Date Night Ideas in Winter Haven, FL

Mid-Florida Milers Walk at Celebration

In 4 days · Sat, Apr 18, 4:00 AM–3:59 AM UTC · Starbucks Celebration · 715 Bloom Street, Celebration, FL

Island Nights (21+)

Happening now · Mar 28 – Sep 27 · Island H2O Live! · 3230 Inspiration Drive, Kissimmee, FL

Grove Roots Brewing

Grove Roots Brewing · 302 3rd St SW, Winter Haven, FL

Outdoor Space in Winter Haven, FL

Red, White & BOOM! at LEGOLAND® Florida Resort

Sat, Jul 4, 4:00 AM–3:59 AM UTC · LEGOLAND® Florida Resort · One LEGOLAND Way, Winter Haven, FL

Margaritaville Run Orlando

Sat, Sep 26, 4:00 AM–3:59 AM UTC · Margaritaville Resort Orlando · 8000 Fins Up Circle, Kissimmee, FL

Sky Zone Lakeland

Sky Zone Lakeland · 6220 US Highway 98 N, Lakeland, FL

Trampoline in Lakeland, FL

Banana Ball

May 29 – May 31 · ESPN Wide World of Sports Complex · 700 South Victory Way, Orlando, FL

Catch Me If You Can 5k

In 1 week · Apr 25 – Apr 26

Urban Air Lakeland

Urban Air Lakeland · 3800 US Hwy 98 N, Lakeland, FL

Outdoor Space in Lakeland, FL

Disney H2O Glow After Hours

Jun 2 – Sep 6 · Disney's Typhoon Lagoon Water Park · 1145 East Buena Vista Drive, Lake Buena Vista, FL

Gatorland’s Holiday Ho, Ho, Ho-Down

Dec 5 – Dec 21 · Gatorland · 14501 South Orange Blossom Trail, Orlando, FL

Swan Brewing

Swan Brewing · 115 W. Pine St., Lakeland, FL

Brewery in Lakeland, FL

Gators, Ghosts & Goblins

Oct 10 – Oct 26 · Gatorland · 14501 South Orange Blossom Trail, Orlando, FL

GayDays Orlando 2026

Jun 4 – Jun 9 · Holiday Inn & Suites Orlando SW - Celebration Area by IHG · 5711 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Medieval Times Orlando

Medieval Times Orlando · 4510 W Vine St, Kissimmee, FL

Food Drink in Kissimmee, FL

Gatorpalooza!

May 30 – Jun 1 · Gatorland · 14501 South Orange Blossom Trail, Orlando, FL

Altitude Trampoline Park Kissimmee

Altitude Trampoline Park Kissimmee · 2703 W Osceola Parkway, Kissimmee, FL

Trampoline in Kissimmee, FL