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. Newcomers like the Porch and 2 Cents have stepped things up a notch with unique appetizers and fine wine and spirits. Those looking for a place to watch the game should head to JDL's Big Ten and the Rum Barrel. During Happy Hour, visitors can get a sneak peak at the Island House, rated as one of the world's top gay resorts with free drinks for guests and half-off for those scoping out the scene.  Just remember, no matter where you are, it's Happy Hour somewhere!

Consistently voted the "best gay men's resort in the world" by readers of Out Magazine and numerous other gay publications, Island House in Key West is setting the bar for other guesthouses and opens its doors to the (male) public during Happy...  Read More

In 2012 entrepreneur Pat Croce became the owner of this no-frills hot spot, adding to his empire of successful Key West restaurants and bars including the Green Parrot, Rum Bar, and Island Dogs. The Half Shell Raw Bar is popular with local...  Read More

Duval Street

The staff at The Porch claim that it is haunted by the spirit of Dr. Porter (ask them about the dimes), but the ghost stories aren't enough to scare off those seeking craft beer or a quality glass of wine at discounted rates during Happy Hour....  Read More

While many parts of Key West have seen modern changes, Schooner Wharf maintains that "old Key West" atmosphere - from the salvage wreckage decor, to the interesting characters that linger around the waterfront. It is also the home of the largest...  Read More

Known for their oysters, this waterfront restaurant in the historic seaport has indoor and outdoor dining and arguably the best happy hour deals in Key West. Alonzo's has arguably the best deals on the island: drinks are half priced everyday...  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's a perfect spot after a day spent milling around Duval Street and offers a more laid-back bar and grill vibe than...  Read More

Part gastropub, part wine bar, 2 Cents offers a nice selection of craft beers and wines, with an ambiance is decades away from the flood of cruise ship passengers. The newly-opened restaurant (January 2012) features funky decor consisting of...  Read More

Rum Barrel

Launched in 2006 by former Philadelphia 76ers President Pat Croce, the Rum Barrel offers a happening place to watch the game (particularly when Philly is playing) with plenty of spirits and great food to boot.There are over 150 rums and an...  Read More

Southernmost Beach Cafe
Photo courtesy of Latitudes

Waterfront dining in Key West often comes with a steep price. Not so at the Southernmost Beach Cafe. Here you'll find reasonable deals on casual local fare for breakfast and lunch. You don't have to be staying at the Southernmost Hotel to enjoy...  Read More


Meet Amber Nolan

Originally from upstate New York, this restless traveler has a knack for befriending interesting characters. You can usually find her just about anywhere that has a hammock. Amber's favorite...  More About Amber