10 Romantic Ideas for Celebrating Valentine's Day in Winter Garden

SPONSORED — From a concert under the stars and Cinderella horse drawn carriage rides to unique restaurants and a special “love potion” beer release, we're head over heels for Winter Garden's amorous Valentine's Day happenings this year. If you need a little help in the planning department, look no further than this list of 10 romantic ideas for celebrating Valentine's Day in Winter Garden.

1. Be serenaded under the stars

Friday, February 14, 6-9pm
Centennial Plaza Gazebo, Downtown Winter Garden
101 W. Plant St.

On Valentine's Day, husband and wife musical duo Forget Me Not will be performing your favorite love songs at Centennial Plaza Gazebo. Snuggle up on a bench swing with your sweetie and enjoy the tunes. Best of all, the concert is totally free! More details here.

Forget Me Not duo

2. Cuddle up on a private horse drawn carriage tour

Friday, February 14, 6-10pm (last tour departs at 9:40pm)
Tours depart from the Winter Garden Downtown Pavilion
104 S Lakeview Avenue
$80 (groups of 2-4)

Ready to live out your fairy tale dreams? Soul Haven Ranch is offering private horse drawn carriage rides in a Cinderella coach on Valentine's Day. Cuddle up as you take in Winter Garden's charming twinkling lights and sights all along Plant Street on the 20-minute tour. Book here.

Image credit: SOUL Haven Ranch

3. Snap a selfie at the Valentine’s Day Mural Wall

Need an updated selfie with your favorite person? Famed artist Rudy Drapiza will be creating a special chalk mural to mark the holiday. Find the mural at S. Boyd St. and W. Plant St on Friday, February 14.

4. Create a shared piece of art

Saturday, February 15, 2-5pm
SOBO Art Gallery
127 S. Boyd St.
$75/couple (non-member)

Make memories–and art–together at SOBO Art Gallery. The gallery will host a special art workshop on February 15, 2020. Learn to make your very own stained glass painted bottle lamp under the guidance of instructor Kathy Bee. All materials will be provided. Register here.

5. Check out festive decorations downtown

Soak up the romance throughout downtown with a variety of fun lighting displays to commemorate the holiday. City Hall will glow red, the splash pad will be illuminated with purple light and twinkling lights throughout town will add extra sparkle. Take a stroll to soak in the colorful sights or use them as a backdrop for some fun twilight photos together. 

6. Take a couples' historical walking or biking tour

Saturday, February 15, 10am and 2pm
Winter Garden Heritage Foundation

Dress in your date day best and embark on a guided historical tour of town with a Winter Garden Heritage Museum docent. Walking and biking tours are offered, so take your pick! Tours are open to adults only. Advance reservations are required and can be made by calling 407-656-3244.

Image credit: City of Winter Garden

7. Dine and wine

Many of Downtown Winter Garden's unique, award-winning eateries and bars will be featuring dinner, dessert and drink specials, including an aphrodisiac “Love Potion” beer release at Crooked Can Brewing Company. Plus, Winter Garden Food Tours is hosting special weekend brunch tours.


  • Burger Fi: Free Custard Cup with the purchase of a sandwich all day on February 14, 2020.
  • Crooked Can Brewing Company: Special Valentine’s Day beer release – LOVE POTION – on February 14. A light and fruity Aphrodisiac Ale – who can resist?
  • Matthew's Steaknouse: Fine dining experience with special-priced Valentine’s Day dinner menu, including bottle of wine, for $79/person: 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. Reservations required: 407-520-7511.
  • Morthan Cheese at Plant Street Market: Buy one, get one 50% off on Valentine’s Day, February 14, 2020.
  • Pilars Martini: BOGO on all Mini-Splits on Feb. 14, sparkling bottle specials all weekend (February 14-16, 2020), and live music all Valentine’s weekend (Friday-Sunday night). Drop in for “Sparkling & Jazz” to celebrate Valentine’s Day!

winter garden
Image credit: Pilars Martini Bar


February 15 and 16, 11am
Downtown Winter Garden, multiple stops

Want to get a taste of multiple Winter Garden eateries during one visit? Winter Garden Food Tours will be offering Valentine's Brunch Tours on February 15 and 16, 2020. Tour stops include Rosallie Le French Café, The Deli Downtown, The Tasting Room, Thai Blossom and Way Chocolate. Book here.

8. Go for a bike ride together

Ride side by side through the quaint downtown and the adjoining 22-mile West Orange Trail. Winter Garden Wheel Works will be offering two-for-one bike rentals at its outpost at the Winter Garden Trailhead. Or, visit the shop on Plant Street for a 15% discount on the purchase of two bikes OR a tandem bike. Both deals will be offered February 14 – 16, 2020. 

Image credit: City of Winter Garden

9. Indulge in dessert – and don’t forget the chocolate!

Dessert options abound with bakeries, chocolate shops, and coffee houses offering handcrafted holiday sweets for your sweetheart. You can even feast your way through downtown on a Valentine’s Chocolatey Crawl. Your furry best friends are not forgotten with pupcakes, pup truffles, and a variety of custom holiday treats.

Indulge at these local favorites:

  • The Bulk Pantry: A broad selection of custom-made strawberry shortcake donuts, cheesecakes, cupcakes, mini cakes, cookies, chocolates, and more plus Valentine-themed sweets for all diets including low carb, sugar free and gluten free.
  • David Ramirez Chocolates: Handcrafted Valentine’s themed chocolates and macarons.
  • Rosallie le French Café: Transcend to romantic Paris with each bite of delectable French pastries! 
  • Sweet Dee's Cupcakery and Custom Cakes: Custom Valentine’s cupcakes and desserts galore for you as well as pupcakes, pup truffles, pup cookies to treat your pup.
  • Way Chocolate & Coffee: Hand-crafted Valentine's Day chocolates and desserts, chocolate truffles and gift baskets.

Valentine's Day in Winter Garden - Rosallie Le French Cafe
Rosallie Le French Cafe


Friday, February 14, 7:30 pm start time, 7pm early registration
Kick-off location: Rosallie Le French Café, 141 W. Plant St. 

This self-guided walking tour with five pre-set tastings includes a passport to explore the handmade, extraordinary chocolately treats and unique establishments throughout Downtown Winter Garden at your own pace. You'll visit Scoops Old Fashioned Ice Cream Store (Ice cream treat), Rosallie Le French Cafe (truffles), David Ramirez Chocolates (macaroons), Way Chocolate and Coffee (chocolate-covered strawberries) and sip ultra-decadent Hot Cocoa provided by Winter Garden Food Tours. Walk-ups will be welcomed, if space is available. Book here.

10. Stroll and shop

Spend Valentine's Day walking hand-in-hand along the charming, twinkle-lit historic streets and pop into the one-of-a-kind shops. 

Some of the deals offered at shops in downtown Winter Garden include:

  • Driftwood Market: Complimentary champagne in-store from 6-9pm on February 14, 2020.
  • Gee Gee's Gems: 10% OFF all purchases plus a chocolate treat with each purchase on February 14 and 15, 2020.
  • KITLIFE: 20% off on Valentine’s Day.
  • 02 Breath in One Utopia: 15% off all aromatherapy oxygen sessions Valentine’s weekend (February 14-16, 2020). Located inside of One Utopia at Plant Street Market.
  • Plantation Jewelers: Custom-made selection of rings and jewelry with hearts and an assortment of beautiful designs.
  • The Sacred Olive: 15% off any size Chocolate Balsamic and Strawberry Balsamic February 14-16, 2020
  • Winter Garden Wheel Works: 2-FOR-1 bike rentals (rentals at Winter Garden Trailhead: 455 E. Plant St.) and 15% OFF any two-bike purchase or tandem bike, February 14-16, 2020.
  • Woodstone Jewelry Pop-Up at Driftwood Market: 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.
  • Woof Gang Bakery: 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.

For a list of Valentine’s Day activities/dining/shopping special offers, as well as Valentine’s Day downtown event information, visit the Facebook event page or www.cwgdn.com.


Feature image credit: Cricket’s Photo & Cinema

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