Packing for a Caribbean trip can be tricky, especially when you’re curvy or midsize. Finding pieces that are both flattering and functional, while also preparing for the heat, humidity, and resort lifestyle, can easily overwhelm even the most seasoned traveler.
After a week in the Caribbean, I’ve figured out exactly what worked and what I could’ve left behind. This guide breaks down what to pack, outfit by outfit, plus the essential extras that made my trip smooth and stress-free.
Evening Looks That Travel Well
If you plan on going to dinners, lounges, or beachside restaurants, pack at least two evening outfits that make you feel dressed up without being uncomfortable. I found that soft, stretchy materials were ideal. They hug your curves without digging in, and they also tend to travel better with fewer wrinkles.
One of my favorite outfits was a rust-toned lace bodysuit paired with a high-waisted tan midi skirt. This look felt effortlessly chic, and the midi skirt gave a sleek silhouette while still being breathable. I added a bold statement necklace and clear heels, which elevated the outfit without adding too much weight to my suitcase.
Another standout was a strapless two-tone dress in purple and pink. It had a flattering high slit and was made of a wrinkle-resistant fabric. Perfect for a night out or a fancier dinner, it didn’t take up much space in my luggage and held up well after being packed away for days.
Resort-Worthy Dresses
When it comes to tropical getaways, the goal is to stay cool and comfortable while still looking polished. That’s why I packed a few lightweight, flowing dresses. They work great for anything from lunch at the resort to sunset cocktails.
A white halter wrap dress turned out to be one of the most versatile items I packed. It combined the comfort of a sarong with the style of a cocktail dress, which meant I could easily wear it from daytime lounging to an early evening happy hour. It showed off just enough skin without being too revealing and felt great against the skin in the Caribbean heat.
Another favorite was a blue-and-white maxi dress that I wore while exploring historic landmarks. The fabric moved with me, and the long length helped protect me from the sun while still looking beautiful in photos. Dresses like this are lightweight, easy to fold, and take up minimal space in your bag, a big win for travel.
Casual Sightseeing Outfits
When you’re on your feet walking through town or heading out for a casual lunch, breathable separates are key. Stick with what you know works well on your body and prioritize comfort.
I packed a pair of high-waisted denim shorts and styled them with a white lace bustier-style top. The shorts provided coverage and comfort, while the structured top gave the look a bit of polish. White sneakers were the perfect addition for walking longer distances comfortably.
Another great outfit included pink pleated shorts and a white corset-inspired tank. This pairing was cute, easy to move in, and still felt put together. I added a bright headband and my go-to sunglasses for a little personality. When sightseeing in hot climates, lightweight layers and comfortable footwear are essential.
Poolside & Beach Essentials
No tropical packing list is complete without swimwear. Bring at least two swimsuits that you feel confident in, and don’t be afraid of bright colors. They pop beautifully against Caribbean backdrops and highlight your curves in the best way.
I wore an orange bikini that was both supportive and flattering. It held up well whether I was lounging by the pool or wading into the ocean. To transition easily from beach to casual dining, I often threw on a long-sleeved mesh top and denim shorts. This combo kept me covered, protected me from the sun, and added a stylish twist.
It’s also smart to pack at least one versatile cover-up that you can throw over any swimsuit. This allows you to move around the resort freely without needing a full outfit change.
Footwear Breakdown
Footwear can be a challenge when trying to pack light, but each pair I brought served a specific purpose and got plenty of use.
Clear heels were a lifesaver for evening outfits. They go with everything and don’t take up much room in your suitcase. For beach days and short walks, flat sandals were perfect. My white sneakers were essential for excursions and travel days, giving me the comfort and support needed for longer periods on my feet. I also packed basic flip flops just for poolside lounging or slipping on quickly.
In total, I brought five pairs of shoes and wore each one, so no space was wasted. Prioritize versatility and comfort, and you won’t overpack.
The Essentials I Couldn’t Do Without
Some items weren’t part of my outfits but were just as important for enjoying the trip fully.
Bug spray was absolutely necessary. Evenings in the Caribbean can bring out the mosquitos, and having a small spray bottle kept me bite-free.
I also brought reef-safe sunscreen and applied it daily, especially before heading to the beach. It’s easy to underestimate how strong the sun can be, even on cloudy days.
A mini electric fan turned out to be one of the best things I packed. When the humidity got intense, especially while waiting outside or walking to town, it provided quick relief.
My large beach bag was roomy enough to carry a towel, book, snacks, and water. It was also easy to clean and packed flat in my suitcase.
Lastly, a transparent waterproof phone pouch allowed me to keep my phone with me in the water without stress. I even used it to take beach photos without worrying about sand or splashes.
What I Didn’t Need
To help you avoid overpacking, here are the items I brought but barely used:
I packed two pairs of jeans and only wore denim shorts. The full-length jeans were too hot for the Caribbean climate.
I also brought several swimsuit cover-ups, but rotated the same two over and over. One or two is more than enough.
As for makeup, heavy products didn’t hold up well. I mostly wore tinted moisturizer, mascara, and lip gloss. Heat and humidity don’t pair well with a full face of makeup.
Packing Strategy for Midsize Travelers
Packing as a midsize woman means leaning into what makes you feel confident. I stuck to clothes I already loved and that I knew fit well. That way, I wasn’t second-guessing my outfits on vacation.
Mix-and-match items were also key. I chose neutral tones for my bottoms and bolder tops, so I could create new combinations without overpacking. Rolling my clothes instead of folding them saved space and reduced wrinkles.
To make room for essentials, I wore my bulkiest items on the plane, including sneakers and my largest bag as a carry-on.
Final Thoughts
Packing for a Caribbean trip when you’re midsize doesn’t have to be stressful. With the right outfit choices and travel essentials, you’ll feel both stylish and comfortable. Focus on clothing that highlights your best features and keeps you cool, and don’t forget the practical items that will make each day run more smoothly.
I’ve linked everything that worked for me on this trip, from my dresses to my favorite travel-sized fan and waterproof pouch. Check out the links, build your own checklist, and get ready for your best vacation yet.
Happy packing—and enjoy every moment under the sun.