Are you ready for a challenge?

Kissimmee Main Street is hosting its first-ever Downtown Dining Challenge. Everyone is invited to participate in this restaurant roundup of some of Kissimmee’s favorites — with a chance to win a gift certificate valued at $200 to participating restaurants. 

Downtown Dining Challenge

“We felt this is the perfect time with the many Sunrail visitors we are experiencing, and the perfect place with over 24 independently owned restaurants and eateries to host a dining challenge,” said Kissimmee Main Street Executive Director Diana Marrero-Pinto. “At Kissimmee Main Street we are always brainstorming ways to showcase the beauty and unique aspects of our downtown, this was another way to do just that.”

Marrero-Pinto continued, “Nowhere else in Central Florida will you find this variety of independently owned mom and pop, made-from-scratch, family recipe restaurants. The merchants, the Downtown Business Association and Kissimmee Main Street work collectively and cohesively to create a downtown that can be appreciated and enjoyed by visitors and residents alike.”

Participating locations include: Candyland Designs Co. (103A Broadway), Big John’s Rockin’ BBQ (324 Broadway), 3 Sisters Speakeasy (226 Broadway), Kissimmee Diner (120 Broadway), Abracadabra Ice Cream (520 Main St.), Nati’s Southern Seafood Boil (231 Broadway), Matador Tacos and Tapas (120A Broadway), Savion’s Place (16 E. Dakin Ave.), Vintage Vino (14 E. Dakin Ave.), Diane’s Tea Room (114 Broadway), Broadway Pizza Bar (403 Broadway), Willy’s Wieners (103A E. Dakin Ave.), Main Street Pizza (16 Broadway), Buchito Cuban Cafe (131 Broadway), Shipwrecked in the Islands Ave. (220 Monument) and Big Toho Marina (69 Lakeview Dr.). 

The Downtown Dining Challenge runs now through Nov. 22. Participants must spend a minimum of $5 at each of the participating locations in order to qualify for the raffle. 

Once you have completed the challenge, bring your stamped card to Kissimmee Main Street before Nov. 22 to be entered in the raffle. The drawing will be held at Small Business Saturday on Nov. 24 at 1 p.m. Winner need not be present. 

About Kissimmee Main Street

Kissimmee Main Street was founded in August 1997. Its mission is to preserve and enhance Historic Downtown Kissimmee for the enrichment of present and future generations. 

Kissimmee Main Street is located at 421 Broadway in Kissimmee. 

For more information about Kissimmee Main Street and all of its initiatives, community involvement and more, contact 407-846-4643 or visit