When You Travel, Do You Plan OR Wing It?

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Pink Cockatoos in Australia 500x332 Itineraries vs. Winging It

Steven W. of Philadelphia asks: Do you usually make a general itinerary? Or just figure it out when you’re there?

The simple answer to this question is “Yes and No.” And that’s not a simple answer at all, which is why I’m writing a post about it!

Before I get into specifics, I should differentiate some terms. The word “itinerary” suggest confirmed, paid-for air, hotel/hostel and, in some cases, tour bookings. When I say I’ve “planned” a trip, on the other hand, it means I have a general idea of what I’m going to do, where I’m going to go and on what time frame, but that my schedule is not fixed.

As a general rule, I set an itinerary prior to departure only if (a) My trip is extremely short or (b) I’m traveling someplace expensive.

If you haven’t got a lot of time, you don’t have room for logistical mistakes, like taking the 11 P.M. bus instead of the 6 P.M. bus, or arriving to Saigon one day before you’re supposed to fly out of Bangkok.

Likewise, it’s easy to “wing it” with flights in Colombia, where a one-way segment might only cost you $100, even last-minute. In Australia or Norway? Probably not such a good idea.

Overall, you should “wing” as much of your trip as possible — if you have the time and money not to book in advance, don’t. Playing a trip by ear dramatically decreases the amount of stress you experience when you travel, and thus makes your travel much more enjoyable.

On the other hand, you should remember that unless you have no limits whatsoever, you should have at least sort of an idea of your journey’s route and timeframe. Otherwise, it’s very easy to get stuck.

Do you have any tips for planning vs. “winging it”?


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