I’ve been talking about packing, luggage, and tech gear since I started TravelCommons back in 2005 — how to wring out every last bit of value out of the carry-on and underseat space the airlines give us, and to have the right tools to swerve all the obstacles the travel gods (and TSA) put in our way.
But shifting from road warrior travel to retirement travel isn’t just a swivel from business to leisure. It’s a change in what I’m optimizing for — from doing everything to survive the travel friction that stands between me and the next meeting, to giving myself a better shot at enjoying where I am. Which translates to a few key changes.
First, slower travel. I’m not triangulating across three cities in four days anymore. As I said back in the TravelCommons Redux post, retirement travel means not having to do any more stupid travel — the ORD-MIA-SEA or ORD-LHR-DEN bunny hops. Retirement travel means longer stays in fewer places, which changes what I’m packing for and how I do it.
Second, no corporate travel expense account. I no longer have other people’s money to buy my way out of a jam. In road-warrior mode, I’d pack light and assume I could buy or replace whatever I forgot. I had a company card. I filed expenses. None of that exists anymore. I own the whole stack — research, booking, insurance, disruption recovery, all of it.
Third, I’m older. I confirmed this in the mirror while shaving this morning. Not a complaint, just a recognition of reality. But it does mean I can’t take as much for granted as I could back in 2005 when I started TravelCommons; skipping sleep for red-eyes, heaving heavy bags into the overhead, tossing nothing but Advil and Zyrtec into a random pill bottle.
So, having reset the baseline, let’s get into it.
Core Packing Rules Still Stand — With a Few Tweaks
Rule 1: Pick a single color family for your clothes, and make it black.
A long-time rule that’s still true. Three reasons: black makes everyone look thinner (always nice-to-have), it spans casual to smart dress codes, and black doesn’t show stains (absolutely need-to-have). I can’t be one-and-done on a pair of pants because of incoming from a fork-handling mishap. But the real point of this rule isn’t black, it’s wardrobe discipline. If black gives you PTSD flashbacks from your teen goth phase, then go for blue or grey or earth tones. But pick one. Don’t pack five shirts that all demand their own separate color ecosystem.
Rule 2: No one-and-done outfits.
Every piece has to do at least two jobs. Every shirt has to work under multiple sweaters and with more than one pair of pants. If it can only be worn one way, it doesn’t make the bag. Pack a travel wardrobe, not a series of costume changes. Versatility is key. And yet another reason to pack black.
Rule 3: Pack layers, think additively.
Multiple thin layers beat one bulky piece every time. Thin layers give you range; bulky items are a commitment. A black merino wool sweater has been my long time go-to, but merino has been taking over more of my travel wardrobe — quarter-zips, t-shirts, socks. It’s versatile — naturally odor-resistant so I can wear it multiple times before washing, wicks moisture, and is wrinkle-resistant enough that I can pull it out of a fully-packed bag and wear it to dinner without looking like I slept in it — which maybe I did.
Rule 4: Leave most of the workout gear at home.
Gym shoes take up a lot of space — that hasn’t changed. But in retirement travel, they’re no longer just for the 6 a.m. hotel gym session. The right pair can take you from the gym, through the museum, and into a casual restaurant for dinner. And as we get older, resistance training is important for maintaining muscle mass. So a tweak to the original rule: wear your gym shoes on the plane and stuff a couple of rolled up resistance bands into your packed shoes.
Rule 5: Use a nondescript black rolling carry-on bag.
Black not only makes you look thinner, it makes your bag look thinner to gate agents scanning for bag-sizer bait.. My daughter’s baby-blue roller was a walking invitation to be gate-checked; her current dark-purple bag is much closer to black and mostly sails through. Hard-side versus soft-side still depends on the problem you’re trying to solve. If the risk is a budget carrier’s strict sizer — or if you’re prone to overpacking — a hard shell can help. If the risk is weight, I want the lightest stripped-down bag I can get.
New Rules For Retired Travelers
Rule 6: Laundry becomes part of the itinerary.
Here’s a new rule. When I was doing road warrior travel — one-night hops, weekly returns home, hotel laundry on the expense account in a crisis — I didn’t think about laundry at all. Now my trips are longer; sometimes multiple weeks before heading home, which should mean I need to pack more. But it doesn’t. Slower travel leaves time for laundry. My default itinerary these days is to book an Airbnb with a washer/dryer every 7-10 days. Toss the underwear into the washer and head out for a beer. Come back, swap in another load and go tour a church… or go back for another beer. Longer trip, same size bag.
Rule 7: Medications earn their carry-on slot before your clothes do.
Looking back at my What’s In My Briefcase posts — I did one every 4-5 years — two of the constants were the bottle half-filled with Advil and Zyrtec tablets I mentioned earlier, and a tin of wintergreen Altoids. But age is often accompanied by more medicine — maybe a statin or a beta blocker, or something with a little more oomph than ibuprofen. And pack extra because, where you’re going, they might not be as easily available.
In Croatia, Irene had an itchy rash — must’ve brushed up against something on one of our hikes — and went looking for their version of Cortizone at a pharmacy in Hvar. But she couldn’t get it. In Croatia, hydrocortisone cream isn’t over-the-counter; it requires a prescription. Good thing to figure out before getting on the plane.
Just One Key Change
The through-line from 2006 to now isn’t really about bags or black or merino wool — it’s about who I’m packing for. Road warrior me was packing to survive the trip. Retired me is packing to enjoy it. I’m not packing to survive a bad connection and make a 9 a.m. meeting in an unwrinkled state; I’m packing to enjoy the destination instead of just surviving the itinerary.
That changes a few things at the edges — a pill organizer, scheduled laundry stops, more stylish gym shoes — but the core really hasn’t changed. I’m still pulling out my now-kinda-beat-up black bag, still making sure everything that goes into it has earned its place.
Coming next: 2026 updates to What’s In My Briefcase and My Travel Tech Stack
Leave a Reply