Do You Leave Your Hotels Up to Chance?

I usually love planning trips — second only to taking them! — but a few years ago, as I tried to hammer out a driving itinerary around the South Island of New Zealand, I found myself feeling unexpectedly stressed out. The problem: figuring out how long to spend in each place.

Would one night in Queenstown be enough, or should I tack on another? After driving three or four hours between stops, should we linger a little longer in each place before tackling the next chunk of our itinerary? Would we have enough time to detour through the Catlins in the far south?

Around in circles I went, even though a few friends who’d been to New Zealand advised me not to worry about nailing down an itinerary. “You don’t need to book hotels in advance,” one said. “There are plenty of motels. Just do what you want during the day and find a place to stay wherever you happen to be.”

Her advice made perfect sense — but I didn’t take it. Here are three reasons why:

1. I’m a hopeless planner. While the idea of landing in a new place with no itinerary or bookings sounds like heaven to some travelers, it’s terrifying to me. I don’t have to plan out my day hour by hour, but the basics — activities I’m interested in, where I’ll lay my head — are a must.

2. Booking early gives me time to compare prices and read reviews. I’ve been burned in the past by last-second hotel choices that cost more than I wanted to pay or didn’t live up to my normal standards of service and cleanliness.

3. When I arrive in a new place, I want to spend my time exploring and doing things — not driving around searching for hotels that don’t look too sketchy.

In the end, I compromised. I booked all my hotels before my trip, but made sure I would be able to cancel them without penalty if our itinerary changed. Fortunately, all my exhaustive research paid off. I wouldn’t have changed a thing.

How do you feel about booking hotels in advance?