendly and beautiful enough to make you feel like the main character.
1. Portugal – The Quiet Charms of the Coast
Portugal in May? Perfeito. The weather is warm enough for beach days in the Algarve, but you’ll beat the wave of European vacationers that flood the region starting in June. Lisbon and Porto are also in that perfect sweet spot—sunny days, light jackets at night, and plenty of room at rooftop bars to sip vinho verde and romanticize your life.
Why I love it: Gorgeous coasts, budget-friendly luxury, and the pastéis de nata are worth the flight alone.
2. Japan – Post-Cherry Blossom Magic
Most people chase Japan’s cherry blossoms in April, but May is seriously underrated. You still get stunning landscapes, fewer crowds, and the beginning of festival season. Think lush gardens, clean air, and the kind of calm that makes you feel like you’ve stepped into a Studio Ghibli movie.
Go for: Kyoto’s zen gardens, Mount Fuji views, and Tokyo’s endless energy without shoulder-to-shoulder crowds.
3. Amalfi Coast, Italy – Before the Heat Hits
Everyone talks about Italy in summer, but the Amalfi Coast in May is way more romantic (and about 1,000 euros cheaper). You can still take a boat to Capri, eat your weight in lemon gelato, and enjoy those cliffside views without being packed into Positano like sardines.
Pro tip: Stay in Ravello or Praiano if you want luxury minus the crowds. Bonus—more locals, less Instagram chaos.
4. New Orleans, Louisiana – Jazz, Culture & Heat That Won’t Kill You Yet
New Orleans in May is steamy, but not too steamy. You’ll still catch live jazz spilling into the streets, second-line parades, and the kind of Southern hospitality that makes you want to move there “just for a year.” Plus, it’s one of the best U.S. cities for adult-only travelers who want culture, cocktails, and a little bit of chaos (the fun kind).
Must do: Frenchmen Street at night, brunch at Commander’s Palace, and an adults-only ghost tour because… duh.
5. The Greek Islands – Santorini, Mykonos & Hidden Gems
Before Greece becomes the summer travel poster child, May is the golden window for laid-back vibes and still-warm waters. You’ll find boutique hotels with actual availability, fewer tourists photobombing your shots, and sunsets that feel like they’re just for you.
My pick: Paros or Naxos if you want something quieter than Mykonos but just as dreamy.
6. Puerto Rico – Home, but Make it a Getaway
Okay, I might be biased, but Puerto Rico in May is magic. It’s right before hurricane season, meaning you still get those gorgeous blue skies, warm Caribbean water, and all the flavor and soul the island is known for. Plus, no passport needed for U.S. citizens.
What I’d do: Hike El Yunque, eat mofongo in Old San Juan, and end every night with a piña colada on the beach.
Why May Travel Just Hits Different
May is that quiet pause before summer—when prices are lower, destinations breathe a little easier, and your travel experience feels more personal. Whether you want romance, relaxation, or a solo reset, this is your sign to go now, before the crowds (and their crying kids) show up.
And if you want a custom itinerary built for your vibe—luxury, adults-only, and stress-free—you already know who to call. 😉
→ Ready to plan your May escape? Let’s get you out of here and into your dream destination. Click here to book your free travel consultation or shoot me a DM @thewanderandtravel.
