Valentine’s Day in Winter Garden

Things to do for Valentine's Day in Downtown Winter Garden

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…with…Downtown Winter Garden.

Serenade Under the Stars – Live Music on the Plaza 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

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

Stroll Through an Art Exhibit: Central Florida Watercolor Society: Annual Awards Show

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

February 14 & 15 10am-6pm

Experience a shared appreciation of beautiful art from an award-winning collection of watercolors paintings and 3-dimensional artworks. FREE!

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

Valentines Brunch Tours

February 15 & 16 @11:00 am

Celebrate Valentine’s with a charming brunch tour in Downtown Winter Garden.  Love is in the air at the following tour stops:

$48 pp 

Click here to Reserve your Spot


Couples Historical Walking & Biking Tour

Winter Garden Heritage Foundation

Saturday, February 15 @ 10:00 am & 2:00 pm

Learn about and experience together with the historical and cultural sights of downtown Winter Garden by taking a special Valentine’s Couples Tour with a Winter Garden Heritage Foundation guide. Both walking and biking tours are available. $14 pp (adults only). Advance reservations required by calling 407-656-3244.

Couples Bike Ride

Winter Garden Wheel Works & Winter Garden Trailhead

Call (407) 654-1496

2-for-1 bike rentals and 15% off any two-bike purchase or tandem bike on Feb. 14, 15, and 16.

Couples that bike together, stay together!

A Day at the Award-Winning Farmers Market

Winter Garden Farmers Market
Downtown Pavilion
104 S. Lakeview Ave.

Take in the beautiful weather while enjoying breakfast or lunch from unique food vendors, discover rare gifts, enjoy live music -- a day at the award-winning Farmers Market is an ideal date venue!

Take pictures (or selfies) at 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 (at S. Boyd St. & Plant St.)

(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! 

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!

Dining and Sipping Specials

Capture the heart with delectable sweets, scrumptious meals, secret love potions, and sparkling spirits. Below is just a sample of the many distinct dining options in Downtown Winter Garden:

The Bulk Pantry

An image of keto friendly sweets

103 S. Main St

Valentine-themed sweets for ALL diets: LOW CARB, SUGAR-FREE, GLUTEN FREE…and full SUGAR! A broad selection of custom-made strawberry shortcake donuts, cheesecakes, cupcakes, mini cakes, cookies, chocolates, and more.

Burger Fi

Burger Fi ice cream

360 W. Plant St.

Free Custard Cup with the purchase of a sandwich all day on February 14, 2020.

Crooked Can Brewing Company

Crooked Can Brewing Company Love Potion Beer

426 W. Plant St.

A special Valentine’s Day beer release – LOVE POTION – on Feb. 14! A light and fruity Aphrodisiac Ale – who can resist!

David Ramirez Chocolates

Chocolates with kiss patterns and in heart shapes.

426 W. Plant St. – Plant Street Market

Artisan chocolates handcrafted in an assortment of Valentine’s theme chocolates and macarons to express your love.

Matthew's Steakhouse

Matthews Steakhouse. Valentine's day dinner menu.  Grilled artichoke hearts. 8ounce filet mignon or 10 ounce new york strip served with baked potato, steamed broccoli, and mixed salad. Fresh tiramisu. Bottle of Flor Cabernet or Pinot Grigio Tiamo.

360 W. Plant St.

Reservations required: 407-520-7511

Fine dining experience with special-priced Valentine’s Day Dinner Menu, including bottle of wine, for $79 pp: Grilled Artichoke Hearts, Mixed Salad, Filet Mignon or NY Strip served with Baked Potato and Steamed Broccoli, Fresh Tiramisu, and Bottle of Flor Cabernet or Pinto Grigio Tiamo.

Morthan Cheese

Friday, february 14th. Buy one, get one 50% off. Morthan cheese.

426 W. Plant St.

Buy ONE, Get ONE 50% OFF on Valentine’s Day, Feb. 14
A great way to share your love of cheese!

Pilars Martini

Image of a martini glass with a heart inside. Pilars Martini.

146 W. Plant St.

Valentine’s Day Special: BOGO on all Mini-Splits on Feb. 14
Sparkling Bottle Specials all weekend (Feb. 14-16)
Live music all Valentine’s weekend: Friday, Saturday & Sunday nights! 

Drop in for “Sparkling & Jazz” to celebrate Valentine’s Day!

Rosallie Le French Cafe

An image of chocolate, fruits, macaroons, and other sweets.

141 W. Plant St.

Transcend to romantic Paris with each bite of delectable French pastries! What a Valentine’s Day delight!

Sweet Dee's Cupcakery and Custom Cakes

An image of cupcakes with heart shaped treats on top.

21 S. Main St.

A large selection of custom-made Valentine-themed sweets for your loved ones…including holiday treats for your furry best friend! Valentine’s cupcakes and desserts galore for you to indulge…as well as pupcakes, pup truffles, pup cookies to treat your pup.

Way Chocolate & Coffee

An image of hearts shaped chocolates in a clear wrapper.

50 W. Plant St.

From chocolate truffles to gift baskets, dazzle your loved one with hand-crafted Valentine’s Day chocolates and desserts.

Valentine's “Chocolatey Crawl”

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

A “passport” to explore the handmade, extraordinary, “chocolately” 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

Valentine's Brunch Tours

February 15 & 16 11:00 am

Celebrate Valentine’s with a charming brunch tour in Downtown Winter Garden.
Love is in the air at the following tour stops:

$35.00 pp. Reservations online (limited to 35 guests)

Reserve Online

Kick-off location: Rosallie Le French Café, 141 W. Plant St. Walk-ups welcome, if space available.

Shopping Specials

Driftwood Market

46 W. Plant St.

Complimentary champagne in-store from 6-9 pm
Enjoy a glass of the sparkly while selecting a great Valentine’s Day gift!

Gee Gee's Gems

24 E. Joiner St.

10% OFF all purchases AND a chocolate treat with each purchase on Feb. 14 & 15.
Unique Valentine’s gift treasures – jewelry, body and bath products, apparel, and much more!


100 S. Boyd St.

20% off on Valentine’s Day
Kitlife offers a variety of Valentine’s Day gifts, including 2020 planners to get the most out of life.

02 Breathe in One Utopia

426 W. Plant St. – Plant Street Market

15% off all aromatherapy oxygen sessions all Valentine’s weekend (Feb.14-16) – fun to experience together! (Located inside of One Utopia at Plant Street Market)

Plantation Jewelers

4 E. Plant St.

Custom-made selection of rings and jewelry with hearts and an assortment of beautiful designs to show your loved one that they are one-of-a-kind. Jewelry is a clear symbol of love on Valentine’s Day

The Sacred Olive

125 W. Plant St.

15% off any size Chocolate Balsamic and Strawberry Balsamic, Feb. 14-17
A tasting experience of premium olive oils and balsamic vinegars – fun to select together and makes a great Valentine’s Day gift.

Winter Garden Wheel Works

101 W. Plant St.

2-FOR-1 BIKE RENTALS (rentals at Winter Garden Trailhead: 455 E. Plant St.), Feb. 14-16
15% OFF any two-bike purchase or tandem bike, Feb. 14-16

Couples that bike together, stay together!

Woodstone Jewelry Pop-Up at Driftwood Market

46 W. Plant St.

Feb. 14: 11 am- 2 pm

Get a pewter heart hand-stamped by WoodStone Jewelry! Add a name or initials or just LOVE on the spot for $10. Necklace comes with a silver chain. Aluminum cuff bracelets will also be available for $15-the perfect way to say Happy Valentine’s Day!

Woof Gang Bakery

18 E. Plant St.

Get a FREE Valentine’s Tin with purchase of 10 oz. or more of bulk treats
Buy 2, get 1 FREE Woof Gang Treat Bags

Large assortment of themed Valentine’s Day treats for your furry friends – and a Valentine’s gift tin!


Share This Article

Leave A Comment