Do I check a bag or carry on?
I’ve done both and honestly it depends on the trip and what I need to bring. I Latin dance and sometimes I’ll be on a trip where I’m performing at and attending a festival – that requires a lot of extra gear so a carry on is tough. On the other hand, I’ve done three weeks in Europe with a carry on.
Regardless of whether you check your bag or carry on, DO NOT be that person with the giant rolling suitcase struggling down the cobblestone streets or taking up all the space on the train.
Here are some things to keep in mind as you choose your luggage:
Cobblestone streets and stairs. They are a thing, especially in Europe. I don’t care if your hotel has an elevator, you WILL encounter situations where you have to take a bunch of stairs and you have to walk several blocks on uneven pavement.
Tip: If you choose a rollie – a suitcase tat only rolls – it should be a carry-on size.
Think about a hybrid – a suitcase that rolls but also can convert to a backpack (but don’t get one that’s too big!).
Regional airlines and flights are different than the international ones. You may be able to get away with a slightly larger carry-on bag on your overseas flight (think Air Canada, WestJet, Delta, KLM) but once you are at your destination and hopping city to city or country to country on the smaller airlines, different baggage rules apply. Think more like the budget airlines back home (Flair). You likely won’t be able to carry your bag on and you’ll potentially have a bunch of extra fees for it, depending on its size and weight.
Tip: Always purchase luggage options with your ticket when you book regional flights. You’ll pay way more at the counter.
Caution: Consider the weight of your luggage, not just the size. Regional airlines often have several checked bag categories by size. If in doubt, you can bring a luggage scale with you. Or just drink the wine you’ve picked along the way instead of check it!
Don’t think just because you’re taking trains it means you can bring unlimited luggage. Some trains have luggage limits for specific ticket types. Even if they don’t, there isn’t a cargo hold like a plane where they can store your giant rollie.
There are some racks at the entrance to each train car and then some SMALL overhead racks above the seats and the space under your seat. Depending on when you get on the train, those racks may already be full.
Also, the more luggage you have to leave at the entrance (depending on where your seat is), the less you can keep an eye on it and the higher risk you have of it getting snatched at a stop when there are people coming on and off.
I went on a five week trip to Italy and France with my parents. It was their first time in Europe and I was a stickler. I mandates specific luggage and I was (as my mom put it) the packing police.
I promised them that at least once during the trip they’d thank me for it. Spoiler: it was more than once. Here’s what we used.
*I am not compensated for recommending any of the products listed in this post. These are only my recommendations from my own personal experience.
MEC Rolling Continent Carry On Pack (40L).
My dad used this bag. It was a little smaller than mine and my mom’s but it worked well for him. He got it on sale (it’s regular $229 so a little pricey). It is technically carry-on size (depending on how much you stuff it).
It rolls but also has backpack straps that you can zip in when you’re not using them. It’s hard sided but soft front and has one front pocket.
I don’t recommend getting the bigger size (75L). My friend got that one for our Spain/Portgual trip and it was harder to carry and is definitely not carry-on size.
Hynes Eagle Rolling Backpack 21″
My mom and I both used this bag (it comes in different colours, mine is black). We paid $139 for ours.
It is also a hybrid roller/backpack and the straps can be tucked away when not in use. It is soft-sided and soft front so you can stuff a lot in there. I also love that it has the straps around it so you can cinch everything in.
You can also zip away the rollie arm when not in use. I honestly love this bag.
Lole Expandable Backpack
We all used this as a personal item. We purchased our bags at Costco but you can also buy them on Amazon or directly from Lole.
These are great, high quality backpacks. The extra material on the shoulder straps help when you’ve got heavy items or are walking long distances with them. I also like the strap at the top to carry it and there is a strap on the bag to slide over your rollie bag.
It has many pockets including a laptop sleeve, water bottle pocket and others.
Travel Smart. Roam Free. 
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