Packing for Long Trips: How to Pack Smart and Be Comfortable

How to travel comfortably for months at a time

by Carolyn Ray

For the past three years, most of my travels have been for several months at a time. In 2021, I lived in Merida, Mexico from November to February 2022. In 2022, I lived in Malaga, in southern Spain. And in 2023, my home base was Italy from December to February 2024.

While every year is a different destination and climate, my packing rituals are the same – pack smart and for comfort. Although I still tend to overpack, I am learning that having too much stuff only causes more stress and anxiety. When you pack light, you can move around easily and lift your own bags onto trains or planes. Packing  for long trips is about staying safe as much as anything else. And for me, it’s about being comfortable wherever I am in the world.

Tips for Packing for Long Trips

Find your packing system

There are certain rituals that come with packing, and one of them is having a system. I use a cross-body bag, a small Gregory backpack and a larger bag for clothes. One, two, three. Before I step out of a hotel room, Airbnb, plane or train, I do a mental check that all three are attached to my body. There are no loose items, everything is in a sub-bag and organized. Electronics in one small bag, travel documents in another, clothes in packing cubes. The only thing I have ever lost is a hat and a jacket because they weren’t attached to the bag. I put a business card with my phone and email address inside everything just in case I lose them.

Cross-body bag: My cross-body bag never leaves my body except when I sleep. In it, I keep my phone, passport, hand sanitizer, sunglasses and keys. Many women recommend either the Travelon or Sherpani cross-body bag – whatever you choose, make sure it closes firmly and stays close to your body.

Backpack: My turquoise blue Gregory backpack is decades old, but it works well for me. Inside this, I have my computer, file folders with travel details, and a bag with miscellaneous items including my headlamp, medical kit, bandaids, sunglasses, Kleenex, etc. I use a very cosy Cabeau neck pillow and face mask that collapses into a small circular package and attaches to my backpack with a clip. I also carry a stainless steel water bottle and fill up at airports (why pay $5 for water?)

Luggage bag: I used to travel with a 70L Osprey backpack; in fact, that’s what I did in Mexico. While I like the simplicity of a backpack, I’m into comfort now, so for the past two years I’ve used a soft-sided wheeled Victorinox bag. I have two sizes, a small one for multi-week stays and the other for longer stays, which is still small enough to carry and lift myself (especially on a train) although it’s not considered a carry-on.

I am not one of these people who is obsessed with carry-on only, there is just too much stress trying to ‘keep up’ with some ridiculous idea that we must travel carry-on only, especially on a longer trip. I am a comfort packer now. Whatever bag you use, make sure it is good quality. I have seen people with broken zippers and wheels that fall off — you don’t want that when you’re trying to get everything to fit. My rule is that I must be able to carry and lift my own bag. I am one of the lucky ones who has never lost a bag even though I generally check it. All the valuable things are in my backpack or cross-body bag anyways.