Category Archives: Key West Bars

Key West Cocktails

 There are so many great places to grab a delicious beverage in Key West that it’s impossible to have a favorite. Sunset Watersports has done some collaborating and we’ve come up with an entire list of cocktails from local joints that we know won’t disappoint!  
Key Lime Pie Martini – Schooner’s Wharf Bar

If Key West was an alcoholic beverage, it would be a key lime pie martini. Take alcohol, combine it with a tangy, sweet treat and you’ve got Key West in a cup! Schooner’s Wharf does a great job of serving up these mind-blowing martinis, accompanied with an old-island experience and beautiful waterfront view.
202 William Street (our neighbors at Sunset Watersports!)
Key Lime Martini at Schooner's Wharf in Key West, FL
Key Lime Martini at Schooner’s Wharf in Key West, FL
Kiss Me Katie – Better than Sex

The name of this Key West dessert restaurant says it all, but the name of this cocktail may need some explaining. The Kiss Me Katie is Ayala Champagne served in a caramel brulee’d rimmed wine glass. There’s not much more to say besides GO TRY THIS INCREDIBLE CREATION, then let us know… is it truly better than sex? We promise we won’t judge, as we’ve tasted it for ourselves!
926 Simonton Street

Kiss Me Katie cocktail at Better Than Sex in Key West, FL. Sunset Watersports favorite cocktail.
Kiss Me Katie cocktail (left) at Better Than Sex in Key West, FL
Sangría – Santiago’s Bodega

This hidden spot is a local favorite but often missed my visitors because of its location deep within Bahama Village. Not only are the tapas out of this world, but with fresh cut fruit and deep wine glasses, Santiago’s sangria is arguably the best on the island. You can take a seat at the bar or make a reservation to enjoy a real Spanish dining experience.
207 Petronia Street

Santiago's Red and White Sangria - Key West Cocktails
Santiago’s Red and White Sangria in Key West, FL
Frozen Key Lime Margarita – Willie T’s

Craft-cocktails whipped up by trendy mixologists using fresh ingredients is all the rage these days. Therefore, we understand your skepticism towards frozen drinks dispensed out of a machine at a bar… but you have to trust us on this one. With the perfect mix of sweet and tart, Willie T’s frozen key lime margarita is one of the most refreshing concoctions on the island. It’s the perfect drink to quench your thirst and cool you down as you make your way down Duval.
525 Duval Street  

Willie T's Key Lime Frozen Margarita in Key West, FL
Iris (your Sunset Watersports blogger!) enjoying a Willie T’s Key Lime Frozen Margarita in Key West, FL
Mojito – Jimmy “Mr. Mojito’s” Drink Cart in Mallory Square

Sunset at Mallory Square is a spectacle in itself. Add these mojitos, and you’re officially in paradise. Jimmy, or “Mr. Mojito”, slays mojitos out of his antique car turned bar at an incredible speed with flawless precision. You can find Mr. Mojito outside of the Westin Key West Resort right on the water. We suggest you grab one before heading over to Mallory Square to watch the famous Key West sunset.  

Hemingway Daiquiri – The Other Side

As mentioned earlier, we are very aware of the trendy, craft-cocktail mixology movement happening all around us…. so is Caroline’s Other Side. That’s why it’s no wonder that this bar wins most creative in Key West, hands down. From egg whites to agave, the staff at the Other Side are not bartenders. They are truly mixologists who have perfected their craft. It was hard to choose just one cocktail from their creative menu, but the Hemingway Daiquiri deserves a shout out. Papa’s Pilar 3yr Blonde Rum, grapefruit and lime juices, simple syrup, and maraschino liqueur… the end. Now go taste it for yourself!
429 Caroline Street

The Pain Killer – The Rum Bar at Speakeasy Inn

There’s not much pain in paradise that needs to be killed, but that shouldn’t stop you from trying this tasty treat. With a perfect blend of Pusser’s Rum, cream of coconut, OJ and pineapple, this cocktail is more like a dessert, so make sure you bring your sweet tooth!
1117 Duval Street

Now, we know there are a TON of places in Key West serving up creative cocktails, so please feel free to share with us your favorites in the comment section below. We are always looking for new things to try, so we can share with our Sunset friends.

Sunset Watersports – Key West’s Premier Activities, Attractions and Watersports Company
Key West Bight * Smathers Beach * Parrot Key Resort * Hurricane Hole Marina
Key West, FL 33040 (305) 296-2554

List of Key West Bars

Finding the right bars to stop at on your Duval Crawl can be an intimidating, daunting, almost impossible task. Thankfully, Sunset Watersports knows all things Key West…. including the best watering holes to satisfy that drought in your mouth. Here is a list of Key West bars that are our favorites.   
Local Favorites
Green Parrot Bar – Established in 1890, this historical spot was a grocery store opened by the grandfather of famous artist Mario Sanchez. Through generations of change, the Green Parrot remained a haven of relaxation and fun for locals, navy boys and more. Not much has changed, as you can still enjoy a cold one and catch some great live-music.  
Chart Room Bar – Hidden away within the Pier House Resort & Spa, you may have to ask around to find this little hole in the wall. Since 1968, Chart Room Bar has been known to many as “a weird little bar trapped inside a luxury resort.” Mel Fisher often ended days of treasure hunting at the age-old bar. A little different than your island bar with free popcorn, peanuts and hot dogs rather than blender drinks, tiny umbrellas and fruity garnishes.
The Porch – Don’t let the size of this little spot fool you. Located in the downtown area of Old Town Key West, this bar offers the widest selection of fine wine and craft beer on the island. Make sure you take the time to admire all the artwork covering their walls, as there’s nothing quite like it on Duval. If you’re looking for liquor, walk to the other side of the building to The Other Side…. our next local favorite!  
The Other Side – This Key West cocktail lounge is the youngest on our list, but much deserving of a spot. It was recently featured in an article for where to go in 2015 for its new-school craft cocktails. If you’re looking for something a little different than your fruity beach beverage, this is the spot for you!
The Lazy Gecko’s Back Bar – You may be intimidated by the loud music and large crowd within Lazy Gecko…. but if you make your way to the very back, you’ll find a low-key, Red Sox themed bar that has seating and serves some delicious munchies.
Flying Monkeys – Located within Fogarty’s Restaurant, this little bar serves a wide-variety of frozen drinks that will cool you down on a warm Florida night. A great people watching spot, as it’s situated right on Duval.
Rick’s Bar – This is a great place to end your night with dancing and drinks. If you aren’t sweaty when you leave, you didn’t fully experience and enjoy Ricks. There are a number of bars within this complex, so don’t be afraid to explore. However, the best seat in the house is on the upper deck looking out at Duval Street.   
Better Than Sex– Although this spot is called a dessert restaurant, their decadent dessert drinks are just too good not to get a spot on this list. With chocolate dipped wine glasses, caramel rimmed beer and champagnes, you’d be foolish not give this decadent dining experience your time. Make sure you call ahead for reservations, as this spot is loved by both locals and visitors on all days of the week.
Iconic Spots
Sloppy Joe’s – One of Key West’s most iconic, well-known bars that is always bringing in large crowds and playing loud music for all to enjoy. A crawl on Duval is not complete without stopping at this Hemingway favorite.   
Capt. Tony’s Saloon – This bar was the original location of Sloppy Joe’s. Eventually, a local charter boat captain purchased the bar and named it Captain Tony’s. This is the bar where Jimmy Buffett got his start in Key West. Buffett played at Captain Tony’s in the early ’70s, and was often paid in tequila. Buffett sings about Captain Tony and the bar in his song Last Mango in Paris.
Hog’s Breath Saloon – For nearly 25 years, this popular bar has attracted both locals and tourists. With live entertainment, seating, and food, there’s something here for everyone.
Bourbon St. Pub – Gay Key West’s original and only video bar featuring the “Men Of Bourbon” nightly, live VJ’s, live Shows, 5 different bars, and a “MALE ONLY” clothing optional garden bar with a pool and jacuzzi.
Schooner Wharf Bar – One of the best waterfront view bars in Old Town Key West. Its rustic charm and warmth makes it the perfect spot to have a drink while watching the sunset. Make sure you try their key lime pie martini, as it’s one of the best on the island.
Fat Tuesday – There may be Fat Tuesdays all across the world, but that doesn’t change its popularity and success on Duval Street. A trip to Key West isn’t complete without bringing home one of their popular insulated to-go-bottles filled with a delicious frozen mixed drink.
Irish Kevin’s – This Irish pub is a hot spot for live music and entertainment. It’s always packed with groups and parties looking for a good hangout spot.
Willie T’s – It may be a few blocks away from the more popular spots on Duval, but this bar doesn’t let you walk by without taking a second look. With a ceiling covered in dollar bills,
The Bull & Whistle – A great spot to grab a pitcher and play some darts. Grab a barstool on the second-floor porch for some great people watching. If you are feeling adventurous, dare to go upstairs to the Garden of Eden, Duval Street’s only clothing optional bar.
We hope you have the chance to enjoy one or more of these spots during your visit to Key West. If not, we guess you’ll just have to come back again!

Did we leave any bars out that you think deserve a spot on our favorite lists? Let us know and it could find its way onto our list!


Sunset Watersport – Key West’s Premier Activities, Attractions and Watersports Company
Key West Bight * Smathers Beach * Parrot Key Resort * Hurricane Hole Marina
Key West, FL 33040 (305) 296-2554