The Organized Journey

What to Pack for a Two Week Sightseing Trip

Packing Collage

I do my best to follow my own advice on packing, but somehow I always try to shove too much in my suitcase.  I tell myself it’s ok because I’ve taken so much out already that my bag is half the size that it was when I started.  I usually start off packing for a trip by taking out everything that I could possibly ever need out of my closet and laying it on my bed.  Then I fold or roll everything meticulously and try to shove it all in my suitcase.  #FAIL.  That never works.  Even with a list this always happens.

So the next, inevitable step is to pare everything down to basics.  This, people, is where you should start.  Not at the chaotic point I described above.

Start out by thinking about what you’ll spend the majority of your time doing on the trip.  For our Rome trip, we were going to spend most of our time sightseeing, so I wanted to bring more sightseeing clothes than anything else.  I like to have two pairs of pants for this, although I could probably get by with one pair of jeans.  I packed a dark wash, boot cut jean and a pair of army green hiking pants that are super comfy and have tons of pockets.  I will usually wear each pair of pants twice (or more if I’m lazy) before washing them, so I can get 4-5 days out of those two pairs of pants.  Shirts that I wear all day are a different story (at least for me).  I usually don’t wear these more than once, but I will rewear whatever I put on top of that shirt.  Weird KB logic, maybe…but it works for me.  Do what works for you.  For this trip, I packed 5 t-shirts to wear during the day.  Add to that pile, enough underthings and socks for 4-5 days, and you should be set.  Just a note, that I always pack at least 2 extra pairs of underwear and socks.

Since I knew we’d only really get dressed up to go out to dinner or for drinks, I tried to bring less dressy clothing.  I brought a black pair of skinny jeans and a dark wash pair of skinny jeans, which could be dressed up or down.  In hindsight, I should have only brought one or the other.  To go with the skinny jeans I packed 3 dressy sleeveless shirts and a flowy 3/4 top.  I wore all of these at least once during the trip, but could have made due with 2 sleeveless shirts instead of 3.   I also brought a gray, long sleeve cardigan and a black 3/4 sleeve blazer.  I packed a white fitted t-shirt that I thought I would wear, but I didn’t.  I thought that I might need a dress, so I brought one that didn’t wrinkle along with a pair of tights.   Neither of which I wore.  Don’t be like me.  Don’t bring extra stuff!

I’m big on putting on comfortable clothing as soon as I walk in the door from a day of sightseeing, so I brought a pair of black yoga pants, a pair of sweat pants, and two gym shirts to wear around the apartment.  Looking back, I would have been fine without the sweat pants.  I love to layer tank tops under my shirts, so I brought 4 of those in various colors (royal blue, black, gray, and white) and I wore all of them.

As for accessories, I brought three different scarves, but ended up only using two of them.  I brought 2 long necklaces to dress up plain outfits and wore both of them.  I packed 5 pairs of earrings (3 dangly, 2 studs) and wore the studs the majority of the time.  I also brought along a few bracelets, which I did use.  I used this purse for a carry-on, my Vera Bradley wallet as a passport/ticket/money holder, and I also brought along a Vera Bradley small clutch.  I used all of them.  The clutch was great when I didn’t feel like bringing my whole purse.  It was small enough that it fit in my hand, and had a little strap to keep it there.  I also bought this clothes drying line right before we left, which really came in handy when doing laundry.  It was small enough to fit in the little nooks and crannies of our suitcase, but strong enough to hold a load or two of laundry.

My outfit on the plane consisted of another pair of black yoga pants, a plain, fitted black tshirt, a pull over hoodie, and my walking sneakers.  I also wore one of the scarves I brought on the plane in case it was cold.  I brought my jacket with me, and in hindsight I wish I hadn’t since I ended up leaving it in a cab.  I could have done much better by just bringing along a heavier rain jacket with a hood and layering underneath to keep warm.  Speaking of which, I’m glad that I brought along a knit hat, because it was very cold some mornings.  I also brought a pair of gloves that didn’t get enough use to justify having them.

Besides my sneakers, the only other shoes I brought were a pair of black flats and a pair of black boots.  Some days had me wishing for my Uggs, but I couldn’t justify packing them in my suitcase because I knew I wouldn’t be wearing them out sightseeing.

Here’s a list of everything I brought (with a star next to the things that I could have left home):


  • Sightseeing pants (2)
  • Sightseeing shirts (5)
  • Long sleeved shirts to layer for sightseeing (3)
  • Black skinny jeans (1) *
  • Dark wash skinny jeans (1)
  • Sleeveless dress (1) *
  • Dressy sleeveless shirts (3) * [minus 1]
  • 3/4 sleeve shirt (1)
  • Fitted white tshirt (1) *
  • Cardigan (1)
  • Blazer (1)
  • Jacket (1) *
  • Gym tshirts (2)
  • Black yoga pants (1)
  • Sweatpants (1) *
  • Tank tops (3)
  • Underwear (7)
  • Bras (2)
  • Socks (7)
  • Dressy flats (1)
  • Boots (1)


  • Scarves (2)* [minus 1]
  • Purse (1)
  • Wallet (1)
  • Clutch (1)
  • Earrings (5)
  • Bracelets
  • Necklace (2)
  • Knit Hat (1)
  • Gloves (1) *
  • Tights (1) *
  • Clothes drying line (1)

Plane Wear:

  • Black yoga pants
  • Fitted black tshirt
  • Black tank top
  • Pull over hoodie
  • Sneakers
  • Scarf
  • Jacket *

What are some of your favorite packing tips?


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