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Top Date Night Restaurants in Kissimmee

Add exotic global flair to your next date night and let your taste buds lead you on a delicious journey at these romantic restaurants in Kissimmee, Florida. You won’t have to travel far to find yourself immersed in the cuisine of the oldest restaurant in Florida or “oohing” and “aahing” at sizzling Thai platters while seated on colorful floor cushions. If you prefer a high-energy night dancing the night away or catching a live Irish dancer show, I have the top spots for you. 

There’s no shortage of romance at these favorite date night spots in Kissimmee. Let’s go explore my favorites at Celebration Town Center, Promenade at Sunset Walk, and Disney Springs.

Holding Hands in Celebration

For a relaxing date, the picturesque town of Celebration offers two authentically delicious international options for lunch or dinner at Celebration Town CenterColumbia Restaurant and Thai Thani
History buffs are bound to enjoy a date at the Kissimmee sister location of Florida’s oldest restaurant, Columbia Restaurant. From the classic Spanish-Cuban dishes which boast recipes created more than a hundred years ago to the many stories the staff has to share, there’s history in every bite. Start with Columbia’s Original “1905” Salad and then share a refreshing pitcher of sangria, or I recommend the sparkling cava for a year-round taste of summer. Created in the 1970s as the alternative to a salad bar, it’s made of crisp iceberg lettuce with julienne of baked ham, Swiss cheese, tomato, olives, and grated Romano cheese, tossed with Worcestershire sauce and garlic dressing.

Meal at outdoor table at Columbia Restaurant in Kissimmee.
Columbia Restaurant. Photos: Christina Thomas, Go Epicurista
Paella at Columbia Restaurant, Kissimmee, Florida

For a deliciously zen getaway with the most soothing vibes, check out Thai Thani. Locally family owned for 12 years, the restaurant has traditional dishes of Thailand in a delightful atmosphere surrounded by a plethora of antique artifacts and statues. The menu, full of fresh flavors that pop using exotic herbs and spices, serves something for everyone. All dishes are made to order so you can request more Thai chili to punch up the spice level if you want to light the fire. Share the Thai Thani sampler with your sweetheart and pair it with a cold Singha beer from Thailand or sweet and creamy Thai iced tea. Request to sit at a low table on Thai cushions in the Asia room or at an outside table.  

Thai dishes on a table at Thai Thani restaurant, Kissimmee, Florida
Thai Thani. Photo: Christina Thomas, Go Epicurista

Tip: If you can’t get enough of the area, stay for a romantic getaway at nearby Bohemian Hotel Celebration, featuring posh modern luxury with lakeside views. Or Meliá Orlando Celebration presents all suite accommodations and a fantastic infinity pool with beach-style entry.

Explore the Promenade at Sunset Walk

For a shopping, dining, and entertainment date, explore The Promenade at Sunset Walk in the heart of Margaritaville Resort Orlando, which offers plenty of options to show how much you love your sweetheart.

Nothing builds excitement like a little danger – at Capone’s Coal Fired Pizza that is. Step into the world of the most notorious gangster of Prohibition Era Chicago for a casual Italian feast – so good I’m glad it’s not illegal. Sip on a fruity Capone Cocktail while indulging in the many classic fairs they have to offer. 

For pizza lovers, create your own made-to-order slice cooked in an 800-degree coal-fired oven for nicely charred, crispy crust. Or you can pretend you’re Lady and the Tramp and share a bowl of spaghetti with giant meatballs. For dessert, Al’s Cannoli made with the traditional crisp Italian shell, stuffed with sweetened ricotta dipped in loads of chocolate chips, and dusted with powdered sugar is all you need to end on a sweet note. 

Cannoli on plate at Capone's Coal Fired Pizza, Kissimmee, Florida
Capone's Coal Fired Pizza. Photos: Christina Thomas, Go Epicurista
Pizza and side dishes at Capone's Wood Fired Pizza, Kissimmee

For a sizzling date night, let the music take you to Estefan Kitchen for a feast that indulges all your senses with an explosion of flavors. The modern decor with a 1950s Havana nightclub vibe will have you singing “Havana ooh na-na.” The live music and dancers at Gloria and Emilio Estefan’s first Estefan Kitchen outside of Miami are absolutely mesmerizing. Start with traditional or flavored mojitos made with strawberry, guava, passion fruit, or mango and end the night with the Tres Leches, a homemade cake soaked in a sweet blend of three milks finished with a sweet, torched meringue on top. 

Dish of paella at Estefan restaurant in Kissimmee, Florida
Estefan Kitchen. Photos: Christina Thomas, Go Epicurista
Tres Leches cake at Estefan Kitchen, Kissimmee, Florida

If your idea of the perfect date night is hanging out at a fun pub noshing on comfort food paired with a cold pint while your favorite team is playing, take your love to the pub at Yeoman’s Cask & Lion. This British pub with a Big Ben Tower on the roof and London Fog filling the room every hour is known for their gigantic portion of fish & chips prepared in their signature beer batter with homemade tartar sauce. Whet your whistle with a Bass pint or one of seven refreshing mule cocktails. My favorite, the Shakespeare Mule with blueberries and cucumber, is easy sipping. The whimsical British icon paintings on the walls, live music, themed trivia nights, and Happy Hour gives you plenty of reasons to plan a date any night of the week. 

Fish and chips and side dishes at Yeoman's Cask & Lion, Kissimmee
Yeoman's Cask & Lion. Photos: Christina Thomas, Go Epicurista
interior seating of Yeoman's Cask & Lion British style pub in Kissimmee

Tip: For a Key West-inspired getaway, book your stay at Margaritaville Resort Orlando and don’t miss indulging in spa treatments at St. Somewhere Spa. 

Fall in Love at Disney Springs

Disney Springs is a foodie happy place with more than 20 full-service restaurants in addition to a plethora of casual quick service options perfect for day or night dining dates. The waterfront restaurants make the most ideal spot to watch the sunset, and what’s more romantic than that?

For an authentic Irish pub experience, do a jig and head over to Raglan Road. Get a cozy spot at the bar and sip on flights of Irish or Scottish whiskey and get ready to immerse your taste buds into a menu of elevated Irish pub classics while you delight in live entertainment featuring some of the best Irish musicians and dancers. Try one of Raglan Road’s Signature Collection local brewed Irish-style beers made exclusively for the restaurant and feast on forks filled with sea scallops in a golden batter served with citrus lime dipping sauce.  

Scallop dish at Raglan Road Irish Pub, Kissimmee
Raglan Road. Photos: Christina Thomas of Go Epicurista
Whiskey cocktail at Raglan Road Irish Pub, Kissimmee

Wine lovers will swoon as they sip, swirl, and delight at this Mediterranean-styled estate. Wine Bar George is guided by a master sommelier, George Miliotes, who is regarded as one of the top wine experts in the country. The fun and approachable, yet eclectic wine list of over 140 wines to choose from is the perfect place to try something new or impress your date with. Snack on small plates or linger over late-night bites. For dessert, The Chocolate Experience pairs three wines with three chocolates for ultimate decadence. And you can’t miss out on the frozen wine cocktails like Frozcato Mimosa, made with DOLE WHIP Pineapple. Request a table in the veranda or in the wine barrel room for an intimate experience. 

Steak and frites with wine at Wine Bar George, Kissimmee
Exterior of Wine Bar George in Kissimmee

As you can see, there’s no shortage of phenomenal restaurants with unique global flair perfect for date night in Kissimmee. No matter what your wanderlust for date night desires, Kissimmee has a lot to offer. Cheers to that!

This guest post was written by Christina Thomas, the creator of GO Epicurista, who celebrates life with great food, wine, and friends throughout Central Florida. Check out her blog here, and drool over even more of her awesome food shots on her Instagram.

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