Opening up my suitcase and sharing everything I packed for five nights in Puerto Rico
It’s a little hard to believe, but there are over fifty packing lists on this blog.
That’s over fifty different packing collages, series of outfit photos, and musings on the packing process.
By now you might think I’ve run out of things to say or outfits to wear (because yes, these posts feature my real-life wardrobe and not a fantasy version), but the truth is, every trip offers its own set of packing challenges.
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The challenges for a recent five-night trip to Puerto Rico? Packing for a mix of hot weather and downpours, chic city exploring, glam dinners, rainforest hikes, and beach days – all while leaving my chilly hometown behind. I felt like I was packing for many separate trips all at once.
Looking for more of the best of Puerto Rico? Find my guides all in one place.
And yet, I still managed to get away with packing everything into my carry-on and personal item, with room to spare.
This experience once again proved that with the right strategy, it’s possible to pack efficiently and stylishly for any adventure:
PACKING LIST FOR FIVE NIGHTS IN PUERTO RICO
Whew.
It feels like a lot, right?
At least, it does to me at first glance.
As someone who is used to traveling for several days at a time with just a backpack and is fine rewearing things, it seems excessive to pack more than one outfit per day. But as I’ve learned from traveling to other destinations in the region (St. Croix, Cartagena), Puerto Rico’s intense heat renders daytime clothing too sweaty to wear again without washing.
So I landed on a suitcase with an assortment of day-to-night dresses, mix-and-match pieces, and comfortable favorites. Let’s dig in:
Tops + Bottoms
The goal here was options. A mix of coverage was important for temperature, modesty, and sun protection. Growing up in Florida and now living in North Carolina, it’s undeniable that there’s a fondness for air conditioning when the sun is scorching, but I wasn’t sure if that would be the case in Puerto Rico. The truth is, I only wore my alpaca cardigan on the plane (though I was grateful to have it!).
As for the rest of my separates, I turned to other natural fibers (cotton, wool, and linen) for ease and comfort. Black isn’t an obvious choice, but I find it looks less sweaty and rumpled at the end of the day. These workhorses make this the least exciting category in my wardrobe for Puerto Rico, but that’s because I’d rather make a splash with dresses and jumpsuits.
Dresses + Jumpsuits
Ah, the one-piece wonders. I like to think of dresses and jumpsuits as a kind of magic trick. Choose the right one, and it’s as comfortable as your favorite pajamas – yet you suddenly have powers that convince everyone around you that you’ve dressed to impress.
I generally have zero patience for uncomfortable undergarments and was unwilling to sacrifice suitcase space for a pesky strapless bra or shapewear. Instead, I reached for a handful of bra-friendly dresses and jumpsuits and a couple of pairs of slip shorts to stay cool. A sheath dress* stood in for a tight strappy mini dress for a night in Santurce, and a fun floral jumpsuit added some much-needed color to a neutral travel wardrobe. A tiered midi dress no longer looks “trendy” but it never looks out of place – and it’s the easiest thing to throw on for a quick coffee run.
Shoes
This is everyone’s toughest category, right? (Please say it’s not just me!). With a celebration dinner, days spent at the beach, kayaking in a lagoon, and splashing beneath a waterfall on my itinerary, I landed on four different pairs of shoes. Chunky shoes are in for now, but a slim pair of low-top sneakers takes up less room. A pair of flats dress up an outfit without relying on heels (I would absolutely recommend that you not pack heels for Puerto Rico). For more active days, a pair of water sneakers and waterproof sandals provide protection while making it easy to rinse off the day’s grime.
Accessories
AKA the fun little outfit makers. Slipping on a pair of cat eye-inspired sunglasses always makes me instantly feel like I’m on vacation, so it was a no-brainer to bring this chic polarized pair from Quince. And my go-to sunglasses for adventure travel? A pair with a lifetime warranty, just in case! For even more protection, I tossed in a crushable bucket hat with a wide brim and a tie in case of wind gusts.
Shall we chat bags? A crossbody satchel was my main bag for the trip, adding another hit of color while leaving my hands free for all of the empanadillas and limber I could eat. A packable backpack was essential for holding the day’s necessities while hiking and exploring the beach, and a waterproof belt bag kept our rental car keys and phones dry during a nighttime paddle. The one bag I could have left at home was this nylon crossbody. I did use it on our most rugged days, but I don’t know that I would consider it an essential (thankfully it takes up almost no room!).
Swim + Activewear
Confession: This is always my least favorite category to pack because while I am always up for an adventure, my style isn’t very sporty. Alas, I needed hard-working clothes that could handle our active itinerary, and a few items in my closet fit the bill.
A pair of swim shorts was perfect for topping my cutout swimsuit for our kayak tour, and a pair of lightweight, quick-drying pants in an activewear fabric kept me cool and clean during our rainforest hike (look how dirty they got! Thankfully a quick rinse in a stream cleaned them right up).
I opted for two one-piece swimsuits for added comfort and security on this trip and found additional coverage for beach snacks at the kioskos with a fun cover-up.
Toiletries
I don’t always include this category in my packing lists, but it feels prudent to do so here. Hot weather means makeup feels heavy, so a tinted mineral sunscreen is a good swap for foundation. A high-SPF mineral sunscreen in the largest size you can pack in a carry-on ensures you’re always covered and a lip balm with SPF is a good idea too.
Personally, waterproof mascara is a must for me when I want to head to lunch after a hike or beach day (just be sure your makeup remover is up to the task!). While I never needed bug spray, I wouldn’t recommend traveling to Puerto Rico without it. Finally, scent always helps create a strong memory, and my favorite beachy perfume oil had to accompany me on this journey. What fragrance will you choose to bring you back to Puerto Rico every time you catch a whiff of it?
PUERTO RICO OUTFITS
ZIPPING IT UP: MY THOUGHTS ON PACKING FOR PUERTO RICO
While I would have loved to pack a suitcase full of bold, colorful looks for my time in Puerto Rico, the reality is that my wardrobe is 90% hardworking basics and 10% fun pieces. Rather than rushing out to buy cheap clothes that may not last, I packed a few bold favorites and left it at that (though perhaps in the future I may consider renting a few fun ‘fits through services like Rent the Runway or local option Cloud Closet to switch things up a bit!).
How I’d rate this packing list
So, how did my travel wardrobe perform? Well, I never felt out of place or uncomfortable with my outfit choices, which is always my primary goal. I also never had to worry about running out of clothes or having the “right” outfit for the occasion, which would certainly add stress to my precious travel days.
Since I made sure to only pack items that weren’t “precious,” I never had to worry about messing up my clothes. For example, rather than reaching for my new, shiny sneakers, I grabbed my oldest pair and splashed in puddles with zero fear. My sneakers and sandals were a hot, dirty mess by the end of the trip, but I never fretted about it.
Looking for more packing list inspiration? Discover what's in my suitcase each season: Spring | Summer | Fall | Winter
When it came to my choices, it wasn’t all sunshine and rainbows though. My water shoes were great for kayaking but barely cut it on our rainforest hike. If you are planning on attempting some of the longer or more challenging hikes at El Yunque, I recommend investing in a pair of waterproof hiking boots or sneakers that you don’t mind getting dirty (and breaking them in well before your trip!)
If I had to pack for this trip again, I would consider leaving my cardigan at home. I thought it might be handy to keep in the rental car, but the truth is, I didn’t reach for it again until it was time to depart for the San Juan airport.
As for rating this packing list, I’d give it an A- for practicality and a solid B for style. I’m lucky to be at the phase of my life where I’m not worried about chasing trends that aren’t going to last and am instead focused on how my clothes will stand the test of time. It is my hope that when looking back on my vacation photos in ten, twenty, or thirty years, I won’t feel embarrassed by the way I dressed.
What else should you know about packing for Puerto Rico?
If I can only talk you into bringing one thing for your trip to Puerto Rico, let it be comfortable, flat shoes that can handle a little grime. Beyond that, you’ll also want to bring a lightweight rain jacket. Michael and I repeatedly found ourselves caught in the rain, which isn’t a big deal at the beach or in the rainforest (where it rains! How novel!), but it is certainly less fun when you’re going out for the evening. This is one of those rare “do as I say, not as I do” moments: bring a good raincoat.
The Weather: As you might expect, the first few months of the year are the coldest, and the temperature peaks toward the middle. Still, with an average temperature of 80°F, Puerto Rico is hot all year long. Rain can occur in any month, but the months coinciding with hurricane season (June-November) are the rainiest. Dress for hot, muggy days with clothes that breathe and dry quickly (linen and lightweight wool will always be my go-to fabrics!).
Local Style in Puerto Rico: I’d read that Puerto Ricans generally dress somewhat casually and conservatively, and I found that was the case during the day. But things are different at night, at least in San Juan. People like to dress up and just about anything seems to fly when you’re partying (not counting places with a listed dress code, obviously!).
In San Juan in particular, the men’s looks tended to be just as flashy, with lots of bling and designer bags. I can’t help but think how nice it would be if Michael started carrying a bag so I don’t have to…
Ultimately, my style takeaways were: don’t dress for the beach unless you’re on the beach, wear breathable fabrics and comfortable shoes, and have a little fun with your look in the evenings.
Final thoughts
Packing for Puerto Rico can be as easy or as difficult as you choose to make it. I’m fortunate to have spent years building a wardrobe with breathable fabric for trips like this (and living in Florida certainly helped with that!), but unless you’re coming from significantly colder climates, I’m willing to bet you do too. I hope this peek inside my suitcase helps you get packed for your next adventure!
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Questions for you
What is your wardrobe’s ratio of “fun stuff” to “workhorses”?
Have I convinced you to not pack heels for your trip? (Please say yes)
Where to next? You may also enjoy these posts:
- Weekend Escape: The Ultimate Guide for Your First Visit to San Juan, Puerto Rico
- From Canopy to Coast: A Perfect Two-Night Rainforest and Beach Itinerary for Puerto Rico’s East Coast
- 13 Things You Should Know Before Renting a Car in Puerto Rico
- Checking In: A Review of El Colonial Hotel in San Juan, Puerto Rico
- Checking In: A Review of Dream Inn in San Juan, Puerto Rico
- Culinary Paradise: A Review of Marmalade in San Juan, Puerto Rico
- Four Days in St. Croix Travel Guide
- Traveling Light: St. Croix Packing List
- Travel Guide: Four Days in Cartagena, Colombia
- Traveling Light: Cartagena, Colombia Packing List
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- All of My Packing Lists
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- Shop My Closet
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