10 Best Happy Hour Bars and Island Restaurants in Key West, Florida

Happy hour has been around since the 20s when sailors in the U.S. Navy needed to unwind after a long day at sea. While a handful of places in the U.S. have banned discounts on alcohol, the island of Key West fully embraces the concept. In fact, happy hour specials are offered at most bars and restaurants between the hours of 3pm and 8pm during the week, while some even add a second late-night happy hour and deals on weekends as well. With so many options, it may be difficult to choose, so we've rounded up some of our favorite hot spots with great specials. Tried and true waterfront restaurants like Schooner Wharf, Half Shell Raw Bar and Alonzo's Oyster Bar are notorious for great deals, relaxing vibes, and tranquil views. Local faves like the Porch and 2 Cents have stepped things up a notch with unique appetizers, craft beer and free bacon. If you want to mix in some live music, the Little Room Jazz Club has two-for-one specials, and Virgilio's has devoted an entire day to $5 martinis on Mondays. Just remember, no matter where you are, it's happy hour somewhere!



Just like the classic waterfront joints of Key West past, the Half Shell Raw Bar serves the freshest seafood in a casual atmosphere. The Shrimp Po' Boy sandwich and the conch ceviche are two of their timeless menu options. Grab a picnic table by...  Read More

Duval Street


Steps from the controlled chaos on Duval Street, The Porch is a craft beer lovers refuge tucked into the front of a 1839 Victorian mansion. They have 18 brews on tap and plenty more in bottles with selections changing with the seasons. Wine...  Read More

The Boathouse
Photo courtesy of Keys Weekly


The Boathouse is a venture from the Commodore Waterfront Restaurant (located upstairs) and has a breezy waterfront location. It hits the spot after both a day on Duval Street or out on the water. This laid-back bar and grill has more of a chill...  Read More

Southernmost Beach Cafe
Photo courtesy of Latitudes


Waterfront dining in Key West often comes at a steep price. Not so at the Southernmost Beach Cafe. Here you'll find reasonable deals on casual local fare, especially during happy hour from 4pm to 6pm Sunday through Thursday. Stroll across the...  Read More

Duval Street


Tucked behind La Trattoria restaurant, Virgilio's (named after the founder of the restaurant) is an elegant indoor/outdoor cocktail bar popular with the swanky over 30 crowd. Instead of a daily happy hour, they created Martini Mondays. From...  Read More



The Little Room Jazz Club & Wine Bar is a refreshing change from the Duval Street Troprock scene. Settle in early to get a great seat for the show and to save some bucks with their happy hour specials. From 5pm-8pm daily, food and drinks are...  Read More



Located in a stunning Victorian mansion on Duval Street, Grand Cafe is known for excellent people-watching and a fantastic happy hour. From 5pm-7pm daily, specials include 50% off all beer, wine, martinis, cocktails and appetizers. It's a great...  Read More



While many parts of Key West have seen modern changes, Schooner Wharf maintains that "old Key West" atmosphere--from the salvage wreckage to the interesting characters that linger around the waterfront. With its three separate happy hours...  Read More



Who knew something as simple as free bacon during happy hour would lure so many people to a restaurant? This funky gastropub hidden down Appelrouth Lane has a fun atmosphere and an eclectic, modern menu. From 4pm to 6pm Monday through Friday,...  Read More



Well-loved for their oyster-fueled happy hour, this waterfront restaurant in the historic seaport has discounts on a wide selection of eats and drinks daily from 4-6pm. Menu items like peel and eat shrimp, spinach Parmesan oysters, key lime...  Read More


Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia