Jack Willie’s Bar

Fun atmosphere with outdoor seating and bar. Quick, pleasant service, and delicious grouper sandwich. Great find!

It was a rainy weekday night so the place was not that busy. Atmosphere was fun and relaxing, ate at the bar and the bartender was extremely nice and fun to talk to. The food was very generous. Calamari was ok not too much flavor but something different than the normal appetizers. The oyster po boy was pretty good. Way to big to hold except in smaller cuts. Oysters themselves tasted pretty good. For a $ 1 more I went with the sweet potato fries with honey and cinnamon. Sounded odd, but very good taste especially with a good IPA. Overall the bartender gave it a 4 star. On just food I would rate a 3, but who doesn’t like a tiki bar?

It is time to upgrade this local bar to a 4 star status despite the occasional presences of heavy smokers and nonsensical drunks at the outdoor Tiki bar. After all, like most of the local folks in Oldsmar, I go to Jack Willie’s for its quality food and relaxing water front atmosphere.
I doubt I will ever complain about the food here. Jack Willie does seafood right. The freshness, flavor and portion aligned to the best that please a picky eater like me. I even liked their onion rings. A large cut of sweet onion coated with a light batter fried to perfect golden color, then serve sizzling hot to satisfy my crave for decently local cooking. Forgive my finger licking eating manner just in case you see me chewing down Willie’s food. I can’t help.
There are many decent restaurants around Oldsmar offer sophisticate atmosphere for folks after a long working day. For that matter, Willie is probably an outcast where pretentious is not required. What matters is simply how much you enjoy your food.

Love this place, come here all the time… Just wanted to brag on Elizabeth our bartender… We had her awesome bloody marys on news year day, for a little hair of the dog… I have to say they were spot on… Thanks girl for a great afternoon once again.

I always try to make it Jack Willie’s when I’m in Tampa. We go for lunch… Sit at the Tiki hut bar, doesn’t get much better than this.
Their fried grouper sandwich is a must!!!
Lori the bartender knows everyone who walks in. Great service… thanks Lori!
We’ll be back again

A fun place with a great outside bar/​patio.
Staff are not super friendly to new comers as this seems to be more of a regulars type of place but they’re nice enough. The food is your basic Florida menu, fish spread, friend clams and calamari, fish sandwiches and pricy entrees. I’d say the food is okay but the point of going here is the fun loving vibe and drinks. There’s been live music or karaōke every time I’ve gone which for me is awesome. Everyone there seems to be enjoying themselves (customers that is). I’ve never dined inside so this review is exclusively regarding the bar and outside area. The bartenders could be a bit friendlier, offer suggestions, introduce themselves, smile, let you know the specials… etc but it is a cool place none-​the-​less.

Loved this place. Only had drinks and a piece of fabulous key lime pie, which looked and tasted homemade. Which we had been hungry, from what we saw going to other tables the food looked great.
Would recommend stopping here for a little local restaurant and bar.

Solid waterfront bar in Oldsmar. I remember being taken here as a kid and ordering the grouper sandwich, now I’m coming during happy hour… and getting a grouper sandwich.
sweet potato fries are delish

Very disappointing, don’t get the seafood and don’t use the bathrooms they are nasty! My husband and I went here last Friday nite. When we arrived the patio was full and we were told there would be a 30 minute wait. We opted to eat inside as there was a table where we could still see and hear the band. Our waitress came by to take our order, we asked about any drink specials. We were told they are $ 2 beers, wells, margaritas and rum runners. We ordered two rum runners. We opted to try the appetizers instead of getting two meals, we had never been there before and thought we could try a few things. My husband ordered the crab cakes and bacon, cheddar fries. I ordered a ½ dozen raw and ½ dozen steamed oysters on the half shell and the fresh cut onion rings. My oysters came out all steamed and on a bed of ice. I told the server that was not what I ordered and she took it back. The server, the cook and someone else stood there and looked at them for a while. A while later the oysters came back out the way I had ordered the except the steamed ones were ice cold. All the oysters were served on the half shell but each oyster was in several pieces (I’m assuming they didn’t know how to shuck them). I decided not to send them back. My husbands items came out as well. We ordered two more rum runners. I decided to order a small basket of scallops to share. They came out. All the seafood items were marginal. We decided to order one more drink and enjoy the band for a while. Then when our check came the total was $ 85 dollars. I was shocked to see that much and asked our server. She said the rum runners were $ 6 each. I asked her about the specials she told us about earlier and her response was she said $ 2 beers and wells and they have margaritas and rum runners. Well that’s not what we heard over the band and crowd. For the $ 100 we spent for everything including her tip we could have had a really nice meal else where. Then to top it off both my husband and I had stomach problems for the rest of the nite. We will never return and if we do it will be burgers and beer. Very disappointing, don’t get the seafood and don’t use the bathrooms they are nasty!

I stopped by with a group of friends, and I am glad I did. The restaurant is a casual waterfront café in the true style of a tiki bar/​restaurant. The special tonight was a nice size ribeye with fries and salad for 11.99. Can’t beat that! For those of us that ordered steak, it was very good and was cooked to perfection. The fries were delicious and crunchy. The portion was so large that we took most of the fries home. Others ordered a sea scallop basket, and a grouper finger basket, both considered appetizers, but it was an ample enough portion for a light meal. Another member had a Grouper Reuben sandwich. All meals tasted great! I will definitely go back because Jack Willie’s has a menu that is chock full of appetizers, entrees sandwiches and salads that I want to try.

Go for the atmosphere and people watching, it’s a great mix. The food is very good, you can’t beat their burgers or shrimp tacos and they usually have a band playing. Yes, it can get loud but if you want quiet you can stay at home. Go to Jack Willies to have some fun!

We found this place on Unilocal!
Older reviews were terrible, but later ones were good. So we tried it, for lunch. Good surprise!
Now we go every couple of weeks, for lunch.
Service is very good, but they cook to order, so not fast food. Usually, fried clams and onion rings are too hot to eat.
Lived in key west for 15 years, and it reminds us of Alabama jacks and hog fish grill.

When you say locals only know about the place, sometimes it’s true and sometimes it isn’t. This is one of those times where it is. Nobody pops by because they see the advertising (there isn’t any). Nobody sees it while driving by on a busy street. Word of mouth doesn’t work either since most are too drunk to remember any specific details.
However, if you’d like a tasty lunch or a drink or four in a nice outside tiki bar, I would recommend it. Just bring a designated driver and you are good to go!

Pleasantly surprised at how cute this restaurant is on the inside and great outdoor patio area too! I have driven by so many times and thought the exterior and parking lot area did not look appealing and so glad we finally went.
Good variety of food offerings — burgers, sandwiches, seafood. Ordered a cheese steak n’ fries — cheese steak was good although much preferred the BF’s Reuben that he shared with me. Waitress was great.
Will be back!

Haven’t been since the renovation and I must say the place looks great. Awesome atmosphere, polite staff, and usually great eats. But our food two weeks ago was sub-​par at best. We started with the fish spread and couldn’t eat much due to the large clumps of cream cheese and the extreme lack of fish taste. Without asking, the waitress took the fish spread off our tab which we were very grateful for. I had the fish and chips and my date had a burger. The burger was ok and so were our fries… But the fried fish was really bad. Tasteless, over battered, and again no fish taste what so ever. Took more than half home and immediately threw it away. I’ve never had any bad food experiences so this was quite a let down. If we do return, I won’t ever order that again.

For the price and it’s close proximity to home, this is a great place.
We arrived around 830 on a Saturday night and sat outside. It was busy but not packed. You could definitely find a table or a seat at the bar. The crowd was interesting. It’s definitely an older, biker, sort of rough around the edges type of crowd. But it was good-​definitely not pretentious and some good people watching.
Our server was slow to greet us or take our drink order, but once she came around she was pretty good.
We ordered the crab stuffed fries mushrooms and they were awesome. For dinner we both ordered the blackened mahi sandwich. Mine with fries, the hubs with a side salad. The sandwich was wonderful. It was served on a toasted sesame seed bun and the fries were nice and crispy. The sandwich had crisp lettuce and juicy red tomatoes on the side.
We ordered an ice tea and a bud light.
For $ 30, this was a great deal and one we will be repeating again.

Love this place, they have good food and cold cheap beer BUT the service is usually on the slow side and could definitely use improvement!
Highly recommend the smoked fish spread, gator nuggets and burgers!

Thankfully Jack Willie’s Original Tiki Bar & Grill is under new management, as the previous ownership had run this place into the ground — netting it several Health Department and «Dirty Dining» citations.
But all of that has changed, and Jack Willie’s is back to being an excellent place to hang out on the northern end of Old Tampa Bay. The restaurant and famous tiki bar sit right against the bay, and you can watch the sunset along with the sandpipers, the cranes, the tarpon, and other critters while you enjoy something to eat or have a frosty cold beverage outside under the thatched roof tiki hut. You’ll find Jack Willie’s right near the intersection of Tampa Road and St. Petersburg Drive in Oldsmar.
If my memory serves me correctly, Jack Willie’s was originally started by a couple of guys from the New York Yankees baseball team as their take on an old Florida fish house /​tiki bar. The back room of the restaurant is filled with autographed photos, bats, baseballs and other Yankees memorabilia.
For years this had been a spot to order their crab cakes, grilled grouper sandwiches, or sushi-​grade tuna served over a big bowls of greens with an Asian-​inspired sesame dressing. And I am really glad to say that the kitchen is back to cranking out some mighty tasty (and thankfully, Health Department-​approved) meals.
The menu is full of seafood prepared as you like it, along with soups, salads, appetizers, burgers, wraps, sandwiches, and full entrees including steaks and chicken.
Jack Willie’s is a great place to visit on the weekends when you can sit outside, under the thatched roof of the tiki hut, and enjoy your favorite drink. On the weekends and in the evenings there is a small house band that plays a lot of classic rock mixed with Jimmy Buffet beach songs. Kind of a funky mix, but it’s popular with the locals.
Don’t be surprised if the parking lot is filled with motorcycles as Jack Willie’s is a popular gathering spot for people on their long weekend rides.
We were there on a Saturday evening after a very filling meal elsewhere, so we found an open table outside and listened to the music while enjoying a few drinks. Later in the evening we split an order of blackened grouper bites, and toasted the fact that Jack Willie’s is back in action!

I wasn’t sure what to expect with the new ownership taking over and practically razing the interior of an old favorite spot, but I think we’re gonna be ok. We’ve lost the pool table, but we’ve got dollar beer. We’ve lost some regulars after the initial closing, but we’ve got flame-​licked burgers. The trade-​offs at this place are alright with me. On every other Thursday they offer bike-​night Jack burgers for 5 buckaroos which pretty much outshine most burgers in the area by simply arranging really fresh ingredients with spot on cooking technique. Still like the place, hope it holds up!

Just went back to try the food since the new management took over, and it was excellent. Grouper sammich was way better than the one offer by the previous owners. The filet was a nice size and pleasantly thick. I love me some grouper sammiches, but I think the story to write about here was the burger my chica got. Damn if that thing was flame grilled to tasty perfection. It’s just hard to find a freaking burger grilled over an open flame these days after the fall of BGR. Honestly, I cannot see going back to Jack Willie’s and ordering anything but this burger!