Packing for a 3 Day Vacation in Key West

Over the years I have made a conscious effort to become a light packer for vacations. Want to dip your toe into not packing the kitchen sink for a getaway? A warm-weather vacation is a great start. Even though the clothes and shoes are less bulky; that doesnโ€™t mean packing six pairs of sandals should fill the place of two pairs of winter shoes. I have found the key to packing light, is to keep the luggage small and not waiting until the last minute to pack. For a three to five-day trip, I use my backpack to carry all of my shoes, clothing, accessories, and toiletries.ย 

The Fall season is officially upon us. However, Key West, Florida does not subscribe to temperatures less than 70 degrees. For my upcoming trip, I have chosen breathable light clothing to keep me cool. Iโ€™ve only allowed myself two pairs of shoes to take along (one of which will be on my feet). 

My first outfit is an easy non-clingy cotton dress. This is my standard uniform for travel when flying to my destinations. There are no belts to take off or pockets to empty out. Shoes can be easily taken off (if I need to enter into the dreaded body scanner) at the TSA checkpoints. This dress feels like wearing a nightgown but looks like you put effort into looking presentable while traveling.

Similar dress HERE & HERE

This second outfit I plan to wear to dinner or while exploring the city. For a beach vacation it can easily go from day to night. This is one of my proudest retail sale finds. I scored this dress at Nordstrom’s last year during a end of the season sale for $7. Not only does it fit perfectly; it was a great (non-thrifting) find.

Similar look HERE & HERE

Outfits three and four I simply changed the top. I anticipate sweating while walking the city. My vacations are usually fast pace and packed with all day sightseeing. If I have a few minutes to run back to the hotel to quickly freshen up; I’ll change tops add another layer of deodorant and dash out the door.

Similar look HERE & HERE


Outfit five and six are the same concept: Shoes and shorts stay the same, tops can be changed. Now, I know what you’re thinking, “Karissa, are you wearing a sweater?!?!”. Technically, yes. But hear me out. I noticed a trend on J.Crew this summer, featuring the “Beach Sweater”. I found this version at the thrift store and thought I would give it a shot. It’s very see through, which will make it a great cover up when I’ve had enough sun. Will I have a heat stroke and collapse in the street? I hope not. If I do, I’ll know this isn’t the trend for me.

Similar look HERE & HERE


Lastly, I packed a pajama set and two bathing suits. I love wearing matching pajamas while on vacation. What if I need to evacuate the hotel in the middle of the night? Or I have to go down the hall to get ice. I still want to live my full glam Real Housewives of Beverly Hills fantasy.

I prefer one piece swimsuits for two reasons: first, I don’t have to adjust them while getting out of the water. Secondly, I won’t have a worry about not being able to find a top or bottom when I’m unpacking and ready for the pool. I especially like these two suits because they don’t require me to tie any of the straps.

Similar pajamas HERE & HERE

Similar swimsuits HERE & HERE

Six outfits for three days still feels like I’ve over packed. I’m still perfecting my packing strategy.

How do you pack for trips? Do you pack last minute and bring a little bit of everything? Do you pack in advance and edit your choices before leaving?

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