I’m approaching 20% of the way through this experience, and I’ve been reflecting on some of the more unexpected things I packed that have served me very well so far. May this be a guide for anyone considering a long trip abroad!

Earplugs

Pico Island is home to an endangered shorebird called Cory’s Shearwater. These birds spend all day out at sea hunting, then return to the island after sunset to seek out their permanent mate. To find their mate, they issue a distinctive call. And by distinctive, I mean truly horrifying. Imagine you’re me for a second. It’s your first night camping on Pico; you’ve been cozily reading in your tent after watching a gorgeous sunset. The wind whistles through the trees; the cicadas and crickets chirp and buzz. And, all of a sudden you hear this monstrous noise just outside your tent. My first thought: “Oh, I guess I’m going to die here.”

Enter the $20 pair of earplugs I bought on Amazon last year, mostly to preserve my hearing at concerts. I keep them on my keychain and didn’t even consciously “pack” them so much as “always have them on me.” They aren’t perfect - sometimes I will wake up with both of them somehow out of my ears, but they do their job defending me from the pure evil of Cory’s Shearwater calls. They have also been incredibly useful on flights, in crowded airports/train stations, at concerts, when teenagers decide to drunkenly revel right outside my window, you name it.

An Inflatable Pillow

A purchase that I almost didn’t make, I bought this mostly for camping, but it has far exceeded that narrow use case. It packs down to fit in the palm of my hand, and it adds a little something extra to any situation where the comfort level is lacking (airports, airplanes, crummy Airbnb pillows). A couple disclaimers: (1) Whipping this pillow out at a café will 100% give you some well-deserved weird looks, but my comfort is worth a stranger’s assumption that I have hemorrhoids. (2) Be sure to properly seal the inflation cap - if it slips midway through use, your head and a hard surface will become rapidly acquainted.

Sketchers Slip-Ins

Just ahead of the 2024 school year, I did a small wardrobe refresh at the mall near my condo in Roxbury. I bought a few new button-downs, a pair of jeans, a blazer, and I stopped into Famous Footwear to see if they had any good work shoes (teachers can go through a nice pair of shoes quickly). I went to their clearance section and discovered, in my size, a pair of the ugliest walking shoes you will ever see: a black-and-gray pair of Sketchers Slip-Ins, which have no-tie laces, a hard rubber heel (to assist in the “slip-in” part of their name), and go with exactly 0 outfits. They were twelve dollars. I bought them, thinking they would be good for walking the dog and little else.

When I say that these shoes have saved my life, both at home and abroad, I’m only mildly exaggerating. I can put them on in seconds; they are comfortable and supportive; and they are durable beyond belief. Since their purchase in 2024, they have been with me on countless dog walks through snow, rain, and heat. They have brought me up mountains in Bali and the Pyrenees. They have eased my passage through airport security. I’ve probably put 500 walking miles into these bad boys, and they are still going strong. When, many years from now, they inevitably walk their last steps, I will probably hold a funeral for them. Sketchers: If you are looking for a spokesman for a single product that you offer, I’m your guy.

Pyrenees Shoes Pictured: The best shoes I’ve ever owned.

Dry Bags

I don’t know how many years ago it was that my brother got me a set of three dry bags as a gift - small, medium, and large. At the time, I was touched by the thoughtfulness of the gift as someone who goes diving and camping regularly (and who just generally enjoys being on boats). But, the magic of the dry bag does not stop at being waterproof. These may be the most thoroughly used gift I have ever received.

Over the course of my experience with them, these dry bags have safely stored (in no particular order): electronics, dirty laundry (they hide the smell), vital documents (they can be locked), and money (again: lockable!). Put dry things in them, they stay dry. Put wet things in them, everything else stays dry. They are also vibrant colors, which helps my simple brain when allocating them roles (“ok, electronics are going in yellow, diving stuff in green, and blue will be for dirty laundry”). They collapse down to whatever size you need them to be. They can be clipped to the outside of another bag or locked to a permanent structure. Get yourself a set of dry bags, and thank me later.

Compression Cubes

Staying on the theme of “stuff that holds other stuff,” I’ll add some more words of praise for compression cubes. When I purchased them, I did so from the perspective of spatial economy - the ability to pack more into limited volume. But their real benefit, I have found, comes from an organizational perspective. I now pack the compression cubes like carry-ons - for a camping trip, I can pack pretty much everything I need into two cubes, which allows me to keep the other cubes (I have 6 in total of various sizes) tightly zipped up and packed away. This has saved me valuable time packing and unpacking, and it helps me to organize myself for upcoming journeys. When packing for Porto and Lisbon, I knew that I will need less of my outdoorsy gear and more of my city gear. Luckily, I had a “city clothes” cube all packed up already. When living out of a suitcase, it turns out that more, smaller suitcases can actually be helpful - a real matryoshka doll situation.

As a related aside, I massively overpacked for this trip, so much so that I ended up donating about a kilogram of excess clothes to a charity shop in Sao Miguel. Packing for multiple months of travel is no easy feat, and I would have certainly benefitted from a harsh critic of my packing back in Boston. To give a sense of just how bad it was, everything I donated in Sao Miguel had either an identical or highly similar item that I continue to schlep. Redundancy might be useful in power plants and security systems, and I may eat these words later when I inevitably lose a critical piece of outerwear down the road, but in the realm of packing, one flannel, one pair of sweatpants, one pair of long underwear is probably enough.

Analog Travel Planner

I love a spreadsheet, and I generally lead an organized digital life. But, nothing replaces an old-fashioned book of dates and appointments. This little book - a dedicated travel planner stretching two full calendar years - has served many purposes: tracking flight/train numbers and schedules, Airbnb entry codes, lists of recommendations, even a de facto diary as I keep track of people, places, and experiences I want to remember. It is also a helpful tool for compartmentalization. When it is open and in front of me, I am in planning mode. The moment I put it away, I am back in the moment, ready to enjoy the current city, the current vibe, the current adventure. With technology, those lines are too easily blurred, and I worry that I will get so sucked into planning and tracking on my phone that I miss the beauty around me at that very moment. Having an analog planner has been the most helpful way to calm my often-overworking brain and keep my phone where it belongs (in my pocket).

Travel Update

I’m writing this from Porto, a gorgeous city with hustle and bustle and absolutely delicious food, likely the best I’ve had so far. I think I’ve probably tried port wine at some point in my life, but for the life of me I can’t remember it being so sweet and so, so alcoholic. It is truly a drink to be savored (and enjoyed with great caution). I’ve treated this brief stay in Porto as a chance to recover from my 9 nights of camping, allowing myself some laziness, time to catch up on work and sleep. My fellow world-travelers have continued to be gracious and welcoming; I spent a really nice evening with a Taiwanese traveler from the guesthouse I am staying at, enjoying fish, ice cream, and port. The weather has graciously turned from overly hot to pleasantly cool and comfortable, so I’ve been going for runs in preparation for my October 17th half marathon in Bilbao. Next comes Lisbon, where I’m excited to get a taste of home by seeing my old friends from university. I’m also excited to start a leg of my trip where I will travel overland, taking trains, buses, and cars across Europe to take in the scenery as autumn settles in.

Wishing everyone back home a great start to spooky season! I hope you all enjoy your favorite autumnal things.

Until next time,

Ethan

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