Fun and Unique Winter Park Date Night Ideas For Valentine’s Day

By Krista Knauer

February is almost here, and we all know what that means. Valentine’s Day has arrived! Check out these Winter Park Date Night Ideas. Whether you love it or feel like it’s just a bunch of corporate nonsense, it seems like Valentine’s is not limited to just the 14th of February anymore. The whole month has become a celebration of love in all forms: romantic, familial, platonic, and self. In the spirit of Saint Valentine, you might be wanting to get out and mix it up with something new. Need some fresh ideas? Our dating and nightlife experts at Park Ave Magazine have a few suggestions for you!


If you’re looking for a creative, activity-based date, head on over to All Fired Up, located at 229 W. Fairbanks Avenue. At All Fired Up “Winter Park’s Original Paint-it-Yourself Pottery Studio”. All Fired Up takes walk-ins only, so there is no need for an appointment. You and your date can walk in, pick a plate, cup, or other ceramic pieces (which vary in price). You can get any instructions from the teachers, and get artsy with the ceramic paints. When you are finished with your masterpiece, leave it with the staff and it will be glazed, fired and ready to be picked up in a week. Prices range from $10 to $150 with most pieces around $25. Creating a custom pottery piece is a creative, affordable date night idea that is perfect for any couple. Plus, there is nothing like spending quality time being creative while enjoying the atmosphere of a local gem.


If you and your date are of legal age, then head on over to The Wine Room to sample a wide variety of wines. Located at 270 S. Park Ave., The Wine Room lets you purchase a tasting card for $3. The Tasting Card acts as a debit card – you load it up with any amount you choose, then take it over to the tasting machine where you can sample from the 100+ wines. Or if you’re into beer and liquor, then head on over to the old State Auto Body building, located at 1288 N. Orange Ave. Sample flights of craft beer and liquor at The Brewstillery, with beer from Bear and Peacock Brewery, and liquor from the Winter Park Distilling Company. Sampling the local flavors can bring the wild romantic out in anyone.


On the second Tuesday of each month, you can watch a free outdoor film in Central Park, sponsored by the Enzian. On February 7th, they are showing Roman Holiday, the classic 1953 romance film starring Audrey Hepburn. Starting at 7:00 pm, bring a blanket and maybe a picnic, and enjoy the feelgood movie with whomever you like.


The first few date nights can be stressful and intimidating. Do they like me? Are we moving too fast? How can I find affordable date ideas? You can make these worries disappear with a date night at an improv comedy show. Improv comedy shows make for great first dates- the laughter and furious jokes dispel any stress or fear that you have and it’s a great way to have a memorable experience. The AdLib Theatre in Winter Park, located on 200 N Denning Drive, Suite 1, hosts weekly improv performances such as Saturday Nights at AdLib Theatre. Tickets are $7 in advance and $8 at the door.


With several galleries and museums in town, art is never too hard to find. For art historians, you can visit the Albin Polasek Museum and Sculpture Gardens at 633 Osceola Ave. to learn about the artist and his life. They are open Tuesday through Sunday (with limited hours on Sundays). Tickets for adults are $10, senior citizens and college students are $8, K-12 students are $3, and children under 4 are free. Here are several other museums and galleries in Winter Park that you can visit with your date:

  • The Charles Hosmer Morse Museum of American Art, 445 N. Park Ave., features a large collection of Louis Comfort Tiffany glass. Tickets are $6 per person, except for free admission on Fridays November through April.
  • The Cornell Fine Arts Museum, located on the campus of Rollins College at 1000 Holt Ave., is always hosting a variety of artwork and exhibitions. Admission is always free.
  • Or if you feel like seeing the latest trends in art, head on over to Ocean Blue Galleries (202 N. Park Ave.) or the Scott Laurent Collection (348 N. Park Ave.). Both are conveniently located off Park Ave., and open to the public to view wonderful awe-inspiring works.

Winter Park Date Night

There are endless date night options in Winter Park, and unfortunately, we couldn’t feature all of the wonderful places and events. Hopefully, we’ve given you a few fresh new date night ideas for your love-filled February that will leave you with wonderful, life-long memories here in our beautiful town. Decided to take us up on any of these suggestions? Be sure to take a picture and tag us on Facebook at Park Ave Magazine!


This article originally appeared in the February 2019 issue of Park Ave Magazine. Titled “Date Night” by Krista Knauer © Copyright 2019 – Park Ave Magazine. If you are interested in reading past issues of Park Ave Magazine, go to the “Editions” tab on the main menu of our homepage. To order past issues of Park Ave Magazine, please call (407)951-5341.