The Best Date Night Ideas in Winter Park FL 2021

If your relationship is anything like mine, your significant other regularly drops hints about going out for a date night. Also, if your relationship is like mine, you struggle to think of ideas that you haven’t done a million times before.

Whether you live in Winter Park, the surrounding areas, or you’re just visiting, developing a date night idea can be overwhelming due to the sheer size of central Florida and all that it has to offer. This list of the best date night ideas in Winter Park, and the surrounding areas, will help narrow it down and provide the two of you with an evening game plan to paint the town red.

Couples Cooking Class

Taking a cooking class together is not only a great idea for an out-of-the-box date night but can also provide you the necessary skills to spoil each other, at home during your downtime, whether it’s a surprise dinner or breakfast in bed. A couples cooking class has the potential to elevate your relationship in aspects other than date night by providing you with acquired skills.

Publix Aprons, Truffles & Trifles date night cooking classes and seasonal classes at Tapa Toro are all great options for a cooking class date. A lot of love can be found and shared through an interactive couple’s experience such as a cooking class. It’s also a great way to determine if a first date will be your last date (hopefully that’s not the case for most of you).

Artistic Date Night Package

Not too far from Park Avenue in Winter Park, Pinspiration offers a unique date night idea via their “Splatter Date Package” located in their “Splatter Room”. As you may have guessed, this involves splattering, throwing, and dripping paint onto a canvas to create unique and memorable pieces of art but also a unique and memorable date night experience.

Included are your canvas, gear, and an option to upgrade to a glow-in-the-dark painting session. They also supply your date night with chocolate and champagne. The three C’s (creativity, chocolate, and champagne) make for an unforgettable and fun evening that you may not have thought of before but surely will consider on your next date night.

Bösendorfer Lounge

If an upscale date night is more your speed, then you cannot get much swankier than a night downtown in the Bösendorfer Lounge at the Grand Bohemian Hotel. Their sophisticated bar makes for an upper-echelon evening out with occasional live jazz and a live DJ on Wednesday nights.

They also offer a charcuterie if you’re looking for a laid-back essence to add to your date night mischief. This upscale cocktail and wine lounge offer signature dishes as well, ranging from escargot and flambee to wagyu beef carpaccio and their lobster & crab bisque. The Bösendorfer Lounge truly implements all the necessary elements for a high-class date night, and it isn’t far enough from Winter Park to deter the locals.

Jazz Tastings

I may have been born after my time if you consider my love for jazz music. If your love of jazz is anywhere close to mine, then you really should check out Jazz Tastings on the cusp of Winter Park. Jazz Tastings offers live music, a great selection of dishes to choose from, and a well-stocked beer and wine bar. All of which is packaged neatly into an elegant, mood-lit, atmosphere.

On Tuesday nights, which may seem a bit odd for a date night, they have scheduled their open mic night. On more traditional date nights, such as Friday and Saturday, they offer live music until 11:30 P.M. EST and are open until 1:00 A.M. EST which gives you and your partner an ample amount of time to participate in the festivities and enjoy each other’s company. With everything they have to offer, it’s no wonder why 761 people have voted them a rating of 4.6 out of 5 stars on Google.

Happy Hour Tour at The Alfond Inn

As the only hotel in the U.S. that is the extension of an art museum, The Alfond Inn offers happy hour art tours by a Cornell Fine Arts Museum staff member. With happy hour beginning at 4:30 and the tour beginning at 5:30, they have left plenty of time for you, and your date, to grease the wheels before the train pulls out of the station and into the art museum.

Taking place, the first Wednesday of every month, this unique date night idea offers plenty of time to schedule accordingly and obtain a babysitter if you simply cannot wait until the weekend for some time alone. The installation is rotated so that you can enjoy date night here again and again while enjoying different pieces of the collection. Afterward, you and your date can enjoy seasonal and popular favorites in Hamilton’s Kitchen. Don’t worry, the cellar at Hamilton’s Kitchen offers award-winning wines, craft beers, and a variety of cocktails so the two of you can keep your buzz going well into the evening; or at least until 9:00 P.M. EST.

We know that there’s plenty to do in the central Florida area but when it comes to date night it can be good to stand out occasionally. These eclectic and intimate date night ideas will supply you with everything necessary for a rememberable date night. From art to music, booze and food it’s no wonder why these venues have been enjoyed by hundreds, if not thousands, of couples over the years. If you haven’t had the pleasure of attending one of these venues before, leap of faith and spice up your date night with something new and unfamiliar. I have personally visited some of these locations myself and I am happy to say that I enjoyed myself and then some. I’m sure that you and your partner will feel the same way if a noteworthy date night is in the cards.

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