There’s nothing worse than a writer on vacation. They pack loads of books, pens and paper. They make plans solely in search of inspiration. They make it look like they’re intensely reading, even when they’re wine drunk and asleep in a beach chair. 

In reality, the writer you know on vacation is not Hemingway. It’s Hamlin. And he’s in a dog fight with page 3 of the first book he’s read in a year. 

What the writers do next is insufferable. They take pictures on disposable cameras. They write prose thinking the town canter is singing to them. Then they make a list of all the places one should absolutely visit before they go home. 

I’m avoiding the list of Googleable tourist traps. Instead of telling you where to go, I am going to tell you what to wear. As you can see from my first installment below – identical to other writers – for the most part, I have no idea what I’m talking about.

Feel this: 85 degrees and a full face sun. Thick sea air and a spritz of lemon float up from the shoreline to the patio. There’s wine, there’s pasta and there are red backed prawns more like lobsters than anything you’ve ever seen in a shrimp cocktail. Before you get too jealous, remember… this is southern Europe. 

The bus is cumbersome, packed and impatient. It’s hard to get around, which makes planning a trip to Pompeii or a ferry to Capri challenging. There are cretaceous sized insects that float through your villa's open windows like tourists. Make no mistake – unlike Americans, the mosquitoes and spiders live here. And they’ll remind you any chance they get. 

I can feel your face melting with pity. 

  1. Bring Breathable Pants

I wore a few different pairs of pants on this trip – all to combat different enemies. Both the Cotton Linen and Seersucker Easy Pants from A.T. feature drawstring waistbands... expansion can be a problem post-pasta. These pants are also super breathable, which makes all the difference in the sticky 85 degree heat. But I can’t say enough about LENGTH. Wearing pants, especially at night, is your best defense against some of the critters that dig into your calves during dessert.

  1. Wear Knit Polos if U want to Live

It’s obviously not that serious but when I’m in Italy I am not wearing moisture wicking Peter Millar with a little squirrel on the chest. I’m just not. I have a personal vendetta against performance polos. I think they all look like you got them at Dick’s. The right knit polo will be just as breathable. That’s how natural fibers work.

There are a lot of knit polos on the market right now. Even sporty brands have caught on and embroider their logo somewhere billboard-y. Bogeyboys and Malbon do it so that’s how you know it’s getting less cool.

I’m never going to wear a polo that feels #merchy so I prefer stuff that’s unbranded. Did I get both the Riptide Polo and Space Dye Polo from work? Yes. Yes I did. Do I wear them often? Absolutely. 

  1. Wear your favorite shirt 

I’m not bragging but I bought this shirt at BODE. I do something crass every time I wear it – I tell people where I got it (they always ask). What’s worse than this ego trip is that I went through a period where I felt like I shouldn’t be wearing it (yes, because of the price tag). I got over it and flexed it on a rental boat. Easily the coolest I’ve ever felt. We sang that Jack Sparrow song by the Lonely Island like 10 times.

“This is the tale, of Captain Jack Sparrow
Pirate so brave, on the Seven Seas,
On a mystical quest, to the isle of Tortuga,
Raven locks sway on the ocean breeze.”

Yes, I do know all the words to that song – and many other songs by the Lonely Island. I guess this is a brag now. But the point is – pack your illest sh&t for vacation. Don’t hold back because you’re worried customs might kill your best come up. 

We toured Pompeii early in our trip and we baked like a brick oven pizza. Felt like all the cardio we needed for the week abroad. I would 10/10 recommend visiting Pompeii but only if you’re wearing a see through shirt like I did. Thing was breeeezy – and it made a difference.


  1. You’re never fully dressed without a smile 

We’re into self-help territory now but you’ve gotta keep it positive on a big trip. Hangovers and headaches are not lost in translation. Mount Vesuvius is less of a threat to blow up than siblings four pinots deep. 

This is where the camera does its best work. People drop their ego and put on a nice face when the flash is on. There aren’t many pictures of people with their chin in their chest. Who wants to tell a story of an all-time vacation where the team didn’t get along? Not me. Not us.