Key West, Florida: Best Happy Hour suggestions to save money on your vacation! (2023)

Vacation can be expensive, especially in Key West! Your food/drink budget can really take a hit if you bring the whole family or if you like to drink alcohol (I mean, it’s Key West, who doesn’t have a few drinks). Why not save a few bucks by planning your dinners and drinking around these favorite Happy Hour schedules?

First Flight Island Restaurant & Brewery

Located a block off Duval at 301 Whitehead Street, First Flight is one of my favorites. Here are the details that you’ll want to know.

• Happy Hours: 4pm-6pm Daily
• Where: 301 Whitehead Street at the “Crash” Bar (21+ only)
• Drink Discounts. $5 well spirits & $6 Margaritas and Glasses of Wine
• Food Discounts. Lots of appetizers for $5, meaty appetizers $7
• Phone Number: 305-293-8484 (Call to confirm happy hour details)

This building is iconic! Well known for being the original birthplace of Pan American World Airways, I can’t help think of the Steven Speilberg 2002 movie “Catch Me if You Can” with Leonardo DiCaprio (which has nothing to do with this building itself) as I’m sitting there having a drink! The building was the same building that the very 1st Pan-Am tickets were sold out of in 1927! Although Pan-Am’s demise occurred in 1991, the Company is still credited with many innovations that shaped the airline industry! This happy hour is like a history lesson on its own (only way more fun)!

Old Town Tavern & Beer Garden

This find is directly on Duval Street. With 1/2 price options for food and drinks 2x daily, Old Town Tavern is a great deal! An extra surprise on Wednesday’s with 50% all Whiskey, Scotch and Bourbon from 9pm-close! What a deal!

• Happy Hours: 4pm-7pm and 11pm-1am DAILY
• Where: 900 Duval Street, Key West, Florida 33040
• Drink Discounts: 50% off wine and house liquors, 25% off any beer
• Food Discounts: 50% share plates and flatbreads
• Phone Number: 305-296-0637 (Call to confirm happy hour details)

One of my favorite things about this bar is the old classic building the restaurant resides in that is right smack in the middle of all the action on Duval! Combine that with the responsive owners, a husband and wife team, who really care about their customers and the restaurant’s success, and you have a big WIN here.

Two Friends Patio Restaurant

This is a local long time favorite where happy hour truly is HAPPY! With live music and a local crowd, you are sure to have a great time at Two Friends. Plus, it’s close enough to Sunset Celebration that you can time it right to have a few drinks/eats and still hit the infamous Key West Sunset!

• Happy Hours: 4pm-6pm Daily
• Where: 512 Front St., Key West, FL 33040
• Drink Discounts. $5.50 Margaritas (on the rocks) and Frozen Rum Runners
• Food Discounts. Special appetizer menu at great prices
• Phone Number: 305-296-3124 (Call to confirm happy hour details)

This restaurant is truly an original! It started in the 1800’s as a saloon started by 2 friends and then after the famous 1886 Key West fire, it transitioned into a bar and restaurant! The casual environment and open-air patio is a great way to experience this old time key west establishment!

Alonzo’s Oyster Bar

If you like seafood, this is the happy hour to go to! Alonzo’s Oyster Bar is a great for families too (think amazing soft Pretzels, loaded pub fries, Chicken Wings, etc.). For the more sophisticated palette, try the Warm Crab and Shrimp Dip and the Baked Oyster Combo (or really anything on the menu, it is ALL good!

• Happy Hours: 4pm-6:30pm Daily
• Where: 700 Front Street Key West, FL 33040
• Drink Discounts. $6 well drinks, $4 draft beer selection, $6 Glasses of Wine
• Food Discounts. Lots of great seafood & American style appetizers from $7-$13
• Phone Number: 305-600-3405 (Call to confirm happy hour details)

As with the other selections in this post, Alonzo’s offers a great atmosphere. This happy hour is located directly on the boardwalk overlooking the water and marina.

Southernmost Beach Cafe

I selected this happy hour simply because the Southernmost Beach Cafe is directly on the beachfront Atlantic ocean. They also happen to have some great Happy Hour bites like Mahi Sliders and Buffalo Shrimp Tacos

• Happy Hours: 4pm-6pm Daily
• Where: 1405 Duval Street, Key West, FL 33040
• Drink Discounts. $5 Well Drinks, 20 oz Drafts and House Wines
• Food Discounts. 1/2 price appetizers
• Phone Number: 305-295-6550 (Call to confirm happy hour details)

A relaxed place to grab happy hour directly on the beachfront. This cafe is located on the Atlantic ocean on the very South End of Duval Street. Just 90 miles from Cuba, the menu is inspired by cuisine from these tropical neighbors! Come for the friendly staff and beachfront location.

You guys!! It’s so hard to stop here because Key West if absolutely JAMMED PACK of great restaurants! It also happens to be one of my very favorite destinations. So, if you have a suggestion that you want me to add to this list or one that really needs to be experienced to appreciate, PLEASE reach out and tell me! I’d be happy to complete my duty and travel back to the Conch Republic to take another look around!