I am a chronic over-packer but I worked really hard to go from a large hard side, down to a medium and a small wheeled carry on for my recent trip to Europe to visit my daughter.
My tips:
Shoes take up a ton of room. Since I knew I’d be walking on cobblestones most of the time, I packed one good pair of walking sneakers with a thick sole (plain white) and I wore a pair of athletic sneakers that I could use as a backup if needed. It pained me not to have shoe choices but there’s no way to do heeled booties or anything other than sports sandals on the cobblestones. Not having multiple shoes frees up a lot of room.
I chose neutral color pallets and planned to mix & match, layer and wear things multiple times (with enough underwear & socks for the whole time). I brought a travel size of fabric refresher in case I needed to freshen anything up. I underestimated how warm I would get, even in 60-degree weather, when walking everywhere, all day. Also, in the cities I visited, the public transportation is either not airconditioned or under-airconditioned, so I probably only needed to bring one light jacket. My daughter and I traveled from her home country to other countries, so I off-loaded some of the stuff I already wore or didn’t think I’d need, and left it in the other suitcase. This allowed my main suitcase to be lighter and easier to handle.
Lots of places in Europe store luggage (including the airports). My hotel stored 2 bags for me for free for 5 days even though I wasn’t checking in there until my last day. It never hurts to ask.
If you think you’ll have to wheel your luggage over cobblestones, make sure you have a set with good wheels! I noticed many people wheeling luggage everywhere. We wheeled our luggage 2 long blocks in Italy from the train station to our hotel and I was very happy that the wheels held up. My set is Travelpro and my daughter’s is Calpak.
I hated having to find bin space for my wheeled carry on. People get very irritated if you (politely) ask if you can shift their item in the bin, to fit yours. Men in particular, don’t seem to want to store their small back packs under their seat. On the way out, I could have checked everything for free as the flight was full, but I worried about lost bags, so I kept the carry on with me. On the way back, the airline again offered to check everything for free and I did (I also had an extra wheeled carry on filled with my daughter’s winter coats and boots that she no longer needed.)
I’ll never be a person with a wheeled carry-on bargaining for bin space again. I now know why people scramble to board. My credit card credits me for checked bag fees, so not a big deal.
I also noticed that in all the airports that I traveled to (Rome, Prague, Barcelona) our checked luggage was either coming out or waiting for us in baggage claim by the time we got down there. I don’t know why it takes so long to get luggage in the US (well, I can guess).
The only thing I would do differently next time is pack lighter travel pants and maybe just one pair of jeans. Jeans are hot and heavy to walk in all day.