Ultimate Happy Hours in Key West: Let’s Get This Party Started! 

This girl likes to kick back with a cocktail or three from time to time and Key West is my favorite spot to do it. So many watering holes, so many fun people, and so much fun!  Happy Hours in Key West are the way to go if you want to save some cash.  Here are some Key West Happy Hours where you can get your elbow in shape.  

1. Kaya Island Eats – 618 Duval St 

I’m into fresh and creative food at fantastic prices. If you’re like me, you’ll love digging into the eclectic menu at Kaya Island Eats happy hour! This spot might fool you from the outside but walk in and check out the food! You will not be disappointed. The food here is some of the best we’ve had in Key West. And it doesn’t get much better than Kaya for a perfect Key West Happy Hour!  

• Happy Hour Daily 4-6 pm Half off drafts, wells, wine, and ½ off small plates.
• Overall: Tuna Poke Nachos and Hawaiin Pork Sliders for the Win!

2. Conch Republic Seafood Co- 631 Greene St

Good things happen when you’re open to them, even if it means your sunset cruise got canceled due to pouring rain! Oh well, belly up to the bar and have a Key West cocktail to shake the blues. We darted through the rain and made a beeline for the bar at Conch Republic Seafood. 

The bar crawls with folks getting their drink on with 2 for 1 beer, well drinks, and wine.  Small plate specials, too, and did I mention the spectacular water-front location?!! Rain, rain, you can stay when there are happy hours like this in town! 

• Happy Hour 4-7pm daily in the bar and on the patio
• Overall: Fun spot directly on the water with spicy specials!

3. Half Shell Raw Bar – 231 Margaret Street

Half Shell – voted the #1 Raw Bar in Key West two years running – features all of the raw bar goodness you’d expect at a waterfront restaurant and bar.  And it’s another option for a fabulous happy hour in Key West, Half Shell is the real deal (they’ve been here since the 1970s)!  Local Key West fishermen fish daily for Half Shell and unload their catch right here!  Sink your teeth into fresh oysters on the ½ shell, peel & eat shrimp, or mouthwatering conch fritters – all at special (cheap!!) happy hour prices.

• Happy Hour 4:30-6:30 daily. ½ price well drinks, beer, wine & a special happy hour menu.
• Overall: This is YOUR place for fish truly FRESH OFF THE BOAT!

4. Mary Ellen’s Bar and Kitchen – 420 AppleRouth Lane

Dive bar vibes and Christmas lights await at Mary Ellens – right off Duval Street. Come for the unique atmosphere and get yourself some Key West Happy Hour drinks. Mary Ellen’s is open 365 days a year almost ‘round the clock. (They take mornings off). 

• Happy Hour: Almost daily (no Thursdays because they’re getting on their vibrator races. For Real!! 
• Cheap Drinks & Eats. Maybe the Best Bloody Mary in Key West!
• Overall: Mary Ellen’s is one place I wouldn’t miss.

5. La Te Da – 1125 Duval Street 

It’s not a trip to Key West without experiencing the odyssey of a Key West drag show. La Te Da also has a killer happy hour in the bar. Here you can eat wagyu sliders, Maryland Crab Dip and more, all in the unique atmosphere of one-of-a-kind LaTeDa.

• Happy Hour Monday – Friday 3- 6
• Overall: Key West & Drag Shows go together like fish & chips!

6. MoonDog Cafe – 823 Whitehead Street 

The vibe at Moon Dog is upscale casual – funky furnishings and along with a little bakery case keep things interesting. That and the food, of course! This local spot does a lot right – 3 meals and a great Happy Hour! Plus, it’s next to the Hemingway House so stop in after you tour (which you absolutely should do!)

• Happy Hour Daily 4:30-6:30 ½ off draughts & bottled beer + wine, under $10 appetizers!
• Overall:  Best Deck for people-

7. The BoatHouse Bar & Grill – 220 Margaret Street

Drinks with a view? Check! This local fav is a bustling spot for good reason – The BoatHouse is one of the absolute best happy hours in Key West! Their happy hour in Key West is award-winning – as in Best Key West Happy Hour! This open-air waterfront spot will knock your socks off with their happy hour specials including ½ price small plates and plenty of drink specials. 

• Happy Hour 4:00-6:30 daily
• Overall:  Casual Happy Hour at it’s best – it’s busy but fun!

8. Two Friends Patio Restaurant – 512 Front Street

Two Friends is one of those places where you just kinda, sorta HAVE TA go!  It’s a legit Key West legend, and one you’re not going to want to miss. This local legend has been a fixture since the late 1800s and it’s going stronger than ever. And it’s a true favorite happy hour in Key West.

• Happy Hour 4-6 daily 
• Overall: come for Happy Hour and stay all night!!

9. Pepe’s Cafe – 806 Caroline Street

Discover some Key West culinary history at Pepe’s. This cafe’s claim to fame is being the oldest restaurant in Key West, and the second-oldest eatery in the entire state! They opened way back in the early 1900s and President Harry Truman was a regular here! Speaking of President Truman, if you’re going to Key West, the Little Truman White House is totally worth touring. It’s cool to see how the upper crust rolled back in the day. The poker table is all setup! At Pepe’s check out the award winning margaritas.

Happy Hour Eats include ½ price peel & eat shrimp; raw oysters under $1, $5 wines, and discounted beer. 

• Happy Hour Daily 4-6 pm
• Overall: Key West Happy Hour in the oldest eatery on the island is worth a stop!

10. Bagatelle – 115 Duval Street

Grab a seat at the bar and chat with the friendly bartenders here. You’re in for a treat no matter what time you roll in, because Bagatelle has not one but two happy hours! The ambiance here is historic and fancy but not pretentious. I love old stuff (history nerd) so the historic building that houses Bagatelle won me over. Not to mention the wraparound porches – so cool! 

• Happy Hour: Breakfast hangover happy hour 9-11:30am & afternoon happy hour 4-6pm.
• Overall – Historic vibes and good selection of happy hour deals.