Interior bar.
a plate of food on a table
Outside seating
Tiki, outside seating, cornhole
Homemade hush puppies.
a glass of limeade on a table
a boom boom shrimp
View dining outside!
menu
Jalapeño Margarita
Tiki bar
Boom Boom Shrimp, tastes like Buffalo pretty spi y but delicious and big!
Great view
Sunset view
Plenty of parking
Water view
Lots of drinks to choose from
Outside
Open for business!
food
Laurie R.
Feb 18, 2025
When we have guest in town our first stop is always Jack Willie's. The outdoor seating is fun and alway friendly staff and helpful about menu. The seafood is great here and large portions. The prices are also very good. Really feel like you're in Florida with laid back water front views. I have had many items on the menu and it's always consistent and fresh.
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Adrizn V.
Nov 1, 2024
Fun tiki bar dive bar. On a quiet water inlet. Cheap beer, ok food, fun ambiance. Shannon our server was spot on. Go for the wings. Excellent. For a tiki bar hush puppies killed it Sorry, to say but today I was picking 1" spines from my Mahi, which was dry. Friends burger was good but a little overcooked But again a fun on the water dive bar.
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Stephanie G.
Aug 20, 2024
A very casual, divey place. It's on the water, which is nice, but the live music did make it a little hard to socialize. I didn't see any games except a ring toss, but the way it was positioned, the rope with the ring kept hitting the wall behind the pole, so I don't believe the toss is solvable.There was a sign off to the side that mentioned gator bites, but they didn't have any when we went (was more of a door prop than an advertisement). We did a split appetizer share with garden salads, fried calamari, boom boom shrimp, and fried scallops. While it may have been a mistake on our part to have so much fried food, they were all good and hearty portions and great for sharing. The food was reasonably priced, so if you stay inside or are coming for the music instead, it can be a nice place to meet up with friends.
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Brian H.
Jul 3, 2024
The wait staff is not friendly, and we asked a bar tender for some Togo boxes and he said "that's not my job". It was just extremely rude. Gratuity was added to parties of 6 or more. Which isn't unheard of, just wanted to let you know. The food was just okay, I got the fish tacos, and it was caked in so much coleslaw that the fish was almost nonexistent, the fish was there but it just tasted like coleslaw. The crab fries was okay, the cheese was too melted that it was hard, and some of the table had a sauce drizzled on it and some didn't, so not sure what that was all about. We did get the seafood stuffed mushrooms, and the filling tasted frozen, not fresh. Over all I was just disappointed with the food. I wouldn't go back the next time I am visiting Florida. It was a neat atmosphere, it was a rustic tiki bar feel, we asked to sit inside. There's not a lot of setting inside, way more outside.
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Kasy S.
Apr 13, 2024
I had a great time with some coworkers, but this joint has some warts.... Just to get it out of the way, it's on the water, so of course there are mosquitos. I didn't dock points, that's to be expected.Our server was friendly but the poor guy was not set up for success. When we were there, the inside beer taps were broken, so the only choices were the few beers that were on tap in the outside bar. The beer coming out of those taps could definitely have been colder. They also didn't have a bartender, so our server had to run to the outside bar to fill beer orders, then run to the inside bar to make the cocktails. He also was the one assembling the salads. All in all, he did a good job with an 8-top, butHe had to work way harder than he should have to take care of us.The fried appetizers were just okay, though the fried shrimp were large and delicious, probably the best thing I had all night. I had the grilled grouper and a side Caesar salad. The lettuce in the salad was kinda gnarly, several pieces had begun to get slimy. The fish was a bit undercooked and under seasoned. Maybe if the back of house gets straightened out and all, I would give it another try on a future business trip.
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Wendy W.
Feb 9, 2024
We met some people from out of town there , and I didn't realize how far out it was. But we'll be worth the drive . The shrimp tacos were the beat I have ever had. My husband got the stuffed shrimp, which was good, not great. Service was excellent. I would like to stop again.
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Barry S.
Jan 20, 2024
It has been maybe 15 YEARS since we've eaten at Jack Willie's and I can't understand why. We would eat here all the time and then when it changed hands I think we lost interest... until today. We were with a large group of friends who had seen it driving into the city and asked about trying it for lunch. We did, and I'm sooo glad! They immediately made space for our large party in the back room, and our drinks and food came out so quickly. Our group ordered scallops, soups, salad, kids chicken fingers, a club sandwich, a Philly, a BLT, a couple orders of fried clam strips, and I had the French Dip. EVERYONE was impressed with the quality of the food! Even the French fries were (in the words of my 10 year old grandson) "pretty much perfect" -- thick and crispy with no grease. The au jus for my sandwich was savory and not overly salty, the roll was fresh with a slight toast, and the meat and mushrooms were more than enough.The wait staff were really attentive, and we didn't have to ask for anything as they kept drinks full and kept making sure we were taken care of. We also have a large group of guys that meet for breakfast each month, and at lunch we decided to move breakfast to lunch at JW's from now on!We will be back -- I love that it's yet another great place to eat here in Oldsmar!!!(I can't believe I didn't take pics!!!)
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Mason S.
May 23, 2024
Always the best service and atmosphere at the bar! Beautiful waterfront views and great food for an amazing value!
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James T.
Aug 16, 2024
Terrible experience here for a lunch. The place itself is a run down shack on an inlet on the water. You would think it would be nicer being on the water, but it's a dump. Limited seating inside the barely conditioned bar area. There is a slightly larger outside area that's too hot to sit during the day. Our server was high or on something, wasn't completely there and fumbled throughout the service. That wasn't even the worst part, the food! I got the blackened Mahi with fries and broccoli and the fish came out charred and tasted spoiled. Didn't get any of my sides and neither did some of the others that were in our party. We got waters to drink, were asked about regular drinks, ordered them and they never came throughout the entire meal. We didn't bother to ask, just wanted to get out of here as fast as possible. We had a party of 8 so they added their own tip to the bill, otherwise it would have been $0.
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Dave P.
Feb 15, 2025
Food is excellent, service was first class, and outside seating very pleasant The sweet potato fries are the best
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