Holiday Packing

Now that you’ve booked your holiday, the countdown has officially begun. The trip is just around the corner, and you cannot wait to have a few margaritas by the ocean in the scorching sun, with sand between your toes.

You’ll undoubtedly have a top-notch week (or two) wherever you’re headed. If you’re planning a luxury vacation, chances are your resort or hotel will provide everything you need and then some. However, you still need to bring a few things from home to make your luxurious holiday 100% perfect, and this post will deal with that.

You can use this luxury holiday packing list to:

  • Make sure you’ve packed everything you need
  • Save some money by avoiding the frankly ridiculous resort-shop prices
  • Pack only what you need rather than hauling around a bunch of unnecessary items

Let’s get started!


Packing Your Carry-On

Whenever you’re setting up a packing list for any vacation that includes flying, you should start with your carry-on.

First, for a genuine luxury experience, you’ll want a high-quality collapsible cabin suitcase.

Once you’re sure you have the right luggage piece for your luxury adventure, you can start thinking about what you should bring with you on the plane, so you’re only mildly inconvenienced if your checked bag winds up on the other side of the planet.

If you’re flying to a luxury resort, you should always pack at least a couple of sandals/flip-flops, beach outfits, and swimsuits. This is doubly important if you have a connecting flight, as this increases the chances of your luggage getting misplaced or delayed.

Even if it only takes a day or two for your checked luggage to show up, not having beachwear and a swimsuit during that time would royally suck, so you don’t want to take that chance.

Of course, the slim chance that your checked bag will get lost is not the only reason you have a carry-on suitcase. If you live anywhere but the Tropical belt, the temperature difference between your departure and arrival will likely be huge.

It is a good idea to change into a summer dress or shorts just before the plane begins its descent. Trust me, wearing leggings or jeans in a humid and hot customs line is not the way to start your luxury vacation. You don’t need anything fancy just getting off the plane, so any casual easy-to-pack dress will work just fine.


Luxury Holiday Packing Checklist

You’ll need to pack more than a carry-on if you want a true luxury experience, so the rest of this post will assume that your checked luggage will reach your destination in time. Let’s talk about everything else you need to pack to enjoy your vacation fully.


1. Evening Wear

Nothing beats a dinner at an all-inclusive resort.

In terms of restaurants, these resorts usually offer a few choices, including both upscale and casual dining options. Typically, both options imply some sort of evening-wear dress code. You should make sure to pack at least three or four different outfits that fit the code.

You do not have to go into full “red carpet” mode here. You’ll likely be OK with a couple of lovely skirts/beach dresses, or even a pair of shorts that combine well with a pretty top.

Things are even more straightforward if you’re a guy. Avoid muscle shirts and tank tops if you want people around you to have a comfortable dining experience. In the more upscale resorts, you’ll need at least a collared t-shirt (preferably a button-down), long pants, and close-toed shoes.


2. Hats

A hat is an essential piece of clothing for a resort vacation. If you have a big floppy hat, it’s an excellent option for sitting by the pool, as long as the day is not too windy. If you plan to spend a lot of time at the beach, though, the wind will kick in at some point, so your big hat will become a liability.

In that case, you’ll want to bring a fedora or at least a firmer, wide-brimmed hat in a neutral color.

Men need hats as well.

Pack at least a couple of hats for an all-inclusive vacation. A bucket hat folds down into nothing, so it’s the most convenient option; plus, it’s coming back into fashion. That said, you should also bring a wide-brimmed option for some extra protection from the scorching heat.


3. Jewelry Travel Case

Nothing says “luxury” like having your favorite jewelry with you at all times and having all your bracelets, necklaces, and rings neatly organized for easy access.

You’ll probably want to wear your flashiest pieces to the restaurant, especially if you’re going to glam up your beach skirt/casual top combo. However, that’s not the only reason to bring a jewelry case — it will also come in handy for anything you buy while you’re there.

Large, all-inclusive Caribbean beach resorts often have clothes and jewelry markets where you can get some gorgeous pieces, and the beach vendors are never far away. Chances are you’ll be tempted to buy at least a pair of earrings, so it’ll be great to have somewhere to pack them safely rather than jamming them into a random corner of your luggage.


What to Avoid

It’s definitely possible to save some space in your luggage by not bringing certain items. We’ll take a look at them here.



Guests at luxury resorts are provided with towels, which they can exchange for clean, dry ones at any time.


High-Heeled Shoes

Shoes take up a lot of space in a suitcase and can be pretty heavy. Avoid packing them if you can help it. The only shoes you need are a few pairs of flip-flops or sandals and maybe a pair of evening sandals for dinner.

If you really love high heels, try to pack a pair of lightweight wedges instead. All-inclusive resorts tend to have a lot of stairs, and any nearby cities and towns have many cobblestone streets – heels are not a great option there.



Yes, we know what you’re thinking. You’re traveling to a tropical destination, and the humidity will curl your hair like nobody’s business. However, there’s no better time or place to embrace the curly awesomeness of your beach hair than an all-inclusive resort!


Tons of Clothes

You don’t need to bring as many clothes as you think. The markets and beach vendors we mentioned above sell all kinds of fashion items, and a cute sundress could be a great souvenir from your luxury vacation in the Caribbean.