Valentine’s Day has arrived and instead of simply being one day of lovey-dovey, rom-com level celebration, it’s a whole weekend full of candy-filled festivities! I’ve selected a few events that would be fun to surprise your significant other with — or to treat yourself to!

First off is a food crawl that will take your Friday to another level. Throw out the normal Valentine’s Day plans of going out to dinner and spending too much money on a set menu and, instead, venture out to Winter Garden for the Chocolatey Crawl!

Where are all the fit couples at? If you’re raising your hand as you read this, Winter Park is where you’re going to want to be this Saturday morning. AdventHealth and TrackShack are putting on a run/walk that is perfectly themed for Valentine’s Day weekend.

Does your husband, wife, girlfriend or boyfriend love craft beer? Take them to the dreamy event listed below and taking place over at Sideward Brewing Company. Sideward is perfectly pairing top notch desserts to its neat selection of beers.

Next, if you’re wanting to make some memories this weekend, I’ve got the ideal night for you. Lakeland’s Nineteen61 is hosting a five-course meal, prepared by Chef Chem, and a special dessert prepared by Pastry Chef Lily. After finishing, head upstairs for a salsa dancing lesson paired with bubbly on the rooftop!

Finally, are you a couple that’s into theater? If so, get dressed up and enjoy a stunning live performance. All weekend long, Orlando Ballet will be performing “Cinderella.” The modern take brings to life this fairy tale that has been making hearts full for ages.

Chocolatey Crawl

When: 7:30 p.m. Friday, February 14

Where: Winter Garden Food Tours

119 S. Lakeview Avenue, Winter Garden

Tickets: $35

Nosh on sweet treats this Valentine’s Day as you bounce around different locations in Winter Garden. Each guest will be given a “passport” that gives them access to exclusive tasty treats at David Ramirez Chocolates, Sweet Dee’s Cupcakery, Scoops Old-Fashioned Ice Cream Store and more!

V-Day Dessert & Beer Pairings

When: 3 p.m. Friday, February 14

Where: Sideward Brewing Co.

210 N. Bumby Avenue, Orlando

Imagine sipping on a “Born in Black” — a bourbon barrel-aged imperial stout with hints of coffee and vanilla — while diving into a rich pot du creme. Would you try Sideward’s Strawberry Skull Tattoo IPA paired with angel food cake, fresh strawberries and cream? Sideward Brewing Co. is pairing desserts and beers like this from 3 p.m. until close!

Valentine’s Rooftop Event

When: 5 p.m. Friday, February 14

Where: Nineteen61

215 E. Main Street, Lakeland

How does this sound for an extraordinary date night? The night begins with a toast and a mouthwatering, five-course meal prepared for you by the executive chef and pastry chef. Next, you wonder upstairs for an hour long salsa dancing lesson on the rooftop! This is as romantic as it gets, people.


When: Friday-Sunday, February 14-16

Various times

Where: Dr. Phillips Center for the Performing Arts

445 S. Magnolia Avenue, Orlando

Tickets: Starting at $19

If you’re looking for a unique date idea, or want to bring the kiddos along for a Valentine’s weekend celebration, I highly recommend checking out “Cinderella,” presented by Orlando Ballet. Watch the pumpkin transform into a sparkling carriage, the stepsisters bicker and true love win before your eyes!

Run 4 Love 4-Mile

When: 7:30 a.m. Saturday, February 15

Where: Showalter East Fields

250 Perth Lane, Winter Park

Let’s face it, this holiday is often celebrated with good food, a few sips of tasty wine and lots of desserts! Run or walk it all off on Saturday morning at the Run 4 Love 4-Mile. Participants are encouraged to show off their Valentine’s Day garb — or Cupid costume — for a costume contest!