25 Winter Park Dates Under $50

25 Winter Park Dates Under $50

Money is a recurring issue for couples when it comes to planning a regular date night, but a night out doesn’t have to cost a significant amount in order to be enjoyable. There are plenty of activities and restaurants to discover as a couple for $50 or less.

To make planning a breeze, we’ve rounded up a list of some of our favorite low cost date ideas in Winter Park. Get out and enjoy some of the best the area has to offer without breaking the bank!

Free/Cheap

Catch an outdoor movie
Popcorn Flicks in the Park is a free monthly outdoor movie series hosted by the Enzian Theatre and The City of Winter Park. Each month features a different family friendly movie screened in Central Park.
FREE

Popcorn Flicks in the Park

Roam the free gardens
If you want to get out and enjoy nature, head to Mead Gardens or Kraft Azalea Garden, both of which offer scenic views and free admission.
FREE

Soak up the sun at the “beach”
Dinky Dock is a 1.5 acre park home to a beach (swimming is permitted), grills, docks, and picnic tables. Slather on some sunscreen and hit the beach right here in Central Florida.
FREE

Have a picnic in Central Park
For a simple weekend date, pack lunch and a blanket and set up anywhere in Central Park. Spend the afternoon lazing away, or pair this activity with another date idea on our list.
FREE

Peruse goods at Winter Park Farmer’s Market
The weekly farmer’s market takes place in the old train depot every Saturday from 7am-1pm. Stock up on goodies for the week or just browse what’s being offered from local vendors.
FREE to browse

Winter Park Farmer’s Market

Catch an improv show
Catch an improv show every Saturday at the AdLib Theatre. No two shows are ever the same, and once a month the Saturday show features an improvised movie.
$5/person

Explore the Albin Polasek Museum and Sculpture Gardens
Recognized on the National Register of Historic Places, the Albin Polasek Museum and Sculpture Gardens features sculptures by the Czech artist in a picturesque setting.
$5/person

Visit an art museum
The Charles Hosmer Morse Museum, home to a large collection of Louis Comfort Tiffany glass, offers free admission every Friday (November-April only) from 4-8pm. Admission is $6/person all other days of the week. The Cornell Fine Arts Museum is always free.
FREE – $6/person

Have a coffee date
Located in the heart of Park Ave., Barnie’s Coffee & Tea is a cozy spot perfect for sipping on a latte while people watching.
$10-$15

Sample sweets along the Avenue
Head to Peterbrooke Chocolatier for gelato, chocolates, and chocolate covered popcorn, indulge in a scoop of ice cream at Kilwin’s, or head to Le Macaron for French delights. Grab something sweet and then stroll the brick-lined streets together.
$10-$15

$30 or Less

Do movie night at Winter Park Village
Movie night is a tried and true date night, but it always works! Head to the Regal in Winter Park Village to catch the latest blockbuster.
$11/person

Enjoy a sunset Shake Shack dinner
For budget-friendly bites with a view, order burgers from Shake Shack and then grab a table out back to watch the sun set over Lake Killarney.
Menu prices vary

Explore by bike
For a fun weekend activity, rent a couple of bikes from Breakaway Bicycles and cruise the bike-friendly streets. All rentals come with a lock, helmet, and a scenic bike route map of the area.
$10/person per hour

Relax on a boat tour
The Scenic Boat Tour of Winter Park is one of the best ways to see several of Winter Park’s lakes while also learning about the area and its rich history. Tours leave every hour on the hour beginning at 10am and ending at 4pm.
$14/person

25 Winter Park Dates under $50

Scenic Boat Tour. Image credit: Stephanie Patterson

Try a yoga class
Full Circle Yoga offers daily classes and beginners are welcome. Check out a single class together, or purchase a bundle of 3 classes if you’re a new student.
$15/class or $25/3 classes (new students)

Take a happy hour tour of the Alfond Inn
This free tour is guided by a Cornell Fine Arts Museum staff member and highlights the contemporary art on display at The Alfond Inn. Afterwards, stick around for happy hour in the lounge of Hamilton’s Kitchen. Tours are offered the first Wednesday of each month at 5:30pm.
Menu prices vary

Treat yourself to fresh pastries
Much loved by locals, Buttermilk Bakery is the perfect place for a casual coffee date. Take your pick of fresh pastries and baked goods as well as coffee.
Menu prices vary

Check out the old State Auto Body building
This corner of Winter Park located on N Orange Ave. is home to Foxtail Coffee, Create Your Nature, and The Bear & Peacock brewstillery. If it’s a nice day outside, stick around and enjoy your drink or meal in the communal outdoor seating space.
Prices vary

25 Winter Park Dates under $50

Old State Auto Body Building. Image credit: The Bear & Peacock

$50 or Less

Give Stand Up Paddleboarding (SUP) a try
Paddleboard Orlando offers hourly paddle board rentals at 115 North Orlando Avenue. Pick up your rental and then head out for an adventure on Lake Killarney.
$25/hour per person

Try Tuesday Date Night at Kona Grill – *no longer available*
Every week, Kona Grill hosts their Tuesday date night dinner. Choose 2 courses per person from the special menu, all for under $50.
$44.95/couple for 2 courses

Rent kayaks and explore the chain of lakes
Peace of Mind Kayak Tours offers kayak rentals and delivery is free throughout Winter Park. Rent a tandem kayak and then paddle your way through the photogenic canals linking the Winter Park Chain of Lakes.
$40 for a tandem kayak for 3 hours

Happy hour hop in Winter Park Village
For less than $50, hop around a few Winter Park Village hot spots for a progressive happy hour date night. Here are a few ideas to get you started.
Menu prices vary

Winter Park Village

Have Sunday Brunch at Dexter’s of Winter Park
Venture slightly off busy Park Ave. for an affordable and delicious brunch at Dexter’s of Winter Park. Most dishes are priced $9-$12, and mimosas are just $3.25 each.
Menu prices vary

Paint pottery
Paint your own pottery at All Fired Up Tuesday-Sunday. Just drop in, select your piece, and paint away for an artsy night out.
$10-$150, average $25/person

Try a Wine Tasting
Simply visit The Wine Room, buy a wine tasting card for $3, load it up with any amount of money you choose, then sample wines from the wine tasting machines until your balance runs out. Or head over to The Parkview and enjoy a flight of red or white wine paired with hearty apps and a cozy, living room vibe. 
Prices vary

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