Packing Hobo Style

Despite the fact that the High Class Hobo is not packing everything in a dirty handkerchief tied to a stick like the cartoons, packing is still one of the toughest parts of the pre-trip preparations, It’s difficult trying to essentially stuff your life into a backpack without any regrets.  When you’re packing it is REALLY easy to think you need certain items only to return from your trip later realizing you used it once or not at all.  Through a series of trial and error packing experiments The High Class Hobo concludes that she has finally discovered how to pack the perfect backpack.  I present these findings below:

Clothing – Like most females I ALWAYS overpack on clothing.  What if I’m hiking, at a pub, going to the market, in the mountains, on the dance floor, going for a run, viewing a temple, on the beach … we need so many different kinds of clothes!  One little word … versatility.  Try to pack clothing that will do double or triple duty for multiple scenarios.  This will also save you money because you won’t need as many items.

2 Bathing suits – one sport and one for beach lounging

2 Bras – one beige and one black, nothing fancy.  Buy ones with the hook on the back straps so it can convert into a racer back bra

1 Sports Bra – you will thank yourself if you invest in one with the “modesty pads”

Yes only 3 bras but bathing suits can convert to bras and unless you have gross amounts of boob sweat bras stay clean longer than most clothing.

5 Dryfit Underwear – now I’m not one to tout brand names but “Lululemon Light as Air” underwear has altered my life. It feels like a glorious cloud swirling around my bottom. I will never wear a cotton, piece of crap, loin cloth again!  Buy a pair of these babies and you won’t experience swAss even if you are walking through the Sahara Desert. Wear them one day, turn them inside out and wear them again the next day to make a pair last longer.  Buy them at the Vaughn Mills Mall where they are half the price of a normal Lululemon store.

Light as Air Dryfit Underwear

Light as Air Dryfit Underwear

Pack of thin sport socks – wait for this deal, socks always come on sale in sport stores sooner or later.  I really like the UnderArmour socks but you can also buy a padded pack of Champion sport socks at Costco for $14 (get that kind relative with a Costco card to bring you shopping)

1 Pair of Wool Socks – You HAVE to get a pair of Redhead socks from the Bass Pro Shop.  I swear these socks must have been woven with a million mini rays of sunshine. You’re feet will be warm and dry all day.

Redhead socks

Redhead socks

While we’re on feet we might as well talk footwear.  Resist taking “those pumps you’ve always wanted to wear out partying” or “that cute pair of strappy sandals that would match your sundress perfectly!” You are on your feet all day and blisters ruin vacations.  My recommendations:

Running Shoes – yes, they’re not stylish but they are meant for running!  Which means they are definitely meant for walking all day.  Also you won’t need to spend money because who doesn’t own a pair of running shoes? (even if they are buried way in the back of your closet from the last time you fell off the New Years Resolution wagon)

My Running shoes with a hiker sole.  Wait for end of summer deals on the clearance rack at Sail.

My Running shoes with a hiker sole. Wait for end of summer deals on the clearance rack at Sail.

Basic Flip Flops – I’m talking about the $3 garbage ones from Walmart.  You will want these on the beach (you won’t be afraid to leave them while you go swimming) and you will want them in the shower (because who knows what kind of fungus grows in hostel showers).  Try to get the really thin ones, they pack better.

$3.99 Clearance special

$3.99 Clearance special

Birkenstocks or another solid sandal – It is nice to have a good pair of sandals that you can walk all day in for the really hot climates or for the times your shoes get soaking wet and won’t dry because the air in Ecuador is so frikkin’ humid! … wait for them to come on sale at the end of the summer season before you buy.

Another versatile footwear option is hiker/sandals.  They are like low cut hiking boots but there are open spots around the toes with a draw string lace.  Can be worn with socks or not, no faux paux there.  Extremely versatile and can be found at sports stores like Sail.  Check the sale rack, Hubby Hobo found his Solomans for $30.

1 Ball Cap, 1 Touque, 1 Scarf, 1 Pair of Gloves – The ball cap is nice to keep sun off your face or when you’ve gone 4 days without showering and your hair is gross.  A toque provides a lot of warmth for only the little bit of space it takes up.  For a scarf I bring a stylish paschmina.  You can get these for under $10, it provides warmth, can dress up an outfit, can cover your shoulders in temples without being too hot, and you can use it as a rope to tie stuff to your bag.  I like gloves because my hands get cold and if I’m climbing or hiking there can be sharp vegetation.

Outwear – I bring one jacket on vacation because no matter where you go, it is always going to get unexpectedly cold.  I remember vacationing in Honduras and wearing a toque and every layer of clothing I had in the evening because they had a record low cold snap.  For my upcoming trip I splurged on a Mountain Hardwear down jacket.  These are incredibly warm and it can be squished and then zipped up into one of its own pockets!  In Canada these usually cost $280 and upwards, but in true hobo fashion I waited it out until I found one on sale for a smokin’ deal!  I am also going to bring a rain jacket because while down is extremely warm, it is not waterproof.  Before I bought my new rain jacket I was wearing my Mom’s old Northern Reflection one (does that place even exist anymore?).  I pretty sure that jacket was made out of recycled nascar tire rubber and chewing gum; it was SO hot and sticky to wear!  The new jackets breath really well and mine also folds up into it’s pocket.  If you don’t want to bring a rain jacket I would recommend the 99 cent poncho from Sail.  But be warned: it’s a one time use only because once you take it out of that tiny little ziplock bag there is NO WAY you are going to be able to stuff it back in.

Super warm jacket

Super warm jacket

Jacket folded into the pocket.

Jacket folded into the pocket.

Tops – One word; DRYFIT.  There is nothing worse than having a dirty, sweaty, pit stained shirt and then having to put it on and wear it the next day, and the day after that… and the one after that.  I’m pretty sure dry fit was invented by a wizard or some magical fairyland creature.  How does it work!?  It just soaks your sweat up and makes it disappear!  I will be packing 4 t shirts and 4 tank tops.  Two of each will be dry fit, one of each will be cotton, and one of each will be a nicer top that I can wear out at night or dress up an outfit with.  I will also be packing two long sleeve dry fit hoodies.  Dry fit hoodies are key when doing any type of hiking because you don’t get too hot yet all your skin is covered which protects you from bugs and vegetation.  You can put a ball cap on and your hood, draw the drawstring tight and not too much can get at you.  For Hobo deals I suggest getting a group of friends and going shopping at the UnderArmour outlets in the States for a weekend.

Bottoms – Pick versatile bottoms because they can take up a lot of room.  I have a great pair of black Columbia pants that fit nicely, dry well, can convert into capris, and have a lot of zippered pockets.  I will also bring a basic pair of tights because they don’t take up much space, can be stylish, and can also be used as an extra layer for warmth. I have a pair of workout shorts, a pair of short board shorts, a pair of longer board shorts, and a pair of jean shorts.  Do NOT bring jeans!  They take up way too much room, provide no warmth, and for the most part are very impractical.

Sunglasses – pick a sport pair with good UV protection.

Sundress – Yes, you may pack ONE sundress because they can go over a bathing suit, be worn out at night, or maybe even worn as a shirt over tights if you get desparate.

Accessories – sorry, you don’t get any.  Pick one pair of earrings to wear.  Make sure they aren’t dangly and that you don’t care if you lose them.  Leave all your jewellery at home, it just makes you look rich which makes you more of a target.  You can, however, bring a headband. This can be a bandana or a thick yoga headband.  This will cover your greasy hair for the days you can’t shower, will soak up sweat, and is key to sleeping on a plane.  When you want to sleep, simply pull the headband down over your eyes and voila, instant night time!

My favourite headband.

My favourite headband.

Medication –  I am going to do a whole post on medications and immunizations, stay tuned.

Toiletries – this is another easy section to overpack in.  I know that “your hair just doesn’t handle the humidity well’ but you’re going to have to leave home your $300 straightener and special salon shampoo.

Toothbrush, Toothpaste – buy travel size, good deals at Target or Walmart

Brush and Hair Elastics – again, buy travel size

Hand sanitizer – you might not always have a chance to wash your hands.


Tampons – these are a pain in the butt to haul around but it is often hard to find Tampons in other countries.  The good news is that as your trip goes on, your load gets lighter.  You could bring a DivaCup but then you have to worry about washing and disinfecting it and those amenities aren’t always available.

Deodorant – .. or not, you can choose if you want to make friends or be alone.  Buy travel size.

Shampoo and Conditioner – sometimes you can buy a two in one.  Try to train your hair before you go on vacation to be washed less.  Simply start washing it less and less (for God’s sake, please still shower though!). You’d be amazed how long your hair can go without looking greasy after you “train” it.  This will make your shampoo last longer and your hair healthier.

Bar of Soap – leave that luffa and body wash behind, a bar of soap is way cheaper and takes up way less space.

Detergent – these mini tide to go packets are genius!  They will save you lots of money on having someone else do your laundry.  You can do your own laundry in the sink with these.  Since you’ve mostly packed dry fit, it will all dry quickly.

Mini Tide packets for laundry in the sink.

Mini Tide packets for laundry in the sink.

Sunscreen – in touristy areas, especially near a beach, they gouge you for sunscreen!  Pack a sport version with a high UV protection.  Even if you have a good base tan, the sun is A LOT stronger than a heatwave in a Canadian summer.

Straightener – now I know I said earlier to leave your straightener at home, but you can get mini styling tools that actually work pretty well!  I have a tiny straightener I will be taking.  It is a good conversation starter too.  Girls are suckers for straighteners and will ask to borrow it if they see it plugged in on a counter.  This is a great conversation starter which might end with an invite to hang out for the evening.

Mini Hair Styling tool

Mini Hair Styling tool

Makeup – If you’re like me and you have blond, non existent eye lashes, people get genuinely concerned when you don’t wear makeup.  They think I am ill and ask me if I’m OK.  For the space a tube of mascara takes up, I will be bringing it so people don’t treat me like I need a bowl of chicken soup and bed rest.

Dry Shampoo – if you know you are not going to have access to a shower dry shampoo is a lifesaver. It’s pretty much baby powder in a bottle and you spray it in your hair. It doesn’t actually clean it but it makes your hair look like it’s not about to transition into dreadlocks.

Dry Shampoo -  a shower in a bottle!

Dry Shampoo – a shower in a bottle!

Toilet paper – in many parts of the world you have to pay for toilet paper in a public restroom or they only offer a spray/budday option. The travel ones are $1 and they come with no roll in the middle and a plastic case so your paper stays dry.

Toilet Paper in a waterproof container

Toilet Paper in a waterproof container

Razor – if you’re going to the beach you might not want to look like a wooly mammoth. You don’t realize how much you miss a razor until you go without. I remember visiting an impoverished rural area in Cameroon, Africa. The students rushed out from the schools because they had never seen white people. They ran their hands up my legs to feel my white skin and I hadn’t had a chance to shave for a week. They must have felt like they were petting a cactus!

Technology: everyone will be different on this department depending on where you’re travelling and how much you choose to shut yourself off from the world.

Smartphone – I bring mine because for the small amount of space it takes up I can take pictures, videos, update my blog, and when I have wifi I can text and FaceTime my friends and family at home. Just make sure you turn your settings to “airplane” mode or you find a nasty phone bill waiting for you upon your return. I also have a waterproof sealable case I bring so I can take my phone rafting for pictures or out if I get caught in the rain.

Camera – I have a FujiFilm XP. This thing is waterproof and virtually indestructible . Perfect for a rough hobo like me!

Indestructible Camera.

Indestructible Camera.

Surface – I was lucky enough to find a Microsoft surface on kijiji for a quarter of the price of what they cost. This is a tablet with an attachable keyboard. Why I chose the surface over the iPad is the USB port. I will not always have wifi but if I have movies on a USB I can still watch them. Not that I plan on watching a lot of movies but sometimes it’s nice for the long bus rides. It is also easier to book flights and other travel arrangements on a computer as oppose to a phone.

Backup Charge – this separate device can recharge your phone for you. It is handy for when you’re camping and going days without electricity but you still want to use your phone as a camera. You get a free one in a 24 of Budlite right now or you can find them cheap on

Charger for phone or computer.

Charger for phone or computer.

Earbuds – sometimes you just need to block out the baby crying on the plane or the chicken clucking in the bag on the bus beside you. Pop in some tunes to reenergize.

Alllll extras:

Flashlight/headlamp – a lot of the rural parts of the world are pitch black when darkness comes. It makes for beautiful star gazing but no vision.

Sleeping Bag – ideally you want your sleeping bag to provide you extreme warmth and take up virtually no space. It seems that the smaller and warmer the sleeping bag, the more money it will cost you. My dad found me a very small bag on sale at Canadian Tire for $50. It is good to 7 degrees Celsius. For the places I will be travelling this should be fine but if you are travelling to Nunavut, a high mountain area, or Antarctica you may want to look into something better.

Pillow – please don’t bring your pillow from your bed at home… No matter how comfortable! One of the blow up airplane pillows or one of the foam squish into a small bag pillows will do. Another options is to forgo your pillow and stuff your sweater into your sleeping bag holder and use that.

Earplugs – aka: sanity savers. A good nights sleep = a good day. There will always be people talking or snoring. You can sleep really well with earplugs, but don’t worry, they let enough sound in that you’ll hear if something major happens and you need to wake up.

Towel – a microfibres towel is key. It takes up very little space and is quick drying. And hey, it’ll make you appreciate that fuzzy, warm, large bathroom towel you have when you get home even more.

My Hand is in the picture for comparison.

My Hand is in the picture for comparison.

Knife – jack knives always seem to come in handy. Don’t bring it in your carry on!

Nuts/protein bars/granola bars/trail Mix – the diet in North America boasts a lot of protein. Oh, and the Germans like their meat too. Anyway, if you don’t want to feel the protein withdraw and watch your muscles shrink bring some protein. The rest of the world eats a lot of rice!

Collapsible water bottle – this will save you money if there is a spot fill up your water bottle with CLEAN water. Once your done it can fold up and be put in your backpack or pocket.

Fold Up water bottle

Fold Up water bottle

Passport, hotel bookings, flight papers, money, credit cards – bring alllll your paperwork, then take pictures of your paperwork, documents, and cards so you have a copy on your phone. Then photocopy everything and put it in 2 different bags (backpack and day bag). Leave a copy of everything with a loved one at home. Always keep your passport strapped to your body. (In Cameroon 4 of us got stopped by the police and they wanted to see our passport. Only 2 of us had them. They weren’t going to let us go and finally the cab driver translated that we could go if we gave them beer or $20 each…. We didn’t have beer so $80 later we were free to carry on). If you’re in a safe hotel you can leave it but hide it somewhere. Also disperse your money and hide some mad money somewhere. I like to hide money in an empty Chapstick tube.

Lonely Planet Travel Book – these take up a lot of room but in my opinion it is completely worth it. These books were written by people who travel a certain country in depth and give accurate and trustworthy advice on EVERYTHING. It also provides any information you could possibly want to know on the country. There are handy maps and suggested itineraries based on the amount of travel time you have. You can buy the books based on continent rather than country to get more bang for your buck.

Journal – even though I have a blog I’ll want a spot for my private thoughts and experiences. It also comes in handy later when trying to figure out captions for pictures.

Other things I will be bringing are first aid kit, mosquito net, Canada stickers etc for the kids I’m going to teach, arm band for running, ankle braces, lip chap, whistle, and donations for the school/orphanage.

Well, that’s all that is fitting in this Hobo’s backpack. Let me know if I missed anything before it’s too late!

One thought on “Packing Hobo Style

  1. Pingback: Tips for Packing a Backpack | The High Class Hobo

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