3 days in key west

searchin' for my lost shaker of salt

last week, i took my almost-sixth annual Warm Weather Winter Getaway™ (skipped 2021 because…COVID) and opted to go to the real life margaritaville aka key west, florida since i’d a) never been and b) my jetblue credit card points covered nonstops to and from boston! it was the perfect little tropical escape and a much-needed reset during these dismal, doldrum days. here are the highlights!

DAY 1:

first of all, y’all…i cannot express the lameness and rinky-dinkiness of the key west airport in words. i figured it would be small, but wow. wow. just wow. the airport in rural cusco, peru was much more upscale than this operation. i’m talking walking-on-the-tarmac-from-the-plane, one working baggage carousel (with a small, adjacent bar doling out daiquiris, obv), and one gate area where everyone congregates to board their flights. one. i mean, i couldn’t beat the convenience, but i’m still blown away that this airport exists in the united states. yowza.

anyway, once i arrived and stowed my bomber jacket in my suitcase because it was a balmy 75 degrees and sunny, and hailed a lyft downtown, my first order of business after storing my luggage was lunch al fresco since i couldn’t check into my rental just yet. i popped over to two friends patio, where i housed a crab cake sandwich, sipped a mint limeade, and delighted in the live music stylings of a young surfer-like troubadour with sun-kissed locks. we were off to a great start!

i strolled down to this little mini-mall to window shop at a couple of the boutiques and vintage stores like boutique alexandra and in one era and snagged a cafe con leche at the famed cuban coffee queen because caffeine was NECESSARY.

then it was finally time to check into my room, and i was SO happy with my accommodations for this trip! i stayed at travelers palm, which bills itself as a boutique hotel, but is really more of a collection of three studios and three suites with separate entry and a beautiful heated pool in the center of the property. my room, the sugar palm studio, was perfect for my purposes, and i loved that i was only a short walk to all of the action of duval street, etc. (but not in the middle of it). as a bonus, it was quite a bit less $ than most of the airbnbs and hotels i was looking at — which was great because key west is EXPENSIVE, especially as a solo traveler. highly recommend!

i was still feeling kinda full and wasn’t in the mood to drink or eat again yet, so i took a long stroll down to key west cemetery. i’m pretty sure i was the only person in there, but it was very peaceful and reminded me a lot of a much bigger version of cemetery #1 in new orleans (minus nic cage’s tomb).

fun fact: judy blume has a bookstore down there called books and books!! sadly, she was not there when i stopped in, but there was a sweet older lady working there and they were playing the harry’s house album; i was like “great soundtrack choice!” and she’s like “i love harry styles!” and i was like “same, girl!” and it was adorable.

despite still not being very hungry and losing steam because i had gotten next to no sleep the prior night, it was starting to get late and i figured i should have SOMETHING rather than go to bed on an empty stomach and waste a meal on my lovely vacation. enter nine one five, a chic eatery in a historic victorian home. i ordered a raspberry lemonade mocktail and some ahi tuna tacos (both delicious) and chatted with the bartender about how she used to work in nantucket. relatedly, the amount of new englanders i met in a few days was insaaane. we’re everywhere!

DAY 2:

i had one of my favorite experiences of the trip at blue heaven, a KW institution where i enjoyed a late breakfast. i sidled up to the very tropical-feeling outdoor bar, ordered myself an iced coffee and stack of their self-proclaimed “very good” pancakes, and got to talking with the woman sitting next to me — who was from new jersey and also on a solo adventure — as a guy-and-gal duo serenaded the courtyard with four non-blondes and roberta flack and nutty roosters ran around. sidenote: everyone told me about the notorious key west roosters, but i was truly unprepared for the amount of them on the island. and the cock-a-doodle-dooing! at all hours of the day and night! bananas. anyway, the conversation was lovely, the pancakes were truly the best i’ve ever had, and it was the perfect way to start the day.

one of my 2025 to-dos was to stand at the southernmost point in the continental united states, which is marked by a colorful, picture-perfect buoy. to my surprise and confusion, there was a line halfway down the block to take photos next to it. but because i’m all about working smarter, not harder, i surveyed the situation and simply stood atop of the bench in front to get my photo without the wait, joking with another woman who was doing the same thing. come on, people!

after a quick pass by higgs beach — perhaps contrary to popular belief, key west isn’t really a beach town, but it does have a few purdy ones — i was on to the hemingway home and museum. GUYSSS, the cats there have my whole heart. they were snuggling and sleeping all around the property and i wanted to take all of them home with me.

and while the hemingway home is a must-do, i actually enjoyed the key west butterfly & nature conservatory the most. it’s this beautiful greenhouse, filled with lush plants and colorful, tropical butterflies flying all about — plus a couple flamingoes, too! loved it.

after a couple hours of being a tourist, i was more than ready for a late lunch in the form of my much-anticipated sloppy joe at the namesake bar, sloppy joe’s. as soon as i sat down, the fun began when a man in his late 50s from maryland started chatting with me and 20 minutes into the conversation, we’re having a deep talk about his 20-something kids and music and life, as a man who looked like he used to be in an ‘80s hair band sang a folky rendition of “bohemian rhapsody.” it’s my gift, man. dads and are just meant to be.

but speaking of which! i’ve said it before, but it bears repeating: if you’re reluctant to travel by yourself or worried it’s going to be boring or sad, PLEASE know that at least for me, the opposite is always true! i quite literally met people at every single place i went on this trip. that being said, one thing i did observe about key west is that some staff members at restaurants/bars seemed a bit bewildered by the fact that i was solo in a way i haven’t encountered in other cities, which was honestly just funny to me? fortunately, i’m experienced and confident enough to stand my ground when a couple of them tried to do silly things like banish me to a dark indoor bar (“no, i’d like a patio table outdoors, please!”).

moving on! i grabbed a post-lunch hazelnut iced coffee at keys coffee co., which was just the late-afternoon boost i needed.

about a month ago, i had read about the seafood-centric little pearl, a vibey little restaurant with a tasting menu, and immediately jumped to make a dinner reservation. from the service to the food and the ambiance, everything was pitch perfect. i ordered: grilled oysters, seared scallops, ahi tuna, and bourbon eggnog ice cream, with a glass of chilled sauv blanc to wash it all down.

and because i obviously needed to indulge in the famed key lime pie, i snagged a slice to go after dinner from kermit’s key lime pie shop; there are a lot of opinions on the best purveyor and about what makes a true key lime pie, but this one’s tart flavor, cheesecake-y texture, and dollops of whipped cream got high marks from me.

before i enjoyed it in my king bed, though, i had to make the most of the pool and the fact that it was still 73 degrees at 8pm; the ideal occasion for a quick dip.

DAY 3:

one thing that i very much appreciate about the key west lifestyle is that there are so many almost euro-style little sidewalk cafes where you can sit on patios and enjoy your coffee and breakfast. la grignote was one such spot, and i grabbed a street-side counter seat to people watch and chow down on their “southernmost verde” sandwich (smoked salmon, swiss cheese, arugula, tomato, and zesty green sauce on a croissant). i met a couple here from cape cod who were enjoying the eatery’s specialty: a multi-layer honey cake, the owner’s parents’ recipe.

i had decided to enjoy one of the many water excursions on my final day, and chose the “sandbar safari with dolphin playground encounter” because all of those things sounded fantastic to me. it was so much fun! i took a boat with about 20 other people out to a sandbar in the gulf of mexico, waded into the 70-degree water for a bit, ate chicken fingers on the boat, and then saw like a dozen dolphins swimming and jumping all around us! it was magical.

the hardest part of spending only a few days in a place with lots of great food is making the tough choices of where to eat for each meal. i had been going back and forth between a&b lobster house, a swanky seafood spot, and bagatelle, a slightly more laid-back but still upscale bistro. but when it comes down to it, i just tend to go with the flow of what i’m feeling that day. the historic-house charm of bagatelle and the cocktail and food menu were speaking to me, and it ended up being an excellent choice for multiple reasons. one: the cherry jubilee cocktail with amaretto, bourbon, muddled black cherries, and lime juice. two: the pan-seared hogfish with coconut rice, grilled asparagus, and piquillo pepper cream. three: the fact that i was sitting next to a 21-year-old server at the restaurant who was enjoying a post-shift bite, and by the end of our delightful conversation, he paid for everything. hehe. #stillgotit!

so, the only liiiittle bit of FOMO i had during the trip was that i didn’t visit general horseplay, a craft cocktail bar that was at the top of my list. but ya know when you walk by a place and the vibe just seems kinda “meh” and you’re not feeling it? that was me with general horseplay on wednesday night. next time!

instead, i went to 22&co., a colorful and fun little bar full of unicorns and tutus and glitter, where i indulged in the most delicious (and perhaps the only?) peanut butter martini i’ve ever had. still dreaming about it.

my sweet tooth was still achin’, however, so i swung by moondog cafe for a mini rum cake that was absolutely delicious. “don’t get drunk!” the animated cashier quipped at me as i left.

DAY 4:

i needed one more warm-weather outdoor cafe experience before i caught my afternoon flight home, and frenchie’s fit the bill. this danish with fresh berries was heaven sent!

after killing some time house stalking, checking out of my rental, and soaking up the final drops of sun, i rolled my carry-on up to the bar at mangoes, an open-air restaurant i’d walked by a few times during my visit, and enjoyed a shockingly good mahi sandwich and pasta salad. relatedly, i am now on a seafood detox for like two weeks. maybe one, because i can never stay away for very long.

overall, key west is fun, quirky, and has a little bit of everything for every kind of traveler — great food, great drink, great live music, great weather, and great people watching. if you haven’t been, i definitely recommend it as a laid-back island vacation!

p.s. my trip theme songs, because i always have at least a couple!

momma - “i want you (fever)”

royel otis - “nack nostalgia”

heidi montag - “i’ll do it”

the criticals - “mother of style”