Updated August 28, 2022.
Packing is one of my least favorite parts of travel, but somehow, even I can admit that I’m really good at it! Steve and I recently visited Key West for the first time, which was amazing, but one of the best parts was the fun, summery weather so I could wear my cute clothes! We went in January, but thanks to Key West’s tropical climate, this packing list can go for any time of the year!
No matter how long you’re staying, whether it’s three days, a week, or two weeks, I recommend taking only three of any one item (three dresses, three bathing suits, three tops, etc.), and it helps if those items go together to create more outfits. The links to clothing below are Amazon affiliate links. When you click the links to shop with me, you’re supporting my small business at no additional expense to you!
Out on the Town (pick 3 outfits)
Choose three of the outfits below (one of each, or three of one category), and if you can interchange the pieces or change them up in fun ways, even better!
Dresses
Check out the skirt below… it doubles as a strapless dress and is made in the USA!
Rompers
I love a fun, easy, breezy romper! They make great outfits for dinners out, bathing suit cover-ups, or lounging!
Related: Visiting Hemingway’s House in Key West
Tops and Shorts
The right combo can be interchanged to create multiple outfits!
More here: 9 Ways to Style a Midi Dress
Shoes (choose one of each)
Sandals
These are the most comfortable sandals I own, and they’re supportive for all that walking, too!
Water Shoes
I never get in the water without water shoes, especially when there are coral and shells to contend with!
Walking Shoes
Because you’ll be walking around the Old Town on uneven surfaces, I recommend bringing a pair of sturdy walking or running shoes. Who cares if you look a little “touristy?” Almost everyone in Key West is a tourist!
Podiatrist approved: Your Travels and Your Feet
Accessories (choose a few that go with multiple outfits)
Kimono Cardigan
Kimonos are awesome for travel because they are so versatile!
Read next: How to Style a Kimono Cardigan
Scarves
Scarves, like kimonos, can be changed up and worn in multiple ways.
Read next: 5 Ways to Wear a Scarf
Jewelry
Jewelry is one of my favorite ways to change up any outfit and stretch my wardrobe! Here are a few pieces to give you some ideas:
Read more: The Ultimate List of Things Every Woman Should Pack
Swimwear (choose two or three)
Be sure you take at least one that will stand up to swimming in the ocean, possibly with dolphins! Function is as important as fashion in the waves!
Read next: The Ultimate List of Summer Gear
Active Day Trip or Excursion Gear (choose as you feel appropriate)
Whether you’re heading to Dry Tortugas National Park, a dolphin encounter, a kayaking excursion, or something just as adventurous, make sure you pack the right gear!
Activewear Tops
Activewear Bottoms
Hat
Sunglasses
Dry Bag
Reef Safe Sunscreen
Read next: What to Know Before You Visit Key West
Want more packing help? Check out all my strategies and the best tips out there on my Packing Page!
And for all my posts about Key West and Florida, head over to my United States Page!
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