Top Valentine outdoor productions in Orlando

Top Valentine outdoor productions in Orlando

A lot of local Orlando organizations are getting creative when it comes to giving the most comfortable and safe place for their audiences. They are all bringing back live music and theatrical performances but in a safe outdoor environment. This helps out a lot with the most romantic holiday coming up. The Orlando arts scene is alive and well with a host of upcoming outdoor arts experiences couples will love. Here are our top picks for the best upcoming outdoor shows in Orlando, perfect for your next date night outing.

Down The Rabbit Hole


This event occurs Wednesdays-Sundays February 6 – March 14, 2021, multiple showtimes
Location: Mead Botanical Garden

The Creative City project is at it again with another spectacular outdoor show you don’t want to miss out on. This is truly one of a kind Orlando experience. Down The Rabbit Hole is a performance held right in the middle of the beautiful Mead Garden in Orlando. Follow Alice as she travels through wonderland meeting all of your favorite characters from the classic children’s bedtime story.
You can expect a combination of circus arts, dance, music, comedy, theater, incredible costumes, theatrical lighting, and more. Groups are limited to 10-15 people at a time. So go on out to Mead Garden to truly take your partner on a real magical adventure for Valentine’s day.


This performance is held at the outdoor courtyard tent at Orlando Shakes. It will be held on February 12 – 14, 2021, multiple showtimes
Recently, Orlando Shakes transformed the outdoor Garden Courtyard into an out door performance theatre tent. This covid safe tent will be hosting two outdoor productions this month. But first up is the romantic production of Kiss Me, Shakespeare! A Valentine’s Cabaret, combining classic Broadway show tunes with along with the most romantic scenes from Shakespeare.
Tickets are $30 for a two-person table.


February 13, 2021, noon-10pm
Outdoors at Swirlery Wine Bar (SoDo District)

This outdoor show in Orlando at Swirlery Wine Bar will combine music and wine into one fun, day-long outdoor festival. The outdoor stage will host a lineup of musicians and live DJs, and food from local purveyors (like Neopolitan pizzas and ramen) will be available for purchase alongside craft beer and wine.

Tickets are just $10 per person. VIP table tickets will be available soon.


February 17 – March 21, 2021, multiple showtimes
Outdoor courtyard tent at Orlando Shakes

Kicking off in mid-February at Orlando Shakes’ inventive outdoor courtyard tent, Josephine is a one-woman burlesque cabaret starring Tymisha Harris. The must-see show is a combination of cabaret, theater, and dance telling the story of Josephine Baker, the” first African American international superstar and one of the most remarkable figures of the 20th Century.” Highlights include the icon’s most famous acts, including songs “Blue Skies” and “La Vie en Rose,” plus “the dance routine that established her stardom, the dance Sauvage, also known as the banana dance.” Tickets begin at $30 for a two-person table and will be on sale beginning January 26, 2021, at noon.

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