Quick Take:
Location: Winter Haven
What Mike Ordered: Cheese slice and Bee-Gees Knees Sicilian Style (pepperoni, basil, herbed ricotta, hot honey drizzle)
What Katie Ordered: Cheese slice and Tie Die (
Mozzarella Base, red sauce, pesto cream, basil, Parmesan) Sicilian style
Gluten Free Options: Yes (10” Cauliflower Crust)
Vegetarian Options: Yes
Final Score: 4.75/5
Price: ~$10–20 per person
For our twenty first stop on our Polk Food Quest, we are back for more pizza at Upper Crust Pizza in Winter Haven.
Upper Crust came in at number four among The Best Pizza In Polk County, and number three on the list of The Best Pizza In Winter Haven.
If you've been reading our reviews and articles for a while you'll know already that we prefer New York style pizza, but we're pizza people in general, so we still love to grab some wood fire and thin slice here and there as well.
But, if you ask Katie and I, it's our number one for Winter Haven.
We like to say we're a bit picky when it comes to pizza, being from New York and New Jersey — and always tell the story about how our marriage consists of competing for who grew up with the best pizza and bagels. 
By the way: if you're new here, the concept of my Polk Food Quest is simple: every week I try a local spot, order the most common thing people get, try a few extras, and rank it on taste, value, vibes, and overall.
This week: a cheese pizza!
Which means I ordered a cheese pizza and "Bee-Gees Knees" Sicilian slice and Katie ordered a cheese pizza and tie-die Sicilian.
How Does This Work?
I order the standard item for that category (for Upper Crust that means a cheese pizza), plus a few extras so I can get a full feel for the menu.
Then I rank the experience on four things:
Taste | Value | Vibes | 
Overall
Taste focuses on the standard item.
The rest reflects the entire experience.
Taste: 4.5/5
If this was just a taste ranking compared to all of Winter Haven pizza that we've had so far, I'd be giving it a 5/5.
BUT, while it's my favorite in Winter Haven, it's not my top choice in all of Polk County, so I'm giving it a SOLID 4.5/5.
This is definitely somewhere I'd bring my family visiting from New York or New Jersey, but I'd still likely remind them that we're in Florida and not to expect what they're used to!
Here's a quick breakdown for my quick scanners, though:
- Cheese Pizza: Great slices. Order by the slice. Each time we've been there the plain cheese slice has been great. Solid and reliable.
- Bee-Gees Knees: Their Sicilian slices are REALLY good, and I'd definitely recommend giving this one a shot if hot honey drizzle sounds good. This one consists of pepperoni, basil, herbed ricotta, and hot honey drizzle — and it came together perfectly.
- Tie-Die: This one also came Sicilian and Katie was very impressed. She usually grabs a tie-die slice if it's available, and this consisted of mozzarella Base, red sauce, pesto cream, basil and parmesan cheese.
Every slice was awesome.
The only reason I'm taking half a point off is because while it is always reliable and always great pizza, it's not blow you out of the water pizza.
Vibes: 5/5
The Vibes at Upper Crust Pizza deserve a 5/5.
They're right outside the heart of Winter Haven, with an easy walk into the main strip and only a block from the library and Lake Silver, which make the location nearly perfect.
Their branding is fun and quirky.
The hospitality is always great.
And the location itself is great, with nice outdoor seating.
We can't complain about anything about the vibes.
The Lean Squeeze
The lowest-calorie, highest-protein, most satiating picks on the menu — chosen by Mike, who spent a decade in the fitness industry before The Polk Squeeze.
Mike's Pick: Plain Cheese Slice
It's not going to win any awards for being the "healthiest" thing on the menu, but let's be honest, you're at a pizza shop. A single cheese slice comes in around 280-300 calories, and it's by far the most reasonable way to satisfy a pizza craving without derailing the whole day.
Alternative Picks: Side Caesar Salad
If you want something on the lighter side, ask for the dressing on the side to keep it in check.
Mike's Note: If I'm being strict, I'll do one cheese slice and call it a meal instead of grabbing two or three. Pair it with the Side Caesar if I want some volume without piling on calories. It's not a "diet" order, it's just the smart way to still get pizza.
Value: 5/5
Coming in with a 4.5/5 for taste and a 5/5 for vibes, Upper Crust Pizza also deservers a 5/5 for value.
When it comes to a pizza joint I prefer being able to go in and order by-the-slice, so that is another bonus and factors into the value for me.
Katie and I got 2 slices each and a soda and it cost around $25, which you can't beat, especially considering two of the slices were specialty Sicilian slices that had me leaving full, and Katie almost unable to finish!
Tack that on to the fun branding, great location, and good hospitality, and there's no deduction here on value.
Overall: 4.75/5
With almost a perfect 5/5, Upper Crust Pizza is one of Winter Haven's best pizza joints.
If you're in the mood for a NY-Style slice of pizza, they're reliable and their plain cheese slices are awesome.
And, if you like adventuring out a bit, their speciality slices keep us coming back to try something new each time as well.
They get a solid 4.75/5 and our recommendation.
Would I bring my visiting family there?
Definitely.
They'll be coming from either New York or New Jersey, so I'd warn them to lower their standards from what they're used to — but I know they'd be pleasantly surprised compared to what they think of Florida pizza!
Here’s how I’d sum up Upper Crust Pizza:
Upper Crust earns its spot on the lists for the Best Pizza in Polk County (and Winter Haven), and after this visit, it's easy to see why.
The cheese slice is exactly what you want from a New York-style pie: reliable, solid, and satisfying every time. But the Sicilian slices are where they really show off.
The Bee-Gees Knees and the Tie-Die both landed as genuine standouts, the kind of specialty slice that makes you want to come back and try another next time.
You also get a great bang for your buck and are able to order by-the-slice.
Two specialty Sicilian slices, two regular slices, and a soda for $25 is hard to beat anywhere in Polk County, let alone right outside the heart of Winter Haven.
The vibes match the food. Fun branding, great hospitality, and outdoor seating near Lake Silver make it an easy hang, not just a quick bite.
With a 4.75/5 overall, Upper Crust is about as close to a complete package as you'll find in Winter Haven pizza.
Before You Go....
Hey!
I want to know what you think of Upper Crust Pizza in Winter Haven.
Leave a comment below.
The more you share, the better, but anything is appreciated.
Each comment helps The Best Of Polk articles and eventually, the yearly awards!
Have a place you want me to try?
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