Austyn Ryli · Dining · Winter Park, FL
My Birthday Dinner at Fleming’s
Fleming’s Prime Steakhouse · Winter Park
Okay so I need to talk about my birthday dinner because it genuinely might be one of the best meals I’ve ever had. My fam and I went to Fleming’s Prime Steakhouse in Winter Park and — I don’t even know where to start. Everything was just perfect.
We went on a Tuesday, which is actually strategic because Fleming’s does Tomahawk Tuesday. If you haven’t heard of it, keep reading, because you need this information in your life immediately.
Walking In
First of all — the ambiance. Fleming’s has this really gorgeous warm lighting that makes the whole place feel intimate and special without being too formal or stuffy. It’s the kind of restaurant where you feel like you’re genuinely treating yourself, but you can still relax and actually enjoy the night. Perfect birthday energy, honestly.
I wore a white top and brown linen pants, both from Aritzia, with my Steve Madden wedge sneakers. Cute, elevated, but still comfortable enough to enjoy a full dinner without thinking about it once. You know the assignment.
Shop what I wore to dinner ♥
The Food (Oh My Gosh)
Okay this is the part I’ve been waiting to get to. My brother and I did not hold back. Here’s everything we got:
The Tomahawk Steak — Tomahawk Tuesday Special
THE moment of the whole night. We split one between us and it was absolutely the right call. When this thing came out I genuinely almost lost it — it’s that impressive. Perfectly cooked, stunning presentation, and honestly one of the best steaks I’ve ever eaten. Tomahawk Tuesday is real and it is a gift.
Calamari
Really solid starter — crispy, not greasy, the perfect light way to kick things off before the main event.
Caesar Salad
Simple but really well executed. Exactly what a Caesar should be.
Fleming’s Potatoes
Okay these are everything. Crispy, cheesy, so good. Don’t come to Fleming’s without ordering these — I’m not joking.
Mashed Potatoes
Buttery, smooth, perfect alongside the Tomahawk. We got two potato sides and I stand by that completely.
Non-Alcoholic Champagne
We toasted with this and it felt so fun and celebratory. You don’t need alcohol to feel fancy — this was such a cute touch for a birthday.
Chocolate Lava Cakes
The grand finale. Warm, gooey, rich — honestly could’ve been their own event. The perfect way to end a birthday dinner.
More Than Just a Meal
I have to talk about how special the whole night felt beyond just the food. It was one of those moments where you just think, okay, this is exactly how a birthday is supposed to feel.
The service was so attentive and genuinely warm the whole night. You could tell everyone there actually wanted you to have a great time. That kind of hospitality makes such a difference when you’re celebrating something.
If You Go
A few things I’d tell anyone planning a trip to Fleming’s:
- Go on a Tuesday for Tomahawk Tuesday — it’s a whole moment and you need to experience it.
- Split the Tomahawk with someone — it’s huge so I recommend splitting it.
- The Fleming’s Potatoes are non-negotiable. Just trust me.
- Save room for the lava cake. Please. You will regret it if you don’t.
- Make a reservation ahead of time, especially for a special occasion.
- The non-alcoholic champagne is such a fun option — you still get the full celebratory feel.
Whether it’s a birthday, an anniversary, or honestly just a Tuesday you want to make special — Fleming’s in Winter Park is the move. And with Tomahawk Tuesday, you get a luxury steakhouse experience that is absolutely worth it. 10/10, no notes, already thinking about when I’m going back.
Reserve at Fleming’s See More
What do you think? Share your thoughts below — I’d love to hear from you!