Fleming’s Prime Steakhouse & Wine Bar — Restaurant in Winter Park

Update: Christmas Eve at Flemings, WP was simply fantastic. There was only two of us, and they wanted to seat us in the back room, in between large group tables, so we weren't agreeable to that. (Sorry..) We were reseated promptly, so that's great. Our server, Diana, was absolutely perfect. The quickness of drinks, taking our whole order at one time always turns bad for us, but not here. The courses were perfectly timed. We visited with the best, most gracious manager, Grace, who we've met multiple times. She is a total asset to the restaurant. She is one of the reasons this is our favorite place. We had the Oysters Rockefeller, and we were gifted the shrimp cocktail. Both were delicious, especially the shrimp cocktail. Four large prawns with cocktail sauce with extra horseradish. We then split the best caesar salad in town, with heavy anchovie paste. I had the eight ounce filet with a twelve ounce lobster tail. Tom had the ribeye with Diablo Shrimp on top. Add a side of mashed potatoes. Carrot cake for home to round out the meal. Really, Diana and Grace made our night, and a special shout out to the lady who assisted at out table whose name we didn't get. She stayed on top of our glasses, water, and plates. Thank you Fleming's, for making our Christmas Eve special.

Went to Fleming's last night for Easter dinner. We had never been there before, despite dining at all the other upscale places around. Well, I suppose somewhere would be the last. But it's true what they say about saving the best for last. What set this visit apart, wasn't so much the food, which was perfectly delicious, it was definitely the experience and the service we received. Andrew was our server, and Jennifer was his wonderful assistant. We had such a great time. We were never rushed, and were given perfect, thoughtful, personable service from both of them. Truly great service here, from the valets, the hostess, servers and from the manager Grace who truly lived up to her name. She came to talk to us when we were finished to see how everything was, and we ended up talking for a bit. She then brought us over two glasses of champagne with a box of truffled chocolates. What a gracious ending on a perfect night. For the food, they first bring out fresh, warm sourdough bread with two different flavored butters. This was so good. We then moved on to our appetizer of beef carpaccio. This was incredibly good and we'd order this again, for sure. We then each had a Caesar salad, which was the best Caesar I've ever had. The crispy prosciutto and capers gave it a big taste nudge, and the dressing was very heavy on the anchovy paste, which I loved. I got the filet and lobster and my husband got the huge pork chop, and we shared a side of the brussel sprouts. All was great and as expected. Overall, this was one of nicest dinners we've had since covid. We will absolutely go back. I can't recommend it more than I do. It's very pricey, but worth it. I just wish we could afford to eat...

We chose Fleming's for the first time primarily because my mother-in-law wanted great steak, and I was treating her and my wife for Mother's Day. We expected it to be very busy and were pleasantly surprised to get seated in the bar area immediately upon request.

What went wrong:

The restaurant was either severely understaffed or they took on way more reservations than they could handle for the staff and kitchen.

Service was rather slow at times. Our entrees took close to an hour to come out, and my mother-in-law's 16 oz. New York Strip was grossly undercooked; it was medium rare, and she asked for medium well. The server brought it back, and it still came out undercooked again.

They forgot to bring the caviar that complements my wife's lobster tail on top of her sea bass. Then, after the food runner said he'd go get it, he just forgot and never returned. My wife had to wait for the server to bring it instead so she could take pictures of her food.

They didn't bring enough bread plates or app plates for three people; only brought two.

The lights and A/C went out multiple times and no explanation was given. My wife and her mother started sweating because of it as did many other women in the bar area.

Several flies made their way into the bar area from the front door lobby which was quite disgusting and obnoxious. Lots of guests were complaining about it. And the waiter said there's nothing they could do about it because they had to keep the front doors open. That's not an acceptable strategy. Need to figure out that problem. Cannot have flies hovering over your food at a 5-star restaurant.

What went right:

The server was very kind and pleasant, however, we were laughing because he must've apologized a thousand times for various gaffes.

Our food, including the bread, calamari, salads, steaks(mother-in-law's notwithstanding), fish, and NY cheesecake were all delicious.

We were seated immediately and comfortably.

The waiter explained dishes and recommended some good items and drinks.

The waiter ended up giving us the two salads, a coke, a cocktail, and dessert for free for all of the troubles during our experience. He was a very friendly, nice guy which is why I still tipped him very well.

Overall, we expected a more seamless, quality experience, especially on Mother's Day. Have to deliver a better experience for the amount of money you pay to eat there. We'll try again and I hope it will be better when it's...

We arrived early and sat on a mini booth that really was not ideal for a date night but it was not as big a deal with what was to come yet. Our server arrived and got our drink orders but forgot the lemon in the tea, attention to detail at a Flemings is expected. We received our salad and soup that were good so we thought well things are turning positively. Well till the food arrived. I needed the steak knife and it was the Chilean Bass which is supposed to flake with a fork. My dates pork chop was so hard jus cutting it was a task but he managed and thought it was cause it was so thick till he bit into it and it was so hard. We are looking around for our servant cannot find him and then we spot him. They take that pork chop back and then I also say to him about the Chi, but I said it’s not terrible so I don’t wanna make a big deal of it. They’ve been bringing the pork chop back and it was so salty, but it was like the head just taken a whole bottle of salt and it just dumped it on top of it. Now my date is VERY upset. They ask if they can make him something else or if you want something to take home at this point he just wants to get out of there. A manager a different one from the first time comes around and says they’re very sorry but we’re gonna take care of the bill. We then see the server and we say to him I’m sure we have to pay for the drinks which we’re happy to do. He says no no but this is what the bill was if you’d like to tip me and if you don’t have cash, I can put it on a credit card we were dismayed at this point. He cared more about his tip than what our experience had been, and I thought that to be very, very out of place at a five star restaurant. Maybe if he had come to the table with the right tea and lemon and maybe if he’d come back once our food had been set down by yet another server and checked on us to see if our food had been good I would’ve said well fantastic really it’s not really the service problem. It’s the kitchen however he hadn’t done any of those, but did Still expect a tip Of course to say the least, this is not what we expected out of a night out on the town going out in Winter Park to a lovely restaurant, hoping to have a really good date night and came away from that very very, very disappointed We enjoy going out for a meal in fact, I think that Eddies and Hillstone are places we’ve had a...