Gray’s Packing Guide, Vol. 1: Tropical Getaway Edition
As a luxury travel planner, one of the questions I get most often is: What should I pack? And I totally get it — packing can either set the tone for an easy, effortless trip or start things off in a mild panic. I’m always more than happy to share suggestions for maximizing suitcase space, curating outfits that actually make sense for your destination and making sure your wardrobe works with the weather and your itinerary.
Personally, I think the vacation mindset starts the moment the suitcases come out. Packing should feel fun, intentional and (dare I say?) even a little exciting. That’s why I’m launching a new series of destination-based packing guides — to help you pack smarter and start your getaway with less stress and more ease.
It only felt right to kick things off with a tropical destination packing list — because there’s nothing quite like stepping off a plane and into that warm, sunny air. Whether you’re headed to the Caribbean, Mexico, Hawaii or a dreamy Southeast Asian island, this guide is meant to feel like your first taste of vacation: easy, light and full of anticipation.
Now let’s talk about the elephant in the overhead bin — overpacking. I know the temptation (I’ve definitely tried to justify packing eight pairs of sandals for a five-day trip), but I’ve traveled enough to know that the extra options usually just create more decisions and more clutter. And isn’t the whole point of a tropical vacation to keep things simple?
Let’s dive in.
A Few Thoughts to Consider:
Tropical destinations often come with a mix of casual beach days, outdoor adventures and the occasional dressy dinner. Before you start throwing things in your suitcase, take a moment to think about:
What activities you’ll be doing (hiking, snorkeling, spa days?)
How much time you’ll spend on the beach vs. exploring
Any dress codes for restaurants or resorts (resorts often have at least one restaurant that requires pants for men!)
The weather, of course! You can expect it to be warm, but nights might get chilly and you’ll likely experience at least one afternoon rain storm.
Hotels and resorts often provide all of the beach gear you need: think umbrellas, chairs, towels, etc. I always suggest paying the extra fees for these items rather than attempting to bring anything with you. A Turkish towel that doubles as a sarong is the only thing I’d consider adding to the list!
Once you’ve considered this list, you can start to build your packing list.
Wardrobe At a Glance:
Tropical Vacation Packing List
Here’s the general formula we love for packing light but fully prepared (this is designed for a 5-day trip, so adjust accordingly!):
3 - 4 swimsuits (if you’re strictly a bikini gal, I recommend throwing in a fun one-piece for practicality)
You could plan to reuse one or two, but I don’t mind packing as many as I’ll need since they take up little storage!
2 - 3 cover-ups
One more functional, one cute enough to wear to lunch and always a sarong.
2 - 3 pairs of shorts
Linen, cotton or comfortable denim (I love Pistola’s new Paige style!)
3 - 4 sundresses
I always prefer a dress for dinner to keep it easy and flowy.
1 flowy set or jumpsuit
Change things up without adding too many game-time decisions.
2 tanks + 2 tees
I like to bring a few dedicated tops for my adventure days that will be worn once, and then pack a few good white tops that I can rewear for mornings or lazy afternoons. I love this little white ruffle tank.
1 lightweight button-down
I always end up wearing this 3+ times for mornings or sometimes as a coverup — sharing my fav below.
1 light sweater or wrap
Think airplanes and breezy evenings — a neutral is a must.
Workout or activewear set
Especially if hiking or excursions are on the agenda — love a good athletic dress!
Sleepwear + undergarments (self-explanatory, but don’t forget)
3 (or 4) pairs of shoes:
Sandals, sneakers and a fun shoe (or two) for fancy dinners! Emphasis on the comfortable here. No one wants to be hobbling around the resort on day two because of blisters.
Pro Tip: Stick to a complementary color palette so everything can be mixed and matched. No need to change your entire aesthetic or purchase a new wardrobe for a trip. I love to stick with my favorites and then add in a few fun pieces (think a fun Monday swimsuit or Farm Rio dress) to add colors that feel like the destination.
Staples I’d Recommend
A Striped Button-Down: Frank & Eileen is always my favorite for a breezy button-down. I would size up in this one to serve as a beachside coverup and a good pair-with-denim shorts top.
Beach-to-Dinner Sandal: The Twiggy Sandal is great because it’s an easy throw-on for the beach or pool but it’s also a beautiful sandal and pairs well with any day-time or evening outfits.
Quality One-Piece: Like I said, even if you’re a bikini girl through and through, packing a one-piece is still a great decision for diving off the bow during your boat excursion or covering your sunburnt belly button (oops!). I love Hunza G because they are excellent quality and work for all seasons of life since they stretch well.
Skincare, Sun Essentials & Makeup
The sun hits differently in the tropics, and sunscreen/aloe are the last things you’ll want to spend money on once you arrive as it’s generally marked up beyond standard pricing.
Must-haves:
Mineral sunscreen (face + body — and make it reef-safe!)
Aloe gel or after-sun lotion
Hydrating mist or toner (so refreshing post-beach)
Lip balm with SPF (an absolute must!)
Bug spray (especially if you’re going somewhere humid)
A note on makeup:
It’s always tempting to pack the whole line-up of makeup items, but, especially for the tropics, I recommend a simple glowy look. The sun will give you a natural base, and I promise you won’t want to feel your face dripping off at dinner!
And of course, you’ll want a wide-brim hat and sunnies. This hat is packable and perfect imo.
Niche Packing Favorites
You know the ones — small items that make travel smoother, more comfortable and less chaotic:
Packing cubes: They aren’t over-hyped. A game changer for smart packing! I love the Away set.
Reusable water bottle: A must.
Portable phone charger: Also a must.
Cadence cubes: I discovered these this year. Think packing cubes for your shower products!
Mini first-aid kit: Bandaids, ibuprofen, motion sickness meds.
Wet bag or extra Ziplocks: For sandy swimsuits or leaky toiletries.
Foldable beach tote: You can’t beat an L.L. Bean Boat Tote.
Portable speaker: I love the JBL Go for travel.
Hat clip: Whoever first created this is a genius. If your hat isn’t packable or you’re worried about it losing shape, this is perfect to keep it in tow!
Waterproof phone case: Especially if you’re planning any water excursions!
Deck of cards: I know, so random. But how fun while you’re in the airport or sipping drinks post-dinner? This is a great way to keep you engaged and off your phone to truly unwind.
A rain jacket: Because you never know. This one packs down easy and is still cute!
Should you need any luggage suggestions, I have a whole ‘travel shop’ with recommendations here!
Travel Day Attire
If at all possible, make your travel day outfits work for the destination too. You’ll always want something fresh to go home in, but if you can rewear your travel-there outfit, it cuts out extra fluff!
Our go-to combo:
Lightweight joggers or linen pants
Comfy tank or tee
Oversized button-down or sweater
T-shirt dress (maxi, of course!)
Slip-on sneakers or flats
My ‘Jet Setting Style’ page shares all of my favorites!
TSA Tips for Toiletries
Remember the 3-1-1 rule: liquids must be under 3.4 oz and fit in one 1-quart clear bag. Most resorts or rentals will have basic toiletries, but if you want to bring yours from home, the following list is a good starting point. The Cadence cubes I mentioned above are super handy for these items!
What to pack in your carry-on toiletry kit:
Face cleanser + moisturizer
Sunscreen + after sun
Toothpaste
Travel-sized shampoo/conditioner
Deodorant
Contact solution (if applicable)
Liquid makeup products
Non-liquid items to remember:
Toothbrush
Hair ties, comb, dry shampoo
Feminine products
Hair tools (I like to pack a straightener or curler and that’s it!)
Final Thoughts
Don’t underestimate the joy of feeling prepared and not lugging an overstuffed suitcase through the airport or ferry terminals. Packing smart lends to a smoother overall travel experience.
Ready to pack?
You can find all of my Tropical suggestions here or visit my ShopMy page for various travel recommendations. And if you're planning a trip and need help with logistics or resort recs, you know where to find me!