How to Pack for a Two-Week Trip . . . and Not Forget Anything

Mar 14

Packing is an overwhelming task.  Even when I pack a simple overnight bag, I ALWAYS forget something.  My de-tangling hairbrush, a phone charger, a book, my moisturizer — there’s always one little thing.  Or more.  😉

When I packed for a week in London/Scotland, I did pretty well.  I remembered the power converter, my toothbrush, AND my passport.  Definite win in my book!  Now, however, I’m getting ready for my longest vacation ever: 2 weeks in Italy.

Here’s how I’m keeping myself organized while packing for such a long trip:

Make a List . . . and Check it Twice!

As a tried and true list maker, there’s only way I’m going to tackle this!  For several weeks now, I’ve been adding items to my Italy 2018 Packing List on Wunderlist.  If you haven’t tried Wunderlist yet, you should!  I’m usually a paper and pen girl through and through (I use a Simplified Planner to live!), so I’ve never loved online list tools.  Until Wunderlist.  There’s something so aesthetically pleasing about the way its organized.  It just works for me!

So, whenever I start thinking of things I’ll need or listen to a travel podcast about packing necessities, I add to my Wunderlist.  When it comes time to actually start filling the suitcases, it will be super easy for me to print off the list and check things off on pen and paper, just like I like!

Carry On Travel

Robert and I aren’t exactly backpacking on this trip, but we are definitely not staying in one place!  In each of the 5 cities we’re visiting, we have different hotels/AirBnBs.  That way, we can keep our luggage in one place, but we are still huffing it on 2 layovers, 5 different train journeys, water taxis, cobblestone streets, and more.

We decided that the simplest thing to do would be to pack carry ons with a messenger bag or backpack each for day trips.  (I’m going messenger bag because it feels safer from the infamous pickpockets!)  This way, we won’t have to worry about losing checked luggage and our luggage will be small and light as we travel between cities.  Plus, nothing makes you look more like a tourist than hauling a suitcase bigger than you onto a train.  When I’m traveling, I want to fit in, not stand out!

carry on travel tips

Space Saving Tricks

When we were getting back in from London, a TSA agent hand-checked my luggage.  He gingerly poked around and said, “I don’t want to mess up your packing job here.  It’s the most organized suitcase I’ve ever seen.”

I feel like that’s like Gordon Ramsey telling you you’ve made great eggs.  It’s like Joanna Gaines telling you you’re good at decorating!

My trick to keeping my suitcase organized and fitting 2 weeks of stuff into a carry on?  Packing cubes.

I use these babies from TravelWise in teal, of course.  They have gone to London, Scotland, North Carolina (a few times!), and Ohio.  Now, they’re about to go to Italy!

I like to have one cube for toiletries, one for shoes, and one for all the clothes.  I also keep a Sainsbury’s bag in the front pocket to stash dirty clothes.  Our AirBnBs do have washing machines, so we will probably have to take advantage of that.

Lay it Out

If I don’t physically lay out outfits on my bed, I will 100% pack 3 pairs of pants and 175 shirts, and none of them will will go together.  I clear off my couch and plan out OUTFITS.  I’ll think to myself, “I like to wear these pants with these 3 shirts.  I would pack this shirt, but it doesn’t really go with either pair of shoes I’m bringing.  I’d love to pack these pants, but they’re not as versatile as these.”  And so on.  That’s the best advice I have for getting to your destination and having stylish but supremely versatile and comfortable outfits!

Roll ‘Em Up

Once I have all those outfits, I roll them up like so.  It saves a TON of space.  And yes, this is how I get everything back home WITH souvenirs! Which brings me to my next point . . .

Leave Space for Souvenirs

My souvenirs are my photos, so I don’t spend a lot of money on souvenirs.  I spend money on cameras!  But there’s one thing I always save to bring back: papers.  When I travel, I save ALL the tickets, restaurant receipts, boarding passes, museum passes, metro cards, etc.  When I get home, I toss them all in this fake book that opens up.  As weird as it is, I LOVE sifting through this hodgepodge of memories.  In this book, I have ticket stubs from every movie Robert and I have gone to, horse race passes, concert wristbands, our program from Wicked in London, etc. etc.

So, I keep all the papers in a big pink, faux leather envelope.  When I’m packing and see that I have a little extra space, I RESIST THE URGE to pack another outfit or pair of shoes!  After all, I’ve already strategically planned every article of clothing I need, and I know I’ll want that extra space for cool souvenirs.

Bonus Tip: Travel Journal

I love writing, obviously.  If we’re on a long train ride or on the plane, I write down as much as I can remember in my Kate Spade travel journal.  I try to remember specific places we saw, foods we ate, and how it all felt each day.  If I don’t, I find that it all blends together after awhile!

So, there you have it!  I hope that helps someone else out there get organized . . . and not forget their toothbrush!

comments +

  1. Erin Schrad says:

    Been loving your Italy photos on Instagram (congrats, by the way!) and I can’t wait to see your pics! I’m headed to Italy in July so I need all your tips… particularly how you packed light with travel gear! May have to buy you a coffee when you get back to RVA!

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