an ultimate guide to key west
key west: where the weird are always welcome. this off-the-wall, eclectic & open-minded community is bustling with personality. my family’s been coming to the keys for as long as i can remember. one year we drove straight through - 22 hours from wheeling, wv to key west, florida. it was the first & last time we’ll be doing that. whenever we do go, i can’t leave without visiting these places:
if you like history:
the harry s. truman little white house, florida’s only presidential suite, has been a getaway for various presidents including dwight eisenhower, jfk and of course harry truman. truman spent over 150 days of his presidency here debating changes in foreign policy and the u.s. response to the cold war. what was originally naval housing in 1890, now serves as a presidential museum for tourists to learn about the rich military history that’s intertwined in key west.
there’s no friend as loyal as a book, ernest hemingway once said. the famed author spent many years in key west, overcoming writers block & drinking his worries away with friends. during his ten year tenure here, he lived at 907 whitehead street. walking into the hemingway house is like stepping back in time. original furniture and decor still fills the home. descendants of hemingway’s six-toed cats roam the property. and the original 1930’s in-ground swimming pool (a major feat at the time) still remains glistening in the summer sun. it’s one of my favorite places to visit!
fort zachary taylor is a civil war fortress turned state park. the fort was used to deter supply ships from reaching confederate ports in the gulf of mexico. in the late 1960’s when excavations took place, ammunition and other weapons were uncovered in a buried arsenal. fort zachary taylor, a national historic landmark, holds the largest amount of civil war cannons in the u.s. today, you can tour the grounds, as well as soak up the sun on their public beach.
if you like food:
for true caribbean cuisine, look no further than blue heaven. their menu is ever changing, but you can find a few staples like jamacian jerk chicken and fresh yellowtail snapper on their dinner menu. the restaurant is tucked under vibrant trees and hidden from the hustle & bustle of duval street.
right across the street from blue heaven is la creperie french cafe. i highly recommend stopping here for breakfast because it is to die for!! you won’t find crepes like this anywhere else on the island. dine outside on their patio for a true parisian experience. the crepes are filled with fresh & organic ingredients, drinks are served in upcycled mason jars, and straws & to-go materials are completely biodegradable. this makes la creperie one of the first eco-friendly restaurants in the florida keys!
for a bit more formal option (you know, where shoes & shirts are necessary) try latitudes, on sunset key. a short ferry ride will take you to the ocean front restaurant. here, of course, you’ll find the freshest fish & seafood. i’m not a seafood person at all, but i go weak in the knees over their lobster bisque. pro tip: make sure to book your reservation for dinner time, because there’s nothing more beautiful than a sunset in key west.
if you like nightlife:
duval street is the key west equivalent to new orlean’s bourbon street or nashville’s broadway - but better! this is where the greats came to drown their sorrows & celebrate their accomplishments. ernest hemingway, truman capote and jimmy buffett were a few to seek refuge in the local bars. today, many people take on their own “duval crawl” and bar hop till the sun comes up. the world’s smallest bar - and it’s small, only 72 square feet - lives on duval and has the biggest energy in town. you just have to stop buy and buy a beer. key west has open container laws so you can take your beer to go! everything is very walkable, there’s never a need to drive anyways.
hog’s breath is another popular hangout in town. this watering hole has been a staple in the community for almost 25 years. great food, great drinks & fantastic live music. actually, one time my family was here & kenny chesney stopped by and gave a free concert! and as they say, hogs breath is better than no breath at all!
a self-proclaimed “sunny place for shady people,” the green parrot is one of the oldest bars on u.s. route one. what started out as a grocery store in 1890 morphed into one of the rowdiest and well known bars in florida. if you want to drink like a local, head to the green parrot.
my personal favorite is a place where hemingway frequented, captain tony’s saloon (though it was named sloppy joes at the time - but keep reading, i’ll get there). the bar was bought by local boat captain tony tarracino in 1958, and affectionately named captain tony’s saloon. you could find tony at the bar every week, even after he sold it and up until he passed away in 2008. inside you’ll find dollar bills, business cards, license plates & bras stapled to the walls and ceilings, along with some pretty strong drinks. captain tony’s was also where jimmy buffet got his start. before he made it big, he sang here & was paid in tequila.
in order to truly understand the essence of sloppy joe’s bar in key west, you have to go back to december 5, 1933 - the day prohibition was repealed. it’s also the day sloppy joe’s served it’s first beer. originally located on greene street, the bar quite literally up & moved in 1937 when the landlord raised the rent. the owner, local patrons & employees picked up their drinks - and all the furniture - and moved to a vacant building on duval street, where it proudly stands today. because hemingway was basically a permanent fixture there, they hold a “papa look-alike” contest every year where hemingway’s relatives crown the best impersonator.
where to stay:
where do you stay when you’re on an island? what about another island? sunset key cottages is a tropical oasis located a mile offshore from key west. the only way to get there is by ferry (which runs 24 hours). little white cottages paint the island community, which also has a gym, pool, spa, restaurant, tennis courts, and even private homes! each morning you’ll wake up to a basket of goodies - fresh fruits, pastries, & breads. a few steps off your porch & a private, secluded beach awaits. if that’s not your style, there are countless bed & breakfasts, hotels and bungalows for you to call home (you just won’t get views like this)!
can’t miss photo-op:
did you know that in key west, you’re closer to cuba than you are to miami? there’s a vividly painted buoy to designate the southernmost point of the continental united states. this screams TOURIST but it’s the perfect photo-op! stop by the southernmost house hotel for a drink before you wait in line for a photo. the old victorian home is a bed & breakfast with killer drinks & amazing oceanfront views.
have you been to key west? where’s your favorite place?