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I arrived to a rainy Montreal on Thursday and awoke to snow on Friday. Holding our second retreat in early April couldn’t spare us from the lingering, wintry weather of Canada. First lesson learned: choose a warmer destination for our next meetup.

As a fully remote team, Tortuga Backpacks has a policy of holding in-person retreats twice per year. Our first official retreat was last fall in San Sebastían, Spain. I say official because previous “retreats” were just excuses for Jeremy and me to take a workcation. Lauren joined us in Spain for a three-person retreat.

We recently held our spring retreat in Montreal, Quebec, Canada, with eight total team members. Even as CEO, I was meeting three team members for the first time. A few members of the team had never met anyone else in person.

Everyone arrived on Thursday or Friday, despite the typical air travel mishaps, before the formal part of the retreat which lasted through the weekend.

In this post, I’ll recap how we structured this retreat, what we talked about, and how the decisions we made on the retreat affect you: our readers and customers. Click to continue…

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Medical complications have a way of, well, complicating travel. Between the TSA’s myriad of regulations, customs officials, and figuring out just how to pack your medicines and medical devices, it’s definitely not an easy mess to make sense of.

However, after talking to travelers who need to carry medicines and medical devices, diving down a crazy rabbit hole of travel forums, I’ve uncovered answers to the biggest questions on traveling with medicines and medical devices.

From traveling with a CPAP machine to understanding TSA’s regulations with epipens and injections, it’s all here.

Medicines: What to Bring & How To Pack

Almost every traveler will need to pack medications with them at some point or another. Whether it’s birth control, Advil, or something only a doctor can prescribe, we’re all likely to include some in our packing lists as we travel.

That said, carrying on Ibuprofen, or any other over the counter medication, is usually pretty straightforward. Prescription medications are where things can get complicated. To demystify some traveler’s concerns, let’s cover a few common questions then get to the medication packing tips.

TSA Regulations

Whether you’re packing pills, liquids, or injections a good rule of thumb is to understand that:

  • Medications must be clearly labeled carry proof of some sort (i.e. a letter from your doctor) that it has been prescribed to you
  • Medication is subject to additional screening
  • Liquids are subject to the 3.4 ounce rule even medications

That said, some travelers might still have a few extra questions and want to make sure they’re playing by the rules (because no one wants to get something as essential as medicine confiscated).  Click to continue…

Did you know that major airlines let you bring one bag on your flight for free?

Yes, you read that right.

That’s a second bag in addition to the one carry on you’re allowed. It’s like they want you to pack light.

This free bag I’m talking about — if you’re not flying on a deep-budget airline (think Spirit, Frontier, or Ryanair) — is called a personal item. Standard size is 9 inches by 10 inches by 17 inches; the size of a backpack, or large purse. Think how much you could pack in this personal item — for free.

How can you max out the space in your personal item, pack light, and never check a bag?

I’m glad you asked. Here are packing lists and tips on how to pack 5 common personal items:

Backpack

A backpack is a great personal item because it’s easy to carry and leaves your hands free. Plus, it creates an extra buffer of personal space when you’re queuing up and need it most. But packing a backpack is challenging — everything jumbles together in that cavernous space.

Keep your backpack organized by creating homes for specific items in your pack.

For example, your book always lays flat across the back to avoid crumpled pages. Your water bottle’s home is down the right side next to the zipper. Snacks live in the outside zippered pocket for quick access.

Packing List For Any Trip:

  • Wallet
  • Smartphone (with good tunes loaded)
  • Book for reading
  • Extra set of clothes (if you must check a bag, don’t get stranded without a fresh pair of clothes if your flight is delayed)
  • Important medical needs (prescriptions, glasses, etc)
  • Sunglasses (great for shielding your eyes for a cat nap on the flight)
  • Empty Nalgene or Platypus bottle to fill after passing through security
  • Headphones
  • Gum
  • Mini medical supplies kit (Tylenol, Benadryl, Alka Seltzer, band-aids, safety pins, hair ties)
  • Laptop, or tablet, for watching movies or working on flight
  • Charger for laptop, tablet, & phone

How to Pack a Backpack


Layer the items by weight putting the heaviest on the bottom. Stand up long items so that they take up less space. For example, put a packing cube in length-wise so its space mirrors the backpack’s shape.

Put your wallet, or ID, in an outside zippered pocket for easy access, but shove them deep into the pocket, so pickpockets can’t simply unzip and snatch your wallet off the top.

Your laptop, or tablet, should lay flat against the back, so you can easily pull it out for airport security. Use packing cubes or clear Ziplock quart freezer bags (they’re tougher than standard sandwich bags) to keep like items together. I use a quart bag for my pens, one for snacks, and one for cords.

If you pack an extra set of clothes in your backpack, use a packing cube to keep them clean and organized. Slide the packing cube down one side of your backpack. On top, put the items you’ll need quick access to on your flight: quart bag of liquids, and a book to read.

Messenger Bag


This is the cool kid’s version of the briefcase. I like Timbuk2’s messenger bags due to their padded straps, inner laptop pocket, and water-resistant Cordura fabric that handles all my abuse.

Packing List For a Warm Getaway:

  • Sunscreen
  • Sunglasses
  • Canon Rebel5 camera
  • Honest baby wipes
  • Smartphone charger
  • Smartphone and headphones
  • Wallet/ID
  • Water bottle: Nalgene, Platypus, or Grayl if you’re going to a country with uncertain water standards
  • Snacks (never leave home without them!)
  • Good beach read
  • Sandals, or flip-flops: change into them when you hit your destination

How to Pack a Messenger Bag

Your goal in packing a messenger bag is to balance the weight. When one end of the bag is heavier than the other, suddenly I’m Hunchback of Notre Dame limping around.

Put items of equal weights on the two ends of your bag. For example, your water bottle and camera. Keep your laptop and book in the middle and lay them to mirror the shape of your messenger bag (i.e. with the long side down).

Purse or Tote

A leather cross-body purse is the bag I always reach for. Smaller than other personal items, it prevents me from over-packing.

Being forced to prioritize what’s in my personal item, I avoid lugging around dead weight I’ll never use. Who said restrictions aren’t helpful?

Packing List for Europe:

  • Wallet/ID in zippered inner pocket (or zippered outer pocket worn next to my body)
  • Platypus water bottle
  • Small paperback book (no room for a heavy hardback)
  • Small flashlight
  • iPod and headphones (holds more music than my smartphone)
  • Smartphone
  • Moleskine journal for travel notes
  • Pens in quart freezer bag
  • Burts Bees chapstick
  • Gum
  • Mini medical supplies bag (Alka Seltzer, Benadryl, Tylenol,  band-aids, hair bands, safety pins)
  • Sunglasses
  • Camera (if bringing)
  • Prescription glasses & extra contact case

How to Pack a Cross-Body Purse, or Tote


Use your bag’s shape to your advantage. If your bag has lots of outside pockets, designate each pocket for specific items. For example, one pocket is for your electronics, snacks, or chapstick.

Keep your valuable contents — ID, wallet, copies of any important documents — deep in your bag’s zippered pockets to dissuade pickpockets. Like the messenger bag, balance the weight evenly between the two ends of your bag to make carrying it feel lighter. I put my water bottle and camera in two opposite corners of my bag.

Diaper Bag


The littlest person in your family seems to need the most stuff. Done right, you can dispel that myth.

Strategically plan what’s in your diaper bag — like you do with your carry on — and your diaper bag will no longer overflow. Suddenly you may even have room to sneak in a paperback book, or two, for the long flight.

Packing List for Baby’s First Flight:

  • Washable, or disposable, changing pad
  • Blanket
  • Diapers for 2-3 days: plan for using more on the flight rather than less (my son can go through 3 diapers in 5 minutes flat)
  • Baby wipes
  • Burp cloths for young infants
  • 2 Changes of clothes
  • Snacks (if baby is old enough)
  • Breastfeeding scarf or drape, if baby is still nursing
  • Toys (if baby is old enough)
  • Benadryl (helps baby sleep on flight — always check with your pediatrician before giving your child any medications)

How to Pack a Diaper Bag

Packing cubes! Seriously, these will be your best friend. They keep the little clothes — like those tiny shirts and onesies — neatly wrangled and easy to locate when you need them.

Also, use packing cubes to keep similar items together: one cube for diapers and wipes, one cube for clothes, a third cube for snacks.

Don’t forget baby’s most treasured item, whether that’s a pacifier, or worn blanket, to bring the comfort of home with you on the road.

Briefcase

You lucky dog, you, going on a business trip. It can be stressful to prepare for anything that could happen, but, with some foresight and planning, your personal item will be cool and collected even under the toughest career pressure.

Packing List For a Business Trip:

  • Laptop
  • Laptop charger
  • Extra pair of clothes (if you checked a bag, bring extra clothes in case your checked bag doesn’t show at your destination)
  • Quart liquids bag (for same reason as above)
  • Pens
  • Notepads, or notebooks, for note taking
  • Smartphone & charger
  • Any work documents needed
  • An empty USB drive of at least 32G
  • Reading tablet, or pop fiction book, (like a Lee Child book) to distract your mind and decompress after a long day

How to Pack a Briefcase

Use the designated laptop sleeve or pocket for your laptop. Then, assign a function for each pocket and store specific items in each pocket.

For example: This pocket is for your pens. That pocket is where your chargers live. When you use an item, return it to its home.

Put the quart liquids bag and extra pair of clothes in a larger compartment. Pack the extra clothes in a packing cube to prevent wrinkles or stains.

TL;DR

Major airlines let you bring a second bag called a personal item — in addition to your carry on — onto the plane for free.

The top five personal items are:

  • Backpack
  • Messenger bag
  • Purse (cross-body or tote)
  • Diaper bag
  • Briefcase

Take advantage of this extra space by strategically planning what you bring in your personal item, so you can carry on and never leave home without an important item.

Beware: the standard size personal item dimensions can vary depending on which airline you’re flying. Always check the airline’s baggage regulations.

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