Top 10 Things to Do for Valentine’s Day in Downtown Winter Garden

Downtown Winter Garden’s romantic charm and fun offerings make it the ideal location for this year’s Valentine’s Day celebration. Click the following link for lists of Valentine’s Day Activities | Dining Specials | Shopping Offers!


Create shared experiences…and memories…this Valentine’s Day! There is so much to do in Downtown Winter Garden, and the activities below are guaranteed to make you fall in love and…with…Downtown Winter Garden.

Be serenaded under the stars by Forget Me Not Duo

Centennial Plaza Gazebo
Downtown Winter Garden
101 W. Plant Street

Friday, February 14, 6:00-9:00 pm

Romantic Music under the stars…and twinkling lights


Love and music will fill the air of downtown Winter Garden on Valentine’s Day! Making a special guest appearance from Nashville, TN, the husband and wife duo of Forget Me Not will put a fresh spin on popular songs as well as a touch of romance. 

Your loved one will certainly not feel forgotten when serenaded by Forget Me Not!

Originally from Orlando, FL, Forget Me Not has a strong background in music and performance, having been hired by companies like Walt Disney World and Sea World to do recording work as well as live performances. 

Event Page More in Winter Garden


Cinderella Carriage Tour Experience

Friday, February 14, 6:00-10:00 pm

Downtown Pavilion
104 S. Lakeview Ave.

Fairy tales do come true when you treat your princess…or prince…to a horse-drawn Cinderella coach experience through downtown Winter Garden. Feb. 14, 6:00-10:00 pm. $80 total for 2-4 people. Limited reservations:

Reserve My Tour


Take pictures (or selfies) at the Valentine's Day Mural Wall

A specially-created chalk mural created by famed artist Rudy Drapiza to mark the holiday on social media... and create a lasting memory.

Located at South Boyd Street and Plant Street

(this is not the actual wall art by Rudy, just a representation for promotion purposes ❤️)


Immerse in the colors of Valentine's Day as downtown projects the spirit of the Holiday with special effect lighting.

City Hall will be lit red, the splash pad turns purple, and lighted trees and gazebo will add a touch of twinkle. The perfect backdrop for fun and pictures!

Image of colorful splashing water in the night.


Couples Art Workshop: Create a Stained Glass Painted Bottle Lamp Keepsake

Saturday, February 15, 2-5 p.m

Sobo Art Gallery
127 S. Boyd St.
​Winter Garden, FL 34787

Artist: Kathy Bee

Couples can create a stained glass inspired lamp keepsake this Valentine’s Day weekend. Working together, couples will use a unique form of stained glass paint that is cut with scissors and placed on bottles using combined creativity. Inspirational quotes and decorations will complete the couples’ very own, one-of-a-kind lighted art. Only pay ONE FEE PER COUPLE for this Valentine’s Day Special: $60 members/$75 non-members (supplies included).

Click here for reservations


Valentine's “Chocolatey Crawl”

Friday, February 14
7:30 pm start time, 7:00 early registration

A “passport” to explore the handmade, extraordinary, “chocolatey” treats and unique establishments throughout Downtown Winter Garden. Self-paced, walking tour with five pre-set stops/tastings:

$35.00 pp

*Limited to 35 guests. 

Reservations online. Walk-ups are welcome if space available.

Book Online


Couples Historical Walking & Biking Tour

Guided by the Winter Garden Heritage Museum docent. Reservations: 407-656-3244


Couples Bike Ride

Winter Garden Wheel Works
101 W. Plant St.

February 14-16

Take a romantic bike ride through the quaint downtown and its adjoining award-winning 22-mile trail. 2 for1 bike rentals at Winter Garden Trailhead– or get a discount on the purchase of a tandem bike rental.


Dine and Wine

At the many unique, award-winning restaurants in Downtown Winter Garden. Many feature irresistible dinner, dessert, and drink specials, including aphrodisiac ale release of "Love Potion" at Crooked Can Brewing Company.

For a list of Valentine's Day Dining & Sipping Specials, click here.


Stroll and Shop

Hand-in-hand along the charming, twinkle-lit, historic streets and pop in the one-of-a-kind shops. A perfect time to buy your special someone that special something!

For a list of Valentine's Day Shopping Specials, click here.


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