Finding Serendipity on the Road

Finding Serendipity on the Road

ser•en•dip•i•ty (srn-dp-t)
n. pl. ser•en•dip•i•ties

1. The faculty of making fortunate discoveries by accident.
2. The fact or occurrence of such discoveries.
3. An instance of making such a discovery

Isn’t serendipity a fascinating word? Where did it come from? What experience first caused someone to use it?

I love to imagine. One thing is certain, serendipity is one of the most lovely occurrences that you can bump into. On the road, it takes on an almost fateful quality. It’s as if you were meant to be in a far off place just to stumble upon that brilliant sunset, take the ride with the singing cab driver, discover an out of the way tapas bar, or to make a great new friend. Serendipity travel: it’s the stuff that holiday memories are made of.


It reminds me of the following quote:

“Life is what happens to you while you’re busy making other plans.”

~John Lennon

The plans we make in our lifetime are sometimes not nearly so good as the serendipity travel moments that replaced those plans, and this can be especially true of travel. Have you ever looked back on a trip, and realized that whatever you happened upon was much better than what you were expecting? That little cafe you discovered when you got lost looking for the touristy restaurant was unbelievably intimate and romantic, and is now where you and your partner return each year to celebrate your anniversary. The little park you accidentally found was magical, and surely couldn’t have been bettered by the more famous park, or museum, you were looking for.

There is one problem with serendipity travel. It can’t be looked for, it must just happen. Like many other things, the more you chase it the more elusive it becomes. There are a few things you can do to invite serendipity to join you on your travels though, and here are a few suggestions:

1. Book a travel deal: Rather than deciding on a location, roll the dice. See where the deals are. Go off the beaten track, or against the season. Don’t head to a beach for a warm winter holiday, visit Vienna in the snow instead. It can be magical.  There’s a reason why the STE super specials change every month.

2. Wander: Book a flight, a hotel room and nothing more. Pick up a map and ask the concierge which direction a wanderer should point themselves in. Browse the used book shops, drop in to an inviting place for a glass of champagne, stop at a pub and enjoy a football match, or walk a country road. It could be the most interesting trip you’ll ever take, and it might encourage you to become a wanderer rather than a planner.  If you need help choosing a destination, there’s a travel recommendation tool for that.

3. Be open to what you discover: Try something you’d never think you’d enjoy. I have a friend who went to their first Broadway show at 47 years old (or rather, was cooerced into going), and now wouldn’t dream of missing an opportunity to take in a West End production. So, take a chance and listen to a travel site’s advice. Take a cooking class even if you can’t boil water, snorkel while you’re overcoming your fear of sea life, go to a poetry reading especially if you’ve never been, visit an obscure museum even if you haven’t attended an art appreciation course, watch a cricket match even if you dislike sport. Do whatever is the speciality of the spot you’re visiting. You never know what new interest might be spurred on.

4. Talk to strangers: I know I’m suggesting you ignore your mother’s wise advice, but sometimes we miss out on the best things in life when we’re too cautious. Most people in the world are just like us. They’re nice, normal and would love to tell you about their favourite little spot for wine and cheese. Take advantage of their enthusiasm and try the Rioja and Manchego cheese in Spain.

5. Let go: This may be the most difficult of all the suggestions, but you are on holiday after all. Must every moment be as planned as your daily life? Both children and adults need unplanned time to daydream and discover. So what if you swim in the pool all day and miss the tour of the ruins? Finding unexpected rest and relaxation on a vacation can sometimes be just what you needed, and what is more important, having unplanned time can open up moments for the serendipitous opportunities that do arise, like dinner with the couple you met by the pool.  If you can’t quiet your mind, then write in a travel journal.

Serendipity does happen, even if it sometimes involves stepping outside of your comfort zone. Just ask yourself, what’s the worst that could happen? You’ll at least end up with a crazy, funny story to share about how you missed the last train, and had to take a bus filled with crazy Spaniards yelling “A la playa!”, because you’d stayed longer than expected at the village festival you’d stumbled upon; but that’s part of the adventure. Serendipity travel might not be easy to find, but here’s to it finding you!

Photo by eschipul

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