Valentine's Day 2027 is a Sunday. Monster Bulls at Silver Spurs Arena the night before, a downtown wine bar, lakefront sunsets and Old Town.

Last checked Oct. 9, 2026. This page is updated each year at the same address. Sources: Silver Spurs Rodeo, Vintage Vino, Old Town, the Promenade at Sunset Walk, the City of Kissimmee’s Lakefront Park page and Experience Kissimmee, Osceola County’s tourism agency.

Valentine’s Day 2027 falls on Sunday, Feb. 14, so the big nights out are Friday, Feb. 12, and Saturday, Feb. 13. Kissimmee’s one dated Valentine’s weekend event so far is Monster Bulls at Silver Spurs Arena on Saturday. Restaurants post their own Valentine’s menus closer to the date; we add them here only as each venue announces them.

At a glance

  • Monster Bulls: 7:30 p.m. Saturday, Feb. 13, Silver Spurs Arena, 1875 Silver Spur Lane. Tickets on sale November 2026.
  • Sunset Walk Car and Truck Show: 11 a.m. to 2 p.m. Sunday, Feb. 14. Free.
  • Vintage Vino: 310 Broadway, open 5 p.m. to midnight Friday and Saturday, 917-627-8432
  • Old Town: 11 a.m. to 11 p.m. Friday and Saturday, 407-396-4888

Saturday: Monster Bulls

The Silver Spurs Rodeo’s 15th Annual Monster Bulls is 7:30 p.m. Saturday, Feb. 13, at Silver Spurs Arena at Osceola Heritage Park, 1875 Silver Spur Lane: a night of bull riding only. The event schedule says tickets go on sale in November 2026. The full 158th Silver Spurs Rodeo follows the next weekend, Feb. 18-21. Silver Spurs: 321-697-3495.

A wine bar downtown

Vintage Vino, the Tuscan-themed wine, cheese and specialty beer bar, has moved to 310 Broadway. Its posted hours are 5 p.m. to midnight Wednesday, 5 to 10 p.m. Thursday and 5 p.m. to midnight Friday and Saturday. 917-627-8432. More downtown spots are in our date night in Kissimmee guide.

Sunset on the lake

Kissimmee Lakefront Park, 201 Lakeview Drive, sits between downtown and Lake Tohopekaliga, with the lighthouse, the fishing pier and the Monument of States. Experience Kissimmee notes free Adirondack chairs for watching the sunset. Pontoon boat tours onto the lake leave from Big Toho Marina, run by Florida Everglades Eco-Toon Tours, 407-717-1024; book with the operator.

Old Town: Ferris wheel and car shows

Old Town, 5770 W. Irlo Bronson Memorial Highway, has a Ferris wheel, bars and restaurants on brick streets. Its Friday Night Muscle Car Show (Feb. 12) and Saturday Night Classic Car Show (Feb. 13) both cruise at 8:30 p.m. and are free to watch. Old Town’s FAQ lists a Ferris wheel and dinner ticket.

Sunday, Feb. 14

The Promenade at Sunset Walk holds its Second Sunday Car and Truck Show from 11 a.m. to 2 p.m., which falls on Valentine’s Day in 2027. The Promenade has more than 30 restaurants, shops and experiences; its directory lists them.

Farmers market

The Kissimmee Valley Farmers Market at Lakefront Park is usually on the first and third Fridays. Experience Kissimmee says past markets have included Valentine’s Day snuggles with farm animals. Dates are on our farmers markets page.

Related: date night in Kissimmee, live music and nightlife and things to do this month.

Frequently asked questions

What day is Valentine’s Day 2027?

Sunday, Feb. 14, 2027. The Saturday before, Feb. 13, is Monster Bulls night at Silver Spurs Arena.

What is happening in Kissimmee on Valentine’s weekend 2027?

Silver Spurs Rodeo’s 15th annual Monster Bulls is 7:30 p.m. Saturday, Feb. 13, at Silver Spurs Arena, and the Promenade at Sunset Walk’s Second Sunday Car and Truck Show falls on Feb. 14, 11 a.m. to 2 p.m. Old Town’s car shows run Friday and Saturday nights.

Do Kissimmee restaurants take Valentine’s reservations?

Restaurants post their own Valentine’s plans, usually in January. We list only what venues announce; none had posted 2027 plans when we checked.