When I packed for my first trip to Hawaii, I had no idea what shoes to bring. This is not just a girl thing, so guys don’t stop reading. I was going to a business conference, so I brought a pair of dress shoes and I figured sandals would be good for a warm climate. I bought a new pair because I didn’t really wear sandals in Colorado. I brought my flip flops (called “slippers” in Hawaii) for the beach. Every one of those decisions was wrong.

I wasn’t alone. I remember watching other conference participants slog along the Honolulu beach-walk from conference sessions in one hotel to another in closed-toe shoes. Flip flops were too casual for the meetings but dress shoes were inappropriate on the beach. After the first session, I gave up on dress shoes and wore sandals. That was a reasonable compromise for the meetings. But they were new and I walked a lot more than I thought I would at a conference. My first stop on the second day was at an ABC store for band-aids for blisters on both feet.

The weather was so perfect and the scenery so beautiful that I wanted to walk a lot, both around Honolulu and later on a bus around Oahu. But blisters, and inappropriate footwear, made that unpleasant. I wasn’t even hiking, just exploring the island on foot. Dress shoes were not good for walking long distances or on the beach. Same for the sandals, which were also too new to be comfortable. The flip flops might have worked but they had a closed toe that is very good for not stubbing your toe on rocks in Colorado. However, sand got stuck in the toe when I wore them on the beach making them uncomfortable and impossible to clean.

NOW this is what I would bring for any trip to Hawaii, whether business or pleasure: one pair of comfortable walking shoes that are really broken in. That’s it. They would work for most conferences — even business conferences are more casual in Hawaii than on the mainland. They are also essential for some attractions (such as visiting Pearl Harbor) that involve standing or walking. And they make it possible to experience an impromptu hike on one of Hawaii’s many enticing trails.

I would buy slippers for the beach after I got here, either a cheap pair to use and discard (sold at every convenience store) or a better pair to take home as a souvenir (I now have an expensive pair with arch support that I have worn pretty much every day for a year without a single blister.) After all, who knows slippers better than Hawaii?


  1. Love your advice, and your first-hand experience added a very good authoritative POV. However, don’t forget to always tell your travelers that slip-on, comfortable shoes are BEST when making air travel a big part of their trip. And we all know flying to Hawaii will take at least one long flight, or several along the way.

    And there’s nothing I hate more about being a frequent business & leisure traveler (30+ trips per year for me) than seeing vacation travelers screw-up the TSA lines with having to re-lace knee-high leather boots or struggle with bag upon bag of tchochke.

    I’m not bitter, but I think their experience (and the experience of those around them) might get off on the right foot — no pun intended, of course — if advice is given from curb to curb.

    IMHO, that is. 🙂

  2. ooh, I don’t think I would bring large leather boots to Hawaii. I had hiking boots in Colorado and I have since bought some here after I moved, but not for quick trips.

    But I do think comfy sneakers or walking shoes are a good idea. I wore mine on my most recent trip back to the mainland and was able to slip them off easily at the TSA line.

    Many thanks for the note of caution and for stopping by! I do not travel regularly so I welcome your perspective any time.

  3. I wasn’t sure what to bring to Hawaii either my first time and ended up bringing a small shoe store. Turns out I wore walking shoes most of the time too. The weather is so nice and there’s so much to do that you end up walking quite a bit. Crocs are a good choice too

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