Should I Bring Shoes? Stephen’s Packing Dilemma For 3 Cards 3 Continents


I set off on my 3 Cards 3 Continents trip last night, flying the new airline Norse Atlantic Airways in Premium Economy from JFK to London.

What is 3 Cards, 3 Continents? Frequent Miler loves creating fun and competitive team challenges. This year Greg, Nick, and Stephen are competing to book the most amazing 3-continent dream-trip using 3 credit card welcome bonuses.

I’d wanted to publish a post before setting off sharing what I was going to bring with me, but doing that was a little tricky. My wife and I spent the last month in Europe, only getting back to the US a few days ago. We were busy for the couple of days after that, so I didn’t get a chance to pack for 3 Cards 3 Continents until the night before I took a positioning flight to New York ready for the trip.

With limited space in my backpack and needing enough clothing for a 10 day trip, my biggest dilemma was whether I should bring shoes with me.

Stephen's 3 Cards 3 Continents packing
This is everything I’m bringing with me

It might sound strange that I’d question whether I should bring shoes on an international trip lasting a week-and-a-half, but hear me out. I’m on an 8 year, 50 state road trip and we tend to head south in the winter and north in the summer, so we’re generally in fairly temperate areas. As a result, most of the year I live in shorts, t-shirts and flip-flops.

During the 40K To Far Away challenge a few years ago, I walked 10 miles at a time around cities in flip-flops. On the European trip we just got back from, flip-flops were the only footwear I brought with me and that worked out fine.

As for 3 Cards 3 Continents, most of the places I’ll be visiting will be warm and so relying on flip-flops would be OK, but there’s an exception. The place I’m flying on to over the next couple of days won’t be quite as warm, but should still be a reasonable enough temperature. However, their weather is unpredictable and so it might end up raining while I’m there.

I’m fine walking around in flip-flops in the rain too, but where I’m going rain = mud and I’ve a feeling I could be traipsing around in a lot of mud for a couple of hours. That’s far from ideal, especially as it could increase the likelihood that I’d slip over in the mud, getting my limited clothing supply dirty too.

My Original Solution

A few nights ago I had what I initially thought was a genius solution. I ordered some waterproof shoe covers that I could slip over my flip-flops to keep my feet both clean and dry. Those arrived overnight at our friends’ house where we’d be arriving the next day, but when my wife saw what they looked like, Shae said something to the effect of “You can’t seriously be thinking of dressing like that – I’m glad I’m not going on this trip after all!”

Coming soon to a catwalk near you: Smurf canoes.

Smurf canoes
My original “solution”

In hindsight, this wasn’t such a genius idea. The shoe covers are fairly thin and even when doubling up the covers on each foot, they don’t give the impression of being overly resilient. The covers are also attached fairly loosely, so mud would likely just pull them off.

I didn’t think I had much of a choice though because there was limited space in the hiking backpack I’m using for this trip and there simply wasn’t enough space for my tennis shoes to come along.

The Solution

My real problem was that I’d been laboring under an incorrect assumption. I’m flying with a low cost carrier during my trip as well as taking some flights on small airplanes with fewer than a dozen passenger seats. I thought that meant I was restricted to one bag, but when double checking I realized that I could take both the backpack and a smaller rucksack. That extra room made all the difference, so my pair of tennis shoes have made their way with me even though I’ll likely only need them for a maximum of a few hours on this trip.

What I’ve Packed

I included a photo of everything I’ve packed for my 3 Cards 3 Continents trip at the top of this post, but here it is again so that you don’t have to scroll all the way up:

Stephen's 3 Cards 3 Continents packing

Here’s what’s made it along on the trip:


  • Mountaintop 40L Hiking Backpack
  • Eddie Bauer rucksack


  • Tennis shoes
  • Flip-flops (in case anyone’s curious as to what flip-flops I live in, they’re Reef Rover)


  • 7 t-shirts
  • 3 pairs of shorts
  • 1 pair of pants
  • Underwear
  • Raincoat
  • 1 shirt
  • 1 pair of socks
  • Swimming shorts
  • Hat
  • Microfiber towel (not really clothing unless I want to wear it like a scarf like Greg suggested)
  • Poncho
  • Shoe coverings (I brought these anyway in case my shoes get muddy so that it doesn’t get other items in my backpack dirty afterwards)


  • Laptop
  • Portable charger
  • USB-C charger
  • International plug adapter
  • Webcam (Frequent Miler OnlyFans coming soon)
  • 2 phones (one is spare in case something happens to my main phone)
  • Car charger (I’m renting a car tonight)
  • Headphones (I’m a little annoyed that after realizing I could bring along the rucksack as well that I didn’t think to bring my noise-cancelling headphones as there would’ve been space for them)
  • Phone splitter (I have a Google Pixel 6 & it doesn’t have a headphone jack, so it needs a dongle to use wired headphones. This splitter means I can also charge my phone at the same time)


  • Frequent Miler water bottle
  • Oatmeal bars
  • Gum (because just like Monica in Friends, I will always have gum)


  • Toiletries
  • Pen (to make filling out forms easier)
  • Waterproof phone case
  • Spare glasses & sunglasses
  • Wallet (with more than 3 cards in it)
  • British passport (hopefully this proves to the person watching Ask Us Anything the other night that my British accent isn’t fake 😉 )
  • Face masks (in case anywhere requires them)
  • Plastic shopping bag (for dirty laundry)

I’ve a feeling that some of what I’ve brought might be overkill. If my destination tomorrow hasn’t been raining, I probably won’t need the tennis shoes at all. Similarly, that raincoat could be unnecessary. Seven t-shirts might be more than I need, especially seeing as Nick is relying on only two shirts.

If those items end up being redundant, I could’ve done away with the extra rucksack. However, I’d have been more sad not having them if I did need them than I’ll be having to lug them around and not have to make use of them.

Anyway, it’s almost time for the first of two positioning flights before an experience I’m very excited about. One of those flights is this afternoon and the other is tomorrow morning – stay tuned to find out what I’m up to.

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Where is your flashlight?


7 shirts? Definitely should have gone with Nick’s idea of taking merino wool shirts. They dry quickly (hang drying after a washing will only take a few hours), don’t smell after many days, and are lightweight. Could do the same for the rest of the wardrobe.

As for shoes, there are plenty of brands that offer extremely lightweight, packable shoes like Nike Flyknits or Allbirds sneakers. They’d take up about as much space as the slippers.

Chris Englert

You could have worn the tennies and packed the flips.?


I had a good experience backpacking with barefoot trail running shoes. They worked well enough for hiking/long walks, dried quickly, and were very lightweight to travel with. Brought those and waterproof sandals for 18 months of travel.

MIke D

Adults in flip-flops not at a beach or a pool? Ah, no.


While I never wear flip-flops myself, even at the beach, the majority of the world lives this way.


WaterShoes Walmart $5 not $30 on Amazon.Use them in and around the Pool or sand..U can fall on Flip-flops and heaver too and they crush to nothing…

Last edited 19 days ago by Cavedweller
Michael Tarlow

It is interesting to see what you are packing, but I’m more interested in how much it all weighs. I have no trouble packing what I need for 4 weeks in a couple of carryons. But getting each bag down to the 7kg (15lbs) max that some airlines require is the challenge for me; starting with the actual weight of the bag. BTW, I was pretty surprised to learn that TMA seaplanes in the Maldives limit TOTAL bag weight to 23kg assessing an additional $5/kg for overages. Not that big a deal given the cost of a Maldives vacation, but a surprise none the less. In addition, over weight bags run the risk of ending up on another flight.


It’s the 7 KG carryon limit that usually gets me as well, since I do tend to fly discount airlines around SE Asia. I usually check a carryon sized bag in that scenario since it’s still cheaper than a full service airline even with checked luggage fee added.

Michael Tarlow

Singapore Air 1st/bus is 2 bags not to exceed 7kg / 115cm ea. Other readers have told me they weigh and measure ea bag at check in


Another solution to this problem — where you need something only for the first day or two of the trip — is to bring something disposable. Before the pandemic a friend and I took a three week trip to SE Asia in January, with a busy 16 hour layover in Seoul on the way. We took old motheaten sweaters / coats with us and abandoned them in ICN before boarding our flights to Singapore. With your lifestyle you might not have a closet full of old coats and footwear, but you could probably find something at Goodwill for $5 that would work.

Michael Tarlow

I have a multi pocket safari type vest that I pack all my electronics, sunglasses meds etc in and wear it onto the plane so that several lbs of equipment don’t count against the weight limits.

Shae Pepper

Mrs. Stephen here LOL – I told him this… I said just stop at Primark or a charity shop and then donate it on afterwards if it’s not all beat up.


Looks like my typical packing list except I pack trail runners for hiking (I do a ton). I just came back from 3 weeks in SE Asia & brought 4 shirts. Only used 3. 7 is too many to manage, even if you somehow do need them. Just do laundry:-)

Shae Pepper

For our month over there we did just do laundry but with all the moving around he’s doing on this 7-14 day adventure there wasn’t time to worry about that.


Frequent Miler OnlyFans account – haha, good one Stephen. Looking forward to your upcoming destinations and activities 🙂


Phone splitter
What brand do you use? I have a Pixel also. First one I bought didn’t work.

Shae Pepper

Looking at the one I have ( we use the same) its a Subynanal. *shrug* no clue LOL he probably got it from Amazon after checking the reviews.

Teresa Henning

Thank you


I would have that dilemma also 🙂
I find my Teva Terra Fi sandals are a good compromise. Rugged enough for hiking and walking long distance while keeping feet cool in warmer climates.

Granted your feet would get muddy, but nothing a little water cannot fix


I think you can skip the flip-flops unless you’re going to the beach, a resort with major pool time, or a lake destination.


Right? The easiest solution to me would be to wear the sneakers and leave the flip flops behind. Better for your feet and for your airplane seat mates, not to mention the potential of having to walk through an airport security screening barefoot (ewww). My feet hurt just reading that Stephen spent a month in Europe just wearing flip flops.

Shae Pepper

Oh Stephen Pepper used to walk around his entire town growing up barefoot. He is gross in that way LOL. He does barefoot at the airport check in. I suggested just wearing the tennis shoes but after 18 years with him, I will say, his feet do seem to have some weird heater in them as they are always really warm. I used to roll my eyes too at the constant flip flops but if I can handle that he uses handkerchiefs I suppose I can deal with this. LOL


Real Simple tie them to BP done..V Berine