How to Pack Like a Pro [Part One]

FIVE DAYS PEOPLE. Five days until I roll around the sand begging my friends to bury me in it. Five days until I trip and fall over cobblestones in the streets of the old town while lost in the colors and vibrancy of the buildings. Five more days until my ears bleed from constantly spending my nights in loud salsa bars blaring the classics from the island like Celia Cruz, Marc Anthony, and Tito Puente.

Have absolutely no idea what I’m talking about? Then you seriously need to check this out. Anyway, since I’m packing for a who knows how long trip (really, this could be three months, three years, or thirty years) I needed to do some serious thinking about what was really important in my life and what wasn’t. It has taken me four times to pack and unpack everything from my personal bag to check in bag and I still don’t leave for another five days (I am notorious for packing a month out). Even though you might not be finding yourself in the same situation as me, you still could be thinking about traveling to the Caribbean and thinking wtf do I pack!?!?


Ahhh I can’t wait to be back on this beach


Well, mis amigos, this isn’t my first rodeo. I’ve packed for a “who knows how long I’ll be here trip” before to the Caribbean and I made some ridiculous packing mistakes. I wrote down everything I didn’t use during my first trip to help me decide what to bring this time around. This will be a three part series on how to pack like a pro and today we will be starting off easy, your personal bag.

I’m flying Southwest which means we get two check in bags (who actually does that?), a carry-on bag and a personal bag. The personal bag is the same on every flight, small enough to fit under your seat. So, I’m taking my small backpack. I’m taking a backpack as opposed to a purse because I just don’t really use purses and having small backpack hiking around Puerto Rico is such a good idea, trust me. If you need a purse that badly, pack it in your carry on or check in bag.


Okay, so here is how I pack like a pro when it comes to my personal bag. I’ll just list everything and show you with pictures how I pack my bag. Keep in mind that this is for a trip to the Caribbean or another warm place. You might not need sunscreen or oil blotting wipes if you’re going north but when you visit the Caribbean you won’t be caught dead without them. Let’s get started

Water bottle (empty)

Okay, this is pretty much a no brainer but just make sure it’s empty when you go through security. There are plenty of areas around the airport to refill your bottle and you’ll want it on the airplane. When I forget I always feel needy when I ask for both ginger ale and water.

Toiletries (non-liquid)

  • toothbrush (I found this AWESOME pack of bamboo ones! Perfect for camping trips).
  • bronzer and brush
  • blush and brush
  • eyebrow pencil
  • make-up wipes
  • tissues
  • floss
  • oil blotting wipes
  • nail kit
  • tweezers
  • chap stick
  • Menstrual cup (One day I will write a blog post about this but this product is AMAZING and I can’t believe it took me this long to convert. Sorry dudes. This is a lady item)

Some how all of this fits in my little Victoria’s Secret make up bag and I will honestly use every single thing on this list. Those oil blotting wipes saved me from sweaty nights out salsa dancing and who doesn’t use floss. Tissues will come in handy on your nights out too. When I lived in Spain every single woman carried around tissues just in case the bathrooms didn’t have toilet paper. Some how that was a common occurrence and I wasn’t going to take any chances in Puerto Rico. Anyway, let’s keep going on how to pack like a pro.


Toiletries (liquid)

  • toothpaste
  • deodorant
  • roll-on perfume
  • sunscreen
  • face cream
  • eye cream
  • face wash
  • leave in conditioner (every one asks what I use in my hair so here you go!)
  • body/hand lotion
  • hydrating face spray
  • mascara

Yes, all of this fits in one of those quart sized Ziploc bags. My skin CRAVES moisture during the winter and I’m currently suffering. It gets worse when I travel so staying hydrated internally and externally is super important. That’s why there is like four different creams here. Having a hydrating eye cream (especially one that lifts) is really nice. When we leave next week we have a 13 hour travel time which sucks for my skin but when I apply that soothing eye cream, lifting face cream and hydrating spray I’ll look semi-awake and ready for the day. The roll on perfume and deodorant is a necessity because…obviously you, your partner and your seat neighbors will thank you for smelling good.

Maybe it would be a good idea to switch out the full sized deodorant for a smaller one that way you could fit a small bottle of mouth wash in your Ziploc bag as well. I didn’t really think that was a necessity because there are things that we will end up buying when we’re there too. Mouthwash is one of those things so it made sense for us to just save the dollar something it costs for the travel sized one and just pick up a whole bottle at the Walmart in San Juan. That goes for the shampoo and conditioner as well. You might notice that I don’t have that much make up and that’s because you will not need it when you get to the Caribbean. When I first went, I had two bags of make up! I maybe used the bronzer, one color of lipstick and mascara if I even wore any make up at all. Something about the heat, going from work to beach to night out, or because I was tan, I didn’t feel the need to cake my face with foundation, concealer or highlighter. Save yourself the space, you don’t need it.

Again, with the whole hydration thing, my hair is super curly and it gets dry very quickly. If I don’t drink enough water or put product on it, it starts to get really coarse and dry which isn’t attractive and it just feels unhealthy. That’s why I always carry a leave in conditioner with me so I can get my hair a little wet in the airport bathroom, spritz some of the It’s a 10 in my hair and go! It’s super nifty and I’ve been using this product essentially my whole adult life and I swear by it. Almost done on how to pack like a pro!

liquids to pack


  • Headphones
  • Laptop and charger
  • Phone and charger
  • Nook
  • Fem thermometer (picture will be in the “other” photo)

I’m still not sure if you’re supposed to prove your technological devices can power on while you’re in security. That was a thing back in 2015 when I traveled to Spain. So, let me know in the comments below if you are still supposed to have all your tech stuff charged. Everything here is pretty self explanatory so I won’t go into anymore detail. Just make sure that this stuff isn’t at the bottom of your bag since you’ll have to take all this stuff out during your security check. The fem thermometer is what I use as a more natural form of birth control (again, this is for the ladies, sorry dudes). Since this is a travel post and not a lifestyle post I’ll save it for my other blog but if you want to learn more about it you can check out this link. But since it has a battery in it, I made sure I put it in my personal bag.



  • Wallet + passport
  • Planner
  • Journal
  • Blog notebook
  • Language
  • Cards
  • Reading glasses
  • Pen and highlighter

Okay, more obvious items like your wallet, glasses, and pens you’ll want to keep close to your side in your personal bag but I also need my journals, planner and notebook because those are necessary for my existence. Okay, not totally true but they are still super important and having them with me during a 13 hour travel day is essential for my success. I also don’t trust my glasses being in my carry on or checked bag because they are super expensive and I like wearing them if I look tired so I look a little..less tired. It’s also a really smart idea to bring along a language book if you want to impress the locals while you order tres empanadillas. 


In Puerto Rico, the people there generally speak English although I have found a few locals that don’t speak it at all. Plus, people there are pretty proud to be bilingual but Spanish is usually their go-to language. They will love speaking it with you if you want to practice but if you get lost they switch over to a more “Spanglish” language and you’ll figure it out. I already know Spanish so Italian is my next language I want to learn. I have a little book from The Lonely Planet in Italian but I’ve found a really good one that covers Spanish in Latin America. It’ll come in handy when you visit the Dominican Republic or Cuba too because come on, if you’re moving to the Caribbean or staying there for a long time you should probably make it around to the other islands.

And that’s all my tips/items in my personal bag and how to pack like a pro when moving or visiting the Caribbean long term. Over these next couple weeks I’ll show you what I pack in my carry on and check in bag too! Stay tuned.

Hasta luego!



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