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    Jessie's Lounge

    3.8 (15 reviews)
    Closed 4:00 pm - 2:00 am (Next day)
    Updated 3 months ago

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    4 years ago

    The menu lacked. Staffing lacked. And seating was atrocious. We would not go back there again.

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    8 years ago

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    10 years ago

    awesome bar! staff always remembers you and what you drink . Great live shows and professional sound person!!! Very clean and not smoky.

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    15 years ago

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    Review Highlights - Jessie's Lounge

    JJ Grey was such a great time!

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    Old Man Frank's

    Old Man Frank's

    3.5
    (123 reviews)
    0.6 mi
    $$

    I love dive bars, especially one's with iconic views, fantastic service and reasonable prices…read more What makes it even better is the seafood which is quite good. Stopped here on a Sunday afternoon right after visiting one of my favorite breweries in the area. Had never been here before and didn't know what to expect. Looks can be deceiving, because from the outside the place didn't look inviting. In fact as I was entering the patrons who were leaving were jokingly asking if I was afraid to go in. Well, challenge accepted. The place wasn't as diverse as I'd like, but there was a good mix of people. There was a guitarist playing live and once I was seated the servers, both of the whom were outside, made me feel more than welcome. In fact, it was the best service I have had in quite a while. I was expecting much less and I got way more than I could have imagined. We sat outside. When you enter, there is a bar right there to you right and as you walk in and around there are tables on the outside deck. Once you get to the back, that is where the entrance is to the inside bar. And just as a footnote, the bathrooms were clean which was an awesome surprise. Ordered oysters, 12 dressed and steamed, can't remember what they called them, but there is definitely a picture and 1/2 dozen raw. They were very good. Also ordered some wings, which were both breaded and fatty. Didn't like them and they were gracious enough to remove them from the bill. Also ordered steamed shrimp which were awesome. For drinks we had a blue martini special drink and I had $1 Narragansett specials which is a really great beer. I had 2 and felt really guilty about having a great beer at such a cheap price. I know why it was on special, because it tasted like it was almost ready to go, but it wasn't gone and it really hit the spot. Suffice to say, I will be returning. There are too many great things happening at Old Man Frank's for me to not be craving this experience again.

    This was a spectacular experience. Our server Fuzzy was so fantastic! With her recommendation, we…read moregot the warm peel and eat shrimp and the smoked fish dip. It was sooo delicious! To top it off, we had the Fuzzy Old Fashioned! It was a top ten day and we hardily recommend this place!!!

    Photos
    Inside
    Inside
    Mushroom bites
    Mushroom bites
    Entrance to the outside leads you to the inside around back

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    Entrance to the outside leads you to the inside around back
    Ya'll Come Back Saloon

    Ya'll Come Back Saloon

    4.1
    (18 reviews)
    14.8 mi
    $

    We stopped for a cocktail on our way to Tampa! Food was great- bartender was hysterical! Patrons…read morebought the bar Jell-O shots for a celebration!!

    The very best part was sitting on the patio to hear the live band! I sat in a far corner so I could…read morehave the fan at my back to blow away to cigarette smoke. It didn't work! I traversed inside to place my order as there didn't seem to be service at that time. The waitress seemed off and kept making me wait while she asked the bar crowd who else wanted a drink. I waited and waited. Finally she took my order. I asked for the nachos and a draught beer. She seemed surprised I ordered food. She kept telling me I needed to order chicken or steak. I indicated that I didn't need those add one and was good with the refried beans listed on the menu. I told her I was sitting on the corner outside. That corner is where I sat, for more than half an hour, gasping for air. I was entertained by the music and some people dancing to the tunes. I really wanted my beer which never came. Finally my nachos arrived. They had a nice presentation but no beans. They were dropped at the table as she sped away. I tried to ask for my beer but she never hesitated long enough nor emerged to check on me. My nachos was more of chips and cheese with a lettuce salad on top. I was thankful for the jalepeno slices and made the best of it. After an hour I went inside to pay. The waitress ignored me again. When I finally got the bill it included the illusion beer that was never served. When I questioned it the waitress got frustrated and handed my ticket to an apologetic younger guy. I don't think wild horses could drag me back to this bar. Maybe if some friends were only willing to come hear the music but not venture inside... it's pretty sad as the music was great!

    Photos
    JANET AND LOWELL
    JANET AND LOWELL
    Ya'll Come Back Saloon
    Ya'll Come Back Saloon

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    The Twisted Prop Bar & Grille

    The Twisted Prop Bar & Grille

    4.1
    (105 reviews)
    0.5 mi

    We were visiting this area on vacation and The Twisted Prop Bar & Grille appeared in my search as a…read moreplace to try. You will feel like you are lost as this place is truly a hidden gem. The true experience can be had by sitting on the covered back porch and overlooking the water. The food was very tasty and the service fantastic. Our table tried the gator bites, wings, shrimp wrap, double cheeseburger, fish sandwich and fried shrimp Along with the peanut butter pie. We all left very satisfied with our individual choice. We will return.

    First visit today and probably our last based upon this experience. This is sad as we were looking…read moreforward to this experience. This is a casual restaurant with both indoor and outdoor seating and it is seat yourself. We picked an open table outside and sat there for quite a while before anyone acknowledged us. They then sent the server assigned to our table (Samantha). It was a quick smile-free greeting and she took our drink orders, then when serving our drinks she took our food order. After serving our food, she never stopped by our table again, although she stopped by her other tables around us several times. We had to stop her to ask for a box and our check.....she never offered drink refills even. We ordered a single cheeseburger with bacon and a side of onion rings ($14.74), a Fish Filet with no side ($14.50) and an order of Tater Kegs ($11.50). The cheeseburger with bacon looked great but didn't live up to the appearance. It was kind of tasteless....even the bacon was disappointing. The onion rings were crisp and pretty perfect. Fish Filet was large and tasty although we really would have liked more tartar sauce. The Tater kegs were also large and tasty. It was nice sitting outside with view of the lake and boat activity. This restaurant has potential to be much better....slow, minimum and cold service really takes a restaurant experience down. I hate that I cannot recommend this restaurant.

    Photos
    Listening to the club "Tanners" across the lake.
    Listening to the club "Tanners" across the lake.
    Burger and fries
    Burger and fries
    Great view and a nice beer!

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    Great view and a nice beer!
    Rudy's Lounge

    Rudy's Lounge

    3.3
    (6 reviews)
    8.8 mi
    $$

    Enjoyed it.... good service, well priced drinks, a fun time. Advance notice - probably hasn't…read morebeen redecorated since 1985 but I found that charming. It looks "lived-in"... in a good way. Plenty of parking, cool laid-back patrons and staff... give it a try !

    This is by far the worst bar I've ever been to. While I enjoyed it for a while, a place to go after…read morea long day of work. I never expected this to happen..... on Friday June 28th, 2025 my friends and I were grossed out by guys who I guess never have seen women a day in their life! This man harassed us the entire night, and made sure to go everywhere we went. While talking to our friend that was a regular about it she decided it was best to tell the bartenders, (who did nothing btw). They did nothing, they ignored the situation and kept serving the man drinks. The guy than kept on with harassing and locking in on me and my friends, we decided to leave because nothing was being done about it (keep in mind it's happening right in front of them), the man follows us outside, we get into our vehicle and leave. He follows us all the way to 27 where I had to pull into the police station. That's when he decided not to follow anymore. So I was able to make it back home and safe. No thanks to the bartenders and the facility. The point of this is, the bartenders knew what was going on! And instead of trying to help multiple women they focused more on getting a "good" tip from a creep and allowed him to stay at the bar. They are fully aware of the man because one of the girls told us he was weird. We've spoke to one of them days before about this and she said "if it happens again, let us know" welllllllll you see how that went. Ladies. I don't recommend!

    Harborside

    Harborside

    3.9
    (851 reviews)
    1.6 mi
    $$

    Here is a polished, detailed review for your visit to Harborside…read moreExcellent Meal with Top-Notch Service! We had a wonderful dinner at Harborside in Winter Haven! The atmosphere was great, and for the most part, the food absolutely delivered. To start, the crabcake appetizer was fantastic, and the clam chowder cup was rich, creamy, and packed with flavor. For our mains, the power greens salad, with chicken and maple salmon were all beautifully prepared and delicious. The only hiccup of the night was the rice that came as a side with the salmon--it was unfortunately quite dry and lacking. However, our server handled it perfectly and quickly brought out a baked potato substitute instead, which was excellent. Great food, lovely views, and accommodating service that knows how to take care of guests. The view is great.

    More than 25 years experience with travelling to the US (yearly to Florida) we just discovered this…read moreplace Already our last day before departure... decided to go for resting near the water. Happy Hour: just for some drinks and unfortunately not explained by the waitress and not indicated on the menu we got We had a watermelon smash (12 dollar) and a harborside margrita (13 dollar) which were very good. We ordered the gator bites (18,50 dollar) ... hugh portion. The drunken mussels (16.50 dollar) were delicious but too fast too cold We ended with a pineapple rum cake (13.50 dollar - for me too sweet) and a NY cheesecake (10.50 dollar) which was delicious. Total of the bill: 116.63 dollar. We decided NOT to tip, due to the fact we got a surcharge fee because we paid with a credit card ‍ In all these years, we NEVER had this Sorry guys, it's that or a tip. In spite of the beautiful view on the lake, we will not come back.

    Photos
    Bar area
    Bar area
    Ribeye steak with a side of lobster tail and snow crab legs
    Ribeye steak with a side of lobster tail and snow crab legs
    TIME FOR SOME SEAFOOD... TIME TO EATZ...

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    TIME FOR SOME SEAFOOD... TIME TO EATZ...
    Cherry Pocket Steak n Seafood

    Cherry Pocket Steak n Seafood

    3.6
    (336 reviews)
    11.5 mi
    $$

    Out day tripping and shopping and the DIL had this spot recommended for an early dinner. It was out…read moreof the way for us, but we went for it and are glad we did. Looking at the reviews already posted makes this place seem bipolar. Maybe it has everything to do with the day of the week, the cooks/chefs on staff and/or managers/wait staff present. This was a Saturday, so.... The better half wanted to sit indoors and the DIL outdoors. A compromise was made and the table selected was in between. The service was exceptional by our waitress (I wish we could recall her name). A solo musician played mellow music and had good vocals. Very relaxing atmosphere. All the food ordered was tasty and abundant. The highlight was the Grouper sandwich the better half raved about, even the day after she was talking about it. The meals came with a tasty brown bread and house salad, which was a nice addition. The drinks were not watered down and well made, at a price point that was quite acceptable. We all look forward to returning; but it may need to another Saturday if that's when they have the A-Team working.

    Disappointed doesn't begin to cover how I felt about my poor experience at Cherry Pocket. The…read moreoverall vibe was chaotic, hot, humid, and sub-par cleanliness with profanity-laced dollar bills stapled all over. Florida! I'm certain the condiment bottles in scattered baskets never get cleaned. I never leave poor reviews, but potential guests must be warned of this place. My elderly aunt and I arrived at 4:10pm after driving an hour to this place for a late lunch. It was Father's Day, so the place was packed and busy. So busy, that the wait staff were frantically running around the place. Upon arrival, we were greeted by a young hostess who looked as if she were in a total daze. We were told there would be a wait, though an approximate time was not given, so we decided to saddle up to the bar outside which was filthy with wet coasters and squeezed lime wedges and trash littered all over the floor. When we were finally texted that our table was ready, at 4:50pm, we were sat outside at a table with a dirty ashtray. We placed our order and waited for another 30 minutes for a two salads and bread (served with "butter", which was really an oily margarine with herbs). Only one salad made it to the table, and the fried pickles were brought 10 minutes before my salad was served with nervous laughter by our waitress. The manager did come to our table to apologize for our waiting, so I politely requested a free beer for our trouble, which was denied. I work at a brewery and give free draft beer if someone has to wait more than 5 minutes! So, she offered a cheesecake instead, which we thanked her for (and which costs their business more than a free draft pour, but I digress). Another 25 minutes pass, which places us at 5:45pm, over 1.5 hours past our arrival. The food finally comes to the table. I placed two orders for hushpuppies, but only one order made it to the table. They were not very good at all. My aunt ordered shrimp with cocktail sauce, but it wasn't cocktail sauce. It was salsa! The waitress explained to us that seating had recently been expanded, but the kitchen staff had not, which was more than obvious. In the end, our food was comped 100%, but the poor experience really ruined our appetite, so we didn't finish our food. While we did have some beers and a cocktail, at no point were we offered water, and the free cheesecake the polite yet condescending manager offered never made it to the table. They didn't have the good sense to tell folks at the door that the wait time was closer to an hour, completely overwhelming themselves instead of taking care of the large parties that were already dining. Gators aren't the only thing to beware of at Cherry Pocket!

    Photos
    The place
    The place
    Table bread is a solid plus!
    Table bread is a solid plus!
    Patio seating

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    Patio seating

    Jessie's Lounge - divebars - Updated July 2026

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