Carry on suitcases plus backpack

I take a small carry on and a small backpack style purse, plus I pack an average size backpack so that on the return trip I have space for any purchases. Then, so that I still have only two bags, I pack the small backpack style purse inside one of the other two bags.

I'm going on my 8th RS tour in October.
The only real issue is that you need to be able to handle your luggage by yourself. I usually check a 22" bag, but might do carry on this year because of all the airport issues.

In addition to the above, I usually used a wheeled backpack.
I have not decided my exact plan, but will figure out something. I usually travel with trekking poles and a CPAP, which cause some challenges.

Most people travel with (at least) one "main" bag and one smaller item for daily necessities. (You can call them whatever you want, what they're called doesn't mean anything to the airlines, what matters to them are dimensions and weights).

There is really no mystery about what can be brought on board and what can't. Every airline posts their bag limits and policies on their website. Go take a look and note the limits for your flights on your airlines. The info is very easy to find. Then measure and weigh your bags (and be honest with yourself). Compare the dimensions and weights of your bags with the posted policy for your airline. There's nothing more to it than that.

There seems to be a lot of confusion as to what people are referring to, when they say backpack. You can get backpacks big enough to carry a whole camping trip worth of supplies, or small like a schoolkid's backpack for their books. There are carryon-sized soft bags with straps that let you carry them on your back. You can see Rick's versions them on the website. And then there are small ones like the Civita and Ravenna backpacks that people use as personal items both on and off the plane, that I think more people refer to as "daypacks".

So for example, look at the Rick Steves, luggage page, and see the Classic Backdoor bag (a backpack because of the straps and no wheels) which is my preferred carryon. I use the Civita as my personal under-the-seat item.

I take a sub-regulation size carry-on plus my "personal item", which is a small (8½x11x2½) case containing my netbook size pad, along with its USB charger and mouse, and some papers with important itinerary information (backup for what's on a spreadsheet on the computer).

I am not sure my bag can actually be carried on, but I am packing small and hopefully light.

Danger, danger! You must check the allowed sizes and weights on your airline and measure your bag. If it’s a no go buy or borrow another one. If you are connecting with another airline use the most restrictive measurements. This is a very bad time to be checking bags. They are getting lost/delayed at alarming rates mostly in Europe. Do not try to board with a bag that is just a smidgen too big. More people are carrying on to avoid losing a bag so the gate agents are becoming more vigilant. As for a backpack-as has been said there are backpacks and then small daypacks and lots in between. Many airlines don’t give measurements for the “personal item” but give examples such as a purse, computer bag, etc. Key point: it must fit under the seat.

I am not sure my bag can actually be carried on, but I am packing small and hopefully light. Just wondering how others manage.

You will have to measure your bag to see if it conforms to the carry-on size for your airline. I have a Travelpro 'international size' roller bag as my primary bag.

My 'personal item' is a bag like this--

https://www.eddiebauer.com/p/82300168/stowaway-packable-20l-backpack?sp=1&color=Onyx&size=ONE%20SIZE

I do not have it filled to capacity, so it always fits under the seat.

Use it as the day pack for water bottles, fruit, snacks; guidebooks. etc. Wearing it as a back pack or carryit by its straps works for me.

For your Rick Steves tour you can take anything you want as long as you can manage it between the coach and your room and return.

I have a wheeled carry on and a personal item. My personal item is a backpack that has a luggage pass thru that fits over the handles of my wheeled bag.

Thanx to all who have posted so far. I have an Away Bigger Carryon, which I know does not meet the carryon requirement to take it on the plane. So I plan to bring a backpack and a small crossbody bag. I want to pack light enough so that my luggage isn't a burden or something I have to think about all the time. I figured if I brought the carryon (4 spinner wheels) and my usual PacSafe backpack with a trolley strap to put it on the suitcase, I should be okay (as long as I keep them light!). I don't know how anyone packs a light carryon ad doesn't bring a backpack/bag of some sort to carry necessities (like pills).

As an aside, anyone going on the Best of Tuscany 9/26/22?

OP:
Again....check the rules for ALL the airlines you will be taking on your trip.
Check their carryon sizes and weights.
Bring the bag that conforms to the smallest size allowed out of all your airlines you will be taking.
Don’t forget to measure your carryon including the wheels!
Some airlines care about weight, some about size, some about both.
I think this year the rules will be stricter.
You can buy whatever you can’t bring from home....European shops are so much more interesting than ours!
Best of luck!

i have been traveling the last few years with a 20" travelpro 4 wheel spinner. no issues on any airlines from international carriers like qatar, klm and delta to regional and short-haul companies like ryanair, eurowing and vistara. i figured when my bag passed the ryanair test i was all set! my other carry-on is a camera bag (basically a shoulder/messenger bag) that fits under the seat. in addition to my camera gear i put all my paperwork, daily medication, and an ms surface in there as well.