Romantic Events and Things to do in Winter Haven, FL
Plenty of intimate outings and couple-focused dates shape the romantic events and things to do in Winter Haven, FL. Couples often gravitate toward the walkable downtown core for candlelit dinners, craft cocktail lounges, and intimate live music settings. Historic venues and lakeside dining spots provide classic backdrops for evening strolls and memorable dates.
- Downtown Winter Haven serves as the social heartbeat, where spots like Gram Parsons Derry Down offer intimate listening room experiences for couples.
- Historic spaces such as The Historic Ritz Theatre host live concerts and classic film viewings tailored for evening outings.
- Lakeside dining locations throughout the Chain of Lakes area provide relaxed, scenic backdrops for sunset dinners and weekend dates.

PW Charters Presents Festival of Lights St. Augustine
Sun, Nov 22, 11:30 AM
Mascotte · 219 W Myers Blvd

PW Charters Presents Festival of Lights St. Augustine
Sun, Nov 22, 11:30 AM
Mascotte · 219 W Myers Blvd
TAMPA WATER LANTERNS & KITES FESTIVAL 2026!
Sat, Dec 12, 2:00 PM
Tampa · Mary Help of Christians Center
TAMPA WATER LANTERNS & KITES FESTIVAL 2026!
Sat, Dec 12, 2:00 PM
Tampa · Mary Help of Christians Center
Psychology of Your Love Life: Understand Patterns & Date with Confidence
Sun, Nov 22, 1:30 PM
Orlando · Orlando Public Library
Psychology of Your Love Life: Understand Patterns & Date with Confidence
Sun, Nov 22, 1:30 PM
Orlando · Orlando Public Library
SHAKE SUMTHIN’ | Mixology Date Night & Social Experience in Ybor City
Wednesday at 7:00 PM
Tampa · Centro Lounge and Kitchen
SHAKE SUMTHIN’ | Mixology Date Night & Social Experience in Ybor City
Wednesday at 7:00 PM
Tampa · Centro Lounge and Kitchen
Author Talk + Book Signing with Gayle Brown at Novel in the Neighborhood
Tuesday at 6:30 PM
New Port Richey · 8507 Old County Rd 54
Author Talk + Book Signing with Gayle Brown at Novel in the Neighborhood
Tuesday at 6:30 PM
New Port Richey · 8507 Old County Rd 54
Movie on the Lawn Double Feature -10 things I hate About You & The Holiday
Mon, Nov 16, 6:00 PM
Tampa · Armature Works
Movie on the Lawn Double Feature -10 things I hate About You & The Holiday
Mon, Nov 16, 6:00 PM
Tampa · Armature Works
Italian Buffet Dinner Aboard the Barbara Lee
Wednesday at 6:00 PM + 101 more
Sanford · St Johns Rivership Company
Italian Buffet Dinner Aboard the Barbara Lee
Wednesday at 6:00 PM + 101 more
Sanford · St Johns Rivership Company
MATCHBOX DOWN + HOOTIE’S WAGON — ONE NIGHT, TWO TRIBUTES!
Fri, Nov 27, 7:00 PM
Cocoa Beach · Heidi's Jazz Club
MATCHBOX DOWN + HOOTIE’S WAGON — ONE NIGHT, TWO TRIBUTES!
Fri, Nov 27, 7:00 PM
Cocoa Beach · Heidi's Jazz Club
Frequently asked questions about Winter Haven