I'd never been to Key West before, but I knew I would love it -- a sleepy beach town with a vibrant history and aesthetic. The spot where Jimmy Buffett and Ernest Hemingway intersect. Cool, but not too cool. It was just what I needed.
A few highlights and tips from my trip:
Most trips I take involve lots of advance shopping/wardrobe planning and elaborate packing lists (that I save for years, because I am a weirdo), but this was really a "drag out a suitcase and throw things in like a madwoman" situation. Surprisingly, it worked. Here's what I took for a quick and casual tropical vacation:
Basics: a pair of jeans // my favorite pair of print shorts // a white button down // one or two good tee shirts // cute sneakers
Good stuff: an easy maxi dress // a not-boring bathing suit (a departure from my usual black tank suit) // a comfy t-shirt dress that doubles as a coverup at the pool // a lightweight sweater for cool mornings and evenings // a romper, the easiest warm weather outfit (I wore my trusty black one, but I wish I had picked up this chic white one or this super-cheery printed option) // cool shades // very walkable sandals // a tote that works for day and night
Travel essentials: a suitcase that holds a ton (and looks so chic as you're schlepping through the hotel lobby or airport) // a cheery bag to hold all of your beauty essentials // the cutest portable electric toothbrush // a great read for lounging poolside (loved this one -- lots of laughs and some really great advice)
My goal for the trip was to do as little as possible, but I did manage a few fun excursions:
Ernest Hemingway House and Museum is a great place to spend an hour or two exploring the legacy of one of Key West's most famous residents. I loved strolling around the gardens and hanging with the current residents, lots and lots of six-toed cats (many of whom are descendants of Hemingway's polydactyl cat Snow White).
Sunsets are a big deal in Key West, and Mallory Square is a great place to watch them. You'll have a great view of the main event and enjoy a carnival-like atmosphere including street performers, tasty food, and lots of cocktails.
I came away from this trip with a new favorite phrase: nuisance chicken. There are chickens everywhere in Key West! I kind of liked seeing them strut around (and I may or may not have done a bit of chicken dancing down Duvall Street after a few rum-based beverages), but not everyone is a fan.
This wasn't a particularly foodie-centric vacation (we bought some groceries on the way and did a lot of snacking in the room, by the pool, etc.), but I can recommend a few good spots:
Cuban Coffee Queen is a fairly tiny food stand that serves up a lot of good Cuban comfort food, great coffee, and another good photo op.
Filed under "it's a small world" is Santiago's Bodega, a great little tapas spot where we grabbed lunch after our visit to Hemingway House. Several people recommended it, and the menu of lots of tasty sharing plates sounded perfect. When we arrived I noticed that this restaurant has a few outposts, including one in Orlando, and I realized it happens to be right across the street from my hair salon -- my hairdresser raves about it! Crazy that I had to drive to the end of the world to try it, but totally worth it.