What to pack for a fun trip

Why is packing for a personal trip so hard? For a business trip I can literally pack in twenty minutes, from outfits to toiletries to boarding pass. For most casual trips I agonize for days over what to pack, making list after list, crossing items out, figuring what I still need to buy…For the Alaska cruise I took with my family in the summer of 2008 my packing list was three columns, and took up three pages! Literally. Now, that was not all clothes of course. I had to figure out what I was taking, then I had to figure out all the different outfits these clothes would make. Then I had to decide on accessories and shoes. And of course there was a page devoted to what I was going to take on the plane (seven hour flight!). Now I may be admitting to a little bit of OCD here. In fact, my mother might say this is the only area of my life where I am OCD at all.  I am very laid back about most things, but packing for a personal trip is not one of them.

I have a few theories about this.  First of all, there are many more situations on a personal trip than on a business trip. For work, I know that I will either be on an airplane, in meetings or trainings, at dinner, or in the hotel the entire time I am gone.  I can basically wear the same thing to all of those places. Once I am in the hotel I change into my yoga pants and I am set. The one crazy thing that *might* happen is that I will go down to the pool, so sometimes I bring a swimsuit.  For a personal trip though, there could be all kinds of activities. In Vegas, I could go to restaurants, go gambling, go to the pool, go shopping, walk around the Strip, go to a show….the possibilities were endless. In Alaska this was compounded by not completely knowing what kind of weather we would have. Plus, what exactly should one wear while whale watching?  (Layers, in case you were wondering.) In Maui, we had the addition of a formal dinner.

I have started getting better at packing lighter, but I still have to make all of those lists. A few weeks ago Home Warrior and I went to Napa for wine tasting, which I followed up with a short trip to Salt Lake City for work. It was definitely tricky combining clothes for a fun trip and a work trip, and still be able to carry on my suitcase. One of my big weaknesses is shoes. I want to bring a different pair for shoes for every outfit. In fact, on my initial Napa list were seven pairs of shoes.  For a six day trip. Sigh.

Although I am evolving it all the time, this is basically what I pack for a fun trip. Obviously add or subtract as needed, and vary as necessary for weather, but start with this list and you will be in good shape.

  • One pair of pants/shorts for every two days (for my 6 day Napa trip I took three pairs of pants), including one pair of jeans
  • A shirt for every day (ideally each shirt will match more than one pair of pants)
  • One or two nice tops/outfits
  • Two pairs of shoes, one pair of flip flops, one pair of tennis shoes**
  • Jacket appropriate for weather
  • Clothes for exercising
  • Clothes for sleeping
  • Swimsuit and cover-up
  • Make-up and toiletries
  • Undergarments

**All of the packing lists I have read say take three pairs of shoes, including the pair on your feet. I think this is a good rule of thumb. I also don’t think flip flops should be included in the shoe count. They are small, don’t take up a lot of room, and are good to have around the hotel regardless of whether you wear them out.


  1. Great list! I would add a large scarf/shawl that can keep you warm in overly-air conditioned restaurants and also jazz up a casual outfit. Pashmina is perfect for this. Takes almost zero space in your suitcase. It keeps you from bringing that same jacket to every single event, too.

    For a swimsuit coverup, I use a pareo, which can also double as a shawl. My pareo is pretty casual, but there are lots of nice ones that would be appropriate to wear over your shoulders into a nicer restaurant. No one but you knows it smells faintly of pool chlorine.

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