There are several great happy hours in Key West to enjoy! Any you stumble on to are usually 7 days a week. This article only touches on a few of them and just use it as a guide - if you don't like the one you are at, just go to the next and enjoy the journey
Kelly’s Caribbean Bar, Grill, and Brewery at the corner of Caroline and Whitehead and Willie T's at 525 Duval. From 4:00 to 7:00 pm they have $1.50 microbrews, $3 margaritas, $ 4 Key Lime Margaritas. Also the hot wings are good too at Kelly's - around $4.
No question - Alonzo’s Oyster Bar at 700 Front Street on the Key West Bight is the best value for happy hour! From 4:00 to 6:30, 7 days a week, the appetizers on the left-hand side of the menu are half price. This means that you can enjoy a half pound of peel-your-own-shrimp or a dozen oysters or clams for about $6.00. Also another great special is 1/2 off all drinks. This includes all mixed drinks, frozen drinks, wine & beers. It is 1/2 off all drinks. When you order present the waitress with your coupon from the See Key West magazine for a free drink at Alonzo’s and sit back and enjoy yourself. (The See Key West Magazine is available free at the airport or in small dispensers all over the island. Pick up several)
When you are finished at Alonzo’s, walk a little farther along the Bight and visit the Conch Republic Seafood Company. They have another great assortment of seafood appetizers and during their happy hour they have two for one beer and drinks (basic drinks and shots, no specials on frozen and speciality drinks). And they are fair – if you order a domestic beer, the free beer is domestic, but ordering an imported draft gets you another imported draft. When you order your drink they give you a small, wooden token to be used to pay for the free one. You can take this with you and use it another day. (As if!) In the afternoons they usually have a small band or just a singer which is a change from the noisier places on Duval. If Royal Reds (shrimp) are in season, try them as well.
As long as you are at the Key West Bight, aka the Historic Walk, make a left turn and follow the walkway to the Half Shell Raw Bar. You can sit at the bar here or on their veranda overlooking the harbor and try some of the best peel-your-own shrimp on the island. Enjoy them with a Key West Sunset Ale from the tap and, if you haven’t thrown away that little magazine, use the other coupon for a second, free drink here. They also offer oyster for .50 each during Happy Hour. They only offer HH at the bar or the outside deck.
Pepe’s at 806 Caroline Street makes a good Bloody Mary at their small, two-sided bar, and usually serves a $1.00 drafts all day long.
Turtle Kraals has happy hour every night where they offer half price appetizers, beer, wine, & house liquor drinks. Their conch fritters and nacho appetizers are great - especially at such an inexpensive price. Also, they have the turtle races on Mondays and Fridays during happy hour which adds to the enjoyment. It is located on Margaret Street - close to the Half Shell.
Schooner Wharf Bar has 2 Happy Hours and sometimes 3 depending on the time of year (7am-12noon and 5pm-7pm are the 2 that are year round) and is on the water at the Bight. They have excellent Bloody Mary's, and a drink called a Dark & Stormy that is worth a try. It is a locals favorite, they have great live music and is a very fun bar to frequent at any time of day.
