Our first post retirement trip was seven months. It included an African safari that limited us to one bag. We had previously met other retirees on our travels who did carry on only for two and three months at a time. Our typical winter trip, pre covid, is 60 days.Pretty impressive that you are able to travel internationally for a month(or more) and only do carryon. I still need to check a bag (sometimes 2) for the family. It's a least two if I try to mix work/holiday into the same trip. If it's strictly work I can easily do a week with carry on. Thankfully due to status I have free checked bags. However, if I can remove one obstacle in getting delayed I will gladly do it. What's your secret? I can't remember if you have multiple stays in Portugal or just set up one home base for the duration.
We decided to do it. Bought international size roller carry ons so that was the max. Each time we return home and unpack we take note of what we did not use or hardly used.
Our issue is also that we have to limit ourselves to what we can each physically handle on trains, ferries, rentals, carrying up stairs etc.
On many flights we also have free baggage check. On one carrier, Australian Jetstar, we actually pay a premium for carry on.
Also did lots of business travel so I was accustomed to carry on. Spouse……more difficult for her.