Are you a type-A plan your face off traveler, or a let's just see what happens traveler?
In the past few years I've done both, employing the ultra-planned and laissez-faire approaches. With each type under my belt, I think there's a time and a place for both. For example, you don't want to show up in Nairobi without a hotel, secure transportation or high-level itinerary, whereas, that's totally doable and almost romantically vagabondish if you visit somewhere for the weekend and figure it out as you go.
Showing up Prepared In mid-fall 2010, I went to Maui with my husband. Since I was only there for 3 nights, and it's a destination I know pretty well {but would like to further explore}, the trip was fairly dialed in terms of what we'd do when. During the day, I planned on exercising followed by relaxing in the sun {not sure why I had to plan that, but I did}, and at night we pre-arranged reservations at our favourite restaurants, so we didn't miss our cherished sunset meals or moments. Similarly, when we visited Europe and Africa in late 2009, we had a 24-hour stop-over in London. Because it was short, I pre-planned our transport, hotel and the show I'd been dying to see to make sure we got it all in. The planning paid-off, we had a fabulous night out at Wicked {the musical} and loved our pod hotel.
Showing up Unprepared Because my personality is planning-oriented, in the past, when I didn't plan every second of an itinerary, I somehow felt I wasn't doing my destination justice. In reading every available guidebook and online review about the area, I had the sense I was using all available resources to embrace the city's highlights. Then, after a few bad tourist attractions and less-than-favorable restaurant visits, I embraced the fly by the seat of my pants side. This rendered great experiences talking to locals and various hotel concierges about where they eat and what they do. My newfound organic approach was a hit, for example, while in Laguna Beach, CA this past summer, we were told to go to a restaurant called 230 Forest by a couple we met while sitting at the Roy's Newport bar. Their suggestion was bang-on, and we had a great meal!
All in all, this semi-reformed ultra-panner has lovingly embraced showing up semi-unprepared. I emphasize semi, because I still like to read articles and reviews pre-trip, in addition to consulting my travel apps while at my destination. Although I will still consult guidebooks in the future, I won't plan every second of my getaway and will always seek local input. Along with a little planning, semi-unpreparedness---or what I call strategic itinerary moments---allows us to discover our destination our way, travel unhindered within it and roam with a looser sense of time. Sounds like a vacation to me!