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How women can 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.

Clothing, shoes, and accessories

Packing clothes: The key to packing for all kinds of weather is layers. I generally bring one of each item. For example, one long-sleeved shirt, one tank top (that doubles as pyjamas), and one short-sleeved shirt. I find jeans bulky and try to avoid packing them, instead, I prefer Spanx leggings, which I can layer under a lighter pair of pants in the winter. Leave room to buy new things – in Italy, I found some colourful, locally made knitted tops and scarves I could not have found at home.

Packing shoes: For shoes, I bring a pair of sneakers for walking and ‘dressing up’, a pair of hiking boots or sneakers and possibly short (not long, they take put too much space) boots for the winter. Again, those boots work for dresses and leggings.

Jacket: I have found that the only jacket required is a puffy jacket, even in the winter. Occasionally, I will bring my ‘angel’ jean jacket but only if I have space or think it will get a lot of wear. I layer my puffy jacket with a hoodie and a vest with pockets. That’s more than enough for most weather, even in Norway, where I was recently.

Underwear and bras: This is one area where I load up. Underwear don’t take up a lot of space so I usually bring 10-15 pairs that I can wash in the sink if needed. I only wear wireless sports bras (mostly from Lululemon) that can double for exercise. (See women-recommended travel bras here)

My staples: There are some items that I can mix and match, that work in both hot and cold weather. My lightweight sleeveless Sweaty Betty black dress is stylish and works well in hot weather. In cold weather I add Spanx leggings underneath and a long-sleeved shirt. I have a Lululemon vest that works well in all seasons that I wear with a long-sleeved shirt or hoody.

Packing cubes: I love packing cubes, not only because they compress my clothing but because they organize it. I generally use three cubes (one large, two medium) and bring an extra one to store dirty laundry. Look for cubes with strong zippers and fabric above all else. I always look for places with a washing machine so that I can cycle clothes around.

Things I always bring for comfort: I never leave home now without my slippers, a light bathrobe, pyjamas and a hair towel. While these may feel like luxuries, they make me more comfortable and many places don’t have carpet anymore. No cold feet for me!

Raincoat or umbrella? Honestly, I don’t bring either. Umbrellas can be easily purchased in a destination if you need them and I find a puffy jacket does the job in windy weather too. In a pinch, you can find a poncho!

Health, wellness, and beauty

Medical supplies: As a migraine sufferer, I need to make sure I have enough medication for at least 3-4 attacks while I’m travelling. I also pack bandaids, aspirin, vitamins, seasickness pills and cold medication as I tend to get sick near the end of trips. Having 2-3 extra pairs of contact lenses is a must for me, plus my backup glasses, although I can usually find cleaning solution anywhere. Make sure you have a copy of your prescription just in case. Pre-menopause, I learned that tampons can be hard to find in certain countries, but thankfully that’s not an issue anymore!

Suncare: It’s vitally important to protect your skin when you travel. I love hats and scarves but I only pack one baseball hat with me as my ‘bad hair day travel hat’. There’s nothing I love more than finding a unique hat or scarf, and it makes a wonderful memento from travels. I always bring reef-safe sunscreen, a pair of strong sunglasses and a small container of bug spray.

Makeup and hair accessories: On some trips, I bring my small travel hairdryer. Generally, I keep makeup to a minimum and avoid liquids altogether. I always bring my own hair conditioner, but I buy moisturizer when I arrive, plus it’s fun to see what’s available. I’ve found some great products and I find that cosmetics in Europe have less chemicals. I also bring a small mirror, face trimmer and hairbrush.

Packing for long trips tips from our readers

Many of our readers are also nomadic or stay longer in places. Here are their tips:

Become acquainted with the second hand/charity shops at your destination. Great for getting a few extra comforts and getting rid of stuff when you leave. I’m in France on a long stay at the moment and was amazed to discover the other day that Galleries Lafayette (upmarket département store) now has a recycled clothing department! — Terri M.

I send a photograph of my checked luggage to myself. I needed that one time, to help describe it to the Lost Luggage staff. — Laura C.

I bring a mushroom sink stopper to do sink laundry, also a travel-size sewing kit. — Lois S.

I always like to carry a mini kettle and a mini rice cooker as it is very practical and one can always use rice with a can of tuna. I always check if the countries allow pepper spray or I do my own chilli and pepper as it has saved my life twice! — Claudia S.

I get my hair cut the day before I leave, and the best walking shoes x2 so I can swap them every day. For my smaller carry-on I use one large simple bag as the shell that fits two smaller laptop-size bags inside, all of them different colours. This way I can keep things separate on the flight, and it means I have 3 bags to use as “day bags” while I am touring around. Like you I travel most of the year and always do carry-on. — Tania C.

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