What To Pack For a Warm Weather Getaway

Since art imitates life, I’m actually posting this article as I finish packing for my trip to Puerto Rico in just a few hours. This is usually pretty simple since I rarely check a bag.

We used to tag along with my flight attendant aunt and fly standby, which meant we took whatever seats were available and we absolutely couldn’t check a bag. I got addicted to the idea of traveling light. And every time I whiz by travelers struggling with mountains of bags, I’m always glad I did. I still pack way more than a lot of seasoned travelers (I like options!) but I’m getting more efficient all the time.

Here are a few packing tips I’ve gathered over the years, as well as a (probably ridiculously) detailed breakdown of what you’ll actually need for a week somewhere warm. (This is a list for make-up and dress-wearing people, but you can adjust it if that’s not your thing.)

Riviera-Maya-Beach
Riviera Maya, near Tulum, Mexico

General Packing Tips:
– Roll your clothes to maximize space
– Choose one dominant color and one or two accent colors so everything in your bag goes with everything else.
– Keep silhouettes simple
– Synthetic and wrinkle-free materials are best — think lightweight, moisture-resistent and fast-drying.
– Stick socks and underwear inside your shoes to save space and help shoes maintain their shape
– Pack the night before and edit the day you leave. Ask yourself is this really the best and most useful option? You’ll probably end up taking a few items out.

First, Pick a Plane Outfit
What you wear to the airport should be both comfortable and strategic. (And ideally, you don’t want to look like a bum either.) I wear the heaviest clothes I’m bringing along and layer so I’m comfortable on the plane.

Here’s what my usual outfit looks like.
– Jeans or lightweight pants (I pack straight leg jeans so I can cuff them into capris and have another option)
– Long sleeved shirt or tunic
– Socks (I personally think it’s gross to walk barefoot through security)
– Sneakers or boots (whichever I’ll need for activities when I land)
– A big knit scarf (to use a blanket on the plane and a layer — or cover-up — when I land)
– A cardigan or light jacket (Now you have a warm layer for the plane and a jacket when you land.)
– A floppy beach hat, if I’m feeling it. (I wear a ridiculous 70s boho thing, which actually works with this outfit.)

Bikinis
My bathing suits clearly don’t follow my color scheme rule…

Now Pack Your Personal Item:
You’re allowed one personal item, so I make sure it’s something portable that doubles as a daypack or beach bag. Then you can throw it over your shoulder and bring it to the beach, fill it with snacks for a hike or tote with you on a day trip. Just don’t fill it so full that you can’t fit a few souvenirs in on the way home.

I always pack this bag first, filling it with everything I need for overnight, just in the overhead bins are full and they need to check it at the gate. (I did this on the way back from Japan and my bag got lost temporarily, so now I’m really, ridiculously cautious. Did I mention I hate checking bags?)
– Purse
– Camera
– Phone
– Charging equipment for all electronics
– Medicines
– Something to read
– A pen (especially if you’re traveling internationally — you’ll have forms to fill out)
– A journal or notebook
– Earplugs or noise canceling headphones
– A sleep mask (I’m a diva like that)
– Make-up bag and toiletries

A quick note on the make-up and toiletries: I only include liquids I can’t readily find at my destination, like minis of my favorite perfume, my foundation etc. Sunscreen and shaving cream can wait. Then you have an excuse to visit the drugstore at your destination, which can be surprisingly eye-opening. And then you’ll get addicted to things you can’t have. I’m looking at you, fabulous Spanish sunscreen…

Suitcase

Finish with the Actual Carry-On Bag
– 2 bathing suits (so you can wear one and dry one)
– 1 cover-up (I like tunics, caftans and sundresses so you can take your suit from the beach to lunch and back again.)
– 1 pair of beach shoes (I do flat sandals so I can wear them out as well)
– 1 pair of dress up shoes (mine are low-heeled sandals so I can wear them for casual stuff as well)
– 2 dresses (to dress up or dress down — at least one should work for a night out)
– Underwear for 8 days (you know, in case your flight is delayed on the way back)
– Socks for every day of the trip you think you’ll need them, with a pair to spare
– 1-2 pairs of shorts or capris (Even if you love dresses, it’s good to be prepared in case you get an opportunity to do something active.)
– 1-2 skirts
– 2-3 short-sleeved shirts
– 2-3 tank tops
– 1 pair of leggings or yoga pants (I wear mine under tunics and for, well, doing yoga)
– 2 or 3 pairs of statement earrings that go with everything (necklaces and bangles get hot in the sun!)
– 2 or 3 colorful scarves (to distract from the fact that I might repeat a tank or T-shirt now and then)
– Small evening bag (if desired — I dance a lot and a leather camera bag gets in the way)
– A woven or slim leather belt for jeans and shorts (it can also belt dresses or add shape to tunics)
– A statement necklace for when the sun goes down
– 2 pairs of sunglasses (You might be able to get by with one. I squint in cloudy weather, so I come prepared.)
– Dry laundry detergent if you’ll be gone more than a week (or if you sweat a lot or will be really active)
– Super basic first aid kit (I pack Tylenol and bandages and that’s about it.)

What’s on your packing list? Where are you traveling this winter?

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