Packing for my next trip just got interesting. There are theme nights for the festival (anti-fascist, colorful, Hawaiian, white shirt), so my evening-wear is set for me. I am also running a 5K one of the days so I need running stuff. I am shooting for just a carrry-on since the trip is 4 days.
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These can be easily covered by a single aloha shirt!
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Yes, but at the end of 6 hours of being in the pit of punk show, the shirt will be unwearable 
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We travel a fair amount, but I detest packing. Have to do it though to travel
I also use the guest bedroom to stage my stuff. Mostly start with things that are very specific to the trip. Wedding clothes if heading to a wedding, hiking shoes and poles if visiting the national parks etc. Of course, the last couple of years, we’ve combined a wedding with a couple of national parks - so packing for those was interesting!
We have status on almost all airlines, so we can check bags. If we are headed for just a regular trip less than a week, it’s always just a carryon and a backpack (each of us has our own). But if we are headed for a cruise or a wedding or a longer trip, we usually take one big bag and a smaller carryon.
I have separate bags for toiletries, medications, makeup (very minimal) and another bag for sunscreen/bug repellent/laundry sheets etc. Use packing cubes for clothes. Always pack a light sweater, a hooded sweatshirt, a swimsuit and a quick dry microfiber towel.
Ziploc bags and a few reusable tote bags are always tucked into my suitcase - never know when you might need them!
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