millennial in debt

SURPRISE… I’m going to Cuba!!

And so is the rest of America so it’s nothing new or special… but to me it is. I wanted to head to Cuba before you know who completely ruined the relationship we’ve been enjoying for the last few years. So I text my best friend, we aligned our forces, days off, and finances with the quickness. Long story short, I’ve been sitting on this secret since December and the cat is now finally out of the bag. It hasn’t been easy keeping such a secret from you, and it certainly has been a bit stressful. So much so that I want to make your future trip to Cuba way less stressful.


Traveling The World As A Millennial With Student Debt
My Trip To Italy and Croatia Recap 

So ya’ll know how terrible I am with series writing (well besides my actual web series… that I’m pretty great at and you should totally check it out here if you haven’t alreadyBut I’m going to try my best to really keep up with this Millennial In Debt Travel Guide series because 1) I love to travel and 2) I want my fellow Millennials In Debt to know that traveling can be possible during various parts of your debt repayment life.

I’ll be sharing more deets on how I booked this trip for less than 400 dollars (including airfare and lodging), what I’m going to be doing while in Cuba and more. It is surely in your best interest to sign up for our mailing list here so you don’t miss any part of the series. I’ll be sharing more than just deets on Cuba as well! I’ll have a little something for everyone at every level!

what to pack for cuba

Millennial In Debt Travel Guide: What To Pack For Cuba

Over the last few months, it has been a slightly difficult to prepare for this trip, especially since it was a very well kept secret. I also was trying to spend as little as possible, and be fiscally responsible. I didn’t buy much of any new clothes for Cuba (I bought one dress and one bathing suit), but I did buy a new carry on suit case from Macy’s Backstage. The way I see it, it was an investment for all the future travel to come.

Because I’m trying to pack smarter and fit into a smaller space, I’ll be very particular with what comes along for the ride. If you remember my Italy packing checklist (which I actually used while packing) you’ll know that I like to be prepared for what may come. So a lot of stuff on this list is precautionary, and the other stuff is absolutely necessary. I’ve made the necessary stuff bolded below so you are able to tell the difference. Hopefully this list makes a certain someone proud! (I’m doing better…)

Natural Hair:

For a trip to Cuba I definitely recommend you going the protective styling route. It just makes life ten times easier, especially when you can’t carry a majority of products with you, and don’t want to use the hotel shampoo and conditioner. I’ve got my hair in box braids for this trip so I won’t need to bring too many natural hair products at all. Which is going to be a god send when it comes to saving space. Here’s what I will be bringing, and what you should consider bringing on your trip to Cuba or anywhere away from home in all reality.

  • Hair Scarf
  • Hair Accessories
  • Optional: Shampoo, Conditioner and Leave In Spritz/Spray


8 Must Haves When Traveling With Natural Hair 


In my previous packing ventures I’ve always for the most part over packed. When I went to Italy/ Croatia last summer I think my packing was pretty good. I used 80% of the things I brought along. This time I’m going to try and use 95% of what I’ve brought with me, and that starts with my clothes. I’m going to Cuba for 5 days, and this is what I’ll be bringing along:

  • Underwear/Bras: Unless you plan on going commando the entire time you’re obviously going to need some undergarments. The rule I usually follow is to bring double the amount of underwear for the amount of days you are going to be away. And bring 1 bra for each day minus 1. So I’m bringing 10 underwear and 4 bras. Potentially I may bring a sports bra in case I want to work out while on the trip.
  • Dresses: I suggest 1-2 maxi dresses that can double as a daytime or night time outfit depending on your destination and your accessories. Plus they are easy to pack, don’t take up a lot of space and you don’t have to coordinate more than one piece garment.
  • Tank Tops: I’m probably going to wear tank tops to bed but I always suggest 2-3 tank tops for any vacation just to have options.
  • Shorts: I’m bringing 3 pairs of shorts because Cuba is very hot/humid. Linen/athletic shorts are probably best so you have some space to breath. I’ll be bringing 1 pair of linen shorts, 1 pair of athletic shorts incase I want to go for a run, and 1 pair of denim shorts just to have some variety.
  • Pajamas: I sleep with very minimal on (sorry for the over share) so I only need a teeshirt or tank top for the most part. Pack your pajamas at your own discretion but you should bring something to sleep in.
  • Cardigan/ Sweater: Cuba does get a little chilly at night so this is at your own discretion as well. Bring a cardigan or sweater to wear for your night time excursions.


I learned my mistake in previous  trips about bringing heels… so this time around it’s not even an option. These are my recommendations for footwear to pack that will fit the best and take up minimal space in your carry on.

  • 1 Pair Of Sneakers (this may become two… but for now it’s one) I’ll be bringing my running sneakers, but I’ll be wearing them there and back so they won’t take up too much space in my suitcase.
  • 2 pairs of sandals: One pair that I can wear to outings, and another pair that I can walk around with all day ( definitely not flip flops). I’ve got a bad knee so my Birkenstocks are going to definitely come in handy.


You’re going to need the basics obviously, but just in case you forget what that means I’ve got the list ready for you (plus ready for me… I use my own posts to help myself pack… go figure)

  • Toothbrush & Toothpaste 
  • Deodorant (I’m not sure if you can bring spray deodorant on the plane, so I’ll be bringing my regular old TSA approved stick deodorant)
  • Sunscreen– Uh… that is a given. The sun is going to be beaming in Cuba and you need to protect your skin. I’ve heard that there are sunscreen wipes or solid sunscreen (looks like a deodorant stick). I haven’t seen those around but they can be found on Amazon.
  • Tampons- The last two times I’ve traveled internationally I’ve gotten my period by surprise. So this time I’m taking no chances.
  • Body Wash
  • Lotion/Moisturizer
  • Facial Cleanser
  • Bug Spray/ Repellant


Well… this is really based on what you want to bring but here are the things I’m bringing along:

  • iPhone X: This wil be what I use to take the bulk of photos and random video while on my trip
  • Sony A5100 (plus 4 extra batteries): This will be used to record most of the photos and video for the Vlog/ Blog I’ll be putting together when I get back.
  • iPad: This will strictly be for reading purposes though I’m certainly thinking of leaving it behind and focus more on writing in my downtime.
  • Macbook Air: I’m taking my MacBook, though I know many people are thinking I shouldn’t. I’m bringing it along for ONE main reason: WRITING. I’ve been writing a book for the last two years and I’m determined now more than ever to get it done this year. So during my down time on the trip, and my travels on the plane I’ll be focusing on writing.


  • Packing Squares: These can be used to organize your toiletries or keep your dirty and clean clothes separate. Minimalist packers, and those who have mastered packing 100 things into a tiny carry on swear by them.
  • Toilet Paper: I’ve heard that not many places will have toilet paper when you head to the bathroom, so my friend and I are bringing these “toilet tissue to go” packages. They cost about 10 bucks for a pack of 6 and are easy to pack in your carry on without taking up too much space.
  • Emergency First Aid Kit: I like to be prepared instead of being caught off guard. I ended up having to wrap my knee up last time I was on vacation, and thankfully there was an emergency first aid kit available. This time I’m bringing my own just in case. It cost me 8 bucks and comes in a cute little push that fits into my carry on with ease.
  • Hand Sanitizer:
  • Aloe Vera Gel: For any cuts, scrapes, or sunburn. I told you… I like to be better safe than sorry.
  • Basic Makeup: Don’t bring a ton of make up to have a full beat face. Cuba is not the time nor the place for that. Your face will melt off. Instead bring basic makeup when ever you think you are going to want to a look just a little extra cute. BB cream, or tinted moisturizer should do the trick (use one with SPF to double as sun protection), mascara, some cute lippies and that is it.
  • Cheap Jewelry: Bring something you think you can afford to lose, don’t bother bringing your fancy expensive stuff. Save that for home.
  • Makeup Organizer: Even though you’re bringing basic makeup, the makeup organizers are amazing for organizing your toiletries. I got mine for 15.00 bucks on Amazon and I plan on using it even when I’m not traveling, because I’m trying to be more organized instead leaving ish lying around all over the house.
  • Vitamins: As always, bring your vitamins and minerals that you usually take.
  • Chargers: Take all your chargers and make sure your tech is fully charged when you leave. Nothing sucks worse than going to take a picture to realize your camera is dead. I mean a mental picture is great… but … that won’t take you very far on Instagram (JK disconnecting is totally okay)

I can’t wait to share my trip with you when I return. If you have already been to Cuba let me know if there is anything that I missed and should add to my list let me know in the comments below.

millennial in debt