Valentine's Weekend Adventures 

Dining Specials

Friday, February 14th

Guests will be given a passport, where they can take their own time and explore the different shops in Downtown Winter Garden. Featuring treats from 5 businesses: 
Rosalie Le French Cafe
David Ramirez 
Way Chocolate
Winter Garden Food Tours 

$35 per person - Claim your spot now! 

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Dine, Stay and Relax at Hyatt Grand Regency

Love is in the air at Hyatt Regency Grand Cypress, recognized as the #1 Resort in Orlando by the Condé Nast Traveler Readers’ Choice Awards. See Dining Specials below! 


Valentine Brunch Tour ~ Winter Garden Food Tour 

Saturday, February 15th

Love is in the air!
Treat your partner to a charming brunch tour in Downtown Winter Garden. Featuring food from 5 locations...
Rosalie Le French Cafe
The Deli Downtown
The Tasting Room 
Thai Blossom
Way Chocolate

$48 per person - Claim your spot now!

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Burger Fi in Downtown Winter Garden

With any purchase of a Sandwich, you receive a FREE Custard Cup on Valentine's Day! Perfect to share with your sweetest friend.

Crooked Can 

LOVE POTION - A special Valentine's Day Ale Release! A nice fruity, light and romantic beer.


Matthew's Steakhouse

For the holiday, dine at Matthew's Steakhouse for a delicious pre-set dinner including an Appetizer, Entree with sides, Dessert and your choice of a bottle of cabernet or pinot grigio.  Only $79 per person, so call to make your reservation today at 407-520-7511!



Valentine's inspired chocolates and macaroons with a handcrafted touch for your valentine!

Morthan Cheese

For Valentine's Day on the 14th, Buy One cheese creation, Get One 50% off!
It's the perfect day for cheesy goodness! Located in Plant St. Market. 



Buy On Get On for all the Mini-Splits for Valentine's Day!
There are Sparkling Bottle Specials with Live-Music all Weekend.
Swing by for jazzin' good time!


The Bulk Pantry 

Stop by on Main St. for Sugar-Free, Gluten Free, Low Carb Options of custom-made cheesecakes, cakes, mini-muffins and more, with Valentine's twists! 



Valentine’s Day Evening Carriage Tours

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

Love is in the air.... Enjoy an unforgettable evening with your sweetheart aboard our lighted Cinderella Coach along Plant Street in Historic Downtown Winter Garden. Book Below! 


Valentine's Day Parents Night Out Gymnastics USA

Parents Night Out events are suited specifically to allow you to have some "me time" while the children have a blast at Gymnastics USA! Enjoy dinner and a movie while the children enjoy pizza and cartwheels (not at the same time of course!) Coaches are there to ensure safety and fun, as well as organize group games and activities. Oh and Pizza is on us! Register Below!

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Theo Moon Live at The MoonCricket Grille

Come spend a romantic evening at The MoonCricket Grille with the smooth sounds of Theo Moon!

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50’s & 60’s Sweetheart Sock Hop Shoe Drive

Come celebrate Valentine's at the 50's & 60's Sweetheart Sock Hop Shoe Drive!
Price of Admission is new shoes for needy pre-school/kindergarten children (sizes: 8-12)
Dance the night away with live band Scotty K and The Corvairs

Delicious Diner Food at Retro prices. More details below! 

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Serenade Under the Stars

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

Stroll on by the Centennial Plaza Gazebo for music and love under the stars performed by Forget Me Not Duo from Nashville, TN. This husband and wife duo is originally from Orlando, Fl and will play popular and classic songs with a romance twist all night long.


Valentine Sock Hop at Sonata West

On Thursday, February 13th dress in your favorite greaser gear or poodle skirt. If you don't have one, go with a plaid shirt, high waist paints and penny loafers. For the ladies, don't forget your scarf and cat eye glasses! Get your dancing shoes ready, this Valentine's Sock Hop with be complete with a DJ and 2 dance hosts! More details below!

Stroll through an Art Exhibit

Central Florida Watercolor Society: Annual Awards Show at the Sobo Art Gallery! 

February 14 & 15 10am-6pm

A free event of award-winning water color paintings and stunning 3 -dimensional artwork!


A Walk of Color

The Splash Pad will be lit with purple lights, City Hall will have a red glow and the gazebo with have an extra special touch of lights and magic.


Take Your Picture With the Holiday Mural 

Artist Rudy Drapizo will create a chalk mural that is a perfect way to take a snapshot a memory of this loving holiday!
(at S. Boyd St. & Plant St.)

Shopping Deals

Driftwood Market

Join WoodStone Jewelry for their Pop Up Jewelry Making Workshop from 11am-2pm on February 14th. Making starting at $10. Stop on by for complimentary champagne from 5pm-9pm for evening shopping. 


Couples Biking

Winter Garden Wheel Works & Winter Garden Trailhead

On Feb. 14th, 15th and 16th Bike Rentals are 2-for-1 and 15% off any two-bikes purchase or tandem bike.

Bike together and stay together!


Stained Glass Painted Bottle Lamps Workshop

Create your own stained glass inspired lamp using a unique form of stained glass paint that is cut with scissors and placed on bottles using your own instincts and creativity with design. Inspirational quotes and decorations complete your one of a kind lighted art.

Fee: $60 members/$75 non-members

Hosted by Sobo Art Gallery and Artist Kathy Bee on Saturday, February 15th from 2pm to 5pm. Register Below!


The Sacred Olive

From February 14th to 16th, find any size Chocolate Balsamic and Strawberry Balsamic, 15% off! At Sacred Olive, enjoy a tasting experience of balsamic vinegars and premium olive oils for Valentine's Day. 


Gee Gee's Gems

Come in for a chocolate sweet treat and 10% Off All Purchases on February 14th & 15th! Stop by for all the new treasures and troves, perfect for the holiday.  



For Valentine's Day, KitLife has a variety of holiday gifts, including 2020 planners. Stop by for 20% on Friday!