I’ll try to make this short, LOL. I benefited so much from reading the posts on this thread, thought I should share my own experiences.
We four 70+ travelers, 2 couples, spent 3 nights in Lisbon, 2 weeks on a small luxury cruise ship and 3 nights in Rome. The weather ranged from 70-80 degrees and late in the trip, we had a few rain showers. I checked my older Travelpro carryon, and managed to get everything in without expanding it until returning with a more stuff. My personal item was a Sherpani Soleil tote/backpack.
Positives/Glad I Brought:
Coordinated black, white and grey basics
Lightweight Eddie Bauer hooded rain jacket instead of an umbrella
Lightweight Eddie Bauer Stratify pants with zippered pockets
Zella yoga pants and cashmere cardigan for plane; ended up wearing more than I expected
Compression socks for plane
Coolibar SPF 50 cotton long sleeve wrap
Inexpensive H&M cream blazer for dinners on the ship
Eileen Fisher black waxed cotton moto jacket-very versatile for day and night
2 dresses, 1 midi, 1 maxi
20-year-old black leather Mephisto sandals instead of sneakers for hot days
Flip flops, swimsuit and caftan coverup for pool area
Eddie Bauer crossbody bag for excursions
2-bra laundry bag and bag for dirty laundry
Detangler brush for shower
Chi travel flatiron
Small plastic water bottle; glad I left nice larger, insulated bottles at home
Negatives/Wish I Didn’t Bring:
Sunscreen that left white marks on black clothing
A few cosmetics I never used
Stashbandz belt for security; I ended up wearing my RS money belt instead
Short sleeveless dress only worn once
Wish I’d brought:
Lightweight hooded yoga-type jacket with zippered pockets
More garments with pockets
PS. I’m still 50-50 on the Sherpani Soleil bag. As others have pointed out, it’s a bit heavy, and doesn’t carry as much stuff as some duffels or totes, but it has a ton of security features and I was able to get everything I needed into it for the plane. I’m also disappointed it’s kind of difficult to get the sleeve on the back to slide easily onto the handle of my carryon bag.