Some people don’t plan enough, and end up paying for it. Others plan too much, which can have its own costs. I tend to fall into the latter group.

Case in point, in preparing for my upcoming road trip, I had planned each day’s ride months in advance, booking hotels (and thus predetermining the route) for pretty much the whole thing. That felt pretty extreme, even for me, and the more I thought about it, the more my ‘planning’ began to feel like handcuffs.

So, I cancelled the majority of the hotels, keeping just a few bookings in place, mostly at the beginning and end of my journey. It may end up costing me a little more this way (although, that’s far from certain), and may lead to one or two dodgy moments when I feel like stopping but there aren’t any rooms available. But that’s part and parcel with an adventure. And that’s what I’m hoping to have.

I’ve been on road trips before where the place we’d planned to stop didn’t have any rooms – or only rooms at exorbitant rates – and we had to come up with a Plan B. It’s always worked out, and I have no reason to believe it won’t this time, too, even though this time it’s just ‘me’ in place of ‘we’.

The first time was on the first long motorcycle ride I did, a twelve day jaunt through seven U.S. states and two Canadian provinces with my friend Scott. We were both in our late 30s, and riding bikes not that much younger than ourselves. In the middle of our trip we had a string of three nights where accommodations were an issue.

The first night was in Phoenix, when the house we’d lined up – with air conditioning and a pool, two things we were sorely looking forward to in mid-August – turned out not to be available. After some scrambling, we ended up in a hotel that I’m betting frequently served guys fresh out of jail. It was conveniently located next to a strip mall containing a tattoo parlour and a liquor store. Sadly, not only was the A/C simultaneously loud and ineffective, the shower in my room didn’t work.

The next night, we rode for several hours to reach the small town of Kanab, UT, around supper time. After eating in a local diner, we decided that it was too early to quit for the day, and we pushed on to the town of Panguitch. When we arrived we encountered one ‘No Vacancy’ sign after another. Finally, we found one motel that had one room remaining – a room that could have slept eight or more – and we took it, as it was beginning to get dark. We asked the proprietor what was going on, and he said there was a high school rodeo in town. Who knew such things even existed?

The following day we set out in the hope of reaching Great Falls, MT. A trucker we met at a gas station in Idaho – who was hoping, back then in 2007, to vote for Hilary – said he thought we could make it. No such luck, though, as we rolled into Bute around 10 p.m., only to find that every hotel room in town was booked. Surely, in a city the size of Bute, this couldn’t be due to a high school rodeo! I asked at the Best Western, and no, it wasn’t that. They were having an “Irish Festival”, I was told. I tried vainly to convince them that Scott and I were the keynote drinkers, but they were having none of it. They suggested we try Helena, a mere 70 miles away. There was nothing else to do, so we set off again, into the night, which became foggy – not a good mixture for motorbikes. Every time I rounded a curve in the highway, I said ‘there are no deer here’, which happily turned out to be true.

About two-thirds of the way to Helena, we pulled into a gas station, mainly to let the adrenaline fade, and I asked the gas jockey if there were any places to stay nearby. Down the hill from the highway, he said, in Boulder, we could ‘try the O-Z’, and if that didn’t work out, there was a ‘resort’ another 20 miles from there. We rode down the hill, got a room at the O-Z, and a very late (but extremely entertaining) dinner at P.K.’s Pub. (It was nearly midnight when our pizza arrived. It had to be ordered in from the resort, as the pub’s kitchen had closed, and the kitchen staff were down at the end of the long bar playing dice with the bartender, Cricket, a former stripper who also worked part time at the women’s prison, she told us. She was particularly fond of Scott.)

I wouldn’t have any of these stories to tell if we’d booked all our hotels in advance and ridden from one to the next each day. And I want stories to tell at the end of my trip. It’s part of why we travel. To meet people, to do things unscheduled and unscripted, to deal with things as they come.

So while I will still plan, I will try not to over plan. I’ll leave room for improvisation, for discovery, and for adventure.

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