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Florida Keys Most Expensive Bars
Rooftop Cafe
photos map Smoke-Free REVIEWED Rated 7 310 Front Street
Key West, FL 33040
Phone: 305-294-2042
The only thing bad about the Rooftop Cafe is that if you have never been there before you may miss it entirely... and if you do see the people dining and drinking and having fun above you on Front Street you will have to keep an eye open to find the door that lets you go up and join them. Finding and getting into the Rooftop is entirely worth it - the bar is very clean, very beautiful and well ...Read more
Bagatelle Restaurant Key West
photos map web page Smoke-Free REVIEWED Rated 9 115 Duval Street
Key West, FL 33040
Phone: 305-296-6609
Bagatelle is more of a classy restaurant than a bar. They have a small bar area for waiting or downing a quick drink, but it's not a hang out type of bar. Being located on Duval it's also a great place to people watch while resting your feet after shopping all day. The building itself is over 125 years old and the current owners have tried successful to keep it's old charm while still offering ...Read more
Rick's Entertainment Complex
photos map web page Dancing Smoke-Free REVIEWED Rated 8 202 Duval Street
Key West, FL 33040
Phone: 877-659-9719
Rick's is a great little place to see a live band on Duval Street. Upstairs is The Red Garter, one of only three strip clubs in Key West and one of two on Duval Street. Around the back is Rick's Upstairs which is a large dance club aimed mostly at the college crowd and all around Ricks you can find various offshoots of the same business but with the same attitude towards excellent service. While ...Read more
Lazy Gecko
photos map web page Smoke-Free REVIEWED Rated 7 203 Duval Street
Key West, FL 33040
Phone: 305-292-1903
This place is a lot bigger than it seems from the outside. The bar itself goes back 20 or so yards and beyond that is another room for bar visitors who want to play pool or foosball. During my visit the bartender I had was extremely friendly and even suggested other places I should visit while in town. I never saw a customer wait for a drink, or a refill and both bartenders actively chatted up ...Read more
Bull & Whistle Bar
photos map Smoke-Free REVIEWED Rated 7 224 Duval Street
Key West, FL 33040
Phone: 305-296-4565
One of the biggest bars around, this building has 3 themed named something different. The first floor is The Bull. It's dirty and unapologetic about it. There is always someone performing on the stage in the corner and it could be a band, a guy with a keyboard or an extremely talented vocalist who sings along to Karaoke tracks.Upstairs is where I can usually be found when I'm in Key West. It's ...Read more
Fat Tuesday
photos map web page Smoke-Free REVIEWED Rated 7 305 Duval Street
Key West, FL 33040
Phone: 305-296-9373
A lot of people will tell you that the best thing about Fat Tuesday is the long wall of frozen drink machines. I don't know how many there were because I simply can not count that high... what do you want, I review bars for a living. What I like best about Fat Tuesday is that they don't cram everyone together just to fit in another 4 tables. You can sit down and still have a lot of room to spread ...Read more
Jack Flats
photos map Smoke-Free REVIEWED Rated 7 509 Duval Street
Key West, FL 33040
Phone: 305-294-7955
If the sun has beaten you up while shopping Duval Street and you want to take a break from the heat to let your sunburn develop a little then Jack Flats is the place for you.It's dark inside and only a very small corner of it actually gets sunlight. The reason for the darkness may be because they have 25 televisions (and one large projection screen) nailed to the wall and on every screen is a ...Read more
Duffy's Steak & Lobster House
photos map Smoke-Free REVIEWED Rated 7 1007 Simonton Street
Key West, FL 33040
Phone: 305-296-4900
What's not to love about steak and lobster? Duffy's specializes in both and the clean quite atmosphere is miles away from the big corporate places that look like they were built with a cookie-cutter and a blueprint from the 60's. Duffy's is cleaner than most other steak and lobster places and the staff are top-notch professionals. There is a small bar, mostly suitable for waiting for your date ...Read more
Pisces
photos map web page Smoke-Free REVIEWED Rated 8 1007 Simonton Street
Key West, FL 33040
Phone: 305-294-7100
Sister Restaurant of Duffy's  Pisces even shares the same address but they are actually two different buildings. There is a small bar  suitable for waiting for your date or for you and your date to wait for a table. However Pisces is an intimate dining experience complete with an extensive original Andy Worhal collection. They have been in business since 1982 and have won numerous awards for ...Read more
Mangoes
photos map web page Smoke-Free REVIEWED Rated 8 700 Duval Street
Key West, FL 33040
Phone: 305-292-4606
This is the kind of place you fall in love with before you even sit down. Everything about it is perfect. The view is beautiful, the design is wonderful, and the staff is fun and energetic. The massive outside bar has a drink selection that you can normally only find in places like Vegas and behind it is their wood fired brick oven that they make pizza in at night.The upstairs is a banquet room, ...Read more
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