Packing Light: 4 Days in a Backpack

I recently booked a last-minute trip to Jamaica to visit my mom (she’s originally from Jamaica and lives there part-time). Making the plan for this trip went something like this: two friends who are close to my mom decided they were going to visit her in Jamaica. Upon hearing their plans, I started thinking maybe I should visit her too. I mentioned my ambitions to another friend who was also interested in going. And then we linked up with the original two friends, and soon the four of us booked tickets together, just 10 days before our departure date.

As if spending four days in Jamaica isn’t wonderful enough, this trip was made even sweeter by the fact that it was incredibly budget-friendly, considering all that we experienced. This was thanks to two key factors: 1) We stayed with a combination of my mom and friends for $free.99. This eliminated the largest expense, and if I can make one plug for anyone who’s looking to travel more while spending less, it would be to start with visiting places where you know people and can stay for free! And 2) we scored basic economy flights on United for $395. This is big, considering that roundtrip flights to Jamaica from NYC during the busy winter season can easily be as much as $600-700.

Now, let’s be clear: paying for a basic economy flight may cost you less money, but it will cost you some sacrifice — in the area of convenience, to be exact. Our basic economy flight meant we couldn’t choose our seat, and it meant we could only travel with a bag that fit under the seat in front of us. Think backpack or small duffel bag.

United included lots of bold text on its website and confirmation emails intimidating reminding us of this fact. And if you’re wondering, like I did, how they’d really be able to track whether or not you had just one small bag — well, when we got to the kiosk to download our boarding passes, we weren’t allowed to check in until an attendant had reviewed our items and confirmed, in the flesh, that we had met the one small bag standard.

I’m sure some of you are reading this and thinking, “Nah, sis. You can miss me with all of this.” I know many people who have trouble not checking a bag when they fly, let alone not being able to even bring a carry-on that can go in the overhead bin. If you’re a checked luggage kind of person, you’re perfectly entitled to bring as much stuff on a trip as you’d like.

BUT, the fact is, airline travel isn’t cheap. And depending on the airline/class, when you throw in extras for seat assignments, baggage fees, headphones, wi-fi, and snacks, things can really add up. Add to that the fact that I’m trying to take as many trips as my schedule/responsibilities/wallet permit, and so saving some coin is important.

While packing light can be a challenge, it does help in the saving money department. And I wholeheartedly believe that less luggage tends to make for an easier, more enjoyable travel experience all-around.

I first started to learn this lesson when I studied abroad in Spain after my junior year of college. I packed a HUGE duffel bag with clothes — it was so large, I could have easily been zipped up inside of it. It was an enormous pain to move it around to my different stops, and it was embarrassing to carry it up three flights to my host family’s apartment.

Over the years, I got better and better at packing light. I learned how to roll my clothes. I learned how to make clothes work for multiple occasions. I learned how to use most of what I packed. And knowing how to pack light was an extremely valuable skill by the time Jordan and I went to Italy on our honeymoon, where we picked up our rental car and learned it was a SmartCar, with two seats for us and just enough room for two carry-ons in the back. Learning how to pack light was even really helpful when I created my capsule wardrobe.

So I’m a pack light evangelist (cue Erykah Badu’s “Bag Lady,” which I have playing in the background). For anyone who might be interested in trying this whole packing light thing, I’m sharing what I packed for my four-day trip to Jamaica. An island vacation is the perfect time to try something like this, because if push came to shove, you could pretty much stay in a bathing suit, a cover-up/shirt, and sandals the whole time.

Here’s a list of what I packed for four days in a backpack:

• 4 shirts (including the ones I wore to travel)
• 3 dresses
• 1 pair of shorts
• 1 pair of jeans (worn to travel)
• 2 bathing suits
• Shorts and t-shirt for lounging/sleep
• 1 pair of sneakers (worn to travel)
• 1 pair of sandals
• Undergarments
• Toiletries
• Misc. objects (sunglasses, passport, etc)

Here’s a look at what I wore each day on my trip…

Day 1: 

Outfit: Jeans | White tank | Denim shirt (similar) | Sneakers | Trench (similar)

I try to wear my heaviest items on my travel day, so they don’t take up space in my bag. I also layered, knowing I’d be going from 20-degree weather in NYC to 85-degree weather in Montego Bay. When I arrived in Jamaica, I could easily ditch the denim shirt and swap the sneakers for sandals. I ended up putting on a bathing suit within an hour of arriving, so it worked great.

Day 2: 

Outfits: T-shirt | Jean shorts (similar) | Romper (old) | Sandals (boutique)

I started the day wearing a t-shirt, shorts and sandals to drive our crew to another part of the island. Once we arrived at the home of friends, I changed into a swimsuit, and for our dinner in the evening, I put on a romper and the same sandals.

Day 3:

Outfit: Breezy blouse (similar) | Jean shorts (similar) | Sandals (boutique) | Tunic

After a morning in one bathing suit, I changed into a different suit and put these clothes on top to drive to Negril. After lunch, I peeled off the clothes and jumped off the cliffs at Rick’s Cafe! I used the navy tunic as a cover up for the drive home. This tunic is a real MVP of my trip — I probably wore it for some period of time every day.

Day 4:

Outfits: Sundress (old) | Sandals (boutique) | Jeans | White tank | Navy tunic | Sneakers

This was our last day, and we spent the morning at the beach. I wore the dress above over my swimsuit. When we got home, I changed into an outfit similar to what I traveled down in, but I swapped the denim shirt for a navy tunic.

Bathing suits:

The striped suit (new design) is from a company called Seea. You can find them on their website and other retailers like ShopBop and Anthropologie.  The pink suit is from Mara Hoffman. Madewell is selling a version in black, and this leopard print one is pretty fire.

Spent a lot of time in both of these, and sometimes both in the same day. :-)

An extra dress:

This white dress (similar) was intended to be for if we went out one night during our stay. We opted to relax at home instead, so this never got worn.

Misc. items:

Starting in the top left:

• Head scarf
• Manual breast pump
• Wallet
• Sunglasses
• Camera (I only included a lens in this photo, because I had to use my camera to take this pic. Ha!)
• Travel-size hair products
• Collapsible travel hair diffuser
• Jewelry satchel
• Passport
• Phone/watch charger
• AirPods
• Toiletry bag

It’s pretty amazing what you can fit in a small bag. It definitely takes being thoughtful about what you pack, but the freedom I felt traveling this light — and in saving money — was a fantastic feeling.

A few additional things to keep in mind if you want to pack lighter for your next trip:

• Save space by rolling your clothes instead of folding them.
• Don’t be locked into thinking you can wear every item you pack only once. Even if you take photos of yourself while traveling, you likely won’t really notice when you may have worn the same shirt on two different days. Plus, traveling should be more about the experiences and memories, not that you had a different outfit on for every occasion.
• If you have a lot of hair/beauty products that you can’t live without while traveling, invest in some good travel-size containers, so you don’t have to cart the big bottles around.
• I find the things that takes up the most space in packing is shoes. Whenever possible, I try to travel with no more than two pairs of shoes, including the ones I wear to the airport. Sometimes the itinerary requires three pairs, but I really try to pick pairs of shoes that can go with several things in my bag.

What’s your philosophy when it comes to packing? Any tips to share?