One vacationer learned the hard way to book hotel rooms in advance. The other learned he prefers not to be tied down. Which is the best way to travel?
We sat in our rented Chevy Cavalier at a rest stop at midnight near Bryce Canyon. Every local hotel was booked, our tent leaked, it was starting to snow, and I was in big trouble. The fog was icing up the car windows, but Margot’s seething glare kept the interior quite warm.
I had convinced my then-girlfriend to visit from her native Germany to “experience the real America” by renting a car and driving from Chicago to Los Angeles. She was being uptight, I told her dismissively, by wanting to plan everything in advance. I insisted we’d get so much more out of the trip by winging it.
In the days before cell phones and iPad apps, trying to reserve on the road meant reading a guidebook under a street lamp, calling from a phone booth, or knocking on hotel doors. Now a room’s just a click away: In 2009, the U.S. Travel Association estimated 85 million Americans used the Internet to book trip reservations, with 82 percent of those surveyed saying it was “very useful or essential” for planning overnight stays.
Planning travel may also be “useful or essential” in keeping your girlfriend. After two weeks of lodging hassles, I took to hiding the car keys at night, worried that Margot would leave me behind in a cornfield and head for a spa she’d booked in secret. When she did depart, late for her flight because I hadn’t planned for traffic, I knew I wouldn’t need any advance planning for another visit—there wasn’t going to be one.
Having learned that lesson, I took a different approach to my next trip, a multiday biking journey through Glacier National Park. When pedaling 50 miles a day through the mountains, planning becomes more than a convenience: It can be a lifesaver.
Choosing the time to avoid risky weather conditions, packing the right equipment in case of a breakdown, and mapping the route helped ensure success when failure would have meant more than overnight discomfort. Without my advance reading of park service reports, my path could have led me face to face with an angry grizzly. And a startled bear has even less sympathy than a cranky girlfriend for those who don’t plan ahead. —Bill Fink 
It’s generally not a good idea to fling open the shutters in Paris’s budget hotels: Intimate views of heating ducts and garbage-strewn alleys tend to kill the romance. So I don’t know what compelled me to check the vista from my room at Hotel Muguet, an unassuming two-star hotel in the 7th arrondissement. We had arrived in Paris without reservations after fleeing bad weather in the Alps, and the Muguet’s biggest selling point was the chambres libres sign on the front door: vacancies.
I gasped, and my wife came running. Together we stood at the window, gawking at the perfectly framed view of the nearby Eiffel Tower, lit dramatically at night. It took us completely by surprise and was our own discovery, which made it all the more precious.
That’s only one of the reasons I like to travel without prepaid reservations tying me down. I can flit about on the winds of serendipity, which for me is always the best way to travel.
I’m free to grab my duffel and jump off a Greek coastal ferry as it rams its bow onto the beach of a Kodak-perfect fishing village that’s not in any guidebook. Or decide that I’ve had enough of Koh Samui after 24 hours, and push on to an island without stoplights or Starbucks. Or flee a Boston hotel whose hallways are overrun with shrieking school groups.
I’ll concede I’m probably in the minority on this one. But a new breed of Internet-savvy travelers is coming pretty close to winging it by taking advantage of last-minute “flash” deals. According to the Ypartnership/Harrison Group 2010 Portrait of American Travelers, nearly one in three travelers took a last-minute trip last year, booking an average of just six days in advance.
I can think of only one reason to book far ahead: so you won’t find any surprises when you arrive. You can scrutinize 360-degree photos of your hotel room, check the balcony view at varying sun angles, and parse a hundred reviews by previous guests, including some not written under alias by the hotel owner.
At that point, though, your vacation becomes less a journey of discovery than a fact-checking expedition. That may be someone’s idea of travel, but it’s not mine. —John Flinn 
Photography by dotshock/Shutterstock
This article was first published in May 2011. Some facts may have aged gracelessly. Please call ahead to verify information.