I Got 99 Problems but Overpacking Ain’t One

packing travel extended backpackWhen I was a little kid, the phrases ‘vacation’, ‘going out of town’, ‘going up north’, and ‘weekend getaway’ meant I would find my old suitcase or my brother’s stinky duffle bag and load it up two weeks before we were leaving town!

Now I find myself hours before a flight flinging clothes around and wondering ‘what the hell am I going to pack this time?!’

I feel like this trip should be the easiest to pack for, but for some reason, it is becoming incredibly hard! And the awesome procrastinator that I am, I have been avoiding even thinking about packing like it’s the Black Plague.

I haven’t totally figured out what has changed since I was a child; I still can manage to wear the same shirt a couple days in the row, I switch between a couple pairs of pants… why am I struggling so badly?

I’m sure it comes down to the fact that I won’t have my options with me. I will be forced to wear the same clothes for months. Since we have decided to start our adventure traveling, which will be a cruise in the Caribbean and then heading over to Europe for 3-4 months, I have been referring to other travel bloggers and reading their packing tips. Amanda over at A Dangerous Business has an awesome page about what is in her backpack.

It has been helping me keep things in perspective and hopefully the power to not overpack. With my new Gregory Cairn 48pack and my Magellan’s packing cubes, I feel I will be able to pack everything I want to. So with that, here is my list of what I plan to pack:

Cairn 48:

  • 1 pair of jeans – I have decided against bringing a pair of jeans. Just because it will be in the summer months where we will be traveling, and I just don’t like to wear jeans in the summer!

  • 1 pair of linen pants

  • 1 pair of workout pants

  • Leggings

  • 1 dress

  • 2 skirts

  • 5 pairs of socks

  • 1 week worth of underwear

  • 5 tank tops

  • 2 t-shirts

  • 1 light sweater

  • 1 rain jacket

  • Swimsuit

  • 1 scarf

  • 2 bras and 1 sports bra

  • Week pill case for carrying jewelry

  • Merrell hiking shoes

  • Skechers city shoes

  • Reef flip flops

  • Toiletry bag (make up, toothbrush, toothpaste, deodorant, brush, lady items,  band aids, body-spray, nail clippers,  hair spray, bobby pins, extra ponytails, shampoo, etc.)

  • 1 travel hair dryer and straightener

  • 1 twin sized sleep sack

Kelty Daypack:

  • iPad/ charger

  • 1 pair underwear/shirt (stuffed into my water bottle)

  • Camelbak water bottle

  • Camera/ Charger

  • Sunglasses

  • Journal/ Pen

  • Lip Gloss

  • Wallet

  • Passport

Of course this is my list of my own personal items. I am packing for what makes me happy and this is just a guideline for anyone who needs a push in the right direction of what to pack. A bonus for me is having Andy there as well, so some things will be stored in his pack. After all, he is a great pack mule :)

In the end, not everything fit into the backpack. Andy had to carry my makeup bag and a few things that we’re sharing. But as we go along, it’ll probably get better since you learn to live with less and the items will start dwindling down. But overall, I’m ready to go and loving my new pack!


  1. The day someone invents truly travel-worthy and summer-appropriate jeans is the day someone will make a billion dollars.

  2. For serious!! Can’t wait for that to happen :)

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