Sports Bars

Aqua 711 Duval St (305) 294-0555 (Gay/Alternative)

Aqua nightclub is the premier gay hotspot in Key West featuring a high voltage sound system and a very friendly staff. A killer happy hour runs 5 days a week from 3pm till 8pm, and Saturdays & Sundays from 2:30pm till 8pm. Aqua is the sister club to one of the nation’s hottest lesbian clubs, “Wall Street“. Aqua is open 7 days a week and there’s something special happening every night of the week, from dueling bartenders to Karaoke, to Texas Hold-em poker games. The “Aquanettes” perform their “Reality is a Drag” show 7 nights a week and no two shows are the same. It’s definitely worth checking out and something not to be missed. Aqua is open late every night and features a DJ and dancing nightly after the shows.

Bare Assets 1029 Truman Av (305) 809-7660 Facebook

Bare Assets is Key West’s largest exotic night club featuring exotic and nude dancers from all over the world, a full service bar, and can accommodate large groups or parties. They offer the only private champagne rooms on the Island and have 4 VIP suites as well as 15 private lap-dance areas. Bare Assets is open 7 days a week from 4pm till 4am and you never need a reservation. You must be at least 21 years of age or older and the dress code is casual. They also offer a 2 for 1 happy hour everyday from 4pm till 7pm and the cover charge is free until 8pm, after 8pm it’s 5 dollars.

Beach Bar @ the Pier House One Duval St (305) 296-4600

The Beach Bar and Grille located at the Pier House Hotel offers a swimsuit casual, dining and beverage experience by poolside or beach front. The bartenders are friendly and welcoming and you can catch some local live entertainment from time to time. Grab a bite to eat, have a cool refreshing beverage in a laid back atmosphere, then just kick back and enjoy the Key West lifestyle. The Bar and Grille is open daily from 11am until around 9:30pm.

Berlin’s Cigar and Cocktail Bar 700 Front St 305-294-5880

Berlin’s is located on the second floor of the A&B Lobster House at the end of Front street and offers patrons a laid back relaxed atmosphere and a myriad of cigar selections for the cigar aficionados, to go along with a full bar, separate rooms for fine dining as well as a dessert bar, comfortable leather couches, and a fabulous second story view of the harbor. It’s not just for men either. Berlin’s also offers many “slim”, less robust female-friendly cigar sizes. Reservations are encouraged.

Blue Macaw Island Eats and Bar   801 Whitehead St   305-440-3196

The Blue Macaw is a fabulous outdoor restaurant and bar boasting the largest make your own Bloody Mary bar in the Keys. Live music daily. Open 9am till 10pm,

Blue Mojito Pool Bar and Grille 601 Front St (305) 809-4043

Located inside the Hyatt Key West Resort and Marina, Blue Mojito pool bar is a great place to enjoy a lite bite to eat, have some cool refreshing drinks poolside and take in the fabulous views of the Gulf of Mexico. Happy hour runs daily from 4pm till 6pm. Thirsty Thursdays Happy Hour is extended from 4:30pm till 7:30pm with live music from some of the area’s top notch musicians. Blue Mojito is a romantic spot to watch the sunset or just hang out on their lush, tropical grounds and enjoy the balmy Key West breezes. They are open 7 days a week from 11:00am till 10pm. Reservations are accepted.

Bobby’s Monkey Bar 900 Simonton St (305) 294-2655 Gay/ Alternative

Bobby’s is a great place off the beaten path to stop in and have a cool refreshing drink after a day at the beach. The drinks are strong and inexpensive. Karaoke nights are Sunday, Monday, Thursday and Friday. Pool tournament night is on Tuesday. Bobby’s is open 7 days a week from noon till 4am. Bobby’s is a great gay-friendly neighborhood bar, home to mostly the local crowd. Cash only and smoking is allowed. It’s also close to many of the other premier gay Key West night spots. See map below. http://youtu.be/Ak5y9xvLer0

Bourbon Street Pub 724 Duval St (305) 294-9354 (Gay/Alternative)

Bourbon St Pub is one of Key West’s most popular gay bars featuring music videos, male dancers and fabulous drink specials. Bourbon St offers 4 bars. The Duval St bar, the main bar, the corner nook bar and the garden bar, which is a very casual tiki bar, outdoor theater and night spot, located next to the pool and jacuzzi of the New Orleans House. They’re open daily from 10am till 4am. And it’s one of the hottest spots to be on New Year’s Eve when the giant red shoe featuring the world-famous “Sushi” the drag queen, is lowered at midnight.

Bottle Cap Groove Lounge 1128 Simonton St (305) 296-2807

The Bottle Cap at Groove Lounge is one of the hottest spots on the Island with local and visiting DJ’s spinning House, Top40, Trance and Latin music till 4am. Bottle Cap offers two rooms , a patio area, 11 TV’s Wifi, a virtual jukebox and a liquor store. The store is open from 4pm till 4am daily while the lounge is open from 8pm till 4am daily. Proudly serving thirsty Islanders and tourists alike since 1934.

Bull & Whistle 224 Duval St (305) 296-4565

The World- Famous Bull and Whistle is a Key West icon and a must do at some point while you’re in Key West. The Bull is located on the corners of Duval and Caroline streets. The Bull is on first floor and offers a full bar and live entertainment seven days a week from 10am till 4 am. The second floor houses the Whistle Bar and is a great place to wet your “Whistle”(sorry for the pun), and watch the throngs walk past below on Duval St. They offer flat screen tv’s, darts, pool tables, a full bar and are open from noon till 4am. The third floor, or rooftop, houses the Garden of Eden Bar, which is Duval street’s only “clothing optional” bar for those of you interested in this option. They are also open from noon till 4am. Always a interesting time.

Capt. Tony’s Saloon 428 Greene St (305) 294-1838

The original “Sloppy Joe’s” and the bar Ernest Hemingway frequented while he was writing as a Key West resident between 1928 and 1938. It’s located at 428 Greene St and is the oldest licensed saloon in the State of Florida. “Capt.Tony’s”, as it’s known today, opened their doors in 1958. The history of both the building and the bar are fascinating. Built in 1851, this building housed everything from an Ice House to Bordello and has Key West’s original Hanging Tree growing right through the middle of the property. They are open 7 days a week from 11am till 4am. They also have live music all day and night. It’s a really fun and historic place to chill and have beer.

Caroline’s Cafe 310 Duval St (305) 294-7511

Caroline’s Cafe is a really cool outdoor cafe located on Duval St, in the heart of Old Town and serves breakfast, lunch and dinner seven days a week. The food is excellent and the prices are very reasonable. Caroline’s offers a full liquor bar and is a great place to stop in for a cool drink and people watch along world-famous Duval St. This establishment is amazingly well managed by our pal Rob and the service here is fabulous. Take-out and free delivery are also available. Caroline’s is open at 11am daily for your dining or drinking pleasure.

Charlie Mac’s   404 Southard St   305-320-0204

Charlie Mac’s is famous for their BBQ and seafood and you can also catch your favorite games on one of 11 HD TV’s. Huge selection of draft beer! Happy hour 4:30p till 6p.

Conch Republic Seafood Company 631 Greene St (305) 294-4403

The Conch Republic Seafood Company is a gorgeous open-air restaurant located in the Historic Seaport and Key West Marina and offers a breathtaking waterfront dining experience along with live entertainment daily from local musicians performing a mix of Caribbean and Island style music. CRSC also boasts one of the best happy hours in Key West daily from 4 till 7pm and proudly features one of the largest bars in South Florida and offers patrons a cornucopia of selections of the finest rums and specialty drinks Key West can muster up! The menu is quite expansive and features a mix of Caribbean style dishes, including the best locally caught seafood as well as Black Angus steaks and various other mouthwatering entree options.They are open till around 9:30pm 7 days a week and the bar about a half hour later at 10:00pm. The Conch Republic Seafood Company is available for private parties and special events, offers an online store and weather you stop in for breakfast, lunch, or dinner, the Conch Republic Seafood Company is a must-do and offers the perfect waterfront location for a great meal or cool refreshing libation anytime you’re in Key West.

Conch Town Liquor and Lounge 3340 N. Roosevelt Blvd (305) 296-4343

Conch Town Liquor and Lounge is located off the beaten path, away from the crowds of Duval street and is a favorite watering hole for many of the locals They are.located just a short drive from Downtown Key West on N. Roosevelt Blvd. Conch Town is open 7 days a week Monday through Saturday from 11am till 4am and on Sunday from noon till 4am. The atmosphere here is very casual and relaxed. You can chill out with a game of pool or darts as well as video sports games in the lounge and enjoy Happy Hour daily from 4pm till 8pm.

Conch Town is family owned and operated and the staff are always courteous and friendly. Conch Town offers the convenience of the only two drive-thru liquor stores on the Island. The liquor store is open Monday thru Saturday from 9am till 11pm and on Sunday from noon till 11pm. Conch Town is also the place to catch every UFC fight with no cover charge as well as all the local and national sports on a dozen high definition flat screen TV’s. If that’s not enough, Conch Town also will deliver your favorite party needs right to your front door at no charge!!! With Karaoke every Wednesday night and Ladies night every Thursday, Conch Town Liquor and Lounge is a cool place to relax and enjoy the Key West lifestyle.

Cork & Stogie Wine and Cigar Bar 1218 Duval St (305) 517-6419

Cork and Stogie is the Southernmost cigar and wine bar. Featuring several of the finest cigar and wine manufacturers in the world, it’s a great place for cigar and wine lovers to stop in and enjoy a stogie and sip on a tasty Merlot, while relaxing on their cozy little front porch. Cork and Stogie is open 7 days a week from 10am till 11pm. They also have an online store for ordering your favorite bottle of wine or cigars.

Cowboy Bill’s Honky Tonk Saloon 618 Duval St (305) 295-8219

If you love country music, Cowboy Bill’s is the place for you. It is the Southernmost country bar in the USA! There’s actually 3 bars located in this huge entertainment complex. At the Angela St entrance, there is an open-air bar/restaurant serving Mexican food via a variety of appetizers, sandwiches and entrees. If live music is your bag, Cowboy Bill’s offers up some of the best touring country bands in the nation, outdoors in a huge courtyard with a full bar. If that’s not enough, they have one of, if not the only mechanical bull to ride in all of the Keys. It’s a blast just watching people try to hang on for dear life. You can ride the bull Tuesdays thru Saturdays from 10pm till 2am and there’s a “sexy” bull riding competition every Wednesday at 11:00pm with a 100 dollar first prize! There’s also a expansive covered dance floor if you want to bust a move. This back bar is open till 4am!

Cowboy Bill’s also offers an air-conditioned sports bar which is located in the complex along Duval St with over 24 TV’s as well as pool tables, darts, and a variety of electronic and board games to play. Cowboy Bill’s is open 7 days a week from 11am till 4am and offers great happy hour specials Monday thru Friday from 4pm till 7pm. PBR’s only a buck every day till 10pm! There’s always something fun happening here 7 days a week. So stop by and check it out.

Dante’s Restaurant and Pool Bar 951 Caroline St 305-293-5123

If you happen to be arriving or departing on the “Key West Express” you’ll find Dante’s Pool Bar and Restaurant extremely inviting. It’s located right next door to the ferry terminal. What a great way to start off or end your stay in paradise! They have a huge saline pool with a cascading waterfall surrounded by tiki bars and they offer beverage service poolside! Dante’s also serves up a full menu that will make your mouth water. From appetizers to the freshest “catch of the day”, including a raw bar and kid’s menu, there is surely something to please your palate. They’re open 7 days a week from 11am till 10pm and have a great happy hour Monday thru Friday 4pm till 8pm. While we were there at the end of May, “John” was our server. He did an awesome job for us! Ask for him and maybe you’ll get to hear about the Hollywood movie script he’s writing. They also have live bands, DJ’s spinning tunes 7 days a week and sporting events on 17 TV’s. Try the frozen Pina Colada. Delicious!

El Mason De Pepe’s 410 Wall St (305-295-2620) Facebook

El Mason De Pepe’s is a wonderful, family-owned Cuban restaurant and bar located right in the heart of historic Mallory Square. They offer a casual atmosphere with a full liquor bar and friendly, attentive service, as well as an outdoor, covered patio dining experience. You can also enjoy top-notch, live Cuban style music across from the bar. El Mason’s is open 7 days a week from 11am till 10pm and is a great place to go for a cocktail and enjoy an authentic Cuban cuisine before or after a gorgeous Key West sunset. Reservations are accepted and they serve breakfast, lunch and dinner. Perfect for kids and larger groups of people. Try a mojito! One of the best on the Island.

Fat Tuesday 305 Duval St (305) 296-9373

Fat Tuesdays is a Key West favorite for some of the best 190 Octane tropical frozen daiquiris in Key West. Located in the heart of Duval St, it’s one of the best open-air bars on the Island to get out of the hot sun and enjoy a frozen drink. They have 18 frozen drink machines and a full bar for all your cocktail wishes. Don’t forget, for an extra buck or two, to add the extra shot of rum to enhance your frozen beverage. You can also purchase a souvenir cup and take it with you out into the streets, then come back anytime with it for half price refills . They also offer 8 flat-screen TV’s to peruse the big games and a great sound system to rock you out. Fat Tuesday offers a great Happy Hour from 4pm till 7pm Monday thru Friday and are open 7 days a week till 2 am, and till 4am on the weekends.

They’ve got a large outdoor deck and misters to keep you cool while you enjoy a beverage and people watch along world famous Duval St. Fat Tuesday’s is also available for private functions and can accommodate up to 200 people. Great music, great frozen cocktails and great service make Fat Tuesday’s on of the most popular bars on the Island for a cold libation by day or by late night.

First Flight Island Restaurant and Brewery 301 Whitehead St (Formerly Kelly’s Caribbean) 305-293-8484

Flying Monkey’s Saloon Facebook 227 Duval St. (305-294-7525)

Flying Monkeys Saloon is located at 227 Duval St next to Fogarty’s restaurant. Much like Fat Tuesday’s, they have a great wall of frozen drinks that will really put out the fire on a hot day. They also offer a full bar and live sports on TV, to go along with a casual Key West ambiance and plenty of outdoor seating. If it’s not too hot, it’s a great place to people watch, have a frosty drink and have a bite to eat along Duval St.

The Garden of Eden 427 Caroline St (on the rooftop of the Bull and Whistle Bar) (corners of Caroline and Duval streets)

The Garden of Eden is a “clothing optional” bar located on the rooftop of the Bull and Whistle Bar located at the corners of Duval and Caroline streets. They are open 7 days a week M-S from 10am till 4am and Sundays from noon till 4am and offer a full liquor bar. The atmosphere is casual and the bartenders are friendly and courteous. No photos please. Nobody is judging you here, so have fun and behave yourself!

Grand Vin Wine Bar and Shop 1107 Duval St (305) 296-1020

Grand Vin is open 7 days a week from noon till midnight and on Friday and Saturdays from 11am till 1am. They have a wonderfully extensive selection of wines and beers to enjoy and purchase by the glass or bottle and a relaxed, casual atmosphere in which to enjoy them in, as you people watch along world famous Duval Street. It is a family owned business and a great spot to chill and soak up all that Key West has to offer. They are located between Amelia St and Virginia St.

The Green Parrot Bar 601 Whitehead St 305-294-6133   (Photo art courtesy of Ray Ralston)

The Green Parrot is without a doubt my favorite bar in Key West. It’s located at the corners of Southard St and Whitehead Street. Hands down they have the best live music on the Island! It’s a little off the beaten path but well worth it. They are open 7 days a week from 10am till 4am with happy hour 4pm till 7pm daily. Green Parrot has a full liquor bar including beer and wine at very reasonable prices.Try the Bloody Mary, it’s quite tasty right down to the pickled Caribe bean.

The Parrot also has a juke box filled with some of the best blues and jazz music on the planet, many of whom have performed there previously. If you can’t make it out to the Parrot in person they have a live streaming webcam of the bar and stage that operates 24/7 It’s a great place to hang out with the locals, play a game of pool, or check out some of the best National and local recording artists in the country. The best part is there is never a cover charge! The Green Parrot has an amazing history which dates back to 1890! Check it out. The Green Parrot Bar is truly iconic and your’re sure to have a good time every time you’re there. Don’t forget the Parrot Store located right next door. Make the Green Parrot a destination anytime you’re in town and experience an eclectic, authentic atmosphere that is true Key West.

Grunts Bar and Grill 409 Caroline St (305-294-8280)

Grunts Bar and Grill is a really cool spot with true “Conch” architecture, located just south of Duval St offering patrons a casual, relaxing atmosphere either indoors or in their beautifully manicured outdoor courtyard. The bar opens at 4pm till 2am daily and the restaurant at 5pm till 10:30pm and is one of the best kept secrets in Key West. Beer, wine and homemade sangria only. Grunt’s also offers catering on site or off site for your private function or event. Great food and drinks and a friendly staff make Grunts an under the radar spot, in a convenient location, you’ll frequent whenever you’re in town.

Half Shell Raw Bar 231 Margaret St (305) 294-7496

Half Shell Raw Bar offers customers a full liquor bar and seafood restaurant with a premium waterfront location in the heart of the Historic Seaport on the Key West Bight. Half Shell is open Monday through Saturday from 11am till 10pm and on Sundays from Noon 10pm for breakfast, lunch and dinner and offer a casual, laid back atmosphere. They have a great happy hour daily from 4:30 till 6:30pm. The raw oysters are fabulous and add in a frosty cool drink along with their location on the waterfront and I can guarantee you’ll be back for more.

Hard Rock Café 313 Duval St (305) 293-0230

This marvelous old three-story Victorian style house built by William Curry for his son Robert, contains more rock and roll memorabilia than you can shake a stick at. Hard Rock Cafe is located right in the heart of Historic Old Town on Duval Street and houses two full liquor bars, one inside and one located outside on the patio. Established here in 1996, this world famous bar and restaurant is a great place to stop into for a frosty margarita on a hot day or simply have a relaxing breakfast, lunch or dinner inside or outside, while you peruse the crowds along Duval Street. Hard Rock is open 7 days a week from 11am till around midnight, offers an extensive menu and friendly service in a casual, laid back atmosphere. They also offer priority seating, can host your private party or special event, and of course, has a fully-stocked rock gift shop with everything from t-shirts to jewelry to you name it. If you’ve never been there before, it’s worth checking out.

Hog’s Breath Saloon 400 Front St 305-296-4222 1-800-826-6969   (Photo art courtesy of Ray Rolston)

Hog’s Breath Saloon is famous for it’s great live music, raw bar and relaxed casual atmosphere. The bar is open from 10am till 2am and the kitchen is open from 11am till 11pm… midnight on weekends. Happy hour is from 5 till 7 pm daily and they have a really cool live webcam if you can’t quite make it out to the Hog. They offer indoor and outdoor seating and have a private room available for your wedding or other special event, party or corporate function. Hog’s Breath offers two full liquor bars and an extensive beer and cocktail menu as well as a fantastic food menu. Don’t forget to stop into the ‘Hog Shop’ next door to pick up a world famous “Hog” tee or tank-top. Hog’s Breath is a really laid back bar and a great place to have lunch, dinner, or some frosty drinks, or just hang out after sunset or any time of the day or night while you kick back and enjoy some of Key West’s finest local and national, live entertainment on stage. Around here they always say… “Hog’s Breath is better than no breath at all”.

Irish Kevin’s 211 Duval St (305) 292-1262   (Photo art courtesy of Ray Rolston)

Irish Kevin’s is not only a great place to enjoy live entertainment all day and night long, seven days a week, but is a place where you just might find yourself up on stage participating in some drinking shenanigans that you might not remember the day after. Irish Kevin’s is a full liquor bar offering a lite bar menu to keep you going strong and have a fabulous selection of draft beers that may be one of the best that Duval Street has to offer. Irish Kevin”s is located right in the heart of Duval Street close to all the action and is open Monday through Saturday from 10am till 4am and Sundays from noon till 2am. They are available to host your private party or special function or event. If you can’t make it out to Kevin’s, they have a really cool live webcam so you don’t miss out on any of the fun. They also have an online gift store for those of you interested in a souvenir to take home with you. Anytime, day or night, you can usually have a good time singing along with cocktail in hand.

Island Dog’s 505 Front St (305) 295-0501, 509-7136

Island Dogs Bar is a great place to stop in for a cocktail and a bite to eat from their fabulous menu or maybe catch your favorite sporting event on one of many LCD flat screen TV’s. Off the beaten path, this casual, upscale bar and restaurant is open for lunch and dinner and offers patrons a choice of indoor and outdoor seating and a full liquor bar with a plentiful selection of draft and bottled beers. They offer a generous happy hour that runs from 3 till 6pm daily and great live music Thursday through Saturday. Island Dogs is open 7 days a week from 11am till 4am and serves up a full menu till 3am. They are located on Front street, a block up from Duval street, between Key West Bight and Mallory Square. They also have a retail store and are available for private parties. A great location and a fantastic, personable and friendly staff make Island Dogs a fun place to enjoy the come as you are, laid back Key West atmosphere at its best. The only place to get char grilled oysters!

First Flight Island Restaurant and Brewery (Formerly Kelly’s Caribbean) 301 Whitehead St (305) 293-8484    (Photo art courtesy of Ray Rolston)

Located in one of the most historic buildings in Key West, formerly the birthplace of Pan American Airlines and where they sold the first ticket, lies one of the great treasures of old Key West. First Flight offers its patrons a full liquor bar as well as its own “Southernmost” micro- brewery right on the premises. They also offer a full menu specializing in seafood and Caribbean dishes and serve lunch and dinner 7 days a week from 11am till 10pm. They have seating available indoors and outdoors as well offering a choice of two beautiful garden courtyards. One of Key West’s best happy hours occurs here daily from 4pm till 7pm featuring 2 dollar micro-brews, 3.50 Margaritas and half priced wings. Formerly owned by Hollywood star Kelly McGillis, this fabulous bar and restaurant is available for weddings and private parties, sells gift certificates and even has a gift store on the property. A great place to chill, live the history, and enjoy this romantic, tropical paradise. A “must do” for happy hour!

KWEST Liquors, Fine Wines and Spirits 705 Duval St (305-292-8500, 294-5995)

Newly renovated, this liquor store has a great little bar next door where you can have a cocktail or two, or enjoy breakfast or lunch while planning your days events. They offer free Old Town delivery for orders over fifty dollars and have free Wifi. The store is open Monday through Friday 9:30am till Midnight and Saturday and Sunday from 9:30am till 1:00am.

La Te Da Hotel 1125 Duval St (305-296-6706, 877-528-3320) (Gay/ alternative)    (Photo art courtesy of Ray Rolston)

There are three bars located at the La Te Da Hotel. The “Terrace Bar” is located outside, along Duval street and is a fabulous place to enjoy a cold beer or frosty frozen drink as you peruse the masses as they stroll past this casual, yet elegant Key West property. The “By George” Piano Bar is a very upscale bar and offers nightly entertainment with Island music and classic blues and grand piano tunes and the room features original Picasso sketches. The “Crystal” Bar is where you can see live cabaret theater performances and perhaps mingle with some of the world-famous female impersonaters at their gorgeous marble bar. The Crystal room is also available for weddings, as well as private parties and corporate events. The bartenders and staff are very friendly and accommodating as well. The La Te Da also houses a fine, upscale restaurant 

serving breakfast, lunch and dinner daily, and an elegant, upscale hotel, and is located toward the quieter, artsy end of Duval street.

Mangoes Restaurant Catering and Nightclub 700 Duval St (305-292-4606)

Mangoes is an upscale Restaurant, Bar and Nightclub located right in the midst of all the action of Duval street. Here, you can sip on a refreshing Mango Colada street-side at the fully stocked bar and outdoor patio, while you leisurely watch the world stroll past. The menu is fabulous and quite extensive and they have won several dining awards in the twenty-five years of serving good times in Key West. You can choose to dine inside, upstairs or downstairs, as well as outside on the patio or in their beautiful tropical gardens. Mangoes accepts reservations, offers gift certificates and is available for weddings, special events and private functions. The restaurant and bar are open from noon till 11pm 7 days a week.

Mangoes is also a full service catering company that will happily cater your special event where ever you choose, on or off the property. Saturday nights at Mangoe’s, the DJ turns the upstairs into one of the hottest dance clubs in Key West providing high energy techno/ euro-style dance music, starting around 11pm and going into the wee hours of the night till around 4am.

Jimmy Buffet’s Margaritaville Café 500 Duval St (305) 292-1435   (Photo art courtesy of Ray Rolston)

Located in the heart of Duval street is this Key West icon and arguably one of the most famous establishments in North America, inspired by legendary musician Jimmy Buffett. Margaritaville Key West is a full service bar and restaurant that welcomes people of all ages, and offers a full, Island-inspired menu served by an attentive wait staff, sensational margaritas prepared by friendly mixologists, and live entertainment 6 nights a week. Jimmy Buffett’s is open 7 days a week from 11am till 2am. If you’re in the hunt for a gift, the Margaritaville gift shop is located right next door offering everything from t-shirts to CD’s and DVD’s. and is open from 11am till 2am. Jimmy Buffett’s Margaritaville Cafe is also available for groups or special events.   (Photo art courtesy of Ray Rolston)

Point 5 915 Duval St (305-296-0669) (lounge)

Point 5 is an upscale, but casual wine bar located above the Nine One Five Restaurant, on Duval street. It’s a great place to sip on a glass of wine while you peruse the sights and sounds on world famous Duval Street. They offer a full, top shelf liquor bar as well as a variety of beers and an impressive fine wine list. If you’re in the mood, you can also grab a bite from their lite bar menu. On Friday, Saturday and Sunday nights, a DJ is in the house to entertain from 10pm till close. Point 5 is open Monday through Thursday from 5pm till midnight and Friday through Sunday from 6pm till 2am. The restaurant is open from 6pm till 11pm daily. This wonderfully historic property was built in 1906.

Rick’s and Durty Harry’s Entertainment Complex 202 Duval St 305-296-4890

Photo art courtesy of

Ray Rolston Artisit

This huge complex houses 8 bars! Drink Specials galore! Rick’s is a cool place to hang out along Duval St and enjoy a couple of cold ones while you are being entertained 7 nights a week till 4 am by some of the areas top local musicians. Down the alleyway from Rick’s is the world famous Durty Harry’s. Here you can find live rock music every night, 10 flat screen TV’s and drink specials during all the big games. Rock On! In the same alley you can find the Red Garter Saloon, one of Key West’s premier Adult entertainment hotspots. In the front of the building, along Duval St you can find Rick’s 208 Tree Bar. It’s another cool place to hop off your journey and enjoy a tropical drink made with fresh hand-squeezed juices.

Located on the 2nd floor you’ll find Key Wests hottest disco dance club, Rick’s Upstairs High energy! Hang out, dance, have a cocktail and people watch along Duval St. Also upstairs across the patio, you’ll find another bar called Rick’s Mardi Gras. Famous for their frozen daiquiris and bachelorette parties, it’s another great place to hang out and enjoy Key West. If your a wine or martini fan check out Rick’s Loft, also located on the 2nd floor. Enjoy the air-conditioned comfort as you chill out in this cozy little lounge. Last but not least in the Rick’s complex is The Crow’s Nest. This bar overlooks the stage and crowd downstairs at Durty Harry’s. It’s a great place to rock out!

Rooftop Café 308 Front St (305-294-2042)

Rooftop Cafe is a fabulous, upscale seafood restaurant and bar located just steps away from Mallory Square and Duval street and is the perfect spot to enjoy lunch or dinner and drinks before or after sunset from the balcony overlooking Front street and the crowds below. They offer indoor and outdoor seating, can host weddings and private parties and can provide off-sight catering for special events. They are open 7 days a week from 10:30am till 10pm. Reservations are available, but not required. The culinary expertise of Chef Orr makes this one of the finest restaurants on the Island and one I’m sure will have you coming back time after time. By the way, a great martini list.

Rum Bar @ the Speakeasy Inn 1117 Duval St 305-296-2680

 

The Rum Bar at the Speakeasy in is one of the best, quaint little bars in Key West. Located near the quieter artsy north end of Duval St this little gem is a must do when you’re in town. The rum list here is off the charts and bartender “Bahama Bob” will create a tropical cocktail for you that you will impress anyone!. Ask him about the Bark Juice shot. Its a rum shot that’s infused with a myriad of oddball things like nut and herbs, among other things, that sits inside the bottle. It’s a great place to chill and get your rum on while perusing the Duval St crowds as they meander on by. Rum Bar is open 7 days a week from 11am till midnight and offer a full liquor bar, friendly hospitality and excellent service from the staff. The ambiance is casual and laid back in an outdoor setting on a cool little 15 seats or so patio right alongside World Famous Duval St. Try the “Painkiller”. It’s pure happiness in a glass.

Shots and Giggles Beer and Wine Bar   201 Ann St.   305-414-8272.

Open 6 days a week Monday thru Saturday 5pm till 2am featuring more than 60 craft beers, fine wines and premium liquors.

Schooner Wharf 202 William St (305-292-3302)  (Photo art courtesy of Ray Rolston)

Schooner Wharf Bar and Restaurant is most definitely one of our favorite bars on the Island, located in the historic Key West Bight at the end of William street. They offer up some of the freshest seafood in town and have 3 happy hours daily at their fully stocked, waterfront bar. Schooner Wharf is also home to some of the best live entertainment in town 7 days a week. This open-air gem boasts a breathtaking view of the harbor and is where you can find the “Official Flagship of the State of Florida”, The Schooner “Western Union” docked. Schooner Wharf also hosts some of the coolest events on the Island throughout the year including, the “Wrecker’s Cup Series”, Chili cook-off, Lighted Boat Parade and my personal favorite, the Minimal Regatta, which is a competition held over the Memorial Day Weekend where contestants build home-made vessels made out of minimal materials and race around the inner harbor. It’s one of the coolest and most fun events of the year and is worth checking out!

Schooner Wharf Bar and Restaurant is open 7 days a week for breakfast, lunch and dinner from 8am till 4am. If you can’t make it out to Schooner Wharf, they have a great live webcam so you can never miss out on what’s going on there. They offer an extensive catering menu for your private party or special event, offer gift certificates and have a store on-site for your souvenir needs. Schooner Wharf Bar and Restaurant offers its patrons a casual, relaxed atmosphere and is truly one of the last little slices of “old” Key West.

Shanna Key Irish Pub Grill and Sports Bar 1900 Flagler Avenue 305-295-8880

Shanna Key is the Southernmost Pittsburgh Steelers Bar offering the NFL Sunday Ticket, is Key Wests home for all the major soccer and rugby matches, and is centrally located a short taxi ride from Duval street and only a block away from Smathers Beach. Shanna Key is open 7 days a week from 11am till 4am and serves up a fabulous menu of traditional Irish fare. They offer two happy hours daily from 4pm till 7pmm and from midnight till 2am. The entire staff at Shanna Key will treat you like family and will make your visit enjoyable and worthwhile. They have an extensive selection of Irish beers and drinks that is quite impressive and serve a delicious lunch and dinner menu that will make you feel like you’re in “Old Ireland”. Check them out next time you’re in town.

Sloppy Joe’s 201 Duval St 305-294-5717   (Photo art courtesy of Ray Rolston)

Sloppy Joe’s is a Key West tradition. They’ve been around literally for generations. They first opened their doors in 1933 and then moved into the present location in 1937. Sloppy Joe’s is open 365 days a year from 9am till 4 am (noon till 4am Sundays) and has some of the best live entertainment you’ll find on the Island. They offer a full bar including a variety of tropical frozen drinks and over 16 domestic and imported bottled beers. If you are in need of a bite to eat their extensive menu will surely satisfy your palate with everything from appitizers and sandwiches to seafood, salads and dessert. If you need to pick up a souvenir, Sloppy Joe’s has great gift shop with everything from gift cards and t-shirts to golf balls and hats. If you can’t make it out to Sloppy Joe’s in person, they have a live-streaming webcam of the bar, the stage and Duval St that really makes you feel like you’re there! It’s a really fun, casual place to hang out and have a great time. There’s also a long history dating back to 1933 that you probably find most interesting. Check it out for yourself and see why Sloppy Joe’s is one of the most popular bars in Key West.

Smokin Tuna Saloon 4 Charles St (305-517-6350)

Smokin Tuna Saloon is one of the hottest new establishments in all of Key West. Both a raw bar and a fabulous restaurant, Smokin Tuna Saloon plays host daily to some of the best live music Key West has to offer. This hidden gem is only steps away from Duval street in the heart of Old Town and is a great place to stop in for some drinks and a bite to eat. This expansive bar and restaurant is home to the Key West Songwriters Festival, which occurs May 1st through the 5th. They offer a raw bar, a fabulous menu, and happy hour daily from 5 till 7pm. The Smokin Tuna bar is open 7 days a week from 10am till 2am and the restaurant is open from 11am till 10pm. They are available for private parties and special event bookings, has a store for your souvenir needs and if you can’t make it out to the Tuna, they have a great live webcam so you don’t miss any of the fun.

Southernmost Beach Café 1405 Duval St (305-295-6550)

Southernmost Beach Cafe is the perfect place to stop in for a cool refreshing beverage after a day at the beach or just plain anytime. Located at the southern end of Duval street, Southernmost Beach Cafe is open for breakfast, lunch and dinner, offers a full bar and is available to cater your wedding, special event or private party on their gorgeous oceanfront location. They have daily happy hour specials from 4 till 7pm, the pricing is very reasonable and the staff at the Cafe are friendly, attentive and welcoming. Reservations are recommended for dinner. The breakfast here is fabulous and you can’t beat the location and casual, laid back Key West atmosphere. They offer indoor and outdoor seating and are open 7 days a week from 8am till 10pm.

Sunset Pier Restaurant @ the Ocean Key Resort 0 Duval St (305-296-7701)

Sunset Pier Restaurant and Bar is the perfect place to catch the sunset, enjoy a refreshing cocktail or two, have a fantastic meal and enjoy the ambiance of this breathtaking oceanfront establishment. Located at the Ocean Key Resort, this wonderful restaurant and bar offers live music from some of Key West’s finest musicians nightly, all within steps of historic Mallory Square. They are open 7 days a week from 11am till 11pm and offer a full bar, plenty of outdoor seating and a casual atmosphere to go along with a fantastic menu and simply unbelievable views of the harbor. A visit to Sunset Pier should definitely be on your list of things to do when you’re in town.

Sunset Tiki Bar and Grill 617 Front St (305-292-1553)

Sunset Tiki Bar and Grille is located inside the Galleon Resort and Marina and offers two happy hours daily from 10am till noon and from 4pm till 7pm. The poolside tiki bar is open 7 days a week from 10am till 10pm and is a great place to relax, enjoy breakfast or lunch and sip on a cool cocktail in a casual Key West atmosphere. They offer live music every evening and the grille is open from 6am till 8pm with delivery available those hours as well. They also offer a marina-side bar located next to the grille and is open from 2pm till 9pm daily.

Tiki House 430 Greene St

Tiki House KW offers authentic unique original tiki cocktails! They are open 7 days a week from 10am till 4am.

Turtle Kraals 1 Lands End Village (231 Margaret St) (305-294-2640)

Turtle Kraals is a fabulous restaurant and bar located in the Historic Seaport offering two full bars, with the Tower Bar located upstairs which has a breathtaking view of the harbor and all the magnificent vessels in port. It’s the perfect place for a cocktail and a bite to eat while you catch the world famous Key West sunsets. Turtle Kraals has a great happy hour daily from 4:30pm till 6:30pm and are open for lunch and dinner from 11am till 10pm Monday through Saturday and from noon till 10pm on Sundays. Turtle Kraals offers inside and outside seating and a very friendly and attentive staff that will take great care of you. Turtle Kraals also offers live music and have a turtle museum located on the property that you can visit and learn about the turtle industry which flourished in Key West in the mid 1840’s. It’s free and well worth the time.

Virgilio’s Martini Bar (behind La Trattoria Restaurant ) 524 Duval St (305-296-8118)

Virgilio’s is open from 7pm til 4am and is one of the best martini bars on the Island offering outstanding live entertainment Wednesdays through Saturdays and a simply sensational Italian restaurant right in the heart of Old Town. Virgilio’s is famous for it’s eclectic live music scene offering classic jazz, blues, reggae and R&B from many of the top local musicians as well as from artists outside the area. Great outdoor patio with tree canopy and fabulous martini menu. Late night dancing and a friendly staff make Virgilio’s one of the most happening upscale martini bars in Key West!

Willie T’s 525 Duval St (305-294-7674)

Wiilie T’s is located right in the heart of Old Town and is one of the spots you can’t afford to miss when you’re in town. This fabulous open-air bar and restaurant is open 7 days a week for lunch and dinner, has live music daily from some of the area’s top musicians and is a great place to have a bite to eat, and enjoy the Key West lifestyle while you people watch along Duval street. They have great happy hour specials daily from 4pm till 7pm and offer 31 flavors of mojitos! They offer a food and drink menu that’s quite expansive and the friendly staff and casual atmosphere will keep you coming back time after time. Willie T”s is open Monday through Saturday from 10am till 2am and on Sundays from 10:30am till 2am. Always lots of fun!