What I’m Packing for a Long Weekend in the Bahamas
Very few people want to spend the two days before a trip spiraling over what to pack. Here’s how to avoid that.
If you’re anything like me, getting ready for a vacation can require nearly all of the mental energy you have before you’ve even gotten on the plane—especially when you’re packing not just for yourself, but for your under-one-year-old daughter, too. But over time, I’ve realized that the key to vacation dressing isn't becoming a different person with a hyper-organized, look-by-look packing system. It’s having a few reliable outfit formulas that can do the heavy lifting for you.
I shop and put outfits together for a living, so I’m always keeping a loose mental inventory of pieces that can work across different trips, climates, and travel styles. What I’m not doing is building out some elaborate spreadsheet of looks or photographing every possible combination in advance. That kind of planning has always struck me as a little too aspirational for the reality of actual travel—especially with a baby involved.
I’m also not someone who wants four outfit changes in a day. I like clothes, obviously, but I’m a fairly low-maintenance vacation packer. I want to feel pulled together, but I also want to be comfortable, practical, and able to get from one part of the day to the next without needing to fully reinvent myself each time.
With Memorial Day around the corner, I’ve already started mentally assembling what I’m bringing for an upcoming family trip to the Bahamas. This is not, for me at least, a destination that calls for anything too precious or overworked. The mood is more straightforward: swimsuits, airy cover-ups, surf-inspired jewelry, netted bags, flat sandals, and pieces that can move easily between the beach, nap time, dinner, and whatever else the day has in store. The best vacation wardrobe is one that looks good without demanding too much from you.
Below are the outfit formulas I’m relying on—and the ones I suspect I’ll come back to all summer.
On the Plane
If you’ve ever traveled with a baby on a plane—or, really, anywhere—you know that comfort and mobility are non-negotiables. But that doesn’t mean you have to resign yourself to looking completely shapeless or defeated in transit. There are enough elevated basics on the market now that it’s entirely possible to dress for comfort and still feel like yourself.
For travel days, I’m looking for pieces that are soft, forgiving, and easy to layer: knit pants, a roomy button-down, a lightweight sweater, a simple tank or T-shirt, and a flat shoe I can actually move quickly in. The goal is to feel comfortable sitting for hours, but also prepared to carry bags, pick up a baby, bend down in an airport terminal, and generally function. An oversized zippered tote is essential, too—something that can hold the usual travel chaos and double as a diaper bag if necessary. If an outfit can survive the airport and still work when I land, I consider that a success.
For the Beach
My rule for any beach trip that requires a flight is simple: always pack a swimsuit in your carry-on. It’s partly a lost luggage precaution and quite practical. If your room isn’t ready when you arrive, or you have a window of time before dinner or check-in, it’s nice to be able to change quickly and head straight to the pool or beach instead of waiting around.
Swimwear is one of the easiest things to pack because it takes up almost no space, which means I usually bring a few options without overthinking it. For me, the sweet spot is a small rotation: one polished, minimal suit; one that feels a little more playful; and one that can double as a bodysuit under a skirt or pair of linen pants. Add an easy cover-up, a great pair of sunglasses, a beaded necklace you never take off, and a sandal you can slide into without a second thought, and you’ve more or less handled an entire category of vacation dressing.
Sightseeing
Even on a beach trip, there’s always a point when you want to leave the hotel or house and look like a person with interests beyond lying horizontally in the sun. Maybe it’s lunch in town, a quick walk through local shops, or just an afternoon that calls for something a little more complete than a swimsuit and whatever was closest to the lounge chair.
The key is packing pieces that still read as resort-wear, but can handle a bit more real life—getting your steps in, navigating the heat, and holding up on cobblestone streets or whatever terrain you end up on. A great button-down, easy linen pieces, a matching set, a bag you can wear crossbody, and a simple shoe—even a flip-flop—are all essentials here. Stow away some extra SPF, teething toys (if you know, you know), and water, and you’re more or less set for the day.
Rest Day
There are always a few days on vacation where doing very little feels like the best possible plan—that often just means staying close to the room, the pool, or wherever nap time lands. Your suitcase should leave room for that, too. The same easy leisure dressing that gets you through the rest of the trip applies here: pieces you can wear more than one way, fabrics that don’t wrinkle, and anything you can throw together without a dress rehearsal.
Think soft tanks and tees on rotation, silky pants or easy shorts that can double as sleepwear, a slip dress that works for lounging or dinner, and a swimsuit you actually want to stay in for a while. Maybe there’s a spa treatment on the calendar; maybe you’re simply moving between the shade and a chair by the water. Either way, the goal is to feel comfortable, breathable, and put together enough.
Beach to Dinner
There’s always at least one beach-to-dinner stretch on vacation, and the trick is packing for it without treating it like a separate outfit category. A great swimsuit that can pass as a bodysuit, a wrap skirt or easy trouser, an oversized button-down, and a sandal that works beyond the pool usually does it. Add a few pieces of beaded jewelry and a bag that feels just slightly more dinner than beach-adjacent, and the transition takes care of itself.
