Date night in Kissimmee: dinner, theater, wine bars, late nights

Last checked Oct. 9, 2026. Every listing links to the venue’s own site or, for downtown and Old Town restaurants, the district’s own directory. Hours change; check before you go. Sources: Vintage Vino, Kissimmee Main Street, Osceola Arts, the Promenade at Sunset Walk, Old Town, Silver Spurs Rodeo, the City of Kissimmee’s Lakefront Park page and Experience Kissimmee.

A Kissimmee date night can be as simple as a walk by the lake at sunset and a glass of wine on Broadway, or as loud as a car cruise and a Ferris wheel ride at Old Town. Here are the options, with the hours each venue posts.

At a glance

Plan	Where	When (as posted)
Wine and cheese	Vintage Vino, 310 Broadway	5 p.m. to midnight Wed., Fri., Sat.; 5 to 10 p.m. Thu.
Sunset on the lake	Kissimmee Lakefront Park, 201 Lakeview Drive	Evening
Ferris wheel and cruise	Old Town, 5770 W. Irlo Bronson Memorial Highway	To 11 p.m. Fri. and Sat.
Dinner and a movie	Promenade at Sunset Walk	Daily
Rodeo night	Silver Spurs Arena, 1875 Silver Spur Lane	Feb. 13 and 18-21, 2027

Downtown: wine, tapas and the lake

Vintage Vino, 310 Broadway. A Tuscan-themed wine, cheese and specialty beer bar, now at a new Broadway address. Open 5 p.m. to midnight Wednesday, 5 to 10 p.m. Thursday and 5 p.m. to midnight Friday and Saturday. 917-627-8432.

Dinner on Broadway. Kissimmee Main Street’s dining directory lists Soul Tapas and Bar (24B Broadway), Matador Tacos and Tapas (120 Broadway), The Italian Joint (215 Broadway) and Queens and King Mexican Kitchen (324 Broadway), among others. Experience Kissimmee counts more than 30 locally owned restaurants downtown.

Sunset at the lakefront. Kissimmee Lakefront Park is a short walk from Broadway, with the lighthouse and pier on Lake Tohopekaliga. Experience Kissimmee notes free Adirondack chairs for watching the sunset. For a trip onto the lake, pontoon boat tours leave from Big Toho Marina, run by Florida Everglades Eco-Toon Tours, 407-717-1024.

Downtown parking is free on the street and in the city and county garages; see our downtown Kissimmee guide.

Theater

Osceola Arts, 2411 E. Irlo Bronson Highway. The arts center has a 235-seat main stage and a 90-seat black box theater, and its season usually runs September to August. It has paused its Broadway Main Stage Series during renovations and says the shows will return when the work is complete; check its site for current performances and its Lip Sync Battle fundraiser.

Sunset Walk: dinner and a movie

The Promenade at Sunset Walk has Studio Movie Grill for a dine-in film, Escapology escape rooms, and restaurants including Estefan Kitchen Orlando (open Tuesday to Sunday), Ford’s Garage, The Wharf and El Jefe Tequilas. Live music plays on the Promenade Plaza Stage; its music calendar has the lineup. Parking is free.

Old Town: Ferris wheel and car cruise

Old Town, 5770 W. Irlo Bronson Memorial Highway, has a Ferris wheel, sells a Ferris wheel and dinner ticket with its A and W restaurant, and stays open until 11 p.m. on Fridays and Saturdays, when its free muscle car and classic car cruises roll at 8:30 p.m. Its bars include Bobby’s Garage Bar and Southern Breeze. More in our live music and nightlife guide.

Rodeo night

The Silver Spurs Rodeo at Silver Spurs Arena, Osceola Heritage Park, 1875 Silver Spur Lane, holds Monster Bulls at 7:30 p.m. Saturday, Feb. 13, 2027, and the 158th Silver Spurs Rodeo Feb. 18-21, 2027. Tickets go on sale in November 2026.

Seasonal

• Christmas at Gaylord Palms, Nov. 13, 2026, to Jan. 3, 2027: ICE!, a holiday show and lights. See holiday lights.
• Valentine’s Day: see Valentine’s Day in Kissimmee.
• Jingle Bar Hop: Kissimmee Main Street’s downtown holiday pub crawl, ages 21 and up, in December.

Related: brunch in Kissimmee, free things to do and things to do this month.

Frequently asked questions

Where is a good date night spot in downtown Kissimmee?

Downtown has Vintage Vino, a wine and cheese bar at 310 Broadway open until midnight Wednesday, Friday and Saturday, plus tapas and Italian restaurants on Broadway listed by Kissimmee Main Street, and sunset views at Kissimmee Lakefront Park.

Is there a theater in Kissimmee?

Osceola Arts, 2411 E. Irlo Bronson Highway, has a 235-seat main stage and a 90-seat black box theater. Its Broadway Main Stage Series is paused during renovations; check its site for what is on. Studio Movie Grill at the Promenade at Sunset Walk shows films.

What is open late in Kissimmee?

Old Town is open until 11 p.m. on Fridays and Saturdays, and Vintage Vino until midnight Wednesday, Friday and Saturday.