Week One of Our Summer Abroad, or: The Art of Self-Sabotage

I planned this trip within an inch of its life. I measured distances. I built in buffers. I confirmed reservations twice. In my own mind, I was a logistics genius. And then Europe, a heat wave, and my own nervous system took turns reminding me that a plan is just a story you tell yourself before the actual day happens. Forty days, six bags, one wedding, one ferry, and one very public moment involving a sweater. Here is everything that went sideways, and exactly how I would dodge it next time.

Book direct, or spend your vacation yelling at a spinning wheel.

I booked our ferry through a third-party site to shave off a few euros. The site then declined to give me actual access to my own reservation, and when I paid for upgraded customer service, the chat rewarded me with the eternal spinning wheel of death. The "private" airport water transfer in Venice I booked through Viator? Seven strangers and a thirty-minute wait for them to show up, in an oppressive heat wave, on a boat I was certain we had to ourselves.

The "private" transfer. Note the number 9, the dock, and the seven strangers who were about to join us.

The fix: book direct with the operator whenever you can. 

Even better: use a trusted travel advisor. And remember, "private" is a word, not a promise. Read what it for sure definitely includes before you pay for the upgrade. Read the reviews, twice. 

The rental car will not care that you did your homework.

I knew the distance from the airport to the car station. I knew the distance from the train station to the car station. What I did not know was which to do first, or that the driver named on the reservation needs his own credit card that actually works in Italy, prepaid car be damned. So, my son stood at the counter with a fully paid reservation in his name and got a very polite Italian no. Josh scrambled a replacement at the last minute for roughly twice the price. We won the email dispute later, which felt wonderful and changed absolutely nothing about that afternoon.

The rental car drop-off: a random garage under the Ligurian tunnels where absolutely no one was working. Or, as far as I could tell, ever has.

The fix: rent your own car, confirm the route order and not just the distances, and make sure the human with the working card is the one on the booking. Also, you can often pick the car up right at the train station, which I somehow did not know was a thing.

"Lead with your humanity. It is the cheapest thing you will pack and the thing you will be most grateful for."

Your bags will break you. Send them ahead.

We packed for a month. Day clothes, going-out clothes, workout gear, Thera-bands, swimsuits, the works. Then we dragged every bit of it through a four-day wedding in Lake Como that needed almost none of it. Fifty to seventy pound suitcases, up and down Venice canal stairs, half a mile through Como, four flights with no elevator, all in ninety-five degree heat. The suitcases themselves were great (I grabbed them off Amazon and have zero complaints). The heat was the enemy. So was I, eventually.

Six bags, one moving walkway, one hothouse of an airport, and me: unfortunately, a delicate flower.

The fix: use a luggage-forwarding service to your final destination and keep one carry-on for the detour. I wrote about the closet reckoning that kicked all of this off in The Packing Reckoning, and the actual two-bag math in Two Bags, Forty Days. Your back, your knees, and your marriage will thank you.

The whole fleet, parked in a Como piazza, waiting to see if the rental car could navigate the one-way streets, forbidden lanes, and finger-wagging Italians to reach us.

The heat will win. Plan to lose gracefully.

Mama-bear adrenaline got us to the train on time. My body collected the bill the second we sat down. I had eaten nothing, drunk far too much water and far too much (admittedly perfect) Italian espresso, and I threw up into my own sweater in the middle of the train aisle. A sweater I had, for reasons I cannot defend, packed for Italy in July. There was no fun party to blame it on. Just heat exhaustion and a tidy series of poor choices. We recovered by cleaning up and quietly colonizing the air-conditioned lobby of a Milan hotel we were not staying at, buying just enough drinks to earn our welcome.

Peak morale. That is the face of a man doing luggage math in ninety-five degrees.

The fix: eat something, ease off chugging water, and build a 4x time buffer. If you think you need fifteen minutes, give it an hour. That extra time is the only reason I got to fall apart safely instead of missing a train.

The Milan station steps. We were angry, sweaty, and approaching heat stroke, so no, there is no photo of that part. Here are the steps instead.

Pro tip: In a heat-wave, fancy hotel lobbies are your best friend

Feet up in the lobby of a Milan hotel we were not even staying at. God bless them and their families for life.

The ferry: a full yes, with caveats.

Do it. It was one of the coolest modes of transport we’ve taken yet, and not only was it a nice way to travel, but it was also a cultural experience. The boat was headed to Tangiers, filled with mostly Moroccans. This is not a luxury cruise; this is an affordable way to cross an ocean without getting on an airplane or taking half a dozen trains and two days. People were laying out prayer rugs, pitching actual tents on the deck, and little kids were running around unsupervised. World Cup fans with Wifi held devices that folks hyddled around to watch.

The terminals are unmarked, disorganized chaos. It took two hours from car drop to boarding, and at one point Josh was so sure we were in the wrong line that he pulled us out of it, only for us to learn thirty minutes later that I had been right about the very long line all along. So, we Mimi and Grandpa'd for a minute. You know. A travel day. Passport control was very Sicilian. It seemed fully optional.

The ferry ahead of us at sunset. Somewhere between a Best Western and a Holiday Inn, floating on the Mediterranean.

The fix: book the balcony cabin and keep expectations at a 2.5-3 star level (a full yes, worth every euro), arrive absurdly early, and do not pre-book your dockside pickup. Disembarkation timing is wildly unpredictable, and there were plenty of taxis waiting when we finally rolled off.

Queuing to get off. Two hours, chaos, and a passport check that seemed, again, fully optional.

The small mercies are real, and most of them are human.

Two regular taxis beat one giant van every single time. Cheaper, easier, and nobody's knees are wedged under a suitcase. But the mercies I keep thinking about were not logistical, they were people. Porters exist in Venice and are worth every euro. Watching a tiny man trolley our absurd pile of luggage over the Rialto bridge was gob-smacking. A gracious Airbnb host mentioned the fourth-floor walk-up before we were standing under it, then helped us haul. A Milan hotel we were not even guests of let a sweaty, sick mama and her wilting daughter recover in their lobby.

And here is what surprised me most. For all the anti-American talk you brace yourself for, every local I mentioned our struggles to met me with real empathy and care. People will lend a hand, offer a better idea, or just give you a sympathetic ear. But usually only if you extend your hand first. Show up a little open, a little human, a little willing to admit you are floundering, and it comes back to you tenfold.

The fix: budget for the little help, and lead with your humanity. It is the cheapest thing you will pack and the thing you will be most grateful for.

And then this. The part that makes you forget the luggage entirely.

Now tell me yours: what is the travel-day disaster you would go back and warn your past self about? Misery loves a comment section.

Next up: how all of this actually crammed into two bags for forty days, the rule I made and then gleefully broke, and the slightly unhinged outfit math behind it.

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