The Joys of Contrarian Travel

If you want to meet a better class of people, try taking your vacation in lousy weather

I came up with a new angle on travel. The shorthand version is called “good times in bad weather.” It simply means if you want to be where the people are genuine, you will have to go where the weather is lousy.

Today, the first thing someone asks when booking a trip is will it be sunny? Then they compound the error by going at the same time, stay in the same hotels, and go with the same group of people or like my in-laws, bring the same cribbage game. Then when they wonder why the only thing that stands out is how much the vacation cost.

I have a contrarian view not just because I’m contrary, but because I like doing things in an old school sort of way. We need to rethink how we travel, where we go and what we do when we get there. Because travel should be about life and people, and the sun should be secondary. Maybe it’s even more important to impress that on our kids. Otherwise, every time we go on vacation with them it starts to feel like summer camp.

And this is important, you must learn to travel at the ‘wrong’ time of year. Otherwise, you are just replacing a local routine with a sunnier version. Your aim is to break out of the silo where everyone thinks like you, votes like you, eats at the same restaurants at same time as you.

Sunny vacations are a snooze. Golf is boring. Tennis is sweaty. But walking around the Cotswold on a cold, rainy day in your Barbour field coat and stopping in for a pint or a cup of tea at a local pub is heaven. You aren’t looking for luxury, you are looking to luxuriate — in people and experiences.

Your objective is to reset your social clock to a time when we hung out with people who did more than tell us how great our tan looks. Those times where if we couldn’t agree with someone about an issue, we put on a pair of wellingtons and headed to a nearby pub where it all got worked out.

Enjoying lousy weather on vacation isn’t hard but it takes fortitude. The reason is you have to defend yourself to all your friends who are infected with a form of groupthink that extends to travel. If you aren’t visiting a place your brother in law would be impressed with, what’s the point? The point is to go somewhere he won’t be.

There is another special benefit. By avoiding the sun, in addition to staying away from sunscreen drenched crowds wearing bathing suits two sizes to small or seeing dolphin tattoos on 60 year old men, you don’t have to die for your vacation.

There are roughly 100,000 cases of melanoma per year, about 10% don’t make it, and another 5 million other forms of skin cancer. This type of cancer is cumulative, meaning regardless of what you do today, you can still suffer from exposure of long ago. The body’s surface is a smart calculator, when it adds up the sun hours and you’ve passed the limit, it’s your turn. By staying in cloudy climes, you keep the bell from ringing.

Herewith a pictorial guide to the best places I have traveled in the worst of times….

Central Park, New York in January

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Napa Valley winery in March

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Windsor Castle, England in May

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Lake Placid Lodge in July

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West Coast of Scotland in August…

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Near Bushmill’s Inn, North Ireland October

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Big Island Hawaii December

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The pleasures of going against the grain, traveling opposite the rush to find tranquility in places other people don’t want to be may be an acquired taste. But it’s worth the trouble.

Author’s Bio

Jeff Cunningham is an advocate for enlightened global leadership, which he calls the most valuable natural resource in the world.

He is a Professor at ASU’s Thunderbird School of Global Management and was the former publisher of Forbes Magazine, startup founder, digital content CEO, and ran an internet venture capital fund.

He travels the globe in search of iconic leaders. As an interviewer/host, he created a YouTube interview series, Iconic Voices, now co-produced by @Thunderbird, featuring mega moguls from Warren Buffett to JeffImmelt. His articles on leadership have been featured in the Arizona Republic, LinkedIn and Medium via JeffCunningham.com.

His career experience includes publisher of Forbes Magazine; founder of Directorship Magazine; CEO of Zip2 (founded by Elon Musk), Myway.com, and CareerTrack.com; venture partner with Schroders. He serves as a trustee of the McCain Institute and previously as a trustee of CSIS and Middle East Institute, and as an advisor to the Nobel Peace Prize Committee.

He has also been a board director of 10 public companies.

The views expressed in this article do not necessarily reflect those of Thunderbird School of Global Management or Arizona State University as a whole.