Top Bars in Town

There is a lot to see while on this small Island.  The bars in town offer great music and entertainment which usually starts in the morning and goes into the wee hours of the night. Here are some of the ones we have spent some time in and feel shouldn’t be missed:

Margaritaville (500 Duval Street) – This is where it all started.  So, your trip should start here.  We try to begin ours with a perfect margarita from the bar on every trip.  The food has been great every time we have been.  The cheeseburger is truly a “Cheeseburger in Paradise” and the fried conch fritters are fabulous.

Sunset Pier – This is a great place to sit and watch the sunset away from the carnival of Mallory Square.  There are Happy Hour specials, just be prepared to wait awhile for service.  We have never had great service (very slow), but with the view of sunset, you kind of overlook the poor service.

Sunset Pier, Key West Florida


Irish Kevin’s – Ok, My name is Kevin and I am Irish, so …this bar is one of my favorites to tip a few pints. Kidding aside, if you want to go to a bar that you are able to be part of the show with singing, hand clapping, competition with other bar patrons and listening to one man shows with some adult lamguage then this is the place for you.  Their motto of “I Came, I Drank, I don’t Remember” will be yours once you visit Irish Kevin’s.

Grand Vin Wine Bar – (1107 Duval Street) – This is a nice place to sit and have a glass of wine.  Located at the quieter end of Duval it offers a relaxed atmosphere to enjoy people watching.

Hog’s Breath Saloon (400 Front Street) – This place offers live music and food.

Louie’s Backyard – (700 Waddell Street) – Best view in town.  We walked on the deck, mid afternoon and sat down and stayed for most of the day.  Once there, it is hard to leave.  You can see the water and really feel very disconnected from the hustle of Duval.  One of our favorites!  We understand why Jimmy Buffett loved to come here when he lived on the Island.


Louie's Backyard, Key West

Perfect Tuesday Afternoon

The Bull & Whistle and the Garden of Eden – This is three story building with a bar on each floor.  The bottom floor offers live bands and second floor bar has a great balcony to people watch from.  The top floor (Garden of Eden) is Key West’s only clothing optional bar.  We have hit floors one and two, but haven’t had enough to drink to hit the third floor.

Captain Tony’s  – Ok this is a place you really have to walk through to appreciate.  There is   a tree growing in the middle of the place and a headstone located in the back.  There is underwear, bras, dollar bills and business cards hanging from the ceiling.  Usually the music consists of a one man show.

Sloppy Joe’s – This is truly a Key West Tradition.  Who would pass up the bar that Hemingway made famous?  Be sure to look for his Marlin and fishing poles hanging on the wall.  The music is great and is always busy.  Usually the music options before 9pm caters to the older – or shall we say seasoned? – crowd.  Then late night, the dance floor opens up and the music is cranked up.  Be sure to check out their webcams located on our site.  The food really is very good.  The pizzas are fabulous.  In one of Kevin’s adventures (ok he had forgot his glasses) he ordered the Sloppy Joe pizza, which was a very pleasant surprise.  It is a pizza with their famous Sloppy Joe mix, cheddar cheese and fresh tomatoes.  Great choice!

Rick’s – 8 Famous Bars in one place – So if you are with a crowd and you all can’t decide, this is your place. They offer anything from loud music, to intimate spots to “talk”, to adult entertainment at the Red Garter.  The balcony is great to people watch Duval street.

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