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Pay Attention to that “When to Go” Part (and When NOT to Go)

Most popular travel destinations in the world have a well-defined weather pattern that determines when to go and when not to go. Sometime between is that magic shoulder season where you can often find lower prices and still good weather, but if you go in the true off season, you could get stuck. Or worse. 

when to go to the Dominican Republic: not during hurricane season

Every guidebook covering a destination has a “when to go” section and most comprehensive travel articles do too. The problem is, a whole lot of people don’t buy guidebooks anymore and the ones that only do the most surface-level research don’t have the attention span to ever make it to that that part of an article.

Add in the shopping-focused, big brand results that Google is emphasizing now and the problem gets amplified. (Expedia and Priceline are not going to tell you it’s a terrible month to go where you’re going. They’ll just tell you to add on travel insurance).

Many travelers just look at the #beautiful photos on Instagram and assume that’s how it’s going to look for their trip too. Then they arrive to a week of rain, or freezing cold, or closed-up hotels and moan about how unlucky they are.

They’re not unlucky. They just didn’t do their homework.

The off season is usually “off” for a good reason. There are exceptions, but Caribbean resorts don’t close in September and October just because they want to give the staffers a long vacation. It’s because there’s a fairly good chance something like this will head their way:

when to go to a destination - not during hurricane season

That is an NOAA satellite photo from September 7, 2017, when three hurricanes were simultaneously moving across the Atlantic and Gulf of Mexico. The one in the middle was Hurricane Irma, which did a number on Puerto Rico, the Florida Keys, and many other islands that were in its path. It was ugly, to say the least.

When I first wrote about this subject a few years later on the blog, Hurricane Dorian was about to plow through the Caribbean and hit Florida again. Are the people who have to evacuate their expensive hotel suite in Palm Beach “unlucky?”

No. Unlucky is when I got to Palenque and it poured down rain all day and I took exactly one photo. It was just a random storm front passing through. Unlucky was when a freak hail storm hit Mexico City and it took us hours to find a taxi back to our hotel. But for this example we’re talking about something totally predictable: southern Florida and the Caribbean during hurricane season.

The travelers just ignored the advice on when to go (or didn’t bother looking it up) and rolled the dice. Every year, tens of thousands of smart people open up a search engine and put in “best time to go to Cancun,” “worst time to visit Caribbean,” or “when to visit Miami.” Unfortunately, a whole lot of people don’t. Then they complain to the Weather Channel reporter that they’ve been stranded for days in a shelter on their vacation and they can’t get a flight out. 

When to Go: Not Hurricane Season, Rainy Season, or Monsoon Season

When to go to Peru

Peru at the right time of year

Starting back in 2010 and happening many years since, it was an ugly few days for travelers who decided to visit Machu Picchu the last week of January, around the height of the rainy season.

This was a story in the Associated Press in 2010 but it replayed itself again recently. “Helicopters had taken 700 people by mid-afternoon from the remote village, the closest to the ancient Inca ruins 8,000 feet up in the Andes mountains. About 2,000 travelers were trapped in the town for days, strapping resources and testing travelers’ patience.”

The trouble started when train service—the only way in or out—was halted because of rain and mud. People were sleeping in the streets, scrounging for food, and generally being miserable. It got worse as the days went on since hundreds more people per day kept arriving via the Inca Trail, including all the porters who couldn’t get home to their families.

This was a bad rainstorm, but pretty much any guidebook or well-researched article on Peru tells you that mid-January to the end of February is the absolute worst time to visit Machu Picchu and you’re almost sure to get drenched. You might not even be able to see the citadel because of fog. The Inca Trail isn’t even open in February because it’s too slippery and muddy. (Plus they do maintenance work then while they’ve got it closed.)

Whether from ignorance or a “maybe we’ll get lucky” sentiment, a lot of tourists avoid this advice and go anyway. Sometimes it works out, just like sometimes people win at roulette or craps. The odds are not in your favor though, especially if you challenge Lady Luck over and over.

Phrases like monsoon season, hurricane season, typhoon season, rainy season, “green season,” and the like are all telling you the same thing: it’s probably going to rain a lot. If a place has a well-defined “off season,” pay attention and book at a smarter time to go. 

Weather Patterns Are Not a Mystery

I once participated in a public chat session thing for a magazine I used to write for on traveling in Mexico and Central America. The question that kept coming up over and over was different versions of, “Is it really all that rainy during the rainy season in Costa Rica?”

The honest answer is “buckets of rain,” and I said so, but you see they wanted to go during the summer break so they were hoping for some better news. Often this wishful thinking stemmed from when they had already requested their vacation time or when their kids had a long stretch off school.

So maybe it was all a misunderstanding and their vacation would be full of sun and fun? Maybe this historical weather history may be wrong this year?

Costa Rica rainy season

Maybe the seasons will reverse and the best time to visit won’t be December through April?

The problem is, weather systems don’t care one bit about your schedule, whether that’s rainy season in Costa Rica, monsoon time in southern India, typhoon season in the Philippines, or hurricane season in Cancun.

Patagonia will be freezing June through August whether your family vacation time is then or not. Most of the hotels will be closed for the season and some of the roads will be too. Nobody goes hiking then unless they have a death wish. 

Take 10 Minutes for “When to Go” Research

travel to alaska in September
That photo above is from Alaska in September, when we were riding the last week the train was going to be open to passengers. If we had come two weeks later, there would be no train service and the tour company we traveled with would be packed up and done until May. That timing is not hard to figure out: it’s roughly the same every year. 

Sometimes things go from normal to worse though. As I write this in 2024, hurricane experts are expecting a very bad year. During the news coverage, we will eventually see some poor sops being interviewed in a shelter, with the newscaster talking about how they traded a $750 room with an ocean view for a spot on the hard floor in a school building. Some viewers will feel sorry for them. Others will just shout “Idiots!” at the TV.

Here’s my advice, based on 30+ years of regular travel: Find a way to fit your schedule into Mother Nature’s schedule instead of trying to hope she’ll smile down on you and change her historic patterns. Pay real attention to that “when to go” section of guidebooks or spend more than two minutes researching historic weather patterns for where you are going on vacation.

If you want a good shortcut, bookmark this site that provides historical weather patterns that are well-organized: Weatherbase. They drill down to the city level too. 

For the record, although I’m a journalist who knows how to dig and do good research, I still buy guidebooks sometimes. They’re researched, fact-checked, and written by someone who has been there, not an AI bot summarizing past (often erroneous) articles or some $2-an-hour writer in a basement in Bangladesh.

Related post: 10 Steps to Plan a Vacation Better (Beyond Using Google).

For many destinations, the weather stays relatively stable and it’s just the temperature that varies, so in those cases if you don’t mind bundling up, and it’s a city not a beach spot, you’ll probably be fine. In other cases, it’s too cold for anyone but the heartiest of residents or explorers, like northern Alaska, Antarctica, or the top of Norway. 

At the other end of the scale, some places are way too hot for sane humans in the hottest months. I learned that the hard way when I ended up in Aswan, Egypt in July. Greece in August is no picnic either, even though it gets packed with red-skinned tourists.

Tim Leffel in Greece

Very nice in April, may be closed due to excessive heat in August…

Los Cabos in April is lovely. Prices drop quite a bit three months later because it’s too hot to walk on the beach or sit by the pool. 

I can empathize a little with everyone stranded in Aguas Calientes town for days in Peru, or stuck in Cancun during a hurricane, or driving around trying to find gas for their rental car to escape north with in Florida. I’m glad it wasn’t me.

It probably wouldn’t have been me though. I know when to go. If I’m going to make risky bets, I’d much rather do it in a casino. At least those bets come with free drinks.