So, here's what I'd bring if I were tagging along:
- Include a comfortable pair of tennis shoes, no matter what. If you will be walking around for 12 hours for days on end, not even a Sperry boat shoe is going to save you, and it's pretty awful to be in so much pain that you do not care about the 2,000 year old ruins in front of you and then have to spend $12 USD on Italian band-aids that do not help much.
- You can certainly minimize the extent to which you stick out from the locals, but you're still going to look like a tourist because you are the one standing in line for a museum and reading a map. So, it's fine to wear jeans, but dark wash and slim fits will help you blend in a bit more. You won't, however, need lots of shorts. They're not as common away from beaches as they are at home, and if you plan on visiting old cathedrals they may not even be allowed.
- Accept that at some point in three weeks, you'll need to find a laundromat, so there's no need to try and make 25 outfits. However, packing things that can almost all be washed and dried together will make that chore easier.
- Heels/wedges take up lots of room in a bag, so they'll need to stay at home.
- One cross-body purse with zipper that isn't too casual or too dressy will keep your belongings safe (hold on to it when you walk through crowds). Make sure it's big enough for your wallet, camera, sunscreen, guidebook, or whatever else you carry around.
- A couple of statement necklaces will add some interest to your basic outfits
- Make sure everything you pack can be paired with almost anything else in the suitcase, including at least one top layer for chilly nights, such as the cardigan and denim shirt I included.
- Plan to bring a dress or two for nicer restaurants, since denim and shorts are not often seen outside of really casual places at night.
P.S. If you are interested in a blog about packing, I really enjoy following Rachel at Suitcase Secrets and Alex at Travel Fashion Girl. Check our her Pinterest board of packing lists!