Why May is the only month worth traveling (and where to actually go)

May is the only month where I actually like being a tourist. Everything else—July, August, even the ‘festive’ December rush—is just a slow-motion car crash of overpriced lattes and sweating through your shirt while standing in a line for a museum you don’t even really want to see. But May? May is the sweet spot. It’s the Goldilocks zone before the kids are out of school and the sun decides to turn the Northern Hemisphere into a convection oven.

The Crete mistake and why you should go anyway

I learned the hard way that May in the Mediterranean isn’t always postcards and sunshine. In 2018, I flew into Chania, Crete, on May 4th. I had this vision of myself driving a convertible along the coast. Instead, I ended up in a rented Fiat Panda that had the horsepower of a lawnmower. I tried to drive up toward the Samaria Gorge, and the car just… stopped. It couldn’t handle the 15-degree incline. I had to roll backward into a ditch and wait for a guy named Yiannis to pull me out with a tractor. I spent the rest of the day walking four miles in flip-flops because I didn’t pack real shoes. It was humiliating.

But here’s the thing: I’d do it again. The air in Crete during May is like a warm blanket that hasn’t been washed in a year—it’s heavy, smells like wild thyme, and feels oddly comforting. The crowds haven’t arrived yet. You can actually get a table at those tiny tavernas in the Old Town without a reservation. Go to the south coast, specifically Loutro. You can only get there by boat. In May, the water is crisp—about 19°C (66°F)—which is cold enough to wake you up but not so cold your heart stops. I tracked my spending that trip; I spent exactly €42 a day on food and wine, and I ate like a king. You won’t find that in July.

Don’t go to Malia. Ever.

Japan is a trap (unless you do this)

People always talk about cherry blossoms in April. They’re wrong. April in Japan is a crowded nightmare where you’re just looking at the back of someone else’s head. May is better, but you have to avoid “Golden Week” like the plague. If you go during the first week of May, you will suffer. Every train is full. Every hotel is triple the price. What I mean is—actually, let me put it differently: go after May 10th.

Head north to Tohoku. While Tokyo is starting to get humid and gross, the north is still cool. I stayed in a ryokan in Aomori where the nightly rate dropped from 22,000 yen to 9,000 yen the second the holiday ended. It’s quiet. It’s green. It’s perfect.

Total peace.

Mexico City is better when it’s about to rain

I know people will disagree with me on this because they want “perfect” weather, but Mexico City (CDMX) in May is elite. It’s the end of the dry season. It’s hot during the day—usually hitting exactly 27°C (80.6°F) around 3 PM—but then the clouds roll in. There’s this tension in the air that I love. Then, for thirty minutes, it pours. The rain cleans the smog out of the air and cools everything down.

If you aren’t sitting in a cafe in Roma Norte watching the afternoon rain hit the pavement with a mezcal in your hand, you aren’t living.

I used to think you had to go in February to avoid the heat. I was completely wrong. In May, the Jacaranda trees have finished their first bloom, and the city feels more like a lived-in neighborhood than a tourist park. Also, I refuse to stay in Airbnbs there anymore. The cleaning fees are a scam and they’re ruining the local housing market. Stay at a hotel like the Gran Hotel Ciudad de México. It’s expensive, but the elevators are cool and they won’t charge you $80 to wash a towel you didn’t use.

The part where I tell you where NOT to go

I’m going to be blunt: stay away from Paris in May. I know, I know. “April in Paris,” “May in Paris,” it’s all very romantic in movies. In reality? It’s a damp, gray mess. I’ve spent three separate Mays in Paris for work-related stuff and it rained 60% of the time. Not the nice, cleansing rain of Mexico City, but a miserable, persistent drizzle that turns the city into a giant wet wool sock.

Anyway, I digress. The point is that May is for places that are usually too hot or too crowded. It’s for the fringes.

I have this weird, irrational loyalty to the Oregon Coast in May too. It’s not “best destination” material for most people because it’s still 55 degrees and windy, but I’ve gone every year for five years. I like the misery of it. I like being the only person on a beach in Cannon Beach because everyone else is waiting for July. There’s something honest about a place that doesn’t try to be pretty for you.

I’ve tested about six different pairs of “all-weather” sneakers on those cliffs over the years, and honestly, they all leak. Just wear boots and accept your feet will be wet. It’s fine.

Does anyone actually enjoy the Amalfi Coast in May? Or is it just something we say because the pictures look good? I genuinely don’t know the answer. Every time I see a photo of Positano in May, I just think about the bus traffic on those narrow roads and get a headache.

Go to Crete. Rent a better car than I did.