Addirional Carry-on for under the seat.

An airlines won't allow you to bring two carry-on sized bags on the plane, one will be checked. I would stick with the shoulder bag or a computer bag. You don't want to have too much luggage when you are trying to get up the very steep steps on the train.

Donna

I'm planning to use the Rick Steves Ravenna Day Pack as my "personal item" during my upcoming trip. Be sure to check your airline's specs for what they allow.

A small backpack, such a a daypack, works well as your under-seat carry on. We all carried the Osprey Daylite on our last trip. It fits under the seat fully stuffed.

I use a 20" rolling carryon and the Ravenna daypack (or Civita daypack). The Ravenna daypack fits over most rolling carryons.

I carry on board a 20 inch rolling carryon bag and the RS Euro Flight Bag. There's a video about this Flight Bag at the Rick Steves Travel Store, Luggage link.

The key is: will it fit under the seat in front of you.? Several of the RS bags do fit and I also use the Red Oyxx Gator at times.

Some luggage companies like Eagle Creek make a small bag that fits perfectly over the handle of the rolling bag for transport, and then can fit under the seat on the plane. Dimensions are something like 18x10x6. It comes with a shoulder strap as an alternate means of carrying, but Infindnit too cumbersome to use as a day bag, so have that folded up in my luggage.

Laura some airlines publish size restrictions for the "personal item" as well as the carryon. Sometimes you might get away with it, but really, there is no meaningful difference between a "carryon" and an "almost-a-carryon" - sized bag.

Hi Laura, I carry on a 21 inch suitcase and my Personal Item is the Kipling Sherpa Bag, it has a pocket in the back that is made to go over your suitcase handle. It fits perfectly under the seat and meets most airlines personal item size requirement. It is very logically designed for travel. It has a large front pocket for my tablet, boarding passes, passport, etc and two larger pockets in front for medication, hand sanitizer, glasses, snacks...and a very large middle pocket that I use for a scarf, makeup, socks and anything that did not fit in my suitcase.. After purchasing it I noticed so many people with this bag on flights. It is large but when I do carry on only I found that the combination of my carry on and this bag was perfect.

I would go to the airline's website and read exactly what they state for size of both the carry-on and personal item.
Today policies differ per airline and some publish exact max measurements and weights.
I wouldn't want to risk exceeding them.

The RS Veloce bag is perfect! There is a discussion about it in the Packing Thread.

I used to use a Sherpani Sojourn, an early one that I liked better than this: http://www.ebags.com/product/sherpani/sojourn/206394 But I found I tended to carry too much in my underseat bag. I also have a RS Eurobag with the same issue. It was convenient to place it on the handle to wheel, however, I found I liked my absolutely don't lose items attached to me rather than on my suitcase and the sojourn/euro type bag encouraged packing too much. I like my absolutely don't lose items in a smaller bag i.e., purse, cross body. Then I know all I need is that purse and not the rest of my stuff. Whereas, once off the plane there were many items in the sojourn that I didn't need anymore to get by and/or wouldn't be tragic if I lost. Consequently, I found myself juggling three bags even though the purse wasn't huge it was a pain. Lately, my system has been a cross body purse that fits my camera, meds, iPad, phone, Passport, etc. (On my next trip this bag will be the Veloce Guide Bag for iPad.) When I get to the gate or on the plane (if I am carrying my suitcase on, which I usually check now even though it is a carryon) I pull a reusable shopping bag from my carryon wheelie that has the rest of what I need at my seat in it. This reusable shopping bag is large enough to throw my purse in if the gate people balk at my system. This reusable bag also folds into a tiny pouch that fits in my purse for during the day sightseeing for purchases or anything else I accumulate to carry along the way. When I get off the plane I put this bag with contents back into my wheelie, have my purse cross body, and go about my business. That way I have one 20" wheelie and one not too large purse to keep track of...and the purse is attached to me cross body so my wheelie is easy to pick up or wheel as desired and I always have a hand free to hold a bannister, etc. With the bag on the handle of the wheelie, it was always necessary to remove it when going up stairs or onto the tube, etc. and that is a pain. This information is not what you asked for, but I'm just giving you a different option. When in transport the reusable bag with contents is in your wheelie versus on top of your wheelie. I think it helps me to pack light as I see many people say they pack light but their personal item is bursting at the seams, as is their wheelie or backpack.

Here's a type of reusable bag I am talking about:
https://www.reisenthel.com/en/mini-maxi-shopper.htmlvarID=657bd86ea671fd1b1e4d0a1b463e1e82
I also sometimes just use a cotton reusable bag. This being said, I am a bag and travel bag/organization addict so my system changes and adapts, but this is my present system. Have fun searching for your system. Wray

I use the Rick Steves rolling carry-on and the Euro Flight Bag, which slides over the handle of the roller bag and snaps securely. The Euro bag is very roomy. My wife and I actually just used it for an overnight trip for both of us. But it slides easily under the airline seat. Last year, I used the roller bag, carried the Civita day pack on my shoulder and tried to use a third bag for my CPAP (permissible as a medical device) looped over the roller bag handle. It was a huge hassle, as the CPAP bag wasn't very secure, so I was constantly having to mess with it while the day bag flopped around on my shoulder. Now I use the Euro bag to carry the CPAP, camera and stuff I want access to on the plane. The Euro bag solved all my juggling problems and I roll happily along. Color me a satisfied customer.

Like Wray said, I'm also a bag addict. One of the things I noticed from the linked bags is the weight. That's something to pay attention to if you're going to carry them separately at any time.

I like to have a tote as my personal item. It needs to be big enough to hold the little purse I take, along with my meds and electronics, small enough to go under the seat, and designed to slip over the handle of my roller bag which is U-shaped, not T-shaped. My go to brand is baggallini. The ones linked are all ones I own and have used. All can be worn crossbody if desired.

So far I've purchased my baggallinis at TJ Maxx and online on sale. There are many online vendors that carry them. I don't think I've ever paid full price.

Hobo Travel Tote: I have this in red with a light orange interior. I find it a little small for my needs, but it can be used as a purse. It's the lightest at about 13 oz.

Alberta Travel Tote: I have this in purple with a chartreuse interior. I got it because the one below was slightly too big for British Airways. This is the heaviest at 1 lb, 10 oz. The shoulder straps were too tight for me, so I removed them which made it lighter.

Santiago Tote: I have this in charcoal with a bright pink interior. It may no longer be available. It weighs about 1 lb, 5 oz.

Kindred Tote: I have it in light blue with a chartreuse interior. I can't find it available anywhere. This one weighs in 1 lb, 6 oz.

The exception to my baggallini fetish is this reuseit Flip & Tumble bag. It weighs nothing and folds into its own little sack. I found it perfect for carrying anything extra that was too big for my tiny charcoal baggallini Nassau and too small for my tote. Now if I could only travel for a short enough time meds-wise that I could use the Flip & Tumble instead of any tote.

There are so many options that it makes the choice a challenge. Good luck!

Like Wray and Lo, there has been an evolution in my finding the best personal item/day bag for the way I travel. Not too big, not too little, not too heavy, but just right. What I have ended up using is the result of very similar logic that Wray used. I pack light and do carry-on only and want a system that for me is the most efficient to handle. Like Lo, Baggallini is my favorite due to the light weight.

To determine what size bag you want without it being too large, bulky, heavy or too small, I suggest making a pile of what you like to have with you when you leave the hotel in the morning and will be gone until evening. Some people can get by with minimal items. I want enough room for day’s money, camera, phone, water bottle, light sweater or windbreaker, maybe umbrella, snack, small pouch of might need items such as aspirin, Kleenex, bandaids etc. Then consider what additional items you want with you on the plane but wouldn’t be carrying daily. Can you find a bag that will work for both situations? What feature(s) are a must have? Check the empty weight of any bag you are considering. Get the smallest possible that will fit your need. If you need larger for plane, Wray’s solution of a tote bag for plane seat items, and dropping the day bag into it for boarding keeps you in airline compliance.

I did ‘customize’ my crossbody bag a bit by sewing round key split rings into the lining. I then attach coiled lanyards https://www.rei.com/product/862376/seattle-sports-drydoc-coiled-lanyard-package-of-4 to the rings and to any item I want more secure such as coin purse, or camera. These stretchy lanyards allow me to use the item without unhooking, reducing the chance of my dropping or losing it and possibly deter a pickpocket.

If flying on multiple carriers, make sure your personal item bag meets the requirements of each carrier.

I was practicing with my luggage like Rick Steves suggested and found that using a back pack was much handier when pulling my luggage around. It kept my hands free and yet I was able to put stuff in it and not be heavy.

Just put your medium-size shoulder bag inside the larger one you want to bring and put the whole bundle under the seat. Just be sure it's all collapsible, soft material that you could pack away eventually. But, that gives you a choice of bags to carry around during the day. I usually have a day backpack with a small, soft purse inside. Some days I use the purse, some days the backpack, depending on where we are--city or mountains.