In previous posts I talked about different kinds of travellers and ways of travelling: vacationers vs explorers, sightseeing vs experiencing. Today I want to talk about two different types of trips: planned ones and unplanned ones.

To be fair, most trips fall somewhere in between. Few people plan their trip down to the hour, or even the day (although I did try in the beginning). This is a rather futile exercise as even in the most developed countries you’re likely to encounter places that are closed down for renovations, or because the owners have gone on vacation, or perhaps you’re unlucky enough to arrive somewhere during a transportation strike (as happened to me in Greece). Any of those things will throw an inflexible schedule right out the window.

On short trips (two weeks or so) it makes sense to pre-book as many things as possible so that you don’t spend your precious vacation time on the computer doing research and bookings. On a longer trip, you may want to keep some flexibility by only booking your first hotel and then booking the next one while still in the previous one. If you know exactly when and where you want to go, booking your internal train and plane tickets in advance makes sense, especially during busy periods or holidays.

Some countries lend themselves to planning more easily than others. There is usually a direct relationship between the level of development of the country and the ability to make plans. In places such as North America, Western Europe, Australia, New Zealand and Japan, planning is a breeze and you can do most of it online.

In some other places (much of Asia and Latin America for example), you need to have some flexibility. Yet some other countries are complete free-for-all. Or, if you want to look at it in a more positive light: you have to abandon yourself to serendipity. I actually really love that word serendipity. Merriam-Webster defines it as luck that takes the form of finding valuable or pleasant things that are not looked for. It evokes happy discoveries made by accident, unexpected encounters, and unplanned delights. But sometimes, serendipity can have a darker side.

Sri Lanka, the island of serendipity

Sri Lanka, a small country to the south of India, is nicknamed the Island of Serendipity. The word serendipity is actually a derivation of serendib, which used to be the actual name of the island. The country proved true to its name during my two-week visit in 1997. Pretty much every plan I made was thwarted. Most of it was for the best, but not always…

First, I boarded a train in Colombo (the capital), heading to the town of Galle, but spontaneously decided to get off the train mid-way to follow the suggestion of a tout and spend a few nights at a guesthouse fronting the beach near the town of Ambalangoda. I usually ignore touts, but this one was especially nice and compelling. This family guesthouse remains one of the highlights of my entire 20-week trip.

Once in Galle, I planned to go to Matara, then changed my mind and took a bus for Ella (a mountain town) but ended up getting off the bus in a beach town called Tangalla because I needed to pee really badly and couldn’t stand sitting on this bumpy bus any longer. I stayed in Tangalla a few days. In my journal I wrote:  “Once again I didn’t end up where I had planned. Not that it’s bad, but it’s starting to be a little strange…

From Tangalla, I tried once more to get to Ella. And this is where serendipity turned on its head and really pissed me off. I spent an entire morning waiting for the “9:30 bus”. After being told that the bus was really at 9:45, then 11:00, then 11:30, then 12:30, I finally concluded that there really was no schedule and these guys were just telling me what they thought I wanted to hear. By 1:00 PM I was able to climb onto a crowded bus headed the right way, but had to stand up for two and a half hours. And so the plans kept changing.

For the most part, I had a good time in Sri Lanka and met tons of interesting travellers. But the final trip ended up looking nothing like the itinerary I had originally planned!

And now, as I’m about to leave for Asia again, I have the feeling that Burma (Myanmar) will be another one of those serendipitous countries, where plans get spat on and thrown out the window. I just hope it will be for the best.

Have you experienced serendipity on one of your trips?

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