Filled with a mix of local characters and visitors-in-the-know, "The Parrot," is not your typical dive bar. As the oldest watering hole in Key West, they've got nothing to prove, and their motto, "No Snivelling," illustrates their no-nonsense approach to slinging stiff drinks. Enjoy drink specials and discounts on selected beers during their happy hour 4-7pm Monday through Thursday and 4-5: 30 pm on Fridays. Tropical breezes and ceiling fans keep the open-air bar cool, and the old-school jukebox mixes B.B. King with The Temptations and New Orleans Funk. At night, bands from around the country up the ante with a heady mix of gritty blues, rock and funk. Just to keep things interesting, the Green Parrot Ukulele Association plays once a month.
Recommended for Happy Hour because: "The Parrot" is best dive bar to enjoy colorful characters, happy hour drink specials and the best jukebox in town.
Claudia's expert tip: Try the Root Beer Barrel Shot, a Green Parrot tradition for over 20 years. Drop a shot of root beer schnapps into a highball glass of light beer and toss it back.
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 vibe than its upscale counterpart. Small plates are half off during happy hour (from 4-6: 30 pm), making it easy to sample a few. Draft beers and select cocktails are buy one get one free. Try the Boathouse bread, a delicious combination of herbs and cheese that is out of this world. There are several other small plates that aren't your usual spinach and artichoke dip. Selections include beer-battered shrimp, beef kabobs, coconut shrimp, conch fritters and lobster tempura with mango sauce.
Recommended for Happy Hour because: Happy hour at the Boathouse is swamped with locals and visitors alike. Get there early for a seat at the bar.
Claudia's expert tip: If you can't get enough of the waterfront, make a reservation for the Commodore after happy hour ends.
The oldest eatery in the Keys (a Cuban fisherman opened it in 1909), Pepe's is worth a visit for the history alone. While it's still a local's place, visitors have gotten hip to this tiny gem despite its unassuming frontage. Their motto, "A fairly good place, for quite a long while," says it all. People line up each day for a breakfast filled with good-old-fashioned Chock Full O' Nuts Coffee, homemade sweet bread, chipped beef on toast, and eggs Benedict. Their happy hour from 4-6 pm is just as popular with $6 Margaritas made with fresh-squeezed juice, half-price oysters, and discounted well drinks, beer and wine. Their outside patio is charming, but the walls inside are packed with flotsam and jetsam from the past decades that will keep you entertained.
Recommended for Happy Hour because: The oldest eatery in the Keys, Pepe's is worth a visit for the history alone. Happy hour is just a bonus!
Claudia's expert tip: Have a little too much happy at happy hour? Stick around for a hearty dinner like smothered pork chops and mashed potatoes.
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 4 pm to 6 pm Sunday through Thursday. Stroll across the sand and settle in at the bar to sample 50% off a selection of appetizers, wine and beer, as well as discounts on specialty cocktails. You'll enjoy the relaxing vibe and view of the Atlantic at this open-air restaurant so much, you may want to stay for dinner. Start with crab cakes topped with an apple cucumber relish and move on to the herb-crusted local grouper with sautéed artichokes and citrus butter. Finish with their homemade key lime pie with a crisp Oreo cookie crust.
Recommended for Happy Hour because: Southernmost Beach Cafe offers waterfront dining at affordable prices and a killer happy hour.
Claudia's expert tip: You don't have to be a guest at the Southernmost Hotel to enjoy this open-air cafe.
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 5-8pm daily, food and drinks are two-for-one. Find a new favorite glass of wine from their extensive list, as you listen to live jazz, blues and even Cuban-fusion bands. If you're feeling peckish, they have light snacks like rosemary and sea salt kettle chips, as well as meat and cheese plates. Specialty cocktails include Hemingway's "Death by Champagne," which mixes absinthe bitters, lemon and Lillet Blanc with champagne and the Cuban Fig Roast that combines burnt sugar syrup, Cuban coffee, cream sherry, Cardamaro, mission fig bitters and a Bucci ice cube. The furnishings have an elegant, polished look, and both indoor and outdoor seating are available.
Recommended for Happy Hour because: For a change of pace, mellow out at the snazzy Little Room Jazz Club with a glass of wine and top-notch live music.
Claudia's expert tip: When the temperature rises outside, head to Little Room Jazz Club, where the air conditioning is as chill as the music.
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 chance to sample some of their starter items like crab cakes with blood orange reduction and key lime mustard or yellowfin tuna tartare with ginger chive oil. Don't miss their beet salad, which gets high marks. They have an extensive wine list, and their lychee martini made with Stoli Vanilla, pineapple and lychee juice gets high marks. Other tropical cocktails include the classic mojito, as well as a caipirinha made with Espirito Cachaca, line and sugar.
Recommended for Happy Hour because: The happy hour at Grand Cafe is a great way to sample their starter items and specialty cocktails for half off.
Claudia's expert tip: When you make your reservation, try to score a table on the porch for the best viewing perch.
From the outside, Santiago's Bodega looks like an old home that displays a weathered wooden sign above the entrance with a name implying it's a corner store. The interior is romantic, yet casual with mixed-matched furniture, chestnut-shaded wood floors, and dimmed lighting fixtures. The menu, which consists of tapas dishes, is equally surprising. Dine during their happy hour (3-6pm) to sample a selection of hot and cold tapas for $5 each, half-price drinks and $5 off a bottle of wine or pitcher of sangria. Their sparkling sangria is a customer fave. Expect yellowfin tuna ceviche, beef Carpaccio with capers and truffle oil, lamp patties with thyme and sherry, and spanakopita (Greek spinach pie) - to name a few.
Recommended for Happy Hour because: Santiago's happy hour (3-6pm) is the perfect time to sample several varieties of tapas at $5 a pop. Pair with a discounted pitcher of sangria.
Claudia's expert tip: Don't miss the flaming the Saganaki halloumi cheese sprinkled with oregano flambeed with Brandy. It arrives flaming at your table.
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 6pm-close, all of their perfectly mixed martinis are just $5, and you can't go wrong with yummy flavors like mint chocolate chip and key lime pie. If you have trouble choosing from their extensive selection, the bartenders can help you find the right drink to fit your mood. Kick back either on the outside patio or at the second bar under the roof. Every night people hit the dance floor for live music, usually jazz, blues or Latin. If you're feeling peckish, you can order Italian fare from a full menu until 10:30 pm and from a limited menu until close.
Recommended for Happy Hour because: Be there when it opens at 6 pm on Martini Mondays. Their delicious concoctions are only $5, and the place gets packed.
Claudia's expert tip: Dress to impress and wear your dancing shoes. They have live music seven nights a week.
While many parts of Key West have seen modern changes, Schooner Wharf maintains that "old Key West" atmosphere, from the salvaged wreckage to the interesting characters that linger around the waterfront. With its three separate happy hours (8am-noon, 5-7pm and 2-4am), it's hard to pay full price for a drink in this joint! Discounted specialty drinks such as Schooner Lemonade, Rumrunners and Mango Daiquiris are featured, as well as select menu items. Settle into the open-air bar and listen to the daily live music, while you people watch. Animal lovers can bring their dogs, or their parrots, to hang out.
Recommended for Happy Hour because: Throughout the years, Schooner Wharf remains an icon and a local's favorite restaurant and watering hole with a view, especially with three different happy hours!
Claudia's expert tip: Be sure to check their special events listing. Schooner Wharf has theme-night events throughout the year.
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 4-6: 30 pm. Sample peel and eat shrimp, spinach Parmesan oysters, key lime garlic oysters and steamed clams at 50% off. Specialty drinks like mojitos and key lime martinis, as well as select wines are also half-off. Arrive early to get a table, or if you catch the tail end of happy hour, stay for dinner and sample the mango lobster salad, coconut fried grouper or snapper in a spicy Cajun cream sauce.
Recommended for Happy Hour because: Alonzo's features the largest selection of warm and cold water oysters on the island. Sample them on the cheap during happy hour.
Claudia's expert tip: Park at the end of Front Street (on the right) and let the attendant know that you will be eating at Alonzo's. Parking is free when you show your receipt on the way out.