Winter Garden Valentine’s Day Dining Specials

Couple walking down Winter Garden.



His and Hers Food Tour

February 14th ($65 per person)

6:00 pm & 7:00 pm

Valentines Tour - Crooked Can Brewing Company meets Rosallie!

Start off at Crooked Can Brewery with beer and a sensational pairing of Sir Benji's Donuts with bourbon bacon Donuts and Michael's Ali Coal Fired Pizza coal-fired wings drizzled in Winter Park orange blossom honey.

Then enjoy private dining at Rosallie Le French Cafe with wine and a romantic pairing of cheese and truffles, French toast and gelato, finished with a dark chocolate espresso.

Something for him and something for her... This way everyone is happy. To book tour, 407-484-7460; email:


360 W. Plant St.

Free Dessert! Get a free custard cup with purchase of a meal on Valentine’s Day (Feb. 14).


426 W. Plant St.

Buy any 64oz or 128oz Drink Tank on February 14, 15, or 16 and receive a FREE fill of "King of Shoals" New England IPA

MICHAEL’S ALI PIZZA at Plant Street Market

Heart shaped pizza.

426 W. Plant St.

Share a heart-shaped pizza with the one you love at Michael’s Ali Pizza at Plant Street Market. One day only on Thursday, February 14th.

DAVID RAMIREZ at Plant Street Market

426 W. Plant St.

Valentine’s Day Collection 2019 featuring a special assortment of holiday chocolates including Fudge Brownie, Raspberry Champagne, and Cherries Jubilee, as well as your favorite classic chocolates with a Valentine’s print. Please order ahead!


50 W. Plant St.

Indulge in premium handmade chocolate made with world-famous Belgian chocolate and high-quality raw materials in a decadent array of flavors and textures. Select from an assortment of Valentine’s Day chocolates and desserts including crepes.

MORTHAN CHEESE at Plant Street Market

Morthan Cheese Valentine's Day Buy one, get one 50% off.

426 W. Plant St.

Buy ONE, Get ONE 50% OFF on Valentine’s Day, Feb. 14


146 W. Plant St.

Valentine’s Day Thursday “Open Mic” Special - drop in for a love song and a sparkling toast to celebrate - a bottle or a glass -- and a sweet treat. Drink specials available all weekend to celebrate Valentine’s Day.

For a comprehensive list of downtown dining options, please see the Downtown Dining Guide!

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