I enjoy traveling. I do not enjoy crowds, lines, or standing around waiting to get a table at a restaurant. I need a detailed plan for a trip to a city I’ve never been to (this doesn’t happen when I go to someplace I’m familiar/comfortable with, like Vegas or Seattle or Jekyll Island), and the process of planning brings out all my worst qualities: indecision, self-absorption, and an eager willingness to spend more money than I should. Here are just a few of the planning choices I had to make that filled me with the traveler’s dread.

When should I have a milkshake?

There is a soda shop near my hotel. They have real, old timey milkshakes. If I drink I giant chocolate shake, there is a chance it will upset my stomach, possibly even giving me a case of the poots. When do I want to risk the poots? On my first day there, before a hockey game? The last day, before my flight? Or should I just not drink a milkshake? I reorganized my itinerary (shoutout to the Wanderlog app) at least a half-dozen times trying to find the perfect slot for a frosty chocolate milkshake. I ended up going back to where I first had it. Probably wasted close to an hour on this. The milkshake had better be good.

Do I go to the zoo?

I like zoos. But it will be cold. But it will be cold everywhere, not just at the zoo. But I don’t want to bring my good camera. But my cell phone has a decent camera. But no zoom lens. (Can’t spell zoom without zoo.) But they have zoo lights at night. But the animals aren’t out at night, so I’d have to buy a ticket for a day visit, then wait an hour for zoo lights to begin. But there’s a Greek place nearby, so I could get a gyro while I wait. But there’s no convenient public transit nearby, so I’d have to spend close to $50 on Ubers. But I like zoos. It just goes on like this in my head. Currently, I am not planning on going to the zoo. But if the weather is nicer than expected…

What counts as an authentic Hard Rock Cafe experience?

I cannot visit a city that has a Hard Rock Cafe without going to the Hard Rock Cafe and coming home with a magnet and a shot glass. But the Hard Rock Cafe sucks. Do I want to spend one of my meals during my limited time in a new city on an overpriced, overcooked cheeseburger? Could I just stop at the gift shop after the hockey game and buy a magnet and shot glass without getting food? No. No, I cannot do that. I must eat the burger. I must be a true aficionado.

Do I have dinner at a fancy steakhouse?

This is a birthday trip and normally on my birthday trips I have dinner at a fancy steakhouse. The type of steakhouse where they don’t print the prices on the menu, but you know you’re spending at least $60 on a steak. I made a reservation and canceled it. Then I made another reservation. I was confident I was getting steak. I felt good about my choice. But when I went back to the website to make sure it was open on the holiday, I noticed it had a dress code. I don’t want to pack nice shoes. So I canceled the reservation and made one for the Jack Daniels themed restaurant at the same resort. Going to a whiskey themed restaurant even though I don’t drink? That’s the kind of stupid vacation choice I can make without regret.

#travel