I'm home from my 2 1/2 week trip with my mom and sister. We were in Lourdes and Amsterdam and took a week long Norwegian Fjords cruise.
I worked long and hard with my mom to reduce luggage. We ended up with one Rick Steves backpack (for me) and two 21 or 22 inch Travel Pro rolling suitcases (mom and sister) that were shipped through. Sister carried on a backpack and mom used my Sydney Love convertible weekender (no longer made, but this is an example: https://www.amazon.in/Sydney-Love-Dogs-Sport-Convertible/dp/B01IWC6T34)
My mom and I also had a Coach packable tote (super lightweight bag, and not too big: 18x12x8).
My sister and I both wore a backpack and rolled one of the Travelpro's and I carried my tote. My mom had a wheelchair in all the airports and held her tote. We never had a problem with taxis (in terms of space). We also never had an issue with checking baggage and in fact, by the time were were at the baggage carousel, our luggage was there.
Despite my best efforts, I did overpack a bit. I never wore my fleece and should have trusted my instincts (I was swayed by other peoples input). But I used my windbreaker/raincoat frequently. I brought an umbrella but never used it. The cruise was much less formal than I was expecting and I could have easily not taken the dress for gala nights and just used a nice top with the pants I brought. Likewise, I could leave out the dress flats.
I used the same dress for sleeping as I did for my swim cover-up. It was this dress: https://www.amazon.com/32-DEGREES-Sleeve-Dresses-Skipper/dp/B07Q87KMFD/ref=sr_1_4?keywords=32+degrees+dress&qid=1565516283&s=gateway&sr=8-4 purchased at Costco and I LOVED it! A great travel outfit. It would be great with leggings for colder weather, was super comfortable for sleeping and was perfect as cover-up.
I began using hair wax just before I left (I have short hair) and it was amazing. I needed a small amount and it took up so much less room than hair gel and hair spray. I'm a convert!
I didn't bring a water bottle and I regretted it. I use a s'well bottle at home (I like COLD water) and would have liked in while in our cabin or hotel room.
I brought this purse: https://pierrebuy.com/collections/womens-bags-crossbody-bags/products/women-waterproof-nylon-shoulder-bag-corssbody-purse-travel-handbags-111771 It was fantastic. I kept my passport and money in the zipped pocked closest to my body, misc items in the middle pocket and my phone in the smallest pocket. I bought these keychain cables from Amazon: https://www.amazon.com/gp/product/B07FY6M1JZ/ref=ppx_yo_dt_b_asin_title_o00_s00?ie=UTF8&psc=1 and "locked" the pocket with my money and passport, as well as securing both straps to the purse.
I brought but never used a passport holder to wear under clothes. However, we didn't travel in what I would consider a pickpockets mecca. We did see signs at Zaanse Schans (or maybe it was Volendam?) in Amsterdam warning about pickpockets. I asked at a shop and was told that pickpockets were relatively new to the area and they tended to target Japanese tour groups, because of their reputation for carrying large amounts of cash.
My sister really appreciated our limited luggage, my mom less so (LOL). I like the Rick Steves bag, but would prefer to find something slightly smaller (maybe 35 liters?) But the bags I have found seem to have the same weight, which I don't appreciate. (for my height- 5' 3") the Rick Steves bag seems a little long on my back.
Looking forward to my next trips!