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

Key West Restaurants

Sunset Watersports wants to make sure you have the best experience during your visit to Key West. Finding the right places to eat, sleep and play can be tedious, so we’re offering up a variety of lists and guides to the best Key West Restaurants.
Local Favorites

Sandy’s Cafe – Cuban coffee and Cuban sandwiches. Open 24/7 with delivery.

Hogfish Bar & Grill – Fisherman’s local spot for the freshest catch. Located on Stock Island and perfect for right after the boat.
New York Pasta Garden – Authentic Italian dishes served with goblets of wine. Indoor and outdoor seating. Make sure you ask for any specials.
Ambrosia – Fresh sushi and incredible rolls. Make sure you try their signature Playmate Roll, a local favorite.
Santiago’s Bodega – Wine and Spanish tapas hidden in Bahama Village. Don’t forget to make a reservation because this place is always packed.
Onlywood – The most delicious gourmet pizzas on the island. Make sure you ask for the pizza of the day special… it never disappoints!
Camille’s Restaurant – Funky art and decor that matches Key West’s unique vibe. A breakfast favorite with delicious crab cake benedict.
B.O.’s Fish Wagon – Don’t let this rustic shack steer you away because they serve up the best fried grouper sandwich on the island, guaranteed.
Date Night
Sunset Watersports Sunset Dinner Cruise – The best seat in the house for an unforgettable view of the famous Key West sunset. Live music, A/C cabin, open bar, and a Caribbean buffet are included with this romantic cruise.
Hot Tin Roof – A picturesque waterfront view of sunset. Fresh seafood prepared in the most decadent manner with a presentation to wow.
Michael’s – The best steak on the island is served at this small, upscale restaurant. Perfect for two if you’re interested in their delicious fondue.
Azur – An extensive wine list with incredible Mediterranean tastes. Make sure you ask about their pulpo appetizer for the best octopus on the island!
Cafe Sole – A romantic dining experience away from Duval Street. Local caught seafood served with a French and Caribbean flare.
Louie’s Backyard – Fine dining with an incredible oceanfront view. It’s been a local’s romantic favorite for a long time. Always offering up the freshest fish with decadent sides.
Zagat’s 8 Hottest Restaurants in Key West – Check out this list of Hottest Key West Restaurants ranked by Zagat. All information regarding location and menus is available through Zagat’s site here.
Roof Top Cafe
The Stoned Crab
El Siboney
Blue Heaven
Seven Fish
Better Than Sex
Turtle Kraals Restaurant & Bar
Charlie Mac’s

What’s your favorite restaurant in Key West? Did we miss any of your favorites? Let us know in the comment section below!

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