Travel Planning – Packing

I love packing for a trip.  Whether you are going to a warm or cold climate or if you are going to be very active or just lounge around in the same location, the categories for what you need to bring remain the same.

  • Outfits
  • Shoes
  • Toiletries
  • Electronics
  • Outerwear
  • Accessories

Putting the categories aside for a second, I typically plan to NOT check luggage on an airplane. I do not like the idea of my luggage getting lost. It’s just too risky especially if you have multiple stops and layovers.

My credit card covers the cost to replace luggage items, but if you have tight connections or are traveling to a more remote location, you might not be able to replace everything at your destination.

I love what The Budget Minded Traveler says about it in Packing for Long-Term Travel in a Carry On. 

While traveling with all of your luggage on can be exhausting, it is not nearly as frustrating and stressful as traveling without any of your luggage, and having to file reports, follow up with airlines, file claims to insurance (if you have it), and, of course, replace an entire wardrobe at retail price at the last minute.

It’s not something I want to deal with. Also, dragging a huge oversized suitcase around is not fun. I want to be able to easily jump onto public transportation and be able to manage my bags without a lot of fuss.

I’m already thinking about what luggage I will bring on my 2-week excursion to Greece and Italy in May. I’ve had long and multiple conversations with the ladies that are coming along with me on this topic. They are getting used to the idea of not checking luggage, but at first, they were just appalled and immediately thought, NO WAY!

However, after explaining that it is possible and actually more desirable, I might have them convinced.

I currently have an Osprey Aura 50, that I use for true backpacking and camping excursions. I have traveled with it for long extended trips as well. When I went to California for 8 days this past October, I used my Osprey Aura 50 and it was awesome to be able to walk freely without rolling something and I loved not checking my bag, but I didn’t like digging into my bag and pulling everything out to get to something that was at the bottom. I had to spend a lot of time re-rolling my clothes and by the end of the trip, it was pretty disorganized.

I initially considered using it for my big trip this spring, but after researching other more travel-friendly, explorer backpacks, I might be swayed into buying a new one.

I am loving the idea of the Osprey 55 Travel Backpack. It is a backpack that has a zipper open, similar to a suitcase! What? I didn’t even know those existed. I also LOVE that it has a detachable daypack that you can use for your city or day hiking trips. Hint, hint, this might make a great 40th birthday present for me!

Ok, back to packing. Whether you want a backpack or carry on roller bag is completely a personal choice, regardless you’ll need to fit all your crap into a bag and take it with you!


I love having clothing that can roll into a tiny little bundle. I also love clothing that is versatile enough for day and evening wear. Lightweight solid color dresses are my favorite. It doesn’t matter if you are exploring a city by day and have tennis shoes on, you can easily dress up your plain dress with a nice scarf and a pair of sandals and you are set for the evening to literally go anywhere. My list of must-haves include:

  • (1) lightweight breathable black dress
  • (1) cotton cardigan
  • (1) neutral pashmina or large scarf that can roll up into a tiny ball
  • (2-3) neutral cotton shirts, one being a tank top
  • (1) pair of shorts can eliminate for winter travel
  • (1) pair of pants (nicer structured leggings or skinny jeans)
  • (1-2) bathing suits, regardless of summer or winter, you might find yourself at a hotel with a swimming pool or spa, bring your suit. I never travel w/o mine
  • (2-3) sports bras that can be worn with your dress
  • (1-2) pair of workout/running capris*
  • (1-2) workout shirt/tank top*
  • (3-4) pairs of socks

*You need to be honest with yourself on these. Are you going to be super active? Do you exercise on vacation? I always do, so I know I need to have room for these. If you won’t or never do, don’t bother! However, if you are going on a group vacation and you have people in your group that like to, you might feel inspired (or forced, hahaha!) into going along with the group.


  • (1) a comfortable pair of walking shoes, neutral that can go with any outfit and you don’t feel like an American tourist with your big bright running shoes on
  • (1) flip flops for beach, showers
  • (1) a nicer pair of sandals that you can still walk a good bit in or boots for colder weather
  • (1) pair of workout shoes or something you can hike in and could get wet

Toiletries + Medication

  • Go to Target or Wal-Mart and buy the 3 oz reusable liquid travel containers, or buy online
  • (1) 3oz each of shampoo and conditioner, fill reusable ones with your favorite
  • (1-2) 3 oz sunscreen of your choice
  • (1) 3 oz moisturizer that can be used on face and body, I LOVE the Trader Joes Jojoba oil. I use it for my all over body moisturizer, and on my face, lips, and hands. I just pour it into my reusable container
  • (1) 3 oz liquid hair product/gel
  • (1) travel size toothpaste
  • (1) travel toothbrush
  • (1) small travel sized container of q-tips
  • (1) ziplock bag, labeled, of ibuprofen or over the counter pain reliever of choice
  • (Many) packets of Emergen-C, pack as many as you need to cover taking 1x daily
  • (1) bottle of Zicam dissolvable tablets
  • (1) package of Pepcid or other indigestion aid. I typically don’t take this, but if you are eating and drinking things you might not normally do, you don’t want to be slowed down by heartburn
  • Makeup –Try to really minimize your makeup if you wear it. I only travel with the very basics
    • (1) mascara
    • (1) small .5 oz size of concealer/foundation/pore minimizer whatever you prefer. In the summertime, you don’t need much
    • (1) a small container of blush
    • (1) blush brush
    • (1) small eyeshadow
    • (1) lip gloss


  • (1) phone charger
  • (1-2) universal travel adapters. Please read about this more in detail here, if you are traveling outside of US
  • (1) iPad or computer, completely unnecessary for the normal vacationer, but I will be traveling with my MacBook Air, so I can write and record my podcast from the road, also I like being able to research destinations and activities while I am there and don’t like using my phone for all internet related searches
  • (1) computer charger
  • (1) flat iron or curling iron for hair, optional. I don’t bother with packing a hairdryer, most places have them and if they don’t you can buy one for cheap there if you must have one


  • (1) lightweight jacket, ideally waterproof with a hood, go heavier for colder weather
  • (1) hat, I love baseball hats for exercising, hiking, hiding bad hair etc.
  • (1) scarf


  • (1) eye mask for sleeping
  • (A lot) of earplugs, give them to your friends too!
  • (1) waterproof iPhone case – necessary for the beach trips
  • (1) travel towel, I love and have used these, also double as a yoga mat
  • (1-2) sets of packing cubes. I have not tried these yet but my friends and all professional travelers swear by them, so I will be acquiring these for my trip. BTW- this is another great birthday present
  • (1) travel iPhone tripod – optional

I’m confident that this entire list will fit into a carry on bag.

The big takeaways here:

Pack minimally.

Feel confident that you can carry-on for any trip you might take.

Pack outfits that can be interchangeable and that you can wear multiple times without having to do laundry.

Bring comfortable shoes that can be appropriate for any occasion.

Always bring an eye mask and earplugs.

Please let me know your tips or products that you use for travel!







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