Monday, March 7, 2016

field trip: key west, fl

On the work front, this year has proven to be one of the most hectic and exhausting of my career (and it's just March). A few weeks ago I had friends in town, and after their time in Orlando they headed down to Key West for some true R&R...and on a whim, I tagged along. It wasn't a vacation exactly (since I work remotely anyway it was easy enough to just take my laptop and cell phone to stay connected), but it was a nice change of scenery.

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:

to pack

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)

to stay

My friends had the good sense to book a room at the Gates Hotel, a modern and stylish hotel that offers a lovely spot for a peaceful retreat while still being pretty close to the action. I absolutely loved it here. In another city this hotel might be a bit of a scene, but there's really no room for pretension in Key West so I didn't have to worry about trying to compete with the cool kids. I enjoyed several leisurely afternoons lounging by the pool with a tasty cocktail or two (love a good cabana...and a good cabana boy). There's no restaurant, but the on-site food truck serves really tasty bites for breakfast, lunch, dinner, and even late-night snacks. PS -- this hotel is pet-friendly!

to do

My goal for the trip was to do as little as possible, but I did manage a few fun excursions:

The Southernmost Point is the photo op in Key West. A great spot to gaze upon the clear blue waters (and daydream about a trip to Havana, high on my travel bucket list right now).


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.

to eat

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.

There are LOTS of great bars in Key West, and I don't think we ever encountered a bad one. The Rum Bar was small but charming, with all of the rum-based drinks you could want. The Bull and Whistle is one of the better looking dive bars I've been in (and for the adventurous, offers a clothing-optional Garden of Eden roofdeck). The Green Parrot is a Key West institution, patronized by locals and tourists alike. Key West is a good time kind of town, so don't be afraid to do a bit of exploring. You'll have a good time for sure.

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