Summer Travel: All in a Weekender + A Contest!

weekender travel

Happy Thursday! Don’t you just love summer vacations? I’m getting ready for a weekend in Chicago to visit my Brother-in-law and Sister-in-law and I am so excited. Since we typically reserve our long vacations to take place during the frigid Ohio winters, our summer travel is all about spending a quick weekend somewhere with friends or family. To try and expand on the usual trips to Chicago or Nashville, I bought Matt a book all about 36 hour trips within the US and I am excited to dig into it this summer. What might make these trips even sweeter? If we were to win this contest from CheapOair… the winner will get FIFTY plane tickets to explore the U.S. in 2014 (entry details on their app!).

Usually, since these types trips are quick – starting on Friday after we are done with work and ending on Sunday afternoon – it’s best to spend as little time as possible dealing with logistics (e.g. waiting for bags to off-load). I typically pack in weekender bags, and with all of the travel I do, I’ve developed a few easy tips which work well for me when I have to keep luggage to a minimum.




First, always start with what you’ll wear on the plane and plan from there. Not only are planes and airports cold, but I always try to wear my bulkier items. When traveling domestically, I wear a uniform: A pair of jeans, a tank top, a blazer or sweater, and heels. From there, packing is pretty easy.

Dresses take up little space and can be worn with the sandals you’ve packed or the heels you wore onto the plane. One can also be paired with the blazer for cooler nights. Two tank tops can both be styled with the jeans you wore and dressed up or down, depending on the jewelry and shoes. One regular bra and one strapless with two pairs of undies will be all the extra underthings you need. With this formula, you potentially have 4 additional outfits for just two additional days of travel. I use this as a template for all travel, swapping in-and-out other low-bulk items depending on the particular schedule for that weekend. So what about things other than clothes? 


Everything that isn’t clothes, goes into a pouch. This makes identifying what you need a breeze and keeps everything very organized. I typically have four pouches with me at all times, but they vary in size depending on the trip. They all vary in color and texture so that I can find what I need without even looking. Here are the basics:

  • Toiletries and makeup – find a bag that has a separate zipper pocket for jewelry. Stash your liquids in a separate plastic bag until after you’re past TSA, then include them with the rest of the makeup.
  • Business supplies – this pouch varies greatly depending on my travel. For primarily work travel, I have a folio sized pouch which fits documents, notebooks, a calculator, pens, post-it notes, and business cards. If I am not going on a business trip, I bring a much smaller pouch that just holds business cards (you never know when you’ll make a connection!) and a few pens so they’re not swimming around the bag ready to mark up my clothes.
  • Tech Pouch – this is an absolute must for me. This exact pouch is always stocked with an extra computer, phone, and camera charger as well as any memory cards, earbuds, and thumbdrives I would need. Keeping all tech in one place eases the hassle of getting out wires tangled in who-knows-what from under a plane seat when you’re trying to get our your headphones. You can easily feel in the bag for the appropriate pouch and pull out what you need.
  • Money Pouch – Now, I typically carry a wallet, but for countries where coins are so abundant to cities with metro cards, this is where they go. I hate pulling out a whole wallet with passports and credit cards when I just need a metrocard. Stick this in an easy-to-reach side pocket.

Once all of the random items are stashed in their pouches and you have a small stack of clothes, go ahead and pack everything vertically, so you can see the end or edge of basically everything in your bag. For clothes, pile everything in one neat pile, then with your bag lying on it’s side, lay down the stack on one side – not on the bottom of the bag. Top the stack of clothes with your pouches (also vertical). This makes finding what you need a cinch!

So, are you inspired to start a little summer globe trotting? Don’t hesitate to enter the CheapOair sweepstakes (running the entire month of June). Where would YOU go if you have 50 tickets to anywhere in the U.S.?? I am going to have to crack open my book to do a little research in case I win!


Disclosure: Cheap-O-Air has graciously sponsored this post!  Thank you, thank you, thank you for supporting the brands that keep us running over here!

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