10 Ways to Spend Valentine’s Day in Winter Garden

From a romantic and free outdoor concert to a specialty food tour and several artsy couples’ workshops, here’s the best of what’s happening for Valentine’s Day in Winter Garden.


– SPONSORED – We’ve been longtime fans of Winter Garden and its charming tree-lined streets, picturesque West Orange Trail, and dozens of quality restaurants lining Plant Street. While worthy of a visit anytime of the year, it’s also the ideal base for your Valentine’s Day celebrations this year. 

1. Be Serenaded

Love jazz? Breezeway Trio will be performing a 3-hour jazz concert at the Centennial Plaza Gazebo on Valentine’s Day from 6-9pm. Enjoy this romantic and free outdoor concert before or after dinner for two at a nearby restaurant.

2. Make Something Together

Driftwood Market is hosting several workshops at their Winter Garden location where you’ll get the chance to make something special for (or with) your sweetheart. Choose from four artisan workshops happening before and on Valentine’s Day.

  • You Are My World String Art ($30): February 4 and 7 from 7-9pm
  • Couples Make and Take Wood Sign Workshop ($70): February 9 from 10am-12pm
  • Make and Take Class “I Love You” or “Love You More” String Art ($20): February 14 from 10am-7pm

Image credit: Driftwood Market Winter Garden

3. Hit the Trail

Soak up the great outdoors together while exploring the scenic 22-mile West Orange Trail. You can check out some of our favorite stops along the trail here. As an added bonus, Winter Garden Wheel Works will be offering 2-for-1 bike rentals February 14-16, 2019.

Image credit: City of Winter Garden

4. Dine around Plant Street

There are dozens of restaurants to choose from on Plant Street, downtown Winter Garden’s main drag. A few date night favorites include Market to Table, Chef’s Table at the Edgewater, and Plant Street Market.

Here are a few Valentine’s Day specific dining and drinking details to note:

  • Market to Table: Five-course pre-fixe menu on Valentine's Day for $75/person
  • Morthan Cheese: Buy one get one free on Valentine’s Day
  • BurgerFi: Free custard cup with purchase of a meal on Valentine’s Day
  • Crooked Can Brewing Company: Free fill of King of Shoals New England IPA with purchase of a 64 or 128oz drink tank February 14-16

5. Take a His & Hers Food Tour

Speaking of food, local duo John and Jamie Baylor of Winter Garden Food Tours will lead a progressive His & Hers food tour feast on February 14. During the tour, you’ll enjoy:

  • Brews from Crooked Can
  • Bourbon and bacon donuts from Sir Benji’s Donuts paired with wings from Michael’s Ali Coal Fired Pizza
  • Private dining at Rosallie Le French Café including wine, cheese and truffles, French toast and gelato and a dark chocolate espresso

Tour times are at 6 and 7pm and the cost is $65/person.

6. Savor Something Sweet

Valentine’s Day isn’t complete without chocolates, and there are several can’t-miss confections in town. Visit David Ramirez Chocolates in Plant Street Market for holiday chocolates (you can also order ahead) like fudge brownie and raspberry champagne. Kaebisch Chocolate on Plant Street is a romantic stop for a shareable crepe or to pick up sweets to share.

Kaebisch Chocolates crepe Plant Street Winter Garden

7. Stroll & Shop

Outside of the restaurants and coffee shops, Winter Garden boasts multiple shops and boutiques. Highlights include The Sacred Olive (bottles of chocolate balsamic and strawberry balsamic will be 15% off February 14-17), Adjectives Market, and Driftwood Market among others. Kitlife will be offering 20% off on Valentine’s Day.

If you’re looking to gift jewelry for Valentine’s Day, Driftwood Market is hosting a jewelry pop-up on February 9 from 11am-2pm. Stop by, pick out a freshwater pearl and watch it get made into a ring. The cost is $15.

Image credit: City of Winter Garden

8. Share a Heart-Shaped Pizza

There’s no shame in celebrating Valentine’s Day by chowing down on a pizza together. Michael’s Ali Coal Fired Pizza (located in Plant Street Market) will be serving heart-shaped pizzas in honor of Valentine’s Day on February 14.

9. Sing a Love Song (or just listen to some)

Every Thursday is open mic night at Pilars, a lively piano and martini bar in the heart of downtown. If you’re feeling brave, hop on stage to sing a ballad to your boo with the help of a live piano player. Otherwise, sit back and listen to local talent as you sip on a specialty cocktail or glass of bubbly.

10. Attend a Masquerade

If you’d rather celebrate during the weekend, wait until Friday for the Winter Garden Art Association’s annual Splash of Masquerade gala at Winter Garden Pavillion. Held on Friday, February 15 from 6:30-10pm, the event includes cocktails, auctions, dinner and live music from Nova Era. The dress code is black tie or creative costume and masks are encouraged.

Feature image credit: Kelly Berringer Photography

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