How packing for travel changed for me in retirement
“While traveling in retirement is more about enjoying the journey than business travel, it’s been a lot harder to pack for.”
Travel packing wishlist
I’ve written a little bit about traveling in retirement, but I haven’t yet really written about the less glamorous part about packing for this kind of travel. In retirement, I’ve found it more difficult to check items off my small wishlist for packing:
Easy in-airport experience
Ease of use at destination
My crucial items with me even if airlines lose luggage
Nice looking pieces
Though most of my 21st century work life, this was all pretty easy because packing was pretty formulaic. However, as of late, I’ve found a few wrinkles in how I prepare and pack for travel now that I have to carry a CPAP, want a daypack at my destination, and need more clothing because I get cold more easily in my older age.
At the risk of TMI, I’ll share what I’ve been doing. I am also interested in hearing how you all manage this now, too.
Note: I write more fondly of business travel in the 21st century. Back in the 1990’s, doing presentations and demos required a lot more gear. Before doing presentations from computers was common, I remember carrying pre-loaded 35mm slide carousels because trying to load 35mm slides carried flat in plastic sleeves into a carousel right before a presentation was too error-prone. Before we had thin-and-light laptops, I remember having to carry a “luggable” computer. And before large monitors or projectors became common conference room features, I remember having to carry my own LCD projector. Before the LCD projector was invented, I had to carry an LCD panel that could be used with an overhead projector, and sometimes I even carried my own high lumen overhead projector to work with those LCD panels! Business travel used to really suck back then… Fortunately, those days are over!
Work travel needed just a briefcase & garment bag
At the core of work travel was having a great briefcase. Personally, I have a nice Tumi laptop bag. The design of the bag made it easy to access the laptop, access cables and accessories, and get to any paper documents stored in the bag. This all worked very well!
Tumi also used to make some very good bags for carrying around business suits that packed well and worked well at the destination because of all the sewn-in pockets. Two of my favorites were the tri-fold garment bag and the boarding bag.
Because I could carry everything on the plane, I never worried about airlines losing luggage. And the Tumi luggage looked great!
Of course, the problem now is that Samsonite bought Tumi in 2016, and the quality has gone way downhill. The bags I really liked, the tri-fold garment and boarding bag, are both obsolete. To honor a warranty repair for me on a discontinued product, Tumi at least offered me an exchange. This is a letter I got from Tumi in 2019, about a year after I retired.
A duffle replaced the garment bag
Receiving the letter was disappointing, but it was OK, as I was already retired and didn’t really need to carry multiple suits at a time anymore. A Tumi duffle with packing cubes worked well, didn’t need to be checked, and still looked smart.
Both the Tumi laptop bag and the Tumi duffle worked together as carry-on luggage, and I could still walk through the airport hands-free.
The old strategy started to fail
However, once I was diagnosed with sleep apnea, I needed to start carrying around my CPAP machine. A problem emerged. The CPAP didn’t fit cleanly into either the Tumi laptop bag or the Tumi duffle filled with clothing.
As such, the Tumi laptop bag is now no longer a core part of my travel packing strategy. Instead I’ve been carrying both the CPAP and prior contents of the Tumi laptop bag in either a free duffle bag (thank you, SignalWire) or a free backpack (thank you, AT&T Cybersecurity). The duffle doesn’t provide such a great in-airport experience because everything inside is stacked on top of each other, often requiring me to “dig” to get certain items like my laptop, iPad, or headphones. The backpack is a little better at the airport, with a bit more random access to the individual items because of their separate compartments. Neither of these pieces look all that great.
One wishlist item I have for the backpack is an easier way to also use the backpack as a day pack when at the destination. While working, the briefcase also served as the day bag with no need to unpack it. There was also no need in business travel to shove another jacket or sweatshirt in the bag. However, when traveling in retirement, it’d be nice to be able to use a backpack to hold sweatshirts, water bottles, and other things needed during the day, without carrying around all the electronics.
Checking luggage
I mentioned in my last post that we flew Ryanair and checked the CPAP in hard-shelled luggage. I figured I would just carry my laptop, iPad, and Bose headphones on the plane using my Tumi laptop bag.
The immediate sacrifice here was that I had to worry about the airline losing luggage and having to potentially sleep without my CPAP. This was not ideal.
The other problem was that the Tumi bag was too tall! It was 32cm high, but the Ryanair height limit was 25cm. I didn’t want the €75 fine for my bag not fitting in the bag sizer!
So, I had to pull an old crappy-looking Briggs & Riley case out of the archives because it is “shorter” than the Tumi bag. (I kept the crappy-looking case because I thought I’d get it repaired at some point!)
The result was less “smart” looking than the matching Tumi stuff, but it worked for Ryanair. I just tried to keep the trashed side of my old laptop bag turned “inwards.” The other benefit is that I got to pack a “day pack” in the checked luggage.
Going forward?
The net is that in my retired life, I am carrying more now.
CPAP machine
Day pack for leisure activities (my briefcase was the day pack while working)
More clothing because I get cold so much easier than when I was younger
At the same time, I am losing strength, so I want things to be easier to carry.
Marsha and I now have both the Alaska Mileage Plan and United Quest credit cards for priority boarding in hopes of securing space for our carry-on bags, as well as free checked luggage allowances if we need them. However, either way, I don’t want to check the CPAP, so I have to be able to carry-on both my electronics and my CPAP. Checked luggage will just be for clothing, if required.
The key is to make all this stuff look smarter together.
I think I have a solution now. Watch this space! (Hint: I just got my Pacmodo system!)
Do you have a better solution? Please share!
The past couple of trips, I've been bringing overly full roll-away, backpack, CPAP in case, through security. I gate check the roll-away and that gets me into an earlier boarding group, and I just have backpack/CPAP with me, which covers laptop, day pack, chargers, 1 change of clothes. I could also put a mini toiletry in the backpack. Downside is that normally I have to pick up roll-away at baggage claim.
Wow ‘business’ travel depends on where and what you’re doing. I used to wear my steel toe boots through security when they’d wand you at best. Now days those puppies go in the checked bag along with hardhat, hi-viz vest, electronics tool pouch and all the clothes I needed for up to 2 full weeks on longer deployments. After using a Samsonite Oyster hard shell case (you might have been with me in Chicago, running through a closing, lights going out, JC Penny’s to get it to check out to haul a PC back to WTC). I found my low cost, it’ll crap out and I can replace it anywhere; Walmart black full size rollaboard (it lasted longer than the Oyster and cost way less)! I guess standard (if you can call it that) is low cost functional. With the zippered expansion panel I’ve never needed more than one checked item even for an, unbeknownst to me, 6 month commissioning role on site! I had what I needed, laundry every 2 weeks, etc.
I’ve had some lost bag events but only once where I had to make essentials purchases that UNITED gladly reimbursed me (always helps to be million miles 1K).
I remember the luggables, Osborne 1, Kaypro II, Compaq Portable with shoulder bag, I was really stoked to get my first Tandy Model 100 with mouse ears acoustic coupler modem! Dial into WTC and get my VAX-mail or hit a bulletin board via CompuServe! Back when Road Warriors ….. WERE! Looking forward someday to retirement travel, no plans current day. Up in the AIR!