Where to Eat, Drink and Stay in Key West

From where to find the best cuban burgers and sky-high drinks to shadows of Ernest Hemingway, we can make your trip unforgettable.

We found ourselves in Key West for the magical wedding of a friend. She was my roommate while I lived in Paris, hails from the States, but currently lives in London and married a British guy. Key West somehow seemed appropriate for their transatlantic families and friends who hail from all over the world to come to celebrate the blessed occasion. It’s also the perfect place for an agenda full of eating and drinking (and what a wonderful agenda it is)! The Cuban-influenced cuisine is nothing less than exquisite, as is the lively night-life on its main drag, Duval Street.

There is a definite older vibe here, which, quite frankly, is what I am into nowadays. The town is bustling with bars and nightlife, but without the feeling of being surrounded by frat guys or a bunch of fake IDS. My pre-planning suggestions for the trip came from my sixty-something Dad, who makes an annual trip to Mile 0 with his bagpipe band for one of Key West’s annual parades. One thing we didn’t see much of here was children, and I am glad that we left ours at home. This is the place to escape to for the weekend to kick back, enjoy some drinks, chatter at the bar and stuff yourself silly with fresh ocean fish, likely caught off the shore within miles of the restaurant.

STAY

The Lighthouse Court Inn

This charming inn sits across the street from the legendary home once owned by Ernest Hemingway. One can be inspired by the surrounding palm trees and lush banyan trees tilting in their endless mangled splendor. Enjoy breakfast or Happy Hour by the pool or simply relax in their charming “conch” homes that date back to the 1890’s.

EAT

Mangoes

For a touch of the nightlife on Duval Street in a refined and outdoor setting, Mangoes features a local Conch delicacy sampler appetizer, fish tacos and our favorite; a most amazing deconstructed tuna sushi dish. Small plates, an endless outdoor bar and lounge seating make this place something special.

Frita’s Cuban Burger Café

Situated off of Duval Street, exactly where one would hope to find a cool, less traveled and absolutely delicious place, Frita’s serves up some of the most delicious Cuban dishes around. The Frita Burger is a must try and the Cuban Pork Tacos are a house favorite. Top off your meal with some of their house-made sangria—yes, please!

Blue Heaven

No trip to Key West is complete without a trip to this popular outdoor brunch spot. Eat amongst the roosters (literally, we attribute them to the likes of pigeons lingering around your food in New York, but somehow less dirty?), listen to live music while sipping on their famous Bloody Mary and eating a favorite, Blue Heaven Benedicts, or their fresh fish sandwich of the day. You will wait an hour for your table, but you will not be disappointed.

DRINK

Sunset Pier

Take a walk towards the water and find a spot amongst the colorful chairs to sit back, relax and enjoy some of their Tropical and Caribbean culinary delights while sipping on a mojito or margarita. This popular spot boasts the famous mile marker sign to other fabulous destinations all over the world.

Sloppy Joe’s

An entertaining and historically rooted place within the city, Sloppy Joe’s has an elaborate beer list as well as offering quality food and live music to welcome patrons at the door. The bar offers generous drinks as well as dancing well into the wee hours as it closes at 4 a.m. A definite good time to be had by all.

LATE NIGHT

Mr. Z’s Pizza

It’s not New York pizza, but at 2 a.m., it’s pretty darn good.

Garden of Eden

This clothing optional bar is one of those places you have to experience once, whether or not you take your clothes off, just to see all of those brave souls who have decided to bare all.

SEE

Ernest Hemingway House

See where the great Hem wrote some of his most iconic novels. Walk around his pool, visit his writing studio or pet one of the 40-50 descendants of his own six-toed cat that walk the premises today. (A literary and cat lovers’ heaven!)

Mile 0 Buoy

Take a selfie at the “90 miles to Cuba” buoy. With the new surge of tourists now able to visit Cuba, getting within 90 miles somehow seems like one is practically there.

Boats

Lastly, set sail to experience Key West in all its beauteous splendor from the water. Whether it’s to take a fishing excursion or to kick back for a sunset sail, experience just a little bit of heaven on earth in this beautiful place from off shore.

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