14 Day Caribbean Resort Packing List

!4 Day Caribbean Resort Packing List

Grey Tank | Black Camisole | White T-shirt | Airy Blouse | Striped Pullover | Blazer
Light Jacket | Swimsuit Cover | Denim Shorts | Black Shorts | Black Pants | Swimsuit
White Dress | Black Dress | Maxi Dress | Yellow Dress | Slip-ons | Espadrille Flats | Sandals | Heels
Black Necklace | Tassle Necklace | Straw Hat | Wool Hat | Watch | Sunglasses | Earrings
Small Purse | Big Purse | Mason Travel Satchel

Recently I got a message from Darlene. She wanted to know if I have ever made a packing list for a Caribbean all-inclusive resort for two weeks in a carry-on. I told her that I hadn’t but I would be willing to give it a shot. I like getting suggestions and I enjoy compiling these lists so I was looking forward to the challenge.  Having been to a tropical place before I can use that experience as a launching off point. To start, when I went I packed way too much. I think I only used 1/3 of what I brought in my gigantic suitcase. Now that being said, we were there for 10 days and we did not stay at a resort. A resort has more opportunities for dressing up so you may need to bring things that can easily dress up, a heel, a few dressier pieces, some accessories. Easy.

I put together items that all match so you can maximize the wardrobe. Every top goes with every bottom, they can be layered or worn with a light coat. The shoes and accessories can change the look of the outfit completely. On Saturday I will post an outline of day to-night outfits for the complete 14 days and link it here for easy reference. Some pieces can also be switched around or taken out entirely depending on if you are more of a short wearing person or dress person. The rule is: add one, remove one. If you add another pair of shorts, than remove another item to balance it out. I did my best to give completely different outfit options for each day and night for the entire 14 days. That means that this list is easily cut down even more if you choose to wear outfits more than once because you won’t need the extra items for the other days.

Here is a breakdown of what this list includes in general terms. That way you can find something comparable in your own wardrobe. Stick to a neutral base like black, white, and grey, because they are easy to match, then add some coloured pieces. For the swimsuit you can add another suit or choose two bikinis of different colours so you can mix and match the tops and bottoms to have more options.

What I included was a cotton tank, a dressy camisole, a simple white t-shirt, an airy blouse, a pullover with a print or design on it, a blazer for dressing up at night, a lightweight jacket for cooler evenings, casual shorts, dressier shorts, a pair of loose airy pants, two casual dresses, two dressier dresses, canvas slip-ons for walking and touring, espadrilles, easy slip-on sandals, heels, two hats, two necklaces, earrings, watch (if you wear one), sunglasses, a swimsuit, swimsuit cover, a small purse for dinners, and a regular purse for days. That’s about it aside from undergarments pyjamas, and toiletries. Wear the bulkiest pieces on the plane there and back and packing should be easy since these pieces are light and don’t take up much room. Toiletries and jewellery can be stored in the small purse. Also, wear the straw hat on the plane if you are bringing one, they do not pack well. Believe me, I learned that the hard way.

I hope this list of what I would bring on a 14 day trip to a Caribbean resort gives you some ideas of what you could pack too. The outfit options for this list can be found in this post.


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  1. OMG Sara…thank you so much.I have been trying to get someone to give me ideas and have not been successful. Your ideas are so realisitic and easily adaptable. Now I can start packing!!!

    • No Problem! It was fun 🙂 I’ll put up the outfit option ideas on Saturday so you can see how it works out visually.

  2. Thanking you in advance…still can’t believe I finally will get some ideas!!! Forever grateful!!!

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