I’ve been coming to Kissimmee since I was a very little girl. My parents, who honeymooned at nearby Clearwater when Walt Disney World was still being built, made WDW our first grand family adventure… back in the time where tickets per ride was the name of the game, not a daily pass.
For years, many people only knew Kissimmee as the jumping-off point for Walt Disney World.
The city, with a population approaching 80,000 in 2020, lies along the northwest shore of Lake Tohopekaliga, called “Lake Toho” by the locals.
What started as swamp adjacent, a horse town, then Disney World, then Sea World and Universal Orlando, Kissimmee remains very much a small town in the historic district, where they’re proud of their very own restaurant row. Thirty-two restaurants, all independent or family-owned, according to the downtown Kissimmee Visitor Center, reside along this row. Not a single chain in the area.
The specific feel to the neighborhoods is still recognized by “old-timers,” away from the creeping sprawl that retains the Kissimmee mailing address, and many things to see in addition to the wonderful worlds of Walt Disney and Harry Potter.
Outside historic downtown, you can feel right at home with many of your local restaurant chains. BJs, Charley’s Steakhouse, Carrabba’s, Chilis, Checkers, Red Lobster, LongHorn Steakhouse, Olive Garden, Panera, and TGI Fridays. You get the idea. But if you want to have something different than home – or in just a few other locations across the country, you might like to check these Kissimmee restaurants out.
The 7 Best Kissimmee Restaurants
The Italian Pizzorante Joint
215 Broadway // +14074837031
A chef favorite, entering this Italian pizzeria is like walking in to see an old friend. Cases filled with fresh bread lay to your left, in front of the pizza oven. And pizza is the name of the day for me this day. They have gluten-free options.
The Margherita does not disappoint. You can taste fresh tomatoes in the San Marzano tomato sauce. The mozzarella is perfectly dappled across the crust and the fresh basil is neither salted nor grilled but truly fresh. Utterly delicious!
You can create your own pizza or choose one with another descriptive name. They offer the Verdura, the Formaggio, the Alba, the Goat, the Carne, the Double Jointed (pepperoni and more pepperoni), the Calzone, the Stromboli, or the Create Your Own option and even specialty Argentinian pizzas.
If you’re in the mood for great Italian food that is not pizza, my server recommends their Garlic Bombs as a start, Crunchy Calamari for my foodie, and “Grandma’s Goodness: Pasta on Sunday the way you remember.” Looks like I’ve already got my next meal picked out.
Unless the Chef’s Special wins out. Right now it’s “Da Vinci Chicken.” Chicken stir-fry with hints of northern Italian wines, braised peppers, and mushrooms served with penne rigatti. It looks delicious. One of the other customers said she loves it … we all ate out, take away, so couldn’t find it.
Hand-crafted sandwich options include colorful names like “The Gobbler” (turkey), or “The Chooch Burger” (Angus Beef and Pork Belly), “The Hot Gardener” (veggie), or “The Porky Sandwich.” With their freshly baked bread, it’s hard to believe you could choose a bad sandwich.
And, yes, they have soup and salad options. Two names in particular made me smile: “Pasta E’ Fagioli” and “Makin’ Me Caprese Salad.” It reminded me that while living in Italy, several things made me crazy. But the food wasn’t one of them. I found the best gluten-free bread sticks in the world at a supermarket there … not in the frozen section. If you’re celiac, you know what a big deal that is.
Dessert. Glorious dessert. Choose from cheesecake, crème brulee, tiramisu, lemon cake with mascarpone, cannoli, chocolate with gelato, or tasting desserts. It’s easy to imagine how fun it would be to just come in and do a tasting of the desserts.
4150 W. Vine Street // +14074822404
Located on an access road, you should make the time to go out of your way to try the food and baked goods offered at this wonderful local restaurant with locations in Kissimmee and Orlando that’s been bringing Puerto Rico’s authentic flavors to Central Florida since 2006.
My Spanish is rudimentary, at best, so the initial server needed a manager to help assist me. They are well-known for their all-day breakfast service and artisanal sandwiches. The manager told me they’re growing their catering business. The way she described the birthday cake and pastry options made me wish it was time for my own birthday to happen here.
Their menu can be really overwhelming at first, stretching across the entire length of the restaurant. It made me feel a little better when I realized it was only half that long … it’s duplicated over the meal section and then again over the baked goods. Their all-day breakfast includes options like pancake selections, egg dishes, ham and eggs, toast, waffles, or breakfast burritos.
The later-day options include burgers, rice and bean plates with your choice of protein (served with sweet plantains), mofongos rellenos, and jibaritos. If you’re really hungry, try a triplets sandwich with ham, steak, pulled pork, and Swiss. The pulled pork is a Taino special. And they even carry a Montecristo. Last time I saw that, I was on a train.
I had the empanadilla pollo which was utter perfection in its simplicity. It’s as though they’ve taken every cooking show judge’s advice to heart. If you’re going to make something simple, be certain it is perfect. It tasted like it had a double crust, crisp on the outside and easily separating flaky on the inside, packed with diced chicken in a light sauce.
The only problem? It smelled so good I didn’t get a photo.
Check out the baked goods display cases and you may feel as though you’ve gained five pounds. The Bizcocho de Oreo was super tempting, as was the apple turnover. I must take my appetite back to sample more items.
Diane’s Creations & Tea Room
114 Broadway // +14072014733
Walk into this delightful tea room, and you’ll find a festive, twinkle-light festooned ceiling with chandeliers from front to back. The tables flow at varying heights with tastefully mismatched seats. Be careful, though, about taking photos. The proprietress doesn’t care for them. Too many people have tried to copy her design.
Come for lunch or high tea (two days’ notice required) and you’ll enjoy a wonderful meal with your favorite cup of tea. If you’re willing, try a new tea. The list contains 43 hot tea options, and the tea sommelier will recommend them to you by number for your consideration.
For example, I’ve been partial to the English and Irish Breakfast teas for about a year and had more than my share of the Earl Grey and Lady Grey teas. He recommended #33, a British Blend that wasn’t quite as brash as the breakfast teas, and I agreed.
The individual teapot came with a lovely fine china cup and saucer. Ask for water, and you’ll have a refreshing water (not tap) in fine-cut crystal. The teabag is presented on its own caddy for easy reuse.
The water is so piping hot, it’s obvious the teapot was pre-heated with hot water prior to filling with my water. It took an ice cube to cool enough for me to drink the initial cup. By the time I got to the third cup, it didn’t take quite so long before I could drink it.
There are four iced teas as well as lemonade, cans of soda (Pepsi products), coffee, hot chocolate, beer, or wine to choose from. You could even order a White or Black Russian.
In addition to the standard fare of chicken, tuna, or egg salad, deli ham, or turkey breast, there’s often a cup of soup or specialty of the day. Today’s soup was a tomato and the special a Reuben or a thinly sliced beef on a homemade Kaiser roll. Other options include a variety of double-deep quiche (think Chicago-style pizza in depth) or a stuffed tomato.
Today, I chose the chicken salad. Served on a croissant roll, it tasted as fresh as anything I’ve had. It was quite a large portion, enough for two, with both a green olive and a gherkin-sized pickle on top. The garnish was a palate-cleansing thin slice of watermelon.
As a side, you can choose between potato chips, fresh seasonal fruit, or one of their side dishes. Their tomato, green bean, and onion salad with homemade dressing was enjoyed by many customers around me. As was the macaroni salad. After confirming the potato salad was mayonnaise-based with just a little mustard, I ordered that.
But, with the delicious desserts and scones promoted on the menu, ask for dessert options first. Ultimately that choice was a blueberry scone with clotted cream. The server joked the Queen of England had stopped by and said they just haven’t gotten it right back home yet. There are many visitors from overseas and they recognize that their scones aren’t the same. Served with clotted cream alone (not butter or jam as is commonly done in Europe), the scones are a middle level density, served warm and instantly consumed. Yummy.
After the scone, I was only able to finish half the tuna and a couple of bites of the potato salad. Surviving on leftovers would not be a bad gig if you ever decided to move to Florida (there’s no state income tax here, just saying).
If you’re on your own, as I was this day, you can feast your eyes on the goods on offer at the store as you eat, or people watch and marvel at the tea sommelier’s experience. Another young woman came in and, while waiting for her companions, had a lengthy discussion about her tea choice. She went with #26, the true blueberry herbal decaf. It reminds me very much of overhearing conversations about fine wine.
3 Sisters Speakeasy
220 Broadway // +14072013270
As the story goes, the photos of the three women along the bar are of sisters Dodie, Fannie, and Ruth, who provided their delectable drinks and hor d’ oeuvres after the prohibition became law in 1920. The password into the Speakeasy? “Apple pie.” The customers could enter and bask in the sisters’ glow of community spirit.
The restaurant has been sold and bought and sold, and there is no longer a hidden room for a speakeasy, but the zest for the community doesn’t seem to have changed. Everyone was friendly and welcoming to a new face.
This restaurant was especially fun as the chef, Jeff, was available to chat. He walked me through the extensive menu. They serve about twenty-two types of sushi rolls. The Sister’s Special most likely to catch your fancy? “Prohibition Philly,” your choice of protein, steak or chicken, grilled onions, mushrooms, and peppers with provolone on an amoroso roll.
My attention was drawn to Ruthie’s Best Burgers, 3 Sisters Tacos, and their entrees, which include salmon, chicken, pot roast, sirloin steak, Argentinian flank steak, and baby back ribs.
My favorite daughter wasn’t with me, so there wasn’t a chance that I’d try the Firecracker Shrimp, but it would definitely be on her list.
Dodie’s D’Lite included the lighter, salad options. The salmon salad was a strong contender. I can already imagine my favorite daughter ordering the pot stickers, calamari, and fried pickles, in addition to those Firecracker Shrimp. It’s a good thing we’re a Disney family and plan to return often.
When I had my choice narrowed down to two, Jeff helped me choose the fish tacos (tilapia, not breaded, yay!) and substituted mashed potatoes for yellow rice. He’d also offered French fries. You’ll have the option to choose to have the fish blackened, but I chose grilled, and it was delicious. A bit messy, as you’d expect seeing how stuffed the taco shell is with the tilapia, shredded cabbage, mango salsa, tomatoes, and a bracing chimichurri sauce. It is truly a delight for the tastebuds.
It was too large a portion for one meal for me, so I took a taco and the potato salad home with me. I’m impressed to say it was as good the second day.
The bar has a Tiffany-like light fixture believed original to the building. I do wish the walls could talk.
Crack N Roll
3260 Vineland Rd Suite 109 // +14075072667
Early in our stay, we stopped at this Cajun Seafood restaurant in a strip mall not far from our apartment. The Facebook photos of their snow crab and sushi really caught my daughter’s attention.
They were out of crab that day but had plenty of sushi on offer. I’m a fan of edamame, so that would hold me until our next meal. They offered sixteen signature rolls, eight pieces per serving, that could include avocado, shrimp, lettuce, spicy mayo, sesame seed, crab, cream cheese, eel sauce, asparagus, baked spicy sauce, and mushroom. You all know I am not the adventurous eater, so I was interested to see what my favorite daughter chose to join her Mango Green Tea.
Broadway Pizza Bar
403 Broadway // +14078477050
If you like thin crusted pizza, this is the place for you.
From the eclectic chair statue outside, to the regulars at the bar, there’s always more to look at. Prompt service and friendly bartenders make all the difference. The smell of tasty pizza filled the air and made me realize how hungry I really was.
As appetizers, you can order the garlic knots (always my downfall), garlic bread, cheesy garlic bread or mozzarella sticks. Olives or mushrooms more your style? They have those, too. And soup and chicken wings if you have a taste for them.
In addition to pizza, they offer ten penne dishes, a dozen salads, eight different subs, and five types of dessert. I was tempted by the Zeppole, an Italian pastry like a beignet with deep-fried dough topped with powdered sugar, but knew I should wait for my pizza.
After I ordered my margherita, I explored a little further. There’s a corner wine room with impressive labels and a table perfect for a tasting area.
When the pizza arrived, placed on a bar stand to keep it high and close, I was impressed by the smell, which reached me before I could see the mozzarella and basil distribution, and then the touch of the hard crust, and feel and hear the crunchiness with the first bite. That’s what I call five sense dining.
It didn’t taste as salty as I’d become accustomed to which made me rethink some of the pizza sauces I’ve been eating.
The price was quite reasonable, even with a soda, and there was plenty to take home as leftovers (perfect fresh from the oven).
2 Brothers Steak House
16 E. Dakin Ave // +14077506753
My last stop at the independently held restaurants in historic downtown Kissimmee, the staff of 2 Brothers Steakhouse were busy putting up more outdoor seating when I arrived. Friendly and cheerful, they offered their favorite dishes as I entered.
Inside, the glasses-bedecked cow made me smile as I looked to the current customers and staff. It appears to have more seating outside than inside, and many people are still ordering take away meals.
I’d never seen mini–Cordon Blue on the appetizer menu before. And that wasn’t the only unusual thing I spotted. They offer stuffed potato balls and blood sausage. Items I’ve become more accustomed to included empanadas in beef, chicken, shrimp, or picanha (still beef, but a cut popular in Argentina). The stuffed plantain cups can include top sirloin, chicken, or shrimp and reminded me of my time in Central America.
They offer wings with eight choices of sauce, three types of salad, nachos, and samplers for two or four people.
The piece d’resistance remains the grilled steaks. Offered with one side and the house salad, it’s a large meal. The beef is certified Angus, and the choice cuts include porterhouse, boneless ribeye, sirloin strip, NY Sirloin strip, Filet Mignon, top sirloin, or boneless ribeye.
My choice has to remain the filet. It’s a good size at eight ounces, so I asked for it to be butterflied so it can cook evenly and not be overdone or dry. They did a nice job with it and were prompt with their service and water glass refills. For my side, I chose the grilled asparagus. The fried plantain was tempting, but I stuck with the vege rather than fruit.
The house salad was fresh and delicious. It’s a restaurant I can see returning often.
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Gail Clifford, MD, a physician for more than 25 years, has traveled to five continents and all 50 United States. An avid traveler, she happily goes on new adventures, especially on birthdays. Multi-generational travel remains a treasured pastime. She divides her time between Ireland and the U.S. You can find her on Instagram, LinkedIn and Facebook.