It can be hard to explain the appeal of Key West, Florida to someone who’s never been there.
You’ll likely get a confused question that goes something like this: “So Key West is at the end of a long road, three and a half hours from civilization, with no amusement parks, no attractions, and no decent beaches? You just go there to eat, drink, and chill? Am I missing something?”
No. You aren’t missing anything. Because you will eat, drink, and chill in Key West unlike any place else on earth.
Oh sure, Key West is a great place to fish, snorkel or scuba dive. And a tour of Ernest Hemmingway’s house is obligatory for a dash of culture.
But let’s face it. The real reason you come here is to drink mojitos and dine on some of the freshest seafood at the most perfect end-of-the-road tropical atmosphere that can’t be replicated anywhere on the mainland.
So where do you start?
Fortunately for you, as your editor here at Proud American Traveler, I have done the arduous work of eating my way through the best dining spots in Key West and have produced a countdown of the Conch Republic’s top 8 restaurants.
It was hard work. But I did it all for you. You’re welcome.
8. Blue Heaven
You can’t visit Key West without enjoying at least one meal at Blue Heaven. It is the most famous restaurant in the Florida Keys. Heck, Jimmy Buffet sang a song about it, Blue Heaven Rendezvous.
It might be resting a bit on its decades-earned laurels, but there is no question Blue Heaven gets that perfect Conch Republic ambiance down pat.
You’ll sit at an open-air patio between 100-year-old buildings that have hosted Ernest Hemmingway boxing matches, brothels, and impromptu Buffet concerts. Chickens cluck around at your feet as a soft breeze sways the strings of lights hung in centuries-old trees that have witnessed it all.
There is no place else like it.
Unfortunately, the dinner menu doesn’t quite match the laid-back atmosphere. The $35 BBQ shrimp are good, but lack that Key West flair you come to expect. If you order the Florida lobster tail “special,” prepare yourself for a “special” sticker-shock when you see a $53 charge on your bill.
So, that’s why I personally recommend Blue Heaven for breakfast, when the food is at its most creative and the prices are much more reasonable.
But no meal here — breakfast, lunch or dinner — is complete without a slice of Blue Heaven’s famous Key lime pie, a monstrosity of a dessert sporting a tower of meringue half a foot high. Whip out your cell phone and take a picture. Your Instagram friends can’t help but be impressed — and envious.
7. Santiago’s Bodega
A small, quaint place that serves tapas on a quiet side street blocks from the Duval Street revelry, Santiago’s is fun to experience with a group of friends and try lots of interesting dishes.
Tapas, known as “small plates,” are inspired by the bars of Spain that serve complimentary small plates of food when you order a round of drinks.
In the U.S., unfortunately, tapas restaurants don’t give away their food for free. Expect to pay $10-$12 per plate. Three plates per person are usually enough to fill everybody up.
Despite the Spanish name and the tapas theme, the menu at Santiago’s is not strictly Spanish. I sampled braised short ribs, spicy shrimp bisque, grilled pork medallions, and shrimp and chorizo skewers.
Our much more health-conscious friends enjoyed salads, asparagus, ceviche, and various greens. Not that there is anything wrong with that…
…afterall, everything tastes better with homemade sangria.
6. Half Shell Raw Bar
Drinking beer in the tropical sun and slurping back fresh shucked oysters on the shrimp docks at Key West Marina is what vacations are all about.
An afternoon at the Half Shell will be one the most endearing of your Key West experiences, I guarantee it. It is quintessential old Key West.
Despite the hordes of tourists and the decades that have passed, the Half Shell still puts alot of effort into serving delicious fresh seafood.
Steamed clams come swimming in a pool of garlic butter. Conch fritters are deliriously moist and full of tender chunks of conch. And of course you can’t leave Key West without sampling a cup of the Half Shell’s spicy conch chowder.
This is the perfect beachfront restaurant of your Key West dreams – it’s located in a super exclusive resort on an even superer exclusivier private island.
Yes. I said private island — exclusive to rich and famous people like Oprah, whom rumor has it, owns one of the couple dozen multi-million dollar beach homes on this appropriately named “Sunset Key.”
Sunset Key is a man-made island a few hundred yards offshore of Mallory Square. There is no bridge and there are no cars.
The only way riff-raff like you and me can visit it is to book a reservation at the Sunset Key Cottages resort for a night’s stay, or a meal at the resort’s pricy Latitudes restaurant.
The resort will pick you up at Mallory Square on its private boat and whisk you over to this traffic-less paradise in five minutes.
Our lunch table overlooked a turquoise ocean and white sand beach with swaying palm trees that provided shade from the sunshine. The perfect setting to sample fried conch, blackened grouper and a lobster roll.
But with a view like this, does the food and service even matter?
Maybe not. If the sluggish service means lunch lasts half the afternoon and I miss the 3pm boat back to Mallory Square, who am I to complain?
As that great Key West poet Jimmy Buffet once sang, “I wish lunch could last forever.”
4. El Siboney
Hopefully by this point in the countdown you’ve figured out that Key West has some great places to eat. But waterfront views, sky-high real estate, and fresh seafood don’t come cheap.
That’s why I (and my wallet) love El Siboney. It is true authentic Cuban food at rock bottom prices you won’t find anywhere else on this island. I mean, where else can you get a beer for three bucks?
This is where the local construction workers, Navy pilots, and cab drivers come for lunch. But savvy tourists who venture off into this residential neighborhood are warmly welcomed too — and rewarded with the best Cuban sandwich, ropa vieja, and vaca frita this side of Havana.
Maybe that’s because El Siboney is the closest Cuban restaurant to Havana, which lies just 90 miles due south.
3. Hot Tin Roof
Lots of restaurants in Key West have great food. Or a nice view. Or a fun tropical atmosphere. Or good live music. Hot Tin Roof has all four.
Every single table on this outdoor wrap-around terrace comes with a perfect view of those famous Mallory Square sunsets tourists clamor to see every evening. While the tourists down below strain to see over all the sword jugglers and selfie sticks, you are perched two floors above being served world-class seafood paella, or shrimp and scallop risotto.
Start your meal off by toasting the sunset with a local beer or Spanish wine while warming up with a tapa of local shrimp and sweet plantains.
Dining at Hot Tin Roof, named for the famous play by one-time Key West resident Tennessee Williams, is elegant and sophisticated, but still Key West laid-back.
The fun atmosphere is enlivened by its location at 0 Duval Street, literally the end of the road, above the Sunset Pier soundstage that features a live band performing Jimmy Buffet and Chris Stapleton tunes.
Remember, no matter how fancy the restaurant, you’re never far from a party in Key West.
2. Hogfish Bar & Grill
This is where you get to hang out with the natives.
Hogfish Bar & Grill isn’t technically in Key West. It’s a short Uber ride over to Stock Island, which is pretty much covered in trailer parks, boats, and not much else.
A few adventurous tourists may also find their way over here, but for the most part, you’ll be hanging out with the local fishermen and the off-duty bartenders and waiters who served you last night.
What that means is you are going to get the freshest fish around at working-class prices. Sounds like a great combination to me!
Their specialty is their namesake Fried Hogfish Sandwich, a deliriously tender and flaky local fish that tastes way better than it sounds. Gilded with lettuce, tomato, and a homemade sauce all tucked into squishy soft Cuban bread, this is a steal for just $16.1. Louie’s Backyard
Louie’s Backyard is everything you came to Key West for – gourmet, yet oh-so-relaxed, romantic, yet fun, expensive, but totally worth it.
Your friends who questioned why you went to the end of the earth just to eat and drink could never understand the feeling of bliss when you’re seated at Louie’s outdoor terrace, watching the glow from the recently set sun fade into a tapestry of twinkling stars, while the waves gently lap against the shore and the palms rustle in the tropical breeze, and the hurricane candles flicker in front of your favorite dining companion.
Welcome to Louie’s, the best backyard in America.
This is the place Jimmy Buffet was referring to when he sat in the room he rented in the adjacent building and wrote, “I knew I could use a bloody Mary, so I stumbled next door to the bar.”
I’m pretty sure both the food and the prices have been upgraded since the mid-1970s when Jimmy would stumble over for a hangover cure.
At Louie’s you don’t just get the quintessential Key West atmosphere. You get creative delicious cuisine — such as fresh caught snapper topped with salsa and swimming in a decadent tomato cream sauce.
Key lime pie or chocolate peanut butter torte will cap off the Key West dinner of your dreams.