Duval Street – Key West

Margaritaville, another must see in Key West. A monument to the free spirited and alternative life style of Jimmy Buffet or a corporate shell, you decide. They do serve pretty good cheeseburgers, personally I won’t eat there again after seeing Corporate Jimmy Buffet sue everyone in sight. Corporate Buffet has sued people for using the phrase “cheeseburger in paradise”, “conch coconut telegraph”, and even sued Six Flags for having a club called “Carrothead Club” for young fans of Bugs Bunny, because it sounds like parrothead. I’ll probably get an angry letter for this but I think Jimmy Buffet sucks anyway.

yay! margaritaville

Sloppy Joe’s and Captain Tony’s, well Hemmingway lived in Key West for a couple years and ever since then Key West has been milking this for all it’s worth. Hemmingway’s favorite bar in Key West was Sloppy Joe’s and it has been an iconic place to go have a drink ever since. Apparently Sloppy Joe’s is not located where it used to be.  In Hemmingway’s day it was located where Captain Tony’s saloon is now. So you can either go have a drink where Hemmingway physically drank or you can go have a drink in the bar with the same name as where Hemmingway used to drink. Both bars are very popular especially with middle aged tourists. Captain Tony’s has a tree growing through the center of it, which is pretty neat. Sloppy Joe’s is bigger and sometimes has a lot of people in it. They both have live music sometimes.

Capt Tony's

Sloppy Joe's Bar

They are both kind of must sees when visiting Key West.

Another beach in close proximity to Duval street is Simonton Beach. It is located at the north end of Simonton street which runs parallel to duval street. It is a small beach and has a boat launch for small boats. It looks out over the harbor and can be a good place to sit and watch boats.  There is a small dock I see people fishing off of now and again, it would probably be a good spot to fish at night.

Beach at the end of Simonton Street

There are also bathrooms and changing rooms at the beach and some parking but the parking is very limited.

Harbor View at Simonton Beach

Where’s the best place to go for seafood? Anyone who works on Duval Street has no doubt been asked this question dozens of times.  Key West is full of fishermen and women, charter fishing boats, commercial fishing enterprises, lobster trappers, and fresh fish every where you look.  Just stroll the docks at Historic Seaport when the charter fishing boats come in, you’ll see the mates busy filetting up the fish, or snapping pictures of fish with proud anglers.

But which Duval Street restaurants serve up the freshest seafood at the best prices with the best service?  That’s an ongoing debate, and differs according to your needs, but some places have great reputations and others don’t.  If you’re willing to pay a bit more, you’ll get better service, and that can make a world of difference, especially at Duval Street restaurants where service can be the worst thing about your meal if you’re not careful.  In a town known for expensive real estate and hard drinking, good help is hard to find.  You may want to shell out a bit more dough just to have a pleasant dining experience because it’s probably going to be worth it.

Staying on Duval Street while on vacation in Key West can be the greatest thing ever, or it can be a huge mistake.  It all depends on what your vacation is all about and how much money you have.  And of course which  hotel you choose.  Duval Street hotels range from the sketchy accommodations with weekly rates and gruff managers, to the posh historical oases of calm and quiet on an otherwise busy street that sizzles with energy day and night.

Duval Street is the center of shopping, restaurants, bars, festivals, and almost everything that’s exciting and fun and doesn’t involve being on a boat or in the ocean.  Staying in a hotel on Duval Street will put you within walking distance to just about everything you want to do, including boarding boats for water sports, tours, and excursions.

You will be able to park your car if you drove to Key West, which is something you’ll be thankful to do, once you’ve driven here from Miami or Fort Lauderdale.  Key West is a small island, and the less driving you do, the better.  This makes the Duval Street hotels very attractive to the average visitor.

There’s only one drawback to staying on Duval Street, and that’s if you end up in a hotel that’s too small or badly designed to isolate you from the noise at night.  Luckily, this is not much of a problem in most cases.  Many of the Duval Street hotels are small, but they’re clever: they put the rooms in the back so guests can sleep peacefully no matter what craziness is occurring out on the street.  Just ask about where the room is located before booking a room and you’ll have a great vacation staying on Duval Street.

Key West is a small island city with a very diverse population.  While  certainly a wealthy community, there are also plenty of regular folk just trying to make a living in Paradise.  While there are lots of snowbirds here in winter, making the average age tilt toward the retirement generation, there’ s a vibrant youthful energy on Duval Street, with kids, twenty-somethings, rockers, skaters, and even a small underworld that’s kept closely in check by our friendly Key West Police department.

In short, Duval Street is a microcosm of a larger city, with many of the elements found only in larger metropolitan areas without the pitfalls that come with urbanization… like major crime and stress.  This is the start of a long list of reasons why we love Duval Street!

Stay with us and we’ll take you on a photo-video journey up and down Duval, from Key West’s South Beach to Mallory Square.  In addition to streetlife on Duval, you can check out bars, hotels, restaurants, shopping, and festivals.  It’s all here on one crazy street called Duval.

From one end of Duval to the other, you’ll find bars to fit every personality and every mood.  From the anything goes joint to the elegant piano bar, Duval Street bars cover the gamut of entertainment and nightlife in Key West.  There are more bars on this street than anything else it seems, which you and your friends or family can bar hop all day long and never visit the same bar twice.

We even have a term for this action, the ability to visit so many bars on one street, from one end to the other…it’s called the Duval Crawl.  You can party it up, jump from bar to bar, and never ever step foot in a car.  It’s all done on foot, safely thank goodness.  You can hop, jump, or crawl between such a diverse set of bars you’ll feel like you’re at the Epcot Center of bars…a new flavor every few steps.

Go from a old honky tonk three level bar that’s steeped in historical charm, booze, and night after night of rowdy live entertainment to a swank patio bar with Sunday tea dances and gourmet bar food.  That would be The Bull & Whistle and La Te Da, located at opposite ends of Duval Street.  And there’s a whole lot more in between, with so many Duval Street bars you can’t throw a stick without hitting one!

What’s a trip to Key West without a little bit of Duval Street shopping?  Here on the main drag you can find beads, baubles, and bodacious gifts as well as unique items, boutique buys and artists’ renditions of everything Key West, form the Southernmost Point to your favorite Key West hotel.  Buy a cigar and puff up and down Duval as you take in the scene, watch the world go by, or just soak up the sun and good vibes.

There’s a version of Duval Street shopping for everyone: man woman or child.  Buy a gorgeous bikini that nobody else back home will own.  Or collect a flavorful range of “Cuban” cigars to impress your buddies back home.  Get some amazing bling jewelry at discount prices or just get a postcard.  Duval Street shopping doesn’t have to ruin your budget!

Good news is, there are fewer and fewer tacky t-shirt shops these days, and more interesting boutiques and galleries than ever.  And talk about unique storefront ideas: there’s a towel store, a flip-flop store, a hammock store and a store for all things Cuban.  There’s a pricey designer clothing store, a swimsuit store, and a store for all things Jimmy Buffet.  Some peoples’ idea of Duval Street shopping is to just window shop, and that’s OK too, since it can be pretty entertaining.  There are some creative store owners in this town, and if you walk up and down Duval, you’ll see the evidence everywhere.

We all know and love Duval Street for its nightlife, dining, shopping, and center of activity of Key West.  But did you know there are also some beaches near Duval Street within walking distance?  If you’re staying in a Duval Street hotel, you don’t have to get in a car to enjoy the beach in Key West.  So grab your towel, your sunscreen, and a hat and some walking shoes, and let’s hit the beach!

First, there’s South Beach, not to be confused with the one in Miami.  As the name implies, South Beach is on the south side of Key West and totally within walking distance from Duval Street.  In fact, it kind of is on Duval Street.

Next, we have a beach at the other end of Duval, sandwiched between two of the major luxury hotels.  It’s small, but it’s free and open to the public.  And of course it’s totally within walking distance of Duval.

And then we have the beach at Fort Taylor State Park, which is one of the nicest beaches near Duval Street.  It’s just a teensy bit further to walk, but well worth the trek.

For more info on these and other beaches near Duval Street, read our in-depth pages on the individual beaches, and then go out and try them all!