Tipsy Rooster Liquor Store and Bar

151

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748

9 months ago

Walk up window to solo bartender serving quick and delicious drinks. The Pain Killer I had was soooo good. Nothing fancy, but they had a live performer a bit after we arrived. Cool island vibes here read more

Tipsy Rooster Liquor Store and Bar - Outside seating - Bars Near Me - Key West, Florida

Tipsy Rooster Liquor Store and Bar - Outside signage - Bars Near Me - Key West, Florida

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Isabelle S.

0

17

13

2 months ago

The drinks are strong and well priced!!! The service was amazing!! Tim was super sweet and accommodating even when I had a difficult time picking what I wanted! He was super patient and funny! The ambiance of the whole place is super chill and laid back and by the end of the night, everyone there was having fun and chatting which is great! Plus, live music every night which is fun! Just a great place to hang out! read more

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Mark C.

8

277

353

2 years ago

A hidden gem which isn't really hidden. Right on the street next to Southwinds Hotel and just 2 blocks north of the Southernmost Point. Liquor store bar with a guitarist playing music pretty much all day. Good music at that. Any drink that you'd like at decent prices including draft beer. Plenty of room at hightop tables (in sand) with a few couches and chairs. Bartender every night we went there was very nice and friendly. No food but right next door is a very good donut/ice cream food truck. Check it out! read more

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Mark B.

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Claudia C.

4

65

138

1 year ago

Absolutely love this place! We've been coming to Tipsy Rooster every year for the past three years, and it never disappoints. The vibe is unbeatable, laid-back, fun, and full of character. Our favorite drink is the strawberry lemonade, perfectly balanced with tons of flavor, not too strong, just right. Kristin is hands-down our favorite bartender, she's down to earth, hilarious, and always nails our drinks. This time we also had Erika, who was awesome too, she even shared her mango and created a new concoction on the spot: mango lemonade (which was delicious, by the way). We finally bought shirts this trip since we talk about it every time we visit. Whether we're people watching from a stool, playing cards in front of the fans, or just soaking in the great music, it's always a highlight of our trip. Can't wait to come back again! read more

Tipsy Rooster Liquor Store and Bar - Strawberry mango lemonade - Bars Near Me - Key West, Florida

Tipsy Rooster Liquor Store and Bar - Strawberry lemonade - Bars Near Me - Key West, Florida

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Jeff S.

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Erin T.

0

2

0

3 months ago

Bartender upstairs was super slow but our waiter Ray was the best. We were there for 2-3 hours and he was attentive and helpful the whole time. read more

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Paul P.

37

805

900

11 months ago

An excellent spot to stop for drinks on the other end of Duval. Good pours, cold drinks, and you can also buy liquor bottles to go. Live music in the evenings - usually one man guitar singers. Nice folks serving. Not a lot of outside seating but it's in keeping with its intimate fun flavor. If you want to avoid the crazy, this is a great spot to hit. read more

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Brandi R.

0

4

1

7 months ago

Great vibe and great drinks. Their infused liquors definitely set their drinks above. The price was very reasonable and we took food from across the street and had a great lunch with amazing drinks! My husband loved his painkiller and I had a great bloody Mary with Horseradish infused vodka. read more

Tipsy Rooster Liquor Store and Bar - Horseradish Infused Vodka Bloody Mary - Bars Near Me - Key West, Florida

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James H.

Dear Brandi R,…

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B W N.

0

3

0

9 months ago

Visited the Rooster early afternoon last week. Outstanding bartender (female) making wonderful drinks and the personality to match. Returned a couple days later and found a different bartender (male) who was rude, unaccomidating and barely able to handle the bar and the store. Refused to allow examination of T-shirts stating that piles were all marked correctly. Got home to find woman large shirt much to small for my 12 y o niece Looks like the Rooster needs some attention from management read more

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Marissa R.

471

608

1234

3 years ago

This is a cute little spot, right in the middle of all the "Southernmost" things you could imagine! It was within steps from my hotel, and we had a coupon for a free cocktail from the Santa Maria, so we swung by. The infused liquor jars are a great idea... didn't seem too strong, but they were flavorful. Take a moment to relax at a picnic table... they're one of the few places that seem to stay open later down at this end of the island. read more

Tipsy Rooster Liquor Store and Bar - Tipsy Rooster. - Bars Near Me - Key West, Florida

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James H.

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Marissa N.

412

2152

7228

4 years ago

The Live music was nice, small place with walk up service n some outside seating. The stirred Pina colada was delicious. read more

Tipsy Rooster Liquor Store and Bar - Delicious creamy stirred Pina colada - Bars Near Me - Key West, Florida

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James H.

Dear Marissa N,…

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John B.

1

2

0

1 year ago

Nice spot to pick up a six pack or bottle of your choice. Also a nice spot listened to music at night

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Rick O.

0

19

3

8 months ago

Fun place with a cafe vibe. Not a lot of seating, and you get your drinks from the bar - no table service. Great people-watching spot.

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Mark B.

Dear Rick,…

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Angel B.

51

479

511

3 years ago

Came here for a couple of drinks. Out door seating on sand so you feel like you're at the beach. I had a mule. It was okay. Service was perfunctory. read more

Tipsy Rooster Liquor Store and Bar - Signature cocktails - Bars Near Me - Key West, Florida

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Jeff S.

Thanks for stopping by for a couple of drinks and sharing your…

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Ed B.

42

41

9

3 years ago

Tori is AWESOME!!! She's the owner and makes the infusions. I'll come here against & again & again!!! read more

Tipsy Rooster Liquor Store and Bar - outside - Bars Near Me - Key West, Florida

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Jeff S.

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Andrew M.

1

105

2

1 year ago

Great place to go in the afternoon before sunset sit back people watch .. great alcohol prices and good food

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James H.

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Nik H.

41

247

380

3 years ago

Our friends were staying at the hotel next door so we went here to meet for drinks on a couple of occasions. Nothing fancy. They have a few outdoor seats on the sand and offer great drinks that are reasonably priced! You order drinks from a window at the front. The two bartenders that I met were both friendly and made great drinks. The place is also a liquor store but their prices were kind of skewed to the high side. You can get food across the street and bring it back. Music was mostly folk-based and was hit or miss but generally enjoyable. read more

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Jeff S.

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Mariah M.

114

100

137

3 years ago

No photo but had the runner and it was tasty! Easy place to buy a cocktail with friends! Love the little beach vibe and live music too! read more

Tipsy Rooster Liquor Store and Bar - bar - Bars Near Me - Key West, Florida

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James H.

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Adam B.

0

11

8

2 years ago

Amazing singer doing live music. Casual and comfortable atmosphere. Open late even on a Monday!

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Mark B.

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Kathy R.

0

7

0

1 year ago

They have everything Staff is friendly and helpful Enjoyed Will definitely return Nothing else to say read more

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Mark B.

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Krista G.

171

237

276

4 years ago

SHHHHHH... Don't tell anyone about this place. No, for real. This is one of the best-kept secrets in Key West. Live music, relaxed atmosphere, no crowds, and drinks from an amazing selection of alcohols? Yes please. It's tiny but mighty: Sand and palm trees. Songs and drinks. Don't miss this. You will be back. read more

Tipsy Rooster Liquor Store and Bar - people at a bar - Bars Near Me - Key West, Florida

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James H.

Dear Krista G,…

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Cat F.

165

572

1541

5 years ago

Who dreamed this up? A liquor store-slash-bar with a deck? Heaven! Lol. They had a variety of outdoor seating including a boat on its side turned into a sofa. Lots of shade or sunny spots if that's your preference. Inside they have a bathroom and a wide liquor, beer and wine selection. read more

Tipsy Rooster Liquor Store and Bar - What to look for, but if you can't find this place, you are too wasted to go there! - Bars Near Me - Key West, Florida

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James H.

Thank you so much for taking the time leave this heavenly review of…

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Kim D.

5

57

16

2 years ago

We loved this place- it was such a chill vibe and great cocktails - so if the weather is nice stop in for a drink or two and enjoy the atmosphere read more

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Jeff S.

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Tish C.

39

183

723

4 years ago

My daughter lives down the street from the Tipsy Rooster and we decided to close the night out by listening to Marjorylee...one of KW best kept secret. She has the voice of Lauryn Hill (Fugees Lauryn), Adele and Amy Winehouse in one 30 something body. She embodies everything that is KW. I digress... Before you even get to the faux sandy beach area you smell the hot mini donuts which reminded me of funnel cake at a carnival or fair. I'll be honest, I wasn't moved by the house drink of the week. I'm not sure what I even had to drink except it tasted a lot like bananas. But the little nuggets of fried dough with powered sugar and soft serve custard was the melatonin I didn't know I needed. I can't wait to go back when Marjorylee is playing and the donuts are hot like Krispy Kreme...yum read more

Tipsy Rooster Liquor Store and Bar - Marjorylee -- phenomenal singer - Bars Near Me - Key West, Florida

Tipsy Rooster Liquor Store and Bar - The sign says it all - Bars Near Me - Key West, Florida

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James H.

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Sharon B.

0

2

1

2 years ago

Amazing margarita and such! Finally a place in Key west with real margaritas, fresh lime juice and amazing infused spirits. And for a Bonus, Torie the bar tender was amazing!! Super friendly and helpful and makes an awesome drink! Oh, and great location to catch a great breeze even in the hottest months!!! read more

Tipsy Rooster Liquor Store and Bar - Margarita with jalapeño infused tequila!!! - Bars Near Me - Key West, Florida

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Sergio P.

593

31

44

2 years ago

Excellent bar music every night. Awesome drinks highly recommend it when you're in Key West :-) read more

Tipsy Rooster Liquor Store and Bar - Great music every night. - Bars Near Me - Key West, Florida

Tipsy Rooster Liquor Store and Bar - Part of Key West history. - Bars Near Me - Key West, Florida

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Jeff S.

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Steve Z.

8

195

808

4 years ago

First time trying the bloody Mary's at Tipsy Rooster. This is a nice little tucked away gem in KW read more

Tipsy Rooster Liquor Store and Bar - Very good Famous Bloody Mary - the famous has horseradish vodka - yummy - Bars Near Me - Key West, Florida

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James H.

Dear Steve Z,…

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Rick B.

742

1022

2903

6 years ago

Great drinks from a mixology bartender who can satisfy any whim, and interesting package liquor inside. She made us great drinks sith Pineapple Flavoring on request, and we also scored some Key West Vodka made from local sugar canes! The virus is the only thing cheating them out of that 5th star. If we could sit inside in the A/C, I would've gone 5 stars! read more

Tipsy Rooster Liquor Store and Bar - Bartender creates our potions! - Bars Near Me - Key West, Florida

Tipsy Rooster Liquor Store and Bar - One Eyed Willie and some local vodka to-go! - Bars Near Me - Key West, Florida

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James H.

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Claire G.

1

18

1

1 year ago

Adorable little patio bar. Bartenders are kind and drinks are strong ! Had some live music as well

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Jeff S.

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Kristin B.

25

229

99

3 years ago

Ok, so we've stayed at the Santa Maria Suites two years in a row now, and you get free drink coupons to the tipsy rooster as it's next door. This place is great- last year we bought a bottle of rum and tried a specialty drink; this year I used my drink coupon to try another specialty drink(pina colada) as well as bought a holiday drink (a peppermint drink that was amaaaazing) The service was friendly and efficient, as I wasn't sure what I wanted and the bartender gave me a great suggestion for the holiday drink because it was SO good! I also love the little food truck that's right next to them for some late night sweet munchies if you get hungry and their live music is great! read more

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Jeff S.

Kristin B,…

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Ashley S.

Elite 26 All-Star

2131

3416

40902

4 years ago

We stopped here for a cocktail before dinner and the place is adorable. It's a walk up bar with outdoor seating, but also a liquor store inside. We tried the Road Rummer cocktail, which tasted similar to a sex on the beach. read more

Tipsy Rooster Liquor Store and Bar - bottles of alcohol - Bars Near Me - Key West, Florida

Tipsy Rooster Liquor Store and Bar - Road rummer - Bars Near Me - Key West, Florida

Tipsy Rooster Liquor Store and Bar - tables and umbrellas - Bars Near Me - Key West, Florida

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James H.

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Alyssa B.

44

49

8

2 years ago

The Piña Colada ruined all other Piña Coladas for me. So good. Live music! Sunshine! Sand under the tables! Amazing bartender! All good vibes read more

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Mark B.

Dear Alyssa,…

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Jo C.

0

24

17

4 years ago

The afternoon we were there it had a jam up guitar solo that was very entertaining They're pina colada's were fab and seating amazingly Great place for a cocktail pit stop lol!! read more

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James H.

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Tom M.

0

74

8

1 year ago

Hidden place in plain sight at the southern end of the island. You can a myriad of items there, including walk up beers, cocktails, and even fried donuts. Best part is when your time is up there you can go inside and there's a full-blown liquor store plenty of seating, including tables to eat a cheeseburger that you might've brought with you. Good music good times will definitely be back! read more

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Mark B.

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Dre G.

5

99

124

3 years ago

It's a liquor store. What could go wrong? This liquor store has everything you want. Make sure you walk in and check out every space all kinds of liquor. I don't have any food so I can't give it a food rating but I can give the service rating a five because I asked a couple of questions about some unique liquors that I needed for making a drink in within a second they were able to help me out. read more

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James H.

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Ellyn H.

27

266

278

3 years ago

Chill, sand in my toes, reasonable drink prices, and great live music. The cross breeze is awesome. Great place to stop on the way to your next bar. Highly recommend read more

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James H.

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Nadine B.

107

488

1043

7 years ago

This place is great -- a liquor store combined with a bar. The liquor store is inside, but all the seating is outside, including 4 bar stools. If you sit on the bar stools you are looking into the liquor store. The only thing I didn't like was the cigarette smoke. You can smoke outside, and everyone took advantage of this opportunity. read more

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James H.

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Natalya L.

0

1

0

2 years ago

The place is unique, the Food is delicious , presentation . Each dish is Art ! Staff is sweet , friendly and so accommodating ! Keep coming back year after year ! read more

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Mark B.

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Erik H.

3

35

21

2 years ago

Great service from Zuzanna and Alex. Fun live music and it's nice to sit with feet in the sand. No food, but you can go across the street to Ana's for a sandwich and bring it back. read more

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James H.

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More info about Tipsy Rooster Liquor Store and Bar

1325 Simonton St
Key West, FL 33040
Directions
(305) 295-5287
Call Now
Visit Website
https://www.tipsyroosterkw.com

Hours

What time does Tipsy Rooster Liquor Store and Bar open?

Tipsy Rooster Liquor Store and Bar opens at 10:00 AM on Monday, Tuesday, Wednesday, Thursday, Sunday, Friday and Saturday.

What time does Tipsy Rooster Liquor Store and Bar close?

Tipsy Rooster Liquor Store and Bar closes at 1:00 AM (Next day) on Monday, Tuesday, Wednesday, Thursday and Sunday.Tipsy Rooster Liquor Store and Bar closes at 2:00 AM (Next day) on Friday and Saturday.

Mon-Thu, Sun 10:00 AM - 1:00 AM (Next day)Fri-Sat 10:00 AM - 2:00 AM (Next day)

Payment methods

Does Tipsy Rooster Liquor Store and Bar take credit cards?

Yes, Tipsy Rooster Liquor Store and Bar takes credit cards.

Food & Alcohol

Does Tipsy Rooster Liquor Store and Bar have catering options?

No, Tipsy Rooster Liquor Store and Bar does not have catering options.

Does Tipsy Rooster Liquor Store and Bar have a drive thru?

No, Tipsy Rooster Liquor Store and Bar does not have a drive thru.

Does Tipsy Rooster Liquor Store and Bar have a happy hour?

No, Tipsy Rooster Liquor Store and Bar does not have a happy hour.

Does Tipsy Rooster Liquor Store and Bar serve alcohol?

Yes, Tipsy Rooster Liquor Store and Bar serves alcohol. Full Bar

Indoor Amenities

Does Tipsy Rooster Liquor Store and Bar allow dogs?

Yes, Tipsy Rooster Liquor Store and Bar allows dogs.

Does Tipsy Rooster Liquor Store and Bar have TVs?

Yes, Tipsy Rooster Liquor Store and Bar has TVs.

Outdoor Amenities

Does Tipsy Rooster Liquor Store and Bar have bike parking?

Yes, Tipsy Rooster Liquor Store and Bar has bike parking.

Does Tipsy Rooster Liquor Store and Bar have outdoor seating?

Yes, Tipsy Rooster Liquor Store and Bar has outdoor seating options.

Does Tipsy Rooster Liquor Store and Bar have parking?

Yes, Tipsy Rooster Liquor Store and Bar has parking options. Street Parking

Other Amenities

Is Tipsy Rooster Liquor Store and Bar wheelchair accessible?

Yes, Tipsy Rooster Liquor Store and Bar is wheelchair accessible.

Does Tipsy Rooster Liquor Store and Bar allow outdoor smoking?

Yes, Tipsy Rooster Liquor Store and Bar allows outdoor smoking.

Does Tipsy Rooster Liquor Store and Bar have free WiFi?

Yes, Tipsy Rooster Liquor Store and Bar has free WiFi.

From the Business

Specialties

The One Stop, Sip And Shop Liquor Store And Bar In Old Town Key West

History

Established in 2018.

The One Stop, Sip And Shop Liquor Store And Bar In Old Town Key West

More Info

Health Score

Review Highlights - Tipsy Rooster Liquor Store and Bar

“Diamond Dave is the friendliest best bartender and every drink tastes like the first time tasting it!”

Mentioned in 6 reviews

General Horseplay

4.5(179 reviews)

0.9 mi

We were searching for a fun craft cocktail bar on our pub crawl and we were lucky enough to get a…read moreseat at the bar at General horse play, probably because we went early. The vibe here is cocktail den, cozy, intimate, dark. It's like a sexy little vixen in the cocktail world with an air of mystery. The menu was very creative, I mean unique combos with premium spirits including absinthe and the bartender was helpful in that she would suggest a drink based upon spirits & profile you prefer. We each had a cocktail and Ithey were both delicious. We tried the I pity a fool, which is Jamison whiskey, peach, lemon, and black pepper. Also, El Cuerno de Aire , an Espadin Mezcal, lemon, and blackberry combo. Yum, Next time I'm in Key West I am definitely coming back here. Don't miss out on this one.

New bar in Key West, imagine that. This place has inside and patio seating. I found inside too…read moredark, I like to be able to see the floor when I'm walking. We only had a drink here, bartender was great.

Bar

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Unicorn heart and I don't know what my husband was drinking

Green Parrot

4.1(488 reviews)

0.6 mi

One of go to spots in KW! Cold beer, good peeps, and live music! Close to Duval and Hemingway area.read more

While roaming around Old Town we stopped in here on a recommendation from a local. He said it's his…read morefavorite spot on the island. It's a dive bar through and through but I happen to be a big fan of dive bars! However, this one fell flat on it's face with the service. I wouldn't say the place was packed but there were not any open seats at the bar. I posted up the best I could but for the better part of 15 minutes both bartenders didn't even come to my side of the bar. I then moved to the other side and waited another 10 minutes to be served (at which point the bartender said "Didn't I just serve you?" Um, no, you most definitely did not. This place has two saving graces: 1) A water jug full of cold water for the taking, off in the corner. Love that. 2) A popcorn machine that had DELICIOUS popcorn! YES. If you can manage to get a beverage then I think you won't mind Green Parrot's (very) relaxed atmosphere and delightful little perks. My takeaway is for the staff to mix in some work to go along with their chatting with the regulars...

Rum Runners: On the rocks or blended

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Outside

Tiki House

4.3(141 reviews)

Tiki House - A Must Stop KW Vibe We stumbled into Tiki House…read moreright at opening, lured in by their "street talker" promising 2 for 1 beers and wells from 12-3 PM. Who's walking past that? Not us. Inside, it's pure island charm -- rustic tiki décor, laid back energy, and a munchie menu that's perfect for a quick bite. Football season meant TVs everywhere, plus a solo musician on stage (I don't need to hear the game to watch it; music soothes the beast). Enter Mira -- The Tiki Oracle. Bartender, manager, Key West historian, and all around gem. She switched a TV to our game without hesitation and put up with me talking her ear off like a true bartender therapist. We liked it so much we came back the next day, and the vibe was just as good -- friendly, accommodating, and exactly what you hope for in a KW spot. We even dragged the rest of our group over, and they immediately asked why we didn't start there. Tiki House is so Conch Republic vibed it just makes you feel good. I highly recommend it... even though I hate giving away a place this good.

We had a few birthday celebrations in our group, so we decided to stop into Tiki House for drinks…read moreand a little dancing. The vibe for an early Friday afternoon was really good. The DJ was playing some great music that kept the dance floor going, and the bartender did a solid job keeping up with orders and taking care of everyone quickly. No complaints from our group at all. Everyone had a great time, and we'll definitely be back next time we're in the area.

JungleBird Bowl

Inside

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The Dive Bar Shirt Club

4.0(59 reviews)

0.9 mi

They pride themselves on being a dive bar but this is a good one. Such a great ambiance. Both times…read moreI have been here it's a local vibe feel. People were super friendly and it's just a fun place to hang out. The sign says dogs welcome humans tolerable, lol. I got to see the Hemingway lookalike winner being photographed along with some of the runner ups. The brisket tacos and burrito were delicious and the tacos were served with au jus for dipping. This is 5 star in a dive bar category.

Third time and the food did not a disappoint. Wonderful tacos and atmosphere. Bar tender / server…read more"seemed" nice until she came to pick-up the cups and trays. I said I was going to keep the Aluminum cup as i kept mine from last year. She then changed her attitude and said you are only allowed one per person per day. I handed my wife the 2nd cup which she purchased separately after the meal and the lady stormed off visibly upset. I walked up and told her I did not want to upset her a gave her one of the 2 cups back. Now a 5 star review becomes a 2 star. We will have to see how we feel next year when we come back to Key West. "Post the rule"

A Key West Legend.

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Open daily 11am - 11pm Kitchen 11am - 9pm

The Rum Bar

4.5(446 reviews)

0.2 mi

First trip to KW and our hotel was right across the street from The Rum Bar so we finished up there…read moremost evenings Hands down the best Pina Colada I've had .. No BS .. the best The banana daiquiri was awesome also Lindsey, the bartender is beautiful and very friendly as the others were too Highly recommended

This place is a fun stop with bartenders who know how to make all the great cocktails. This is not…read morea restaurant. Comfortable seating both indoors and out. Great people watching.

The other end of an amazing bar.

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Kenny Chesney Island Girls!! Nothing like these island girls to enjoy with the wife!

Sloppy Joe's Bar

3.9(1.6k reviews)

Shout out Security guard Ron! He was so friendly and helpful. He remembered us the next day and was…read moresuch a great guy! We spilt drinks twice and he happily helped us clean up both times. He made us feel really safe and welcome.

When in Key West check out Sloppy Joes. The Sloppy Key Lime Cocktail and rh original Sloppy Joe is…read moreamazing. Check them out! Service was great. Really everything was great.

Famous cat in Key West.

Original Sloppy Joe sandwich

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Sloppy Rita and Sloppy Ginger

Hog's Breath Saloon

3.6(658 reviews)

Cool fans at the outside bar and Coldest beer on Front Street. I'd stop here anytime I'm in Key…read moreWest.

First I want to thank all the wonderful employees that helped get my dog cooled down. You guys…read morewere the bomb! They sat us immediately near the fan and brought ice cold water. The water never stopped coming. Even tho I am a Floridian and I know better to walk around during the heat of the day , we decided to go out. Thank you so much again. The local fish dip was wonderful too. lol. Great southern hospitality. Thanks again.

Live music

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Captain Tony's Saloon

3.9(335 reviews)

I stopped by Captain Tony's Saloon and it was such a fun, classic Key West experience…read more The vibe is exactly what you'd want, laid-back, a little quirky, and full of character. There was live music playing, pool tables, and even some video games, so there's plenty to keep you and the family entertained while you hang out. Kids are allowed in, but they aren't allowed to sit at the bar. It definitely feels like one of those places where you can lose track of time in the best way. They also have a merch area with hoodies, stickers, and other souvenirs if you want to take a little piece of the experience home. And knowing it's one of the oldest bars in the Keys just adds to the charm and history of the place. The service was quick, you walk up to the bar and order then find a place to sit. Super chill and laid back. One fun thing you have to try is tossing a quarter into the fish's mouth outside... test your luck and see if you can land it! Can't forget the drinks! The rum punch is to die for... super refreshing and perfect for the Key West heat. Overall, such a fun stop if you're in town. Definitely worth checking out! Fun fact: - it used to be a morgue and ice house back in the day. it also used to be the original home of Sloppy Joes, before they moved to Duvall St.

We were with friends from CO who were visiting Key West for the first time. After walking around…read moreMallory Square and down Duval Street, we decided to have a drink at Captain Tony's before going out to a different restaurant for dinner. Of course it is an attraction because it is supposedly the original Sloppy Joes where Ernest Hemingway hung out. It is dark inside with low ceilings. People have hung paper currency all over and you will also see lots of bras hanging from the ceiling. There is live music and lots of people watching. We enjoyed our drinks and the fun atmosphere.

Inside

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Better Than Sex

4.5(1.7k reviews)

0.3 mi

I have a sweet tooth, a tremendous sweet tooth indeed, For…read moreice cream and desserts are the things that I need. I've had dessert in the desert near Area 51, And underground in Antarctica, far from the sun. I've had it in graveyards, beneath moonlight so fair, And even in a dessert restaurant, yes, I've had dessert there! At Better Than Sex, the Fever was mine, And it tasted so splendid, so luscious, divine. I tried one of their special coffees as well, And it was so delicious, I nearly swooned under its spell. But the night's grandest moment, the finest display, Was when our waiter arrived with the desserts on a tray. He looked straight in my eyes as he named each delight, With a confidence both curious and wonderfully bright. My dessert was a huge phallus, impressive and grand, With two giant balls resting beneath it in hand. It was covered in "splooge sauce," a curious sweet stream, A dessert of such drama it belonged in a dream! I truly enjoyed this place and would gladly return If I lived nearby, where the sweet candles burn. They are masters of dessert, of flavor and flair-- A deliciously mischievous treasure tucked away there.

We went to Better Than Sex after eating a full meal at Duffy's right in front, so there wasn't much…read moreroom left in us. But oh man was it amazing. An extremely unique ambience and decoration. But it's not too much or too little. The seating is comfortable and private. Our server was very nice, he checked in at all the right times and was sweet. We only ordered one dessert and it got there promptly. Everything on the menu looked excellent and delicious. We settled on the cookie nookie cake, it was super fresh with many contrasting flavors that made every bite a pleasure. Overall had an amazing time and recommend this place for anything from a late night dessert or a full dessert meal. If we're ever around again, we are definitely going back and trying a lot more than just one dessert.

Cream in my coffee

Red velvet cheesecake

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Moscato, white chocolate rimmed glass

Halo Rooftop Lounge

4.4(9 reviews)

0.8 mi

We came on a recommendation, and we heard the music from the street below, which made us curious…read more Popped in to have a quick drink, and stayed a bit longer listening to an amazing musician. I really wish I remember his name. Our bartender Maria was super sweet and very friendly! Cool place to relax, have a drink, listen to some great live music, and people watch on Duval Street.

The location is awesome, a balcony above Duval Street, right in the middle of the Key West action…read more If you only want basic beer or wine, *maybe* you'll enjoy yourself. They offer a *very* limited choice of cocktails, and couldn't even make a daiquiri for us. Bizarre. The bartender suggested we go to another bar with a better choice of cocktails, so we did. BTW, they only serve drinks in plastic cups, like a pool bar, if that matters to you. Halo is located in an expensive upscale hotel, but this is definitely not a high end experience.

Dinner menu

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Menu

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arlene b.

0

2

0

7 years ago

ordered a hat 3/19. Still haven't received it. Now they won't even respond to my emails. i couldn't have been more patient with them. But now they ignore me. Hope they can resolve this very soon We spend 1-2 weeks in KW every spring. Never had an issue before. What gives??? read more

Jo M.

0

32

10

6 years ago

Fun local walk up bar !! The bartender was very nice and gave us great recommendations of other places to eat and try. He was super nice and made GREAT drinks ! Fun atmosphere and great local shop! read more

David B.

0

9

0

5 years ago

Nice place, good location, good nighttime entertainment, drinks are great- try the iguana bait beer, the best, great cuban food truck across street next to Blue Marlin Motel. read more

Cristina H.

140

12

8

2 months ago

So good I drove 45 min to get it and it was well worth the drive. I can't wait to go back again and give it another try

Edward B.

0

41

9

1 year ago

fun and delightful. great entertainment for all ages. This corner stop is a must for all visitors to key west.

Tipsy Rooster Liquor Store and Bar - bars - Updated September 2026

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The Roost

4.4

(113 reviews)

This bar is so incredible, we came three times during our trip! It sounds like a dive bar but it's…read moreactually an upscale craft cocktail bar. Loved their porch sipper and the Sazerac. Black manhattan, rosemary gin and tonic, and blowing smoke up your glass were great too. Service was great and loved the decor. Stumbled upon it walking around and saw the menu, and had to check it out.

The Roost is one of those super cool artsy intimate neighborhood pubs that you feel lucky to wander…read moreinto. And it's not only the drink menu with its custom crafted cocktails, wines, beers & ciders that will wow you but the accompanying snacks and bites are just as divine. And bonus, it's not only a bar, but also a liquor store with an awesome selection of wines and spirits. This bar definitely has a locals vibe. It's small , dark and cozy and the small tables with velvet chairs are very welcoming. We loved it so much. We came back for a second night. We tried the Maria Rita, which was a reposado tequila with fresh lemon, lime, hibiscus, and habanero, perfect version of a margarita. We also tried blowing smoke up your glass, this was made with Papa Pilar, dark rum, pineapple, fresh lime, house made basil syrup & tiki bitters. Absolutely fabulous. We also tried their deviled eggs each topped with unique toppings like trout row, bacon, and scallions. They were absolutely fabulous. They also have a great selection of charcuterie, Key nuts which you can order with different flavor, profiles, caviar, olives & peppers. Also, the most generous happy hour I've ever heard of from 12 to 6 PM every day. Don't miss out on this little jewel when in Key West.

Southernmost Point Bar

4.5

(67 reviews)

Great key lime pina colada at this bar. We weren't sure if it would be good since it's a tourist…read morespot but it was blended so well. Best frozen drink of our trip.

This is a cute bar near the southernmost point. There is usually live music playing and lots of…read morefans nearby to help with the Florida heat. There is a walk up food truck to order food and a bar to get drinks. The drinks are on the pricey side but they were pretty good.

Hank's Hair of the Dog Saloon

4.2

(142 reviews)

I stopped by for a quick bite and cold beverage. Got em! As usual the service was top notch with M…read moreMorgan (first M is silent) was serving up the suds at the back bar and roasting customers with glee. Two thumbs up! Well worth the walk from Duval St. You won't be disappointed.

We stopped here to take in a live musical performance by talented guitar player and singer, Noah…read more We were semi-covered beneath multiple sailcloth strung above us, but still able to see plenty of stars and an enormous bright moon between the gaps. Beer was cold and the crowd was having a great time. A food truck, Garbo's, is also on site to order fantastic food.

Shots and Giggles

4.3

(66 reviews)

What a cute little spot! We heard about the mermaid margarita so we stopped for that and it was…read moredelicious! Very refreshing on the hot day. Inside there are several rooms, all adorable. The outside area is cute too but had no shade at the time of day we were there so that wasn't happening for us. The bartender was very friendly and welcoming. Added bonus- they have a little dog bar with treats and toys for your pup!

Never again. The bartender was more interested in hitting on a guy than acknowledging us. Her…read moreenergy was heavy and clearly annoyed we were interrupting. Once we patiently waited for her to finish flirting and trying to make plans (guy trying to leave as it was that obvious ) she finally asked if we wanted something (umm are you kidding?) we had one shot because we really wanted to give this place a try but after the shot we left . Bad service, whatever shots, and just not the vibe.

Sloppy Joe's Bar

3.9

(1.6k reviews)

Shout out Security guard Ron! He was so friendly and helpful. He remembered us the next day and was…read moresuch a great guy! We spilt drinks twice and he happily helped us clean up both times. He made us feel really safe and welcome.

When in Key West check out Sloppy Joes. The Sloppy Key Lime Cocktail and rh original Sloppy Joe is…read moreamazing. Check them out! Service was great. Really everything was great.

Don's Place

4.2

(39 reviews)

•$

Fun bar with separate indoor and outdoor areas-also has a liquor store. Service was fine. Went to…read morewatch the Buffalo Bills play - big crown of Bills Mafia inside and out. Fun crowd.

Great little place in key west to watch the Buffalo Bills play, fantastic bartenders!!read more

Vinos On Duval

4.6

(154 reviews)

We stumbled across Vino's while wandering Duval Street and ended up visiting twice during our trip…read more The sangria is delicious, especially during happy hour, and there are plenty of wines available by the glass or bottle at reasonable prices. We also shared a meat and cheese board that paired perfectly with the wine. What really made us come back, though, was Sam. She was welcoming, attentive, and just genuinely enjoyable to chat with. The kind of person who makes you feel like you've been coming there for years, even if it's your first visit. This feels like one of those places you could stop into for a glass of wine every afternoon while you're in Key West. Relaxed atmosphere, good wine, good conversation, and no pressure to rush off somewhere else. As an added bonus, Sam helped us secure reservations at Lola's Bistro, which ended up being my favorite meal of the entire trip. We'll definitely be back the next time we're in Key West.

Cute and quaint wine bar/shop. Large selection of wines to try or purchase…read more On this particular night, bartender more concerned with interpersonal conversation with friends than guests.

Smallest Bar

3.9

(176 reviews)