Matthew Garrepy
Google
If there’s a foodie hill to die on, this is it. Hillstone NEVER disappoints me. This is our go-to standard for (almost) every birthday, anniversary, college basketball team win, or even the successful completion of a load of laundry. This is our place - and for good reason.
When other restaurants think about service, Hillstone is the gold standard they aspire to. Every dimension has been thought of. They run their staff like a well-oiled machine, and you’re never without a freshly chilled glass for your dirty martini.
By the way, they have the BEST dirty in town—olives stuffed to the hilt with blue cheese and just the right amount of ice crystals buoyed by the surface tension.
The bar is the heart of this place, and if you can score a seat, you can have dinner and a lively conversation with the bartenders. It makes for a fantastic Saturday afternoon.
The food. My god… where to start? The keyword is consistency. Every time we go, it’s always top-notch. I’ve never had to send back the Hawaiian Ribeye due to the cook being off. It’s always a slam-dunk. We also love the Grouper sandwich, which is only available at lunch on certain days but totally worth the trip.
The burger is insane. Juicy. Sumptuous. And the fries? Dip them in the seasoned mayo and sprinkle on their signature seasoning. Pure Heaven.
Desserts are inspired. They have this concoction served with ice cream, and you pour on warm chocolate sauce and watch your eyesight blur as your brain goes numb. It's insane.
If you’re up for a big night out, add a glass (or bottle) of The Prisoner. They have an exceptional wine list and some knowledgeable staff who can guide your choices.
Parking is tight, so plan to valet. Dress decently - it’s a warm, charming, upscale atmosphere. Even though they don’t enforce a dress code like they used to, I always make an effort to button up.
It's possible to get a seat at the bar, but it's always tight. As far as the dining room goes, I recommend a reservation. Showing up with a party of two has a good shot at getting something when it's busy, but plan to wait. Parties over four aren't a thing, although they've let me sneak a fifth in before. But don't count on it.
In terms of prices, it’s actually quite reasonable. That said, you can easily run up a major bill with a few cocktails, but that’s a risk almost anywhere these days.
Finally… the outdoor patio and lakefront area. This is the pièce de résistance. At sunset, when the weather’s right, grab a libation at the bar and steal an Adirondack chair for the ensuing light show. You’ll be treated to epic views of Lake Kilarney, and maybe catch an amphibious prop plane pulling up to the dock for a dinner reservation. It's a golden hour that can't be topped.
Hillstone is magical. I even hesitate to leave this review for fear of interrupting my access to greatness. But anyone who’s anyone in Winter Park will tell you that this is the place. So go.