travel planning | order or spontaneity?

How many times have you seen this kind of question asked by someone planning travel?

We are going to Italy this summer.
Should we book our rooms now?
Or should we just wait until we get there to get a room?

While I have some very definite personal preferences about planning my own travel, I also recognize that people are different and value different kinds of experiences.

Some people cannot relax unless every possible variable has been anticipated and planned for. Their trips are scheduled on a spreadsheet with every detail accounted for. Hotel reservations are printed out on a meticulous itinerary. Sightseeing has been scheduled to-the-minute with maps and commentary reproduced from guidebooks. Dinner reservations have been made and show tickets booked.

This would drive other people crazy. They want to be spontaneous. They want to relax and enjoy themselves. They want to wake up in the morning, leave their hotel, and just go wherever their whims take them. When they come to a metaphorical fork in the road, they want to make that decision in the moment. Sometimes the road less taken leads to serendipitous discoveries, and sometimes it just goes to the city dump. No matter... this is how they do things!

Using the language of the Myers Briggs Personality Type Indicator, I am describing Judgers (who like things to be orderly and predictable) and Perceivers (who appreciate spontaneity). If you're curious about your own personality type, try this online test .

My perspective? Sometimes a little bit of structure can maximize your freedom.

You don't want to get off your trans-Atlantic flight, jet-lagged and disoriented, and have to spend the next four hours figuring out where to leave your bags. This doesn't make the first day of your vacation especially enjoyable.

You don't want to arrive in a popular tourist destination in high season without reservations, having to settle for what's left (either the least desirable hotel that nobody else wanted or some exorbitantly expensive suite that was cancelled at the last minute).

And you don't want to wait until the last minute to plan a trip for the week after Christmas or Easter. Any remaining plane tickets will be expensive (if there are empty seats at all), and the resorts you really want to stay in may be fully booked. In fact, it may already be too late (and we're only in the first week of May) to make some kinds of bookings for Christmas week.

So should you book your rooms in advance or when you arrive? There is no right or wrong answer. The important thing is to know what kind of traveler you are ... and plan accordingly.


If you have comments on this column, or questions about booking travel, email me or visit my website.