Civita daypack with roller

Perhaps you can take it to a good seamstress or shoe shop and have them sew a horizontal strap or "sleeve" on the back of the Civita bag that will slip over the handle of the roller bag. Do some google searches and find a small bag that slips onto a roller bag. Print out a picture of the back of it and let the seamstress / shoe shop use that as a guide. Just one thought -- maybe others will have more.

My wife uses a carabiner (or two) to attach the Civita to her roller handle (I don't use a roller). The Civita is really floppy so you'll need to experiment.

I realize it's always good to use what we have and just make adjustments but have you checked out Rick's new Ravenna day pack? It has the sleeve to slide over a rolling bag and is a bit sturdier than the Civita so it would probably balance on the rolling bag better.

Or the Euro Tote for over-the-handle. But it doesn't have backpack straps, just a cross-body one (which I use to get on/off trains rather than trying to maneuver roller-plus-tote)

All great suggestions -- thank you! Now, I need to make a choice - quickly! I leave for next trip in just under 4 weeks.

I use the Euro bag, which secures nicely to the handle of my RS rolling carry-on. The Euro bag, which slips easily under the airline seat, holds my CPAP, camera and things I want access to on the plane, but it would be pretty clunky as a daypack. So I pack my Civita bag, which weighs almost nothing, either in the Euro bag or the carry-on, to use for walking around.

I use these 24" Clippable Gear Ties to hold my backpack to the handle of our roller luggage.

My personal item & day bag are not the same bag. I use a 21" rolling suitcase & a 17" rolling backpack that can attach to it. Day bag is soft crossbody used as a packing cube in suitcase. I usually check the suitcase for the flights. The rolling backpack is great in the terminals & fits under all seats. I am 5'1" with very little arm strength. This has worked for domestic & international trips.

Probably TMI for most: But I added a strap to the back of my Appenzell day pack a couple of years ago for just this purpose. I used a length of 1" black webbing, seared the ends with a candle flame, sewed each end to the sides of the back about 1/3 of the way down. (It helped to turn the bag inside out - making it easier to get the sewing machine in there.) This worked very well, but the Appenzell bag has more structure than the Civita.