Sarah Goes to Siena: Episode I: The Perils of Packing

HELLO ALL! This total badass Sarah contacted me a few months ago via email. Sarah is moving to Siena for school and asked if I’d be interested in sharing her journey with all of you awesome readers. My answer: Hell yes. And? She’s a great writer to boot. This series will follow her from her voyage from the US to Italy and her experience as a student in Siena. I’m REALLY excited for this series because who doesn’t want to follow someone’s new and amazing journey into newness? Plus, all of you who live in Italy or made the same journey know that it’s bound to be hilarious and super fun. Stay tuned every two weeks for a new installment of Sarah’s journey. Enjoy!


Packing is probably the least glamorous part of travel. While browsing all the beautiful travel sites out there, the process seems so simple: lay out all these pretty clothing items, take cute Instagram pics of you doing this, then magically all of it fits perfectly in your bag. You forget nothing, and then boom you’re on your way and you have everything you need and you dance through fields with butterflies and small adorable animals.

For anyone who is not a travel magician who writes about these things for a living or anyone, who like me, is fondly referred to by friends as “a mess,” the packing process is slightly more complex. Luckily I have packed for trips to Italy a few times now and done my reading and learned lots things.

As I mentioned earlier I am a complete mess, this means that often times my suitcase also becomes one big hot mess. This leads to sad things like obscenely wrinkled clothes, misplaced underwear, and a mingling of dirty clothes and clean clothes. To remedy my messiness, this time I am going to try using packing cubes to organize my clothing and other various items. These help to prevent messiness on long trips by compartmentalizing your stuff so that you just have to flip through bags instead of taking all of your clothing items out and having to refold them and put them back in. Also you know where everything is (ideally) and that is a win in itself.


Packing cubes, hopefully the best organizing tool yet

What exactly you are going to pack is also kind of important. For the most part, despite what a lot of places want you to believe, what you pack really depends on you. This means that you can make packing into an introspective journey and ask yourself “What do I need in my bag?” or you could just know that flats hurt your feet and that maybe you shouldn’t pack those as your intended walking shoe. On that a few things that you should definitely bring regardless of the length of your trip or who you are and what you need, you should definitely bring: walking shoes because cobblestones want to kill you and your feet, a shirt that covers your shoulders so that you can visit cool old churches without being confused when an old Italian man runs up to you and starts making weird gestures and speaking rapidly in Italian in an attempt to communicate that you need to cover your shoulders with a scarf, SUNGLASSES because it suns everyday, also on that note bring sunscreen too especially if you are pale like my poor ginger self.


My adorable cat Luna helping me pack by wrinkling all of my clothes with kitty love

Blending in is also something people are often concerned with when packing to visit Italy. I personally like blending in because then you are more likely to get shopkeepers to speak to you in Italian so you can practice and you get a more interesting experience, also most importantly you are less likely to be targeted by scams and pickpockets. Personally I have a decent amount of trouble with blending in because I am a ginger. There just aren’t many gingers in Italy. I usually try to keep count of how many Italian gingers I see. After traveling all over the country for two weeks multiple times the highest my count has ever gotten is about twenty five. However for those who have a slightly less red and freckled coloring, wearing solid colors more on the neutral sides of life (black, white, grey, denim, etc) and being dressed on the nicer side will usually do the trick. Personally I think what’s more important is your attitude. If you look confident even if you are not sure of yourself at that moment you are less things will work out much more smoothly. This is really important because although style can be generalized and mimicked if you have a confident attitude you will fit in much better regardless of what you are wearing.  However I still would not recommend wearing neon under armor shorts and a matching sweatshirt and confidently yelling “WHERE CAN I FIND A HAMBURGER AROUND HERE?” if you want to blend in in Italy.

Packing a carry-on is probably my preferred form of chaos as I feel like I am close to reaching the point of perfection in this area. My carry on also holds some of the most important things for my trip that I absolutely cannot forget. For instance bringing at least three to four days worth of your prescription medications with you or bring it all because if you get delayed, or they lose your bag for a little while you want to have that with you. Some more basics that should not be forgotten, glasses/contact case/solution, phone charger, outlet converter, any important electronics that you don’t want to be broken, some form of entertainment, and whatever you need to sleep, be it ear plugs, a neck pillow, medication, etc.

Also something I would recommend is if you bring a reusable water bottle on a plane most of the time the flight attendant will fill it up for you so you have a nice bottle of water at your seat instead of a little cup that will spill. Be smart and pack one that you know doesn’t leak so that unlike me you will feel clever and actually be clever instead of feeling clever and then discovering that your whole carry-on is soaking wet by the end of your journey.

One more, quick note about carry-ons and important things to bring, first off bring your passport, secondly chose a designated and secure spot in which to keep it the entirety of your travels. If you have a specific pocket where you put it and make sure you put it back there any time you have to take it out for security and customs it will save you a lot of stress. My friend was once yelled at by German airport security when he misplaced his passport in his bag and held up the customs line searching for it.

I am currently down to two days to pack for my upcoming two-month trip. As I am an anxious packer I have already had my packing nightmare for this trip. This time I dreamed that I arrived at the airport without a suitcase, which was completely terrifying. However now I feel like as long as I do better than that it will be a successful pack.

I look forward to updating you all on the failures and successes of my current packing plan in the near future! Ciao a tutti!

About the Author:


Sarah is a college student with a minor Italian obsession. She is spending the summer studying Italian language and other interesting things in Siena. She loves cats, old things, pizza, and sarcasm. You can learn more about her crazy self and antics on her Instagram. (@gingersarahb)


7 thoughts on “Sarah Goes to Siena: Episode I: The Perils of Packing

  1. Very cool article! So true about the attitude being more important than the wardrobe. Looking forward to hearing more!

  2. OMG loved this! I’m exactly like her, I’ll be moving to Italy for a whole year it was really fun to read this written by someone like me!

    Sent from my iPhone


  3. Yay! A black cat named Luna!

    The first time I went to Italy, I went with one of my dear friends, who has beautiful long red hair. I have long blonde hair. We got a LOT of attention, but also some really nice art-related compliments from old men.

    Enjoy your stay!

  4. Look around and find plastic bags you put your clothes in and then use a vacuum cleaner to suck out the air. That way you can pack more. Undies, socks, t shirts are rolled tightly to save room. Get a traveler’s scale and weigh all bags to get exact weight. Coats can carry small heavy items in the pockets.
    I use a passport pouch that hangs around my neck. I will never lose it and it is easily available when I go through customs. Plastic baggy holds my coins through the metal detectors. Good luck, Dave

  5. I pack every piece of clothing possible in my carry-on for the trip over. When the Icelandic volcano caused one of our trips to erupt in chaos, I still had plenty of clothes, not only for me but to share with my sister-in-law. LOVE packing cubes!!!!! My latest addition to my travel “accoutrement” is a child’s water bottle, Elsa to be specific.🙂 Way easier to pack and have available then adult size. I remind everyone traveling to Italy to pack a pair of slippers or flip flops if you don’t care for being barefoot on stone floors.

  6. Ciao Sarah! I have been studying in Siena for two months – flying home this weekend. When you arrive, check out Tolomei gardens, La Vecchia Gelateria, concerts at Palazzo Chirchigi, and the films in La Fortezza (plus all the big name stuff). And go to a contrada dinner before the August Palio-it is an exhibition of Italian awesomeness!!!! Siena is also a great city to people watch/take naps in the piazza. Have a great time-Siena is an amazing city!

  7. At last … a fellow hopeless packer. Have you noticed the way they pack in films … just get everything out of the cupboard and fling it into the suitcase. No underclothes or toiletries. Just be glad you don’t have to use cheap flights like Ryanair, as we Europeans do, which means only a small case and no wine or olive oil, because I’m not paying 30GBP (cost of checking in your suitcase) for a bottle of wine or olive oil.

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