Packing for Italy and the Inevitable

On a recent weekend trip to Las Vegas, I was talked into taking a cheap flight instead of road-tripping it by a girlfriend whose status is now in question. I was assured that the price of the ticket more than compensated for gas, traffic, parking hassles, and speeding tickets. That a leisurely stroll through the airport sipping Starbucks was a better use of our time.

After clicking the “Purchase” button, my e-receipt popped up and with it came the fine print….for another three pages. Turns out, this airline is cheap for a reason and deviating from their rules comes with penalties. You may only bring onboard a single personal bag that fits inside exact measurements below your seat. A carry-on option can be purchased for an additional fee of $30. One-way.

“Oh, we’re just going for the weekend!” said my girlfriend, “How much do we need? I just take my little backpack.”

She showed up with her backpack and her purse. I raised an eyebrow. I had taken no chances and fit everything into a single tote, using magical Sherpa powers. Let’s just say that for all I was going to Vegas, I am not a gambler.

Six tops in a gallon ziplock, capris, shorts, two dresses…and I still didn’t wear half of it.

She went up to the gate-keeper just before we boarded and asked about her “two” bags. The man, well trained as a prison guard, attempted to charge her $65. There was an additional fee for waiting till the last minute to break the rules. She came back panicked.

I suggested she put all of her clothing on in layers and wear it onboard.

Instead, she jammed her purse into the top 3” of backpack airspace and called it a single bag.

Mission accomplished. With a little side-eye at the guard as he scanned our tickets.

My point is, that when one travels, one never knows what ludicrous situation will arise in which you wish fervently that you had packed with more efficiency. Our return flight, for example.

We arrived at the departure gate from Las Vegas to San Diego with plenty of time to get our last Starbucks of the weekend and lounge by the windows. We watched planes coming and going and discussed the merits of what age and what color one should get their hair dyed (the minute you start going gray and whatever you do, don’t end up “tweed”) when the loudspeaker announced our flight’s “final departure call”.

In a puff of smoke, my girlfriend disappeared. I stood up, torn by the decision to tidy up our table or take off after her, racing for our gate.

To whoever had to clean up behind us: I’m sorry.

To whoever watched our epic airport dash, flip-flops flapping, bulging bags bouncing, and gray hairs flying: You’re welcome.

Even my little bag felt extra-heavy during that sprint and I’m sitting here pondering a trip to Italy for September and asking myself, “Self, exactly how much baggage do you want to lug with you on planes, trains, and gondolas? Can you justify bringing a flatiron across the planet? Can you trudge along the cobblestones in flat, sensible shoes while the native beauties sashay by in stilettos?”

This is where my Self reminds me that probably they won’t. Probably stilettos get caught in the cobblestones, and I feel slightly better.


I took exactly one pair of sandals to Vegas. They went with everything and we walked for miles without a blister. But Italy is Olympic-size traveling.  I’m gonna need a bigger shoe. And a sparkly shoe.  And a high-heel shoe. And a sprinting shoe.

And a smaller bag.

Which Self will win? The Sensible Sherpa or the “Roman Holiday” Romantic?

I’ve been perusing travel websites, searching for a way to have my cannoli and eat it too, but I’d love to hear some advice in the Comment box!


Comment (3)

  • Andrea| July 3, 2018

    Love it! We definitely need to have tea and discuss!

  • Bon| June 26, 2018

    Everyone needs sensible sandals! But I say take the stilettos and catch a ride to your dinner/dance. Pack large and enjoy every last minute of your trip- no more packing for the kids and their activities – go be you !

  • Nini| June 26, 2018

    Nobody in Italy will care what you wear or walk in. Doubt that hubs will either. Go pack light, but leave a tiny space in that bag to bring home a most gorgeous pair of Italian leather stilettos!!

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