Guide to a Perfect Day Date in Kissimmee

Looking for the perfect day date that can all be found in one place?

Here's your guide to impress your significant other with a mix of the great outdoors, a dash of history, some artsy vibes and, of course, food and drinks that’ll make for a great memory visiting Downtown Kissimmee.

Kick the morning off at Buchito with owners Maria and Alejandro and a Cuban-style café latte. We recommend pairing it with an order of scrambled eggs and homemade salsa which really adds flavor to this traditional breakfast, or a Cuban-pressed style egg and cheese sandwich. It’s not uncommon for locals to sit at the cafe bar and catch up with the family of owners. Just be careful because these popular seats are also right in front of Maria’s locally famous desserts like homemade flan, dreamy tres leches, or warm banana bread. Get there early if you want a sweet afternoon treat for the road. 

Grab coffee and head to the Kissimmee Main Street Welcome Station for a brochure of the art murals. Several of the historic buildings have beautiful murals painted by local artists in partnership with Osceola Arts that highlight important moments in Kissimmee. The walking mural tour is a staple in our local vibrant arts scene and bonuses as a great background series for your Instagram. If you're a bit more adventurous, just outside of Downtown Kissimmee is Shingle Creek Regional Park. Rent a kayak and try not to splash each other too much as you navigate through the headwaters of the Everglades.

By now, you’re probably starving, so make your way to Queens and King by El Tenampa. Order some agua frescas (locals love the lemon agua frescas; think of them like lemonade but sweeter) and enjoy the endless chips and salsa. You can never go wrong with traditional tacos, but we recommend the birria tacos if you’re looking for something different. Birria is a popular dish from Jalisco, Mexico, and these tacos contain shredded beef dripping in au jus topped with shredded cheese and finished on the flat-top grill for a crunchy outer shell.

To work off the endless chips and salsa from lunch, hop in your car or take a quick Uber to the Osceola County Historical Society’s Pioneer Village. It's an immersive journey that allows you to walk in the footsteps of those who pioneered Osceola County, where Kissimmee is located. The village is a walking tour filled with historically preserved buildings and discovered artifacts that will give visitors a glimpse into the daily lives of our founding families, fostering a deeper appreciation for the struggles and triumphs of earlier generations living in Central Florida. 

It’s five o'clock somewhere, so next, grab a drink at 1881 Restaurant and Bar, a new go-to spot for Kissimmee-themed cocktails. The star of the show is the Summer of 1881 cocktail, a watermelon Jolly Rancher in liquid form garnished with fresh mint. Hop over to Breeze Kissimmee for a night cap which is our popular whiskey lounge where something is always going on. If you land there on a Sunday, you can enjoy bottomless mimosas and live karaoke, which is always a fun date-night to-do.

Wrap up your adventure with a visit to Lake Tohopekeliga (pronounced To-hó-pk-i léyk-a), or Lake Toho as the locals call it. The lakeside views are the perfect backdrop at the end of the day, and the park provides free Adirondack chairs to watch the sunset and plan your next date.

From charming restaurants to exciting entertainment, Kissimmee offers countless ways to make each moment special. To keep the magic alive and stay updated on the latest local happenings, sign up for our newsletter. Join us as we continue this journey together, bringing you more ideas and experiences to make every date night extraordinary.